Large group vacation rentals in Rum Point, Cayman Islands

Explore 85 large group vacation rentals, homes, and villas in Rum Point for your next getaway or business trip. With space for everyone, enjoy the comfort and privacy of a home designed for gathering, alongside premium amenities such as Air Condition Homes, Homes with Pools and Homes with Free Parking. Throughout your stay, spend time together, share meals, and relax in spacious living areas that make group travel feel cohesive. With options starting as low as $30 per night and homes offering up to 11 bedrooms and 13 bathrooms, it's easy to book a stay that fits your group. And with 24/7 local support and high-speed Wi-Fi, everyone stays connected and protected. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, making each trip more rewarding than the last. Book your next group getaway with Homes & Villas by Marriott.

85 Great for Groups in Rum Point

Timmy’s Place

Rum Point, KY
3 Bedrooms 8 Guests
Aug 25 - 30
$477 night

***Property Overview*** Welcome to Timmy’s Place, a brand-new oceanfront villa with spectacular views and a sandy backyard beachfront in peaceful Rum Point. This spacious 3-bedroom, 3.5-bathroom home is perfect for families and traveling groups seeking a relaxing island retreat within driving distance to beachfront dining and watersport options in neighboring Cayman Kai. The home’s upper level offers spectacular elevated views of the Caribbean Sea from the living areas to the expansive wraparound deck, perfect for enjoying your morning coffee with inspiring sunrise views. The deck and a lower-level patio are furnished with outdoor dining tables for alfresco meals by the sea. A propane grill sits on the oceanside of the deck, perfect for surf-and-turf cookouts. Inside, the upper level’s open-concept design includes a full kitchen with modern appliances plus a cozy living area furnished with a comfy sectional sofa and wall-mounted SmartTV. All three bedrooms sit on the upper level and feature walkout access to either the wraparound deck or a shared balcony. ***Sleeping Arrangements*** (Licensed to sleep 8 guests, 6 adults max.) -- Bedroom 1: primary suite, upper level, king bed, SmartTV, walkout access to the wraparound deck, ensuite with shower. -- Bedroom 2: upper level, queen bed, SmartTV, walkout access to a shared balcony, shares a Jack & Jill bathroom equipped with a shower. -- Bedroom 3: upper level, queen bed, SmartTV, walkout access to a shared balcony, shares a Jack & Jill bathroom equipped with a shower. -- Additional Sleeping: sleeper sofa in the lower-level den for two children only. On the ground level, a second den has been converted into a hybrid media room and recreation space just beyond the foyer. Guests will find a convertible air hockey & ping pong table, plus a dart board for friendly match play. The den also features a sleeper sofa, a SmartTV for streaming, and walkout access to the lower-level patio. For those who prefer to stay out of the sun, the lower-level patio is a shady retreat with a hammock for siestas by the sea. An outdoor shower also adds convenience to wash off after a day of backyard beach fun. The villa is surrounded by natural beauty, including a large area to the left with sandy pathways, beach chairs, and solar lighting, creating private hideaways for quiet moments or daytime adventures for kids. A public, beachfront gazebo and swing set sit to the right of the villa for everyone to enjoy. Need to work remotely while staying at Timmy’s Place? The villa comes equipped with a dedicated workspace at the end of the top-level hallway for your work needs. Guests can enjoy incredible snorkeling and kayaking (pictured kayaks available for rent) right from the beach with barefoot entry into the crystal-clear Caribbean waters. Plus, Timmy’s Place boasts an exceptional location, less than half a mile from the watersports and beachfront dining at the Rum Point Club and the Kaibo, making it the perfect blend of comfort, adventure, and island charm. *Notes: Bike rentals plus single/tandem kayaks and Seaview boards are available at discounted rates. A signed waiver is required. ================ ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service Fee added to all rates. -- Accidental Damage Protection added to all rates. -- A Departure Cleaning Fee is added for all stays. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays are welcome but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 or older to book and must occupy the property during the entire stay. -- Check-in is 3:00 pm; Check-out is 10:00 am. ***Grand Cayman Villas & Condos Guest Services*** The 10% Guest Service Fee includes the following member benefits: -- Centralized on-island Guest Services & Welcome Center -- Complimentary snorkel equipment for use during your stay -- Complimentary pack-n-plays, booster seats, & baby gates -- 10% advance booking discount towards a private charter -- Guest 10% discount card with preferred vendors (restaurants, watersports, charters, etc.) -- Unlimited use of our Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Referral to preferred vendors, guest services desk assistance -- Complimentary early check-in, if no check-out on the same day -- Tandem kayaks and paddleboards are available for discounted rental* *Signed waiver required. ***Nearby Points of Interest*** -- 1.0 mile west to the Rum Point Club and Bioluminescent Bay -- 2.4 miles to the Kaibo Beach Bar & Grill & Starfish Point -- 3.5 miles to the nearest grocery store, Chisholm’s Grocery -- 5.5 miles east to Over the Edge restaurant and the Cayman Crystal Caves -- 7.9 miles from our Welcome Center -- 11.6 miles east to the nearest supermarket, Foster’s Express, and the resorts at Morritts and Wyndham Reef Resort -- 13.6 miles to Tukka East Restaurant & Bar and the Cayman Parrot Sanctuary -- 14.7 miles to La Casita Taco & Tequilla Bar -- 25.0 miles (48-minute drive) from Owen Roberts Int’l Airport (GCM) ***Getting Around*** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Marshalls, or Hertz. ***Beach Notes*** All beaches in Grand Cayman are technically public, since the Crown extends to the high-water mark. Be advised that the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked before your arrival. Should sargassum be extremely heavy behind your property, we will reach out to the owner for alternative solutions, which may include a partial refund or relocation. We try our best to work around Mother Nature.

Hilltime

Rum Point, KY
5 Bedrooms 12 Guests
Aug 23 - 28
$978 night

***Property Overview*** Welcome to Hilltime, a spacious single-story beachfront villa located in beautiful Rum Point. Featuring multiple bedroom terraces, a private pool, and backyard snorkeling, Hilltime is a fabulous destination along the island’s North Side. Hilltime’s family room has been reconfigured by separating the dining and living areas to free up space for everyone in your group to spread out. The living area has been reshuffled with sofa seating and a wall-mounted television opposite the kitchen area. A new dining table sits against the windows providing beachfront views with every meal. Vaulted ceilings and tall windows allow natural light and sweeping views to fill the home. The new layout makes the best use of the space while accentuating the stunning ocean views throughout. In addition to the family room, a double bunk room has been added to sleep 4 children or 2 adults. The bunk room comes furnished with a SmartTV and plush round poufs for comfy seating. The bunk room shares an adjacent hall bathroom with the East Bedroom. Other upgrades include a Sonos Home Sound System. Set the vibe and let your favorite songs fill the home. A portable Sonos Move is located in the kitchen. Just grab it off its base and take your tunes to the beach or pool deck! The villa’s 5 bedrooms are divided by the family room with 2 on the west wing and 3 on the east wing. ***Sleeping Arrangements*** (Sleeps 10 adults, 12 guests max.) -- West Primary Suite: king bed, ocean views, television, blackout blinds, walk-out oceanfront terrace, ensuite with double vanity, makeup counter, large shower with walk-out access to the pool deck. -- West Suite: king bed, ocean views, large closet, blackout blinds, walk-out oceanfront terrace, and ensuite with shower. -- East Suite: king bed, ocean views, large closet, blackout blinds, walk-out oceanfront terrace, and ensuite with shower. -- East Bedroom: king bed, ocean views, large closet, blackout blinds, walk-out oceanfront terrace, shares adjacent hall bath equipped with shower bath. -- East Bunk Room: 2 sets of twin bunks, SmartTV, blackout blinds, shares adjacent hall bath equipped with shower bath. The home’s freshwater pool sits on the land-side of the villa protecting guests from trade winds in the winter and absorbing most of the sun’s rays. Sail shades and all-new sun loungers circle the pool deck. The pool deck also includes a cabana for shady relief from the island sun. For the grill master in your group, a new Weber propane grill is provided for island cookouts. Inside, the gourmet kitchen comes equipped with everything you need to prepare a home-cooked meal. Modern appliances including dishware, utensils, glassware, and cookware are all provided. Hire a private chef for a night of in-villa dining or start your morning with a champagne brunch! The beach behind the villa is wide and sandy with superb snorkeling inside the reef-protected shallows. Children, and the young at heart, will love the custom wood swing set installed along the beach. The property sits on a deep estate of over an acre with heavily landscaped grounds. Plenty of off-street parking is available with room to turn around in the driveway. ====== ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service added to all rates. -- Accidental Damage Protection added to all rates. -- A Cleaning Fee is added to all rates. -- Additional tandem kayaks are available for discounted rental. A signed waiver is required. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire with your travel dates prior to booking. -- Shorter stays may be accepted but subject to a higher cleaning fee. -- Must be 25 years or older to book and must occupy the property during the entire stay ***Grand Cayman Villas & Condos Guest Services*** The 10% Guest Service Fee includes your Guest Services Membership. Member Benefits -- Centralized on-island guest services & welcome center -- Unlimited Use of Private Fitness Center (18+ yrs.) -- Business Center with computers, printer/scanner, and FedEx/DHL supplies -- Proprietary Guest benefit & discount card -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Referral to preferred vendors and reservations assistance -- 10% advance booking discount for private charter -- Complimentary snorkel gear, pack-n-plays, booster seats, and baby gates for checkout At-Villa Benefits -- Complimentary early check-in (if no check-out on the same day) -- Day-after-arrival guest services follow-up -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Coordinate private chefs, cooks, babysitting & family photographer -- Kayaks available for discounted rental* *Signed waiver required. =============== ***Getting Around*** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Marshalls, or Hertz. ***Nearby Attractions*** -- 1 mile to the Rum Point Club & the island’s Bioluminescent Bay -- 2.5 miles to beachfront dining at the Kaibo, ferry service to Camana Bay/Seven Mile Beach, and a laid-back beach at Starfish Point -- 3.5 miles to the nearest general store, Chisholm’s Grocery -- 5.3 miles east to Over the Edge restaurant -- 5.8 miles to Cayman Crystal Caves -- 8 miles from our Silver Thatch Welcome Center -- 11.6 miles to the nearest supermarket, Foster’s Express -- 25 miles (47 min drive) from Owen Roberts Airport (GCM) ***Villa Cleaning & Sanitation*** All villas are cleaned and sanitized before each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked before your arrival. Should sargassum be extremely heavy behind your property, we will reach out to the owner for alternative solutions which may include a partial refund or relocation. We try our best to work around Mother Nature.

Ocean Kai

Rum Point, KY
6 Bedrooms 12 Guests
Aug 23 - 28
$1,489 night

***Property Overview*** Ocean Kai is built on the oceanfront along a sandy ridge in Cayman Kai. Spanning over 5,500 square feet of vaulted living space and an open design, Ocean Kai sleeps 12 guests across six bedroom suites. Upon entering the great room there is an immediate "wow factor" as your eyes take in the ocean views through a wall of glass doors and windows looking out over the pool deck. The open living area has a cathedral ceiling accentuating the home’s size and grandeur. A mezzanine loft with a glass railing serves as a media room and has an oceanfront windowed dormer with outstanding ocean views. A full-width, oceanfront shaded veranda overlooks a 38-foot private pool with steps leading down to your own sandy beach. The veranda is furnished with plush sectional seating and an outdoor dining area. *** Sleeping Arrangements *** (Sleeps 12 guests total) -- Bedroom #1: primary suite, oceanfront, king bed, television, walk-out access to the pool deck, ensuite with dual vanity, soaking tub, and separate shower. -- Bedroom #2: oceanfront, king bed, television, walk-out access to the pool deck, ensuite with dual vanity, soaking tub, and separate shower. -- Bedroom #3: oceanfront, king bed, television, walk-out access to the pool deck, ensuite with dual vanity, soaking tub, and separate shower. -- Bedroom #4: queen bed, television, ensuite with shower bath. -- Bedroom #5: queen-over-twin bunk beds, ensuite with shower. -- Bedroom #6: queen bed, television, ensuite with dual vanity, soaking tub, and separate shower. Ocean Kai’s kitchen is a vacationing chef’s paradise. Featuring marble countertops, all-white cabinets, and high-end appliances, guests can whip up a home-cooked meal or hire a private chef for a night of in-villa dining. Guests can choose to eat in the formal dining room or step out onto the veranda for a night of al-fresco dining. A propane grill is located near the pool deck for island cookouts. Notes: Additional tandem kayaks are available for discounted rental. Signed waiver is required. ===== ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 12.90% Villa Concierge & Service Fee is added to all rates. -- A Departure Cleaning Fee is added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire with your travel dates prior to booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 years or older to book and must occupy the property during the entire stay. -- Check-in is at 3:00 pm. -- Check-out is at 10:00 am. ***Grand Cayman Villas & Condos Services*** The Villa Concierge & Service Fee includes your Guest Services Membership. Member Benefits -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Proprietary Guest benefit & discount card -- 10% advance booking discount for private charter -- Complimentary use of snorkel equipment -- Guest parcel receipt & hold for check-in -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Referral to preferred vendors, guest services desk assistance -- Airport arrival Fast-Track VIP Process (fee charged by CAA) -- Special event/dinner reservations At-Villa Benefits -- Welcome amenity basket -- Complimentary early check-in, if no check-out on the same day -- Day-after-arrival guest services follow-up -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- $2,500 of Accidental Villa Damage Protection -- Complimentary pack-n-plays, booster seats, & baby gates -- Kayaks and stand-up paddleboards (SUPs) available for discounted rental* *Signed waiver required. =================== ***Villa Cleaning & Sanitation*** All villas are cleaned and sanitized prior to each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. The beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival--we try our best to work around Mother Nature.

Coral Kai

Rum Point, KY
5 Bedrooms 10 Guests
Aug 23 - 28
$1,144 night

***Property Overview*** Coral Kai is directly oceanfront in Rum Point on the north coast. This large one-story villa offers a sizable sandy beach that’s perfect for long walks or just a lazy afternoon. Excellent snorkeling is just steps from the back door! The large, oceanfront freshwater pool is elevated, allowing guests to soak in the wonderful ocean views while they swim. Coral Kai is less than a mile from the Rum Point Club, so guests can easily step out for water sports, drinks, lunch, or dinner. Coral Kai’s full-width, shaded veranda offers a place to relax in outdoor sectional sofas or lounge chairs; cool tile floors and outdoor dining tables make it the perfect place to unwind after a day of surf and sand. A propane grill next to the pool makes for effortless outdoor dining. ***Bedroom Configuration*** (Sleeps 10 guests total) -- Oceanfront King Suite: Gorgeous suite with a king bed, doors to the pool deck, stunning ocean views, two comfy chairs, and an ensuite bath with a soaking tub. -- Oceanfront Queen Suite: Ocean view suite with a queen bed, doors to the pool deck, spectacular ocean views, and an ensuite bath with a combination shower/bathtub. -- Garden View King Suite: Garden view suite with a king bed, TV, and an ensuite bath with a walk-in shower. -- Garden View Queen Suite: Garden view suite with a queen bed and an ensuite bath with a combination shower/bathtub. -- Twin Bedroom: Garden view bedroom with two twin beds and a bath next door. Twin beds can be converted to a king upon request. ***Coral Kai’s Unique Features*** -- Oceanfront windows and french glass doors facing the sea flood Coral Kai with Caribbean sunshine year-round. -- The recently redecorated interior gives the home an airy, beach house feel without sacrificing luxury or comfort. -- The living, dining, and kitchen areas all offer wonderful views of the Caribbean Sea. -- An enormous sectional sofa and a large flat-screen TV in the oceanfront living room allow everyone to hang together at the end of the day, whether they want to watch a movie or just relax. -- Sizable, open kitchen with modern appliances, plenty of counter space, and bar seating for quick meals or evening drinks! Dishware, cookware, cutlery, and a coffeemaker are all provided. -- Separate den with an additional flatscreen TV is perfect for kids, teenagers, or anyone who wants to get away for a few moments. -- Elevated veranda with outdoor sectional sofa and dining area. -- Superb wedding venue for small ceremonies. Excellent for large families, or 2-5 couples. Twin beds can be converted to a king upon request. Pool heat (winter only) is available for a $250 per week surcharge. NOTES: Bicycles and kayaks are available for discounted rental. Signed waiver required. ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 12.90% Villa Concierge & Service Fee added to all rates. -- A departure cleaning fee is added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire with your travel dates prior to booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 years or older to book and must occupy the property during the entire stay -- Check-in is at 3:00 pm -- Check-out is at 10:00 am ***Grand Cayman Villas & Condos Guest Services*** The Villa Concierge & Service Fee includes your Guest Services Membership. Member Benefits -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Proprietary Guest benefit & discount card -- 10% advance booking discount for private charter -- Complimentary use of snorkel equipment -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Referral to preferred vendors, guest services desk assistance At-Villa Benefits -- Day-after-arrival guest services follow-up -- Complimentary early check-in, if no check-out on the same day -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- $1,500 of Accidental Villa Damage Protection -- Complimentary pack-n-plays, booster seats, & baby gates -- Kayaks available for discounted rental* *Signed waiver required. ==================== ***Villa Cleaning & Sanitation*** -- All villas are cleaned and sanitized prior to each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. Should sargassum be extremely heavy behind your property, we will reach out to the owner for alternative solutions which may include a partial refund or relocation. We try our best to work around mother nature.

Olympus Villa

Rum Point, KY
5 Bedrooms 12 Guests
Aug 26 - 31
$1,374 night

***Property Overview*** Welcome to Olympus, a landmark oceanfront estate in Rum Point. Recently acquired by new owners, this striking, architect-designed villa sits on an elevated shoreline, offering panoramic views of reef-protected waters and direct access to world-class snorkeling. With a bold abstract design, a three-level layout, and seamless indoor-outdoor living, Olympus is a masterpiece of modern island luxury. The heart of the home is the main-level great room, where 40 feet of floor-to-ceiling sliding glass opens to a sun-drenched terrace and L-shaped freshwater pool. The pool, heated seasonally from Thanksgiving through mid-April, is flanked by tiled patios and cool artificial turf for barefoot comfort. The home’s angular design provides natural shade throughout the day, creating relaxing outdoor retreats. A sandy backyard stretches to the water’s edge, while a half-bath with exterior entry serves guests enjoying the pool. Indoors, a floating staircase and tropical wood accents lead into a stylish, open-concept space. The living area features a sectional sofa, large HD cable television with Apple TV for streaming, and a PS4, plus an adjacent reading nook for quieter moments. Hidden roll-down shades and five independent A/C zones ensure comfort throughout. The expansive kitchen boasts quartz countertops, top-of-the-line appliances, and a large island ideal for chef-hosted dinners or casual meals. A breakfast bar seats four, while the main dining table accommodates ten. Five well-appointed bedrooms sleep up to 12 guests, 10 adults max. There’s a family suite and bunk room on the lower level, plus three king suites on the upper level. *Sleeping Arrangements* (Sleeps 12 guests total, 10 adults max) -- Bedroom 1: family suite, lower level, king bed, sleeper sofa for 2 small children, television, walkout access to the pool deck, coffee station with minifridge, ensuite with shower. -- Bedroom 2: lower level, twin-over-full bunk bed, television, uses adjacent half bathroom. -- Bedroom 3: primary suite, upper level, floor-to-ceiling oceanfront windows, king bed, television, desk + chair, walkout access to the east + west terraces, ensuite with soaking tub and rainfall shower. -- Bedroom 4: upper level, king bed, television, walkout access to the west terrace, ensuite with shower. -- Bedroom 5: upper level, king bed, television, walkout access to the west terrace, makeup vanity, ensuite with shower. The third-floor rooftop terrace elevates outdoor living with 360-degree island views, an alfresco dining veranda seating 8–10 people, plus a sun deck for daytime tanning and a lounge area for late-night stargazing. An outdoor prep kitchen makes sunset dinners unforgettable. Additional amenities include a private home office with wifi, a full laundry room with detergent and extra linens, a propane Rinnai water system for continuous hot water, two propane grills, and heavy tropical landscaping for privacy. A home security system is available upon request, and mid-week housekeeping is included with 7-night stays. Whether relaxing poolside, enjoying a surf-n-turf cookout on the beach, or late-night stargazing from the rooftop terrace, Olympus offers a one-of-a-kind Cayman experience designed for privacy, comfort, and spectacular views. ========= ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 12.90% Villa Concierge & Service Fee is added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays are welcome but subject to a higher cleaning fee. Please inquire to book. -- Must be 25 years or older to book and must occupy the villa during the entire rental period. -- Check-in is at 3:00 pm; check-out is at 10:00 am. ***Grand Cayman Villas & Condos Guest Services*** The Villa Concierge & Service Fee includes your Guest Services Membership. Member Benefits -- Centralized on-island Guest Services Team & Welcome Center -- Free snorkel gear for all members of your group -- Free access to our private fitness center (18+ yrs.) -- Complimentary business center access: computers, printer, scanner, & FedEx/DHL supplies -- Guest benefit card for 10% discounts at select restaurants and preferred vendors -- 10% Discount towards a private Stingray City snorkel charter -- Guest parcel receipt & hold for check-in -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Airport arrival Fast-Track VIP Process (fee charged by CAA) -- Arrange airport pick-up & rental vehicles (fee applies) -- Special event coordination and dinner reservations At-Villa Benefits -- Welcome amenity basket with locally sourced goods -- Free baby gear including pack-n-plays, booster seats, & baby gates -- Complimentary use of Apple TVs, Bluetooth speakers, beach coolers, and more -- Complimentary early check-in, if no check-out on the same day -- Day-after-arrival & mid-week guest services follow-up -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- $2,500 of Accidental Villa Damage Protection -- Additional kayaks available for discounted rental* *Signed waiver required. =================== ***Villa Cleaning & Sanitation*** All villas are cleaned and sanitized before each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum. Sargassum is a harmless seaweed that is largely seasonal in the summer months. Our owners will remove heavy sargassum and will have the beach raked ahead of your arrival. Should sargassum be extremely heavy behind your property, we will reach out to the owner for alternative solutions, which may include a partial refund or relocation. We try our best to work around Mother Nature.

Fischers Reef

Rum Point, KY
8 Bedrooms 20 Guests
Nov 21 - 28
$6,089 night

***Property Overview*** Located just a mile from the famous Rum Point Club, Fischer’s Reef is a perfectly designed 8-bedroom oceanfront villa ideal for large families or group getaways. The villa’s unique floor plan allows guests to spread out in ample style with multiple living and sleeping areas. A wide staircase separates the floors meaning the noise from one floor won’t reach the others. Renovations completed include luxurious features such as an oceanfront infinity pool with optional heat, beach cabana, multiple indoor and outdoor dining areas, two separate 75-inch LED TVs, and a Sonos home theater system. For remote working professionals, a new high-speed fiber internet connection has been wired to the property. Multiple users and devices can now connect to the web to work or learn remotely with reliable speeds and increased bandwidth. All the attention to detail makes Fischer’s Reef a wonderful venue for entertaining and relaxation. ***Bedroom & Bathroom Layout*** (Sleeps 18 guests total, 14 adults max) -- King Suite #1: Main-level suite with a king bed, garden views, ensuite bath, and an ensuite bath. -- King Suite #2: Main-level suite with a king bed, partial ocean views, and an ensuite bath. -- King Suite #3: Pool-level suite with a king bed, ocean views, and an ensuite bath. -- Queen Suite #1: Pool-level suite with a queen bed, ocean views, and an ensuite bath. -- Queen Suite #2: Pool-level suite with a queen bed, ocean views, and an ensuite bath. -- Queen Suite #3: Pool-level suite with a queen bed, garden views, and an ensuite bath with a shower tub combo. -- Twin Bunk Suite: Pool-level suite with two sets of twin over twin bunk beds and an ensuite bath with a shower tub combo. -- The living area also has a sleeper sofa. ***Fischer’s Reef Notable Amenities*** -- Fischer’s Reef is located within a designated marine park teeming with abundant marine life just steps off the infinity pool. Strap on your snorkel gear and go exploring, but please wear pool shoes for protection and avoid damaging the corals! -- Sandy beach with oceanside cabana and hammocks for hours of relaxing by the sea -- Wonderful sunrises and plenty of privacy -- Spectacular stargazing with minimal light interference -- The indoor living and dining areas upstairs are furnished with high-quality upholstered furniture and decor -- Large modern kitchen on the upper level with a spacious refrigerator, small upright freezer, gas range, microwave, two dishwashers, wine fridge, drip coffee makers, a Keurig, a Nespresso, and ample counter space -- Breakfast table for 8 and two large dining room tables seats 20; both with ocean views -- Oversized great room with multiple couches and living areas allow room for large families to spread out -- Exterior spiral staircase connects the balcony with the pool deck while providing wonderful elevated views of the beach and reef -- Pool-level living area features a kitchenette with a coffee center and microwave, dining table with seating for 6, plus a 75" LED TV for movies, games and sporting events -- Blu-Ray player and Apple TV on each level -- Laundry rooms upstairs and downstairs -- Fiber optic wifi connection with increased speed for multiple device streaming -- 7-zone central air conditioning -- Heated pool set to 88 degrees; additional heat to 88-92 degrees available during winter months for $500/week surcharge -- Home security system available -- Small deposit safe for guest valuables -- 1 single kayak & 1 tandem kayak included with the villa -- Additional tandem kayaks are available for discounted rental. Signed waiver is required. A local professional property manager resides on-site in the small cottage near the gated entrance. Manager’s cottage is heavily landscaped and separated from the villa. Close enough to reach out in case of emergency, but far enough away so as to respect your privacy. Owner requires Saturday-to-Saturday bookings unless otherwise pre-approved. ============== ***Rate Details*** -- 13% Occupancy Tax is added to all rates. -- 12.90% Villa Concierge & Service Fee is added to all rates. -- A Departure Cleaning Fee is added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire with your travel dates prior to booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 years or older to book and must occupy the property during the entire stay. -- Check-in is at 3:00 pm. -- Check-out is at 10:00 am. ***Grand Cayman Villas & Condos Guest Services*** The Villa Concierge & Service Fee includes your Guest Services Membership. Member Benefits -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Proprietary Guest benefit & discount card -- 10% advance booking discount for private charter -- Complimentary use of snorkel equipment -- Guest parcel receipt & hold for check-in -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Airport arrival Fast-Track VIP Process (fee charged by CAA) -- Arrange airport pick-up & rental vehicles (fee applies) -- Special event/dinner reservations At-Villa Benefits -- Welcome amenity basket/arrangement -- Complimentary early check-in, if no check-out on the same day -- Day-after-arrival & mid-week guest services follow-up -- Complimentary use of Apple TVs, BlueTooth speakers, beverage coolers -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- $2,500 of Accidental Villa Damage Protection -- Complimentary pack-n-plays, booster seats, & baby gates -- Additional kayaks available for discounted rental* *Signed waiver required. ============ ***Villa Cleaning & Sanitation*** -- All villas are cleaned and sanitized prior to each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. Should sargassum be extremely heavy behind your property, we will reach out to the owner for alternative solutions which may include a partial refund or relocation. We try our best to work around mother nature.

Sea Biscuit 1BR/1BA Oceanfront Sea Lodge at Rum Point

Rum Point, North Side, KY
1 Bedrooms 2 Guests
Aug 23 - 26
$197 night

Welcome to Sea Biscuit at The Sea Lodges, a charming direct beachfront 1 bedroom, 1 bath hideaway in Rum Point, Cayman Kai. Just a 5 minute walk (about ¼ mile) from Rum Point Beach, this cozy retreat sits along a peaceful stretch of Caribbean coastline with 400 feet of powder soft sand, crystal clear water, and excellent snorkelling right offshore. It’s ideal for couples or solo travelers seeking a relaxing North Side escape with easy access to dining, activities, and top attractions, typically about a 45 minute drive from Owen Roberts International Airport and the Seven Mile Beach corridor. 1 Bedroom | 1 Bathroom | Sleeps 2 (plus pack n play) ACCOMMODATION • Fully updated king bedroom dressed in luxury linens for a calm, restful sleep. • Ensuite bathroom with sleek walk in rain shower for a spa like experience. • Full air conditioning throughout the condo for year round comfort. After a day of Caribbean adventures, drift off in the plush king bed and let the ocean breeze and waves complete the experience. LIVING AREA & INTERIOR FEATURES • Open concept ground floor living area with a cozy 2 seater lounge and smart TV. • Selection of movies and audiobooks for laid back evenings in. • Screened in front patio with table and chairs overlooking the ocean—perfect for romantic dinners or sunset drinks. • Complimentary Wi Fi so you can stay connected while enjoying your island escape. KITCHEN & ESSENTIALS Fully Equipped Kitchen • Stove, refrigerator, microwave, and essential small appliances to prepare simple meals or longer stays. • Gas BBQ grill for relaxed outdoor grilling. • Multiple coffee options for your morning ritual: French press, Nespresso, and drip coffee—best enjoyed on the patio with sea views. Essentials Starter Pack • Kitchen Essentials: Dishwashing liquid and/or dishwasher tabs (if applicable), basic pantry starters such as salt, pepper, and coffee filters. • Home Essentials: Shampoo, conditioner, hand soap, toilet paper, paper towels, garbage bags, laundry detergent, blow dryer, and iron with ironing board. • Towels, linens, and beach towels are all provided. BEACHFRONT SETTING • Directly on a wide, sandy beach with lounge chairs and tiki huts for shaded relaxation. • Calm, clear Caribbean waters ideal for swimming, floating, and easy snorkelling right offshore. • Peaceful Rum Point setting with a quiet, laid back atmosphere away from busier resort areas. INCLUSIONS Complimentary items available (some on request) include: • Two bicycles for exploring the local area. • Yoga mats and snorkel gear for beach workouts and reef time. • Beach chairs. • Pack n play for guests travelling with a little one. When you’re ready to explore, you’re just minutes by foot, bike, or car from Rum Point Beach, Starfish Point, Crystal Caves, Botanical Gardens, Bioluminescent Bay, and several relaxed beachside restaurants. DINING & NEARBY ACTIVITIES • Rum Point Club & Restaurant – About a 3–5 minute walk (1–2 minutes by car) for oceanfront dining, beach bar favorites, hammocks, and a classic beach club vibe. • Red Sail Sports at Rum Point – Also a 3–5 minute walk, offering Stingray City trips, snorkelling, diving, paddleboarding, and kayak rentals. • Kaibo Beach Bar & Grill – Roughly a 5–7 minute drive for casual beachfront lunches, wood fired pizzas, and sunset cocktails. • Upstairs at Kaibo – An upscale fine dining restaurant above Kaibo Beach Grill, also about a 5–7 minute drive. • Kaibo coffee spot – Ideal for coffee, pastries, and easy breakfast starts when you head toward Kaibo. • Over the Edge Café – Approximately a 10–12 minute drive for casual local dining with waterfront views. • La Casita (East End) – Roughly a 25–30 minute drive for Mexican cuisine. • Tukka East and Eagle Ray’s – About a 25–30 minute drive for East End seafood and island style menus. • Morritt’s / East End resort area – Around a 25–30 minute drive, with additional restaurants, beach bars, and oceanfront dining options. Nearby attractions and highlights include Starfish Point (about a 5–7 minute drive), the Stingray City sandbar (via boat tours from Rum Point or Kaibo), Cayman Crystal Caves (around 10–15 minutes’ drive inland), and the Queen Elizabeth II Botanical Garden (approximately 15–20 minutes by car). GROCERIES, SUNDAY CLOSURES & PRACTICAL DETAILS Nearby grocery options such as Foster’s Express and Chisholm’s Grocery are about 15 to 20 minutes away by car. Larger supermarkets are also convenient stops on the drive from the airport. Supermarkets are closed on Sundays in Cayman, though most restaurants and gas stations remain open, and some gas stations sell liquor on Sundays. Grocery items can also be pre-ordered and delivered before arrival. Chisholm’s Market is on the Northside, and is open 7 days a week, and is well stocked with food, supplies, beer, wine & liquor. 15 minutes from the condo. TRANSPORTATION • A rental car is highly recommended for this area so guests can easily explore Grand Cayman at their own pace. • Many guests book directly with trusted local providers such as Marshall’s Rent-A-Car, Andy’s Rent-A-Car, or compare options through Kayak. • Due to limited public transportation in Cayman Kai, having a car offers the greatest convenience and flexibility. ACCESSIBILITY & PARKING • Ground-floor condo. • On site free parking is included. PROMOTIONS Automatic discounts may apply based on travel dates, including seasonal Stay 7, Pay 6 offers from May 1 to November 1, 2026, along with last-minute deals, early booking savings, and extended-stay discounts. Eligible offers are applied automatically, cannot be combined with other promotions or Repeat Guest benefits, and may be subject to blackout dates from December 17 to January 3. CHECK IN & CHECK OUT After booking, you’ll receive detailed arrival information by email, and your unique door code before arrival. Check in is any time after 4:00 PM with keyless entry; early check in may be possible depending on cleaning schedules and can be confirmed with the property manager closer to arrival. Check out is self service at 11:00 AM, with clear instructions provided; late check out is only available if pre arranged, as time is needed to prepare for incoming guests. SEASONAL NOTE During Easter week, guests should expect increased local activity and a livelier atmosphere in the Kaibo Kai area, reflecting one of Grand Cayman’s most vibrant holiday periods. TRAVEL INSURANCE Travel insurance is recommended, especially during hurricane season from August through October, to help protect against trip interruptions and weather-related disruptions. Guests can review coverage options directly here: https://caymanvacation.rentalguardian.com/ Sea Lodges License number: A-598

Gypsy Villa

Rum Point, KY
4 Bedrooms 10 Guests
Aug 23 - 28
$1,029 night

***PROPERTY OVERVIEW*** Welcome to Gypsy, a luxurious island getaway! This elegant Caribbean-themed villa is a true tropical paradise with a private oceanfront pool and backyard beachfront. Gypsy’s backyard oasis offers a private haven above the beach, ensuring your relaxation and privacy. Stairs lead down to a beautiful sandy beach, perfect for sunbathing. The pool deck includes sun beds for your convenience, and large hedges and grassy lawns providing seclusion during your stay. Optional pool heat is available during the winter at $50 per day for added comfort. As you enter the foyer, the tall glass doors beckon your gaze to the private pool area and the stunning Caribbean Sea beyond. Gypsy offers over 4,000 sq ft of living space, with an additional 3,000 sq ft of outdoor paradise, accommodating up to 10 guests across four bedrooms. Sleeping Arrangements (Sleeps 10 guests max.) -- Primary Suite: king bed, ocean views, walk-out access to the pool deck, walk-in closet, ensuite with double vanity, soaking tub, and separate walk-in shower. -- Bedroom #2: king bed, garden views, ensuite with walk-in shower. -- Bedroom #3: queen bed, garden views, ensuite with shower bath. -- Bedroom #4: 2 queen beds, garden views, shares adjacent hall bath equipped with double vanity and walk-in shower. Gypsy’s living areas boast astounding views, high ceilings, and plenty of natural light. The living room and family room offer ample seating for relaxation while enjoying the mesmerizing views. If you love music, the grand piano in the family room can be unlocked for your enjoyment. The gourmet kitchen is a chef’s dream, equipped with modern appliances, a double oven, a built-in Subzero refrigerator, a Keurig coffeemaker, and plenty of counter space. A dining table with seating for 10 allows for memorable meals with your loved ones. A propane grill is available on the pool deck for island cookouts. Please note that the owner does not permit pets, smoking, or events with invited guests on the property to ensure a serene and peaceful atmosphere. Don’t miss the chance to embrace the Caribbean dream at Gypsy! ***NOTES*** -- A Cleaning Fee is added for all stays due to enhanced cleaning and sanitation. -- Tandem kayaks and SeaView boards are available for discounted rental. A signed waiver is required. ================ ***RATE DETAILS*** -- 13% Occupancy Tax added to all rates. -- 12.90% Villa Concierge & Service Fee added to all rates. -- A cleaning fee is added to all rates. ***BOOKING RULES*** -- Christmas & New Year’s are split into two 7-night rental periods. Please inquire with your travel dates before booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 years or older to book and must occupy the property during the entire stay. ***GUEST SERVICES*** The 12.90% Guest Service Fee includes your Guest Services Membership. Member Benefits -- Complimentary snorkel equipment for use during your stay. -- 10% Advance Booking Discount towards a private snorkel or dive charter. -- Guest benefit card for 10% discount with our preferred vendors. -- Jacques Scott Wine & Spirits pre-order & complimentary hold at check-in -- Centralized on-island Guest Services & Welcome Center. -- Unlimited use of Private Fitness Center (18+ yrs.). -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Referral to preferred vendors, guest services desk assistance At-Villa Benefits -- Complimentary pack-n-plays, booster seats, & baby gates -- Complimentary early check-in, if no check-out on the same day. -- Day-after-arrival guest services follow-up. -- Gilchrist & Soames bath products. -- Assistance coordinating private chefs, family-style cooks, babysitting, or family photography -- $1,500 of Accidental Villa Damage Protection -- Pre-stocking of groceries & beverages (delivery fee applies) -- Tandem kayaks are available for discounted rental* *Signed waiver required. =============== ***GETTING AROUND*** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town. Plus, there is no Uber or Lyft in Cayman. For rental cars, we recommend Budget Cayman, Marshalls, or Hertz. ***VILLA CLEANING*** All villas are cleaned and sanitized before each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***BEACH NOTES*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***OCEAN DEBRIS & SARGASSUM SEAWEED*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency over the years during the summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked before your arrival. Should sargassum weed be extremely heavy behind your property, we will reach out to the owner for alternative solutions which may include a partial refund or relocation. We try our best to work around Mother Nature.

Fantasea

Rum Point, KY
3 Bedrooms 8 Guests
Aug 29 - Sep 3
$719 night

==> PROPERTY DESCRIPTION <== Along the beachfront in Cayman Kai is where you will find a newly-renovated and refurnished villa, aptly named Fantasea. This spacious 2-bedroom main villa with a detached 1-bedroom guest cottage has undergone a complete makeover, both inside and out. Plus, the villa’s recently upgraded fiber internet connection provides reliable speeds for work-from-home professionals, as well as reliable streaming options. The renovation included 100% new tile, windows, furniture, kitchen, baths, and high-grade stainless appliances. With multiple large sliding glass doors to the screened veranda and pool deck, guests are never far from views of the water. A new freshwater pool and tiled deck are elevated for privacy and to take advantage of the sun setting directly over Cayman Kai Cove. Ample deck furniture, an outdoor shower, screened veranda, and an outdoor kitchen, complete with a propane grill, make for easy-island living. The spacious open-concept great room links the living area, dining area, and kitchen with breakfast counter seating and a built-in table with banquette seats. Sliding glass doors provide seamless indoor/outdoor living allowing you to open the great room to the outdoors. Quality furnishing and decor have been used throughout the property for an elegant and contemporary feel. ***Sleeping Arrangements*** (Sleeps 10 Guests total; 6 Adults max) -- North Suite - king bed, water views, cable television, walk-out access to the screened veranda, ensuite with double vanity, shower, and bathtub. -- South Suite - two sets of twin-over-queen bunk beds, water views, cable television, walk-out access to the screened veranda, and ensuite with shower. -- Guest Cottage - detached from the main villa with private entry, queen bed, water views, SmartTV, beverage bar, dresser, ensuite with shower. The cove water is shallow with a soft bottom, so recreational swimming and snorkeling are best enjoyed up the street at the Rum Point Club, just a 5-minute walk north. There you will also find watersport activities from wave runners to guided dives, plus a restaurant, beach bar & grill, and a gift shop. Combined with its central location on the Cayman Kai peninsula, walkable to water activities, family-friendly restaurants, and laid-back beach bars, this island getaway is sure to become a guest favorite. Come experience easy island living in beautiful Cayman Kai! *Notes: A Cleaning Fee is added to all rates due to enhanced cleaning, sanitation, and inspection protocols. **Kayaks and stand-up paddleboards (SUPs) are available for discounted rental. A signed waiver is required. ==================== ==> RATE DETAILS <== -- 13% Occupancy Tax added to all rates. -- A 10% Guest Service Fee is added to all rates. -- Accidental Damage Protection added to all rates. -- A Departure Cleaning Fee is added to all rates. ==> BOOKING RULES <== -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates prior to booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 or older to book and must occupy the property during the entire stay. ==> GUEST SERVICES <== The 10% Guest Service Fee includes your Guest Services Membership. Member Benefits -- Complimentary use of snorkel equipment -- 10% Advance Booking Discount towards a private charter -- A guest savings card for 10% discounts at local businesses -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of our Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Referral to preferred vendors, guest services desk assistance At-Villa Benefits -- Day-after-arrival guest services follow-up -- Complimentary early check-in, if no check-out on the same day -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- Complimentary pack-n-plays, booster seats, & baby gates -- Kayaks & Paddleboards (SUPs) available for discounted rental* *Signed waiver required ==> WHAT’S NEARBY? <== -- Home is on the island’s Bioluminescent Bay -- 15-minute walk to Rum Point Beach -- 10-minute walk to the Kaibo Beach Bar & Grill -- 1.0 miles south to Starfish Point -- 5.0 miles to the nearest general store, Chisholm’s Grocery -- 6.9 miles east to Over the Edge restaurant -- 7.4 miles east to Cayman Crystal Caves -- 9.4 miles from Grand Cayman Villas & Condos Welcome Center -- 13.2 miles to the nearest supermarket, Foster’s Market -- 26.2 miles (51-minute drive) from Owen Roberts Airport (GCM) ==> GETTING AROUND <== A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Avis, Marshalls, or Hertz. ==> DAY TRIPPING <== Cayman Ferries operates daily water taxis departing from the Kaibo Marina to Camana Bay. Perfect for day trips to Seven Mile Beach or shopping excursions at Camana Bay. Download their app to purchase your tickets in advance. Just be sure to make it back for the return voyage across the sound! =============== ==> VILLA CLEANING <== All villas are cleaned and sanitized prior to each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ==> BEACH NOTES <== All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ==> SARGASSUM <== Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency over the years during the summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. We try our best to work around mother nature.

Peace & Kai It

Rum Point, KY
3 Bedrooms 6 Guests
Nov 30 - Dec 5
$742 night

***Property Overview*** This redecorated and lively 3-bedroom, 2-bath beach cottage epitomizes easy island living in beautiful Cayman Kai. Located on the shores of Cayman’s Bioluminescent Bay, the new owners have updated just about everything and also provided complimentary kayaks! As you enter the home, your eyes are drawn through a wall of sliding glass doors to the shimmering turquoise blue waters. Coconut palm trees, an elevated sundeck, a private dock, and a seaside hammock beckon you to kick off your shoes and relax. Let the vacation begin! A spacious living room and large kitchen provide all the comforts of home with new furniture and modern appliances. Dual-zone air conditioning, fiber-optic wifi, and SmartTVs will keep everyone cool and connected across their devices. Work-from-home professionals will enjoy the home’s high-speed wifi providing fiber-optic speeds for multiple users and devices. This single-level home positions the primary suite on one side of the home with two additional bedrooms on the opposite end. ***Sleeping Arrangements*** (Sleeps 6 guests total) -- Primary Suite - king bed, water views, SmartTV, ceiling fan, walk-out access to the screened porch, ensuite with shower bath. -- Guest Bedroom #1 - king bed, water views, SmartTV, walk-out access to the screened porch, shares hall bathroom equipped with a walk-in shower. -- Guest Bedroom #2 - 2 extra-large twin beds, island views, SmartTV, shares hall bathroom equipped with a walk-in shower. Twin beds can be fitted into a king upon request only. The newly-renovated kitchen comes complete with modern stainless appliances and a breakfast bar with seating for 4. A separate bar complete with an under-counter beverage fridge and a high-speed blender will keep your favorite frozen cocktails flowing. A full laundry room sits adjacent to the kitchen. The full-width screened patio and raised sun deck are furnished with al-fresco dining tables and comfortable lounge seating. The screen porch has western-facing views to enjoy spectacular sunset viewings at cocktail hour. A charcoal grill comes provided for island cookouts. Enjoy outdoor dining for 8 on the screened patio with 180-degree water views. With sea breezes all year round, it really does not get much better than this! Guests are asked to respect the villa’s non-smoking policy which includes all screened areas. Owners provide kayaks on a complimentary basis for use during your stay. Additional kayaks can be rented at friendly rates. Launch off the home’s private dock to explore the glowing waters of Bioluminescent Bay on moonless nights. Book a private charter to Stingray City and have the captain collect and drop you off on the home’s private dock. Peace & Kai It is a great option for families and group getaways. The adjacent 4-bedroom property, S’Kai Blue, can be combined with Peace & Kai It to sleep a total of 17 guests, or 14 adults, with an added private pool! Please contact us for more info on this bundled configuration. ***IMPORTANT NOTES*** -- A Cleaning Fee may be required due to enhanced cleaning, sanitation, and inspection protocols. -- Additional kayaks and stand-up paddleboards (SUPs) are available for discounted rental. A signed waiver is required. ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service Fee added to all rates. -- Accidental Damage Protection added to all rates. -- A cleaning fee is added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire with your travel dates prior to booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 or older to book and must occupy the property during the entire stay. ***Grand Cayman Villas & Condos Guest Services*** The 10% Guest Service Fee includes your Guest Services Membership. Member Benefits -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Proprietary Guest benefit & discount card -- 10% advance booking discount for private charter -- Complimentary use of snorkel equipment -- Complimentary pack-n-plays, booster seats, & baby gates -- Referral to preferred vendors, guest services desk assistance -- Complimentary early check-in, if no check-out on the same day -- $500 of Accidental Villa Damage Protection -- Additional kayaks and stand-up paddleboards (SUPs) available for discounted rental* *Signed waiver required. =================== ***Nearby Points of Interest*** -- Home is located on the island’s Bioluminescent Bay -- 15-minute walk to the Rum Point Club for snorkeling, watersports, and light dining. -- 10-minute walk to the Kaibo Beach Bar & Grill -- 12-minute walk south to Starfish Point -- 5.0 miles to the nearest general store, Chisholm’s Grocery -- 6.9 miles east to Over the Edge restaurant -- 7.4 miles east to Cayman Crystal Caves -- 9.4 miles from our Grand Cayman Villas & Condos Welcome Center -- 13.2 miles to the nearest supermarket, Foster’s Market -- 26.2 miles (51-minute drive) from Owen Roberts Airport (GCM) ***Getting Around*** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Avis, Marshalls, or Budget. ***Villa Cleaning & Sanitation*** -- All villas are cleaned and sanitized before each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked before your arrival. Should sargassum be extremely heavy behind your property, we will contact the owner for alternative solutions, which may include a partial refund or relocation. We try our best to work around Mother Nature.

Rum Point Resort Penthouse #504

Rum Point, KY
3 Bedrooms 8 Guests
Aug 31 - Sep 3
$841 night

*** PROPERTY DESCRIPTION *** Fifth Floor Penthouse | 2,620 sq. ft. All Rum Point Resort condos feature sleek finishes, designer decor, and an open-concept layout maximizing space, natural light, and stunning ocean views. All the comforts of home are included in this 2,620 sq. ft. penthouse condo including gourmet kitchen appliances, quartz countertops, SmartTVs throughout, and a private open-air oceanfront balcony. All condos strike the perfect balance of modern luxury and seamless indoor/outdoor island living. Central air conditioning and high-speed wifi will keep you cool and connected during your stay. Beyond the entryway foyer, the home flows into a spacious open-concept great room encompassing the living, dining, and kitchen areas. Forever blue ocean views from the great room and primary suite will leave you breathless. Vaulted ceilings and crisp coastal decor throughout accentuate the island scenery. The living area includes a comfy sectional sofa, a large SmartTV, a tray ceiling with a ceiling fan, and coastal decor. Walk out from the living area onto the private balcony overlooking the resort’s pool deck and beachfront. The balcony is also equipped with a retractable sunshade above an aluminum pergola for relief from the island sun. The gourmet kitchen features a suite of Thermador appliances, plus countertop appliances and a kitchen island with breakfast bar seating. Cookware, dishware, glassware, and cutlery also come provided. An outdoor dining table with seating for 6 is furnished on the private balcony for meals with sweeping oceanfront views. The Rum Point Resort fits all condos with blackout window shades, the finest Egyptian cotton bedding, hypoallergenic pillows, duvets, and sumptuous robes. ***Sleeping Arrangements*** (Sleeps 8 guests; 6 adults max.) -- Primary Suite: king bed, ocean views, walk-out access to a private open-air balcony, SmartTV, walk-in closet, desk + chair, ensuite with dual vanity, soaking tub, and shower. -- Guest Suite: king bed, SmartTV, walk-in closet, ensuite with soaking tub and shower. -- Guest Suite #2: queen bed, SmartTV, ensuite with shower. -- Additional bedding: sleeper sofa in the living area suitable for kids. Crib or pack-n-play provided upon request; children under 2 do not count towards occupancy. There is also a rarely used 5th-floor open-air owner’s terrace with dining tables and seating for sunset dinners with 270-degree island views of Cayman Kai, North Sound, and George Town in the distance. The terrace is also a serene setting for a quiet read with elevated island views. Trade the crowds of Seven Mile Beach for an escape to Cayman’s quieter side where life is easy and not so fast. ***Additional Resort Amenities*** -- 500 feet of beachfront with daily beach umbrella, chair, and towel service. -- Resort pool deck with heated infinity pool. -- Resort dock with cabana and ladder for gentle water entry for snorkeling and swimming. -- Our new on-resort restaurant, Blue Flame, is open from 11:00 a.m. to 11:00 p.m. for lunch and dinner service. -- Private chef dining options available*. -- Front desk staff for local recommendations, pre-arrival grocery stocking, chartered excursions, and more*. -- Access to the 5th-floor Owner’s Terrace for group events or sunset dinners*. -- On-site fitness center (18+ and over). -- On-site wellness suite for spa treatments or massage*. -- Xbox Gaming Console or DVD Player Available at the Front Desk+. -- Complimentary snorkel equipment provided during your stay+. -- Complimentary bike share for cruising the Cayman Kai neighborhood+. Discover why the Rum Point Resort is Cayman’s hidden 5-star gem! Resort Amenities Notes: * Pre-arrival reservations are required; additional fees apply. + Provided on a first-come, first-served basis. Cannot be reserved before arrival. *** RATE DETAILS *** -- 13% Occupancy Tax added to all rates. -- 10% Resort Fee is added to all rates. -- Accidental Damage Protection added to all rates. *** BOOKING RULES *** -- Christmas & New Year’s are split into two separate rental periods. Please inquire about your dates before booking for the holidays. -- Guests must be 25 years or older to book and occupy the unit during the entire stay. -- Check-in: 4:00 pm. -- Check-out: 11:00 am. *** NEARBY POINTS OF INTEREST *** -- The resort is next door to the Rum Point Club for food + drinks, snorkeling, watersport rentals, and Stingray City excursions. -- The resort is adjacent to Cayman’s Bioluminescent Bay for nighttime kayak tours. -- 1.2 miles to the Kaibo Beach Bar & Grill and The Kaibo Marina. -- 1.7 miles south to Starfish Point -- 4.4 miles to the nearest market, Chisholm’s Grocery. -- 6.2 miles east to Over the Edge restaurant -- 6.7 miles to Cayman Crystal Caves -- 12.5 miles to the nearest supermarket, Foster’s Market -- 26 miles (49-minute drive) from Owen Roberts Airport (GCM) *** GETTING AROUND *** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget, Avis, Marshalls, or Hertz. *** DAY TRIPPING *** Cayman Ferries operates daily water taxis departing from the Kaibo Marina to Camana Bay. Perfect for day trips to Seven Mile Beach or shopping excursions at Camana Bay. Download their app to purchase your tickets in advance. Just be sure to make it back for the return voyage across the sound!

Kai Vista

Rum Point, KY
4 Bedrooms 9 Guests
Aug 23 - 28
$1,259 night

***Property Overview*** Welcome to Kai Vista, a recently remodeled 4-bedroom/4-bath villa perched on an elevated ridge in Rum Point with a private pool and heated spa. Grab your nice shades and head down to the beachfront sundeck lined with comfortable sun beds to work on your tan. Then, cool off with a dip in the oceanfront infinity pool. As the sun sets, slide into the heated spa and watch the skies turn pink as your troubles effortlessly melt away. Inside, scenic ocean views are captured through 30 feet of sliding glass walls that open and fill the villa with island breezes and natural light. An enormous open-concept living area has two separate seating areas with sectional sofas, a large HD television with Apple TV for streaming, and a soundbar. A fully renovated kitchen includes new appliances, granite countertops, and a wet bar with a separate ice maker. A propane grill on the side of the house is available for cookouts, next to a thatched cabana for the cooks to stay out of the sun! The homeowners have embraced an eco-friendly approach to recent renovations including upgrading the home’s insulation, converting all lighting to warm LED fixtures, installing a high-efficiency air conditioning system, and installing a solar-powered water heating system. For remote workers, a high-speed fiber internet connection has been wired to the property. Multiple users and devices can connect online with reliable speeds and increased bandwidth. ***Sleeping Arrangements*** (Licensed to sleep 9 guests, 8 adults max.) ---Bedroom 1: primary suite, lower-level, oceanfront, king bed, walk-out access to the pool deck and beach, ensuite with dual vanity, soaking tub, and separate walk-in glass shower. ---Bedroom 2: lower-level, queen bed, television, shares adjacent hall bath equipped with walk-in shower. ---Bedroom 3: upper-level, oceanfront, king bed, television, walkout access to a shared ocean balcony, ensuite with glass shower. ---Bedroom 4: upper-level, oceanfront, king bed, television, walkout access to a shared ocean balcony, ensuite with walk-in shower. ---Additional bedding: sleeper sofa on the upper-level loft; suitable for children only. The beach behind the villa is great for long walks in either direction with plenty of privacy. Rum Point is easily accessible via a 5-minute walk on the beach. If snorkeling is on your itinerary, this villa is for you as Kai Vista is located on the Grand Cayman Marine Park. We recommend pool shoes or fins when entering the water. Coral heads and a marine environment prevent barefoot entry. Kai Vista boasts an exceptional location, less than half a mile from the watersports and beachfront dining at the Rum Point Club, in addition to its fabulous at-home amenities. *Notes: 1) A Cleaning Fee is required due to enhanced cleaning and sanitation protocols. 2) Kayaks are available for discounted rental. Signed waiver required. =============================== ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 12.90% Guest Services Fee added to all rates. -- A Departure Cleaning Fee is required for all stays. ***Booking Rules*** -- Check-in is 3:00 pm -- Check-out is 10:00 am. -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire for approval to book. -- Must be 25 or older to book and must occupy the property during the entire stay. ***Guest Services Benefits*** The Guest Services Fee provides the following perks and benefits. Member Benefits -- Complimentary use of snorkel equipment (mask, fins, and snorkel) -- 10% Discount towards a private Stingray snorkel charter -- 10% Guest Discount Card with select restaurants, local charters, watersports, and more! -- Villa Concierge services - upon confirmation, before arrival, and during your stay. -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Guest parcel receipt & hold for check-in -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Airport arrival Fast-Track VIP Process (fee charged by CAA) -- Arrange airport pick-up & rental vehicles (fee applies) -- Special event/dinner reservations At-Villa Benefits -- Welcome amenity basket -- Complimentary use of Apple TVs, Bluetooth speakers, beverage coolers -- Complimentary pack-n-plays, booster seats, & baby gates -- Complimentary early check-in, if no check-out on the same day -- Day-after-arrival & mid-week guest services follow-up -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- $25,000 of Accidental Villa Damage Protection -- Additional tandem kayaks available for discounted rental* *Signed waiver required. ***Villa Cleaning*** -- All villas are cleaned and sanitized before each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased over the summer months. Our owners make efforts to remove heavy sargassum and will have the beach raked before your arrival. Should sargassum be extremely heavy behind your property, we will contact the owner for alternative solutions, which may include a partial refund or relocation. We try our best to work around Mother Nature.

Rip Kai Villa

Rum Point, KY
9 Bedrooms 22 Guests
Aug 23 - 28
$3,163 night

===> PROPERTY OVERVIEW <=== Welcome to Rip Kai Villa, an extraordinary oceanfront estate in Rum Point designed for unforgettable group getaways, extended family reunions, and milestone celebrations. Spanning over 8,000 square feet of seamless indoor and outdoor living, this private sanctuary offers complete luxury and privacy across five Great House suites, two detached Veranda Suites, and a separate two-bedroom Guest Cottage featuring its own living areas and kitchenette. The vacation experience begins with an airport greeting by a professional driver and a 28-seat mini-coach (7-night minimum stay required). Our on-island concierge can coordinate with your rental car company for delivery of your vehicles to the villa in advance. Pre-stocking the home with groceries and beverages is also a popular add-on, as is having our concierge coordinate in-villa chef or butler services for a few nights of stress-free gourmet dining. The crown jewel of Rip Kai is its expansive resort-style pool deck. Step out onto a private backyard paradise, lined with shaded pergolas, a tiered sundeck with 12 chaise lounges, and an invigorating pool and hot tub overlooking reef-protected waters. Perfect for alfresco dining, the large outdoor kitchen and entertainment pavilion features a built-in gas grill, bar seating, dual Smart TVs, and an outdoor dining table under the shade of the wraparound veranda. Steps away on the pool deck, guests of all ages can hang out in the fully equipped game room—complete with a ping pong table, dartboard, Smart TV, and full bathroom. Kids will love their own private paradise at the outdoor playground, equipped with a swing set, slide, and roofed play fort, while adults can enjoy a game on the beachfront volleyball court. Whether you are relaxing by the pool, cooking outdoors, or enjoying beach games, Rip Kai offers the ultimate luxury retreat on Grand Cayman. Inside, the home is crafted for ultimate comfort and entertainment. Prepare gourmet meals effortlessly in the chef’s kitchen and caterer-ready butler’s pantry, or gather at the indoor dining tables and breakfast bar with seating for up to 22 guests. Unwind at the intimate piano bar, enjoy high-speed fiber internet and whole-house SONOS audio throughout, or retreat to the home theater—a state-of-the-art media room seating up to 14 guests for movie nights or the big game. For added accessibility and convenience when moving luggage, the main house includes a private elevator. ***Sleeping Arrangements*** (Sleeps 24 guests total, 18 adults max) The 5-bedroom Great House sleeps 10 adults max, plus 2-4 children in bunk beds. -- Bedroom 1: primary suite, upper-level, king bed, oceanfront, vaulted ceilings, walk-out access to a furnished shared balcony, cable SmartTV, walk-in closet, ensuite with double vanity, beauty counter, and shower. -- Bedroom 2: upper-level, king bed, oceanfront, walk-out access to a furnished shared balcony, SmartTV, ensuite with shower. -- Bedroom 3: upper-level, king bed, oceanfront, walk-out access to a furnished shared balcony, SmartTV, ensuite with shower. -- Bedroom 4: upper-level, 2 sets of full-over-full bunk beds, ocean view, walk-out access to a private balcony, SmartTV, ensuite with double vanity, and shower bath. -- Bedroom 5: upper-level, 2 twin beds, ocean view, walk-out access to a private balcony, SmartTV, ensuite with double vanity, and shower; twin beds can be fitted into a king upon request. -- Bedroom 6: detached exterior suite with private entry, king bed, walk-out access under the west veranda, Smart TV, ensuite with double vanity, and shower. -- Bedroom 7: detached exterior suite with private entry, king bed, walk-out access under the east veranda, Smart TV, ensuite with double vanity, and shower. -- Bedroom 8: guest cottage with private entry, king bed, SmartTV, ensuite with shower. -- Bedroom 9: guest cottage with private entry, 2 twin beds, SmartTV, ensuite with shower; twin beds can be fitted into a king upon request. -- Additional bedding - queen sleeper sofa in the guest cottage living area for 2 children only. Rip Kai is remote enough to be private, but also convenient to local restaurants, beach bars, and water sports. Private transport options are available for restaurant dinners in the eastern districts. Access to our private fitness center is only 15 minutes away for active guests. NOTES: Bicycle and kayak rentals are available at discounted rates. A signed waiver is required. ===> RATE DETAILS <=== -- 13% Occupancy Tax added to all rates. -- 12.90% Service Fee is added to all rates. -- 3.50% Admin Fee added to all rates. -- A Departure Cleaning Fee is added to all rates. ==> BOOKING RULES <=== -- Guests must be 25 years or older to book and must occupy the unit during the entire stay. -- Check-in: 4:00 pm. -- Check-out: 10:00 am. ===> NEARBY POINTS OF INTEREST <=== -- 2 miles to Bioluminescent Bay and the Rum Point Club for food + drink, snorkeling, charter excursions, and water sport rentals. -- 2.5 miles to the Kaibo Beach Bar & Grill and Starfish Point -- 2.8 miles to the nearest general store, Chisholm’s Grocery -- 4.7 miles to Over the Edge restaurant -- 7.2 miles from our Grand Cayman Villas & Condos Welcome Center -- 11 miles to the nearest supermarket, Foster’s Market -- 13 miles to Tukka East restaurant. -- 24.5 miles (45 min drive) from Owen Roberts Airport (GCM) ==> GETTING AROUND <== A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Avis, Marshalls, or Hertz. ==> BEACH NOTES <== All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection--pool socks or aqua shoes--when entering the ocean to avoid injury on coral heads, ironshore, or rocks.

Hidden Cove

Rum Point, KY
6 Bedrooms 12 Guests
Aug 23 - 28
$914 night

***Property Overview*** Welcome to Hidden Cove, a family vacation hideaway tucked back in a quiet corner in the beautiful Cayman Kai neighborhood. Hidden Cove offers a large family, or two smaller families, a home away from home with the amenities of a vacation resort. With a boat dock on a secluded cove, guests can launch kayaks for a day of exploring above the waves. 3 single kayaks and 3 tandem kayaks are provided complimentary during your stay. Better yet, you can even rent jet skis and keep them docked behind the house! Guests wanting to stay on land can use the 15 adult bikes and 4 child bikes included with the home to explore the neighborhood. Round up the entire family for a group bike ride to The Kaibo for a bite to eat or head to the Rum Point Club and Starfish Point- all about a 5-minute ride away. Training wheels, helmets, and a pump are also available. The newly renovated swimming pool and sun deck will be a hit with sun-seeking families. Lounge poolside with your fancy shades on and soak up the sunshine while the kids splish-splash in the freshwater pool. Fire up the propane grill for an island cookout and enjoy a bite to eat under the poolside gazebo or alfresco dining area off the pool deck. Inside, plenty of windows overlooking the pool allow natural sunlight to fill the spacious family room. Complete with a living area and a large formal dining table, the family room is the perfect gathering spot after a long day of fun under the sun. *** Sleeping Arrangements *** (Sleeps 12 guests total) -- Bedroom 1: primary suite, lower-level, king bed, water views, walk-out access to the pool deck, television, ensuite with dual vanity, shower, and whirlpool bathtub. -- Bedroom 2: lower-level, queen bed, garden views, ensuite with shower bath. -- Bedroom 3: lower-level, 2 twin beds, garden views, shares hall bath equipped with shower bath; twin beds can be fitted into a king bed upon request. -- Bedroom 4: lower-level, queen bed, garden views, shares hall bath equipped with shower bath. -- Bedroom 5: upper-level, queen bed, elevated partial water views, shares hall bath equipped with dual vanity and shower. -- Bedroom 6: upper-level, 2 twin beds, elevated partial water views, shares hall bath equipped with dual vanity and shower; twin beds can be fitted into a king bed upon request. *** Hidden Cove’s Notable Features *** -- Great snorkeling nearby! -- The property is wired with a fiber internet connection perfect for remote working professionals. -- Directly across the street, sandy access provides kayaking in Cayman Kai Cove and North Sound. To the east, one can kayak across Little Sound to meander through mangrove passages and enjoy the bioluminescent cove on a moonless evening. -- A short walk to the Rum Point Club for watersports, snorkeling, plus food + drinks. -- A quiet sitting room and an overflow dining area just off the kitchen. -- Outdoor shower. -- 3 single kayaks and 3 tandem kayaks included. -- 12 complimentary bicycles, 8 adult & 4 child bikes, are included with the villa. -- 2 Pack-n-Plays are also available. Come, relax, and enjoy the island life at Hidden Cove! ***IMPORTANT NOTES*** -- A Cleaning Fee may be required due to enhanced cleaning and sanitation protocols. -- Additional kayaks are available for discounted rental. Signed waiver required. ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service added to all rates. -- Accidental Damage Protection added to all rates. ***Booking Rules*** -- 4 nights minimum stay required. -- 6 nights minimum and full occupancy required over Thanksgiving week. -- 7 nights minimum stay and full occupancy rate required over Christmas and New Year’s week. -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 years or older to book and occupy the property during the entire stay. ***Grand Cayman Villas & Condos Guest Services*** The 10% Guest Service Fee includes your Guest Services Membership. Member Benefits -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Proprietary Guest benefit & discount card -- 10% advance booking discount for private charter -- Complimentary use of snorkel equipment -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Referral to preferred vendors, guest services desk assistance At-Villa Benefits -- Day-after-arrival guest services follow-up -- Complimentary early check-in, if no check-out on the same day -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- Complimentary pack-n-plays, booster seats, & baby gates -- Additional kayaks available for discounted rental* *Signed waiver required. ***Nearby Points of Interest*** -- The home is adjacent to the island’s Bioluminescent Bay -- 10-minute walk to the Kaibo Beach Bar & Grill -- 14-minute walk to the Rum Point Club -- 1.0 mile south to Starfish Point -- 5.0 miles to the nearest grocer, Chisholm’s Grocery -- 7.0 miles east to Over the Edge restaurant -- 7.4 miles east to Cayman Crystal Caves -- 9.4 miles from our Welcome Center -- 13.2 miles to the nearest supermarket, Foster’s Market -- 26.2 miles (50-minute drive) from Owen Roberts Int’l Airport (GCM) ***Getting Around*** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Avis, or Marshalls. ***Day Tripping*** Cayman Ferries operates daily water taxis departing from the Kaibo Marina to Camana Bay. Perfect for day trips to Seven Mile Beach or shopping excursions at Camana Bay. Download their app to purchase your tickets in advance. Just be sure to make it back for the return voyage across the sound! ***Villa Cleaning & Sanitation*** All villas are cleaned and sanitized before every guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked before your arrival. Should sargassum be extremely heavy behind your property, we will reach out to the owner for alternative solutions which may include a partial refund or relocation. We try our best to work around Mother Nature.

Flip Flop Kai

Rum Point, KY
3 Bedrooms 8 Guests
Aug 25 - 30
$799 night

*** PROPERTY DESCRIPTION *** Welcome to this lovely private villa situated on a sandy beach with scenic views of the Bioluminescent Bay, in Cayman Kai. Newly redecorated and painted, Flip Flop is a popular 3-bedroom beach cottage with fabulous amenities. This home boasts stunning water vistas from almost every room plus a delightful beachfront veranda and gazebo, where you can listen to the gentle sound of lapping waves and savor beautiful sunsets. Flip Flop ticks almost all the boxes with a pool, sunset views, screened porch, thatched cabana, private dock, and within walking distance to beach bars and restaurants. The owner includes 3 kayaks. Paddleboards are available for discounted rental with delivery. The freshwater private pool is shaded by palm trees, making it a perfect hideaway spot for relaxing with a tropical drink. The spa is located at the end of the pool and can be heated as an optional add-on for the duration of your stay for $50/day, year-round. On the sandy beach, you can enjoy paddleboarding and kayaking. During moonless nights, you can venture out into the bay to witness the incredible light display provided by nature! The owners also own the adjacent sandy lot; perfect for frisbee and soccer. Flip Flop Kai has a private dock with thatched cabana, which allows you to rent a boat or jet skis. Book a charter to Stingray City and coordinate dockside service right off the home’s dock! It’s the ultimate convenience for private snorkeling or scuba charters with our friends at Silver Thatch Water Sports. Inside, this beautifully decorated beach villa is an ideal place for a comfortable family gathering or a fun vacation with friends. Lots of glass brings the Caribbean blue indoors. The open-concept kitchen is fully equipped, perfect for the chef in your group to prepare delicious meals. There’s also a gas BBQ for grilling and a large thatched beach cabana for sunset cocktail hour. ***Sleeping Arrangements*** (Licensed to sleep 8 guests total, 6 adults max.) -- Bedroom #1: upper level, king bed, waterfront views, television, DVD player, ensuite with double vanity and shower. -- Bedroom #2: upper level, two queen beds, ceiling fan, shares adjacent bathroom equipped with shower bath. -- Bedroom #3: upper level, two twin XL beds, ceiling fan, shares adjacent bathroom equipped with shower bath; beds can be fitted into a king bed upon request. -- Additional bedding: sleeper sofa in the media den for children only; uses half-bath on the first floor. Within walking distance of the villa, you’ll discover Starfish Point, a family-friendly beach spot where you can interact with starfish. Along the way, you’ll find The Kaibo, a beachfront dining destination with two restaurants and a coffee shop. To the north, you won’t want to miss the new Rum Point Club, a public beach with great snorkeling, beach service, an open-air beach bar, plus a new restaurant serving lunch and dinner. Red Sail Watersports operates off the dock for excursions to Stingray Sandbar, or a sunset cruise just before dinner. Flip Flop Kai truly offers an ideal place to relax and unwind, Cayman-style, with your loved ones in a sunny paradise...barefooted. ================ ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service Fee includes your Guest Services Membership. -- A $225 Departure Cleaning Fee is added for all stays. -- A Refundable Damage Deposit of $1,500 is required for all stays. -- Refundable Damage Deposits will be returned to the guest 7 business days after departure pending any damages. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 years or older to book and must occupy the property during the entire stay. ***Grand Cayman Villas & Condos Guest Services*** The 10% Guest Service Fee includes your Guest Services Membership. ***Member Benefits*** -- Complimentary use of snorkel equipment -- Complimentary pack-n-plays, booster seats, & baby gates -- Guest Services Discount Card for 10% savings with our restaurant partners -- 10% Advance Booking Discount for a private Stingray City charter -- Complimentary early check-in, if no check out on same day -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Referral to preferred vendors, guest services desk assistance -- Additional single/tandem kayaks & paddleboards are available for discounted rental. A signed waiver is required. ***Nearby Points of Interest*** -- Villa is located on Cayman’s Bioluminescent Bay -- 13-minute walk to the Rum Point Club & the Kaibo Beach Bar & Grill -- 20-minute walk to Starfish Point -- 5 miles to the nearest grocery store, Chisholm’s Grocery -- 6.7 miles to Over the Edge restaurant -- 7.2 miles to Cayman Crystal Caves -- 9.2 miles to our Guest Services Welcome Center -- 13 miles to the nearest supermarket, Foster’s Express -- 26.5 miles (50 min drive) from Owen Roberts Airport (GCM) ***Getting Around*** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Avis, or Marshalls. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. This is VERY RARE for homes along the Cayman Kai Cove.

Wight Away

Rum Point, KY
4 Bedrooms 10 Guests
Aug 23 - 28
$684 night

***PROPERTY DESCRIPTION*** Experience laid-back luxury at Wight Away, where at-home comforts and captivating water views of the island’s pristine mangroves await. This recently constructed waterfront villa boasts 4 bedrooms and 3 bathrooms, providing spacious comfort for a large family or two smaller groups. With a deluxe pool deck, a private dock, and stylish interiors, it offers top-notch amenities and a serene ambiance for your island getaway. The villa boasts a delightful wraparound porch on the west, south, and east sides, each with private lounge areas. The sparkling freshwater swimming pool invites you for a refreshing swim or a cool dip after a busy day. An expansive veranda dining table creates the perfect setting for alfresco dinners. The pool deck also features an outdoor shower, multiple sun lounges, and an outdoor kitchen cabana with a propane grill. Inside the villa, a luminous vaulted great room welcomes you with plush sofa seating and a large high-definition television. The gourmet kitchen comes equipped with a suite of modern appliances providing everything you need for a home-cooked meal. Enhance your stay by hiring one of our local chefs for a perfect gourmet dinner or brunch service. **Sleeping Arrangements** (Licensed to sleep 8 adults, 10 guests max.) -- Primary Suite: lower level, king bed, waterfront views, television, walk-out access to the pool deck, ensuite with dual vanity, and shower with rainfall water head. -- Upper Suite: upper level, king bed, television, walk-out access to a private balcony, ensuite with dual vanity, and shower. -- Bedroom #1: lower level, king bed, island views, shares hall bathroom equipped with dual vanity and walk-in shower. -- Bedroom #2: lower level, queen bed, island views, shares hall bathroom equipped with dual vanity and walk-in shower. -- Additional bedding: queen sleeper sofa on the upper level for 2 children only. We’ve got all your beach and bathroom essentials covered, including linens, bath towels, and plush beach towels. Complimentary high-speed WiFi keeps you connected with loved ones back home and the office if needed. The villa’s central air conditioning will keep you cool and refreshed all day long. Wight Away is perfectly placed within walking distance of two of the neighborhood’s beachfront dining destinations. A complimentary phone allows for free local calls to make restaurant reservations. A short walk to the north, the Rum Point Club provides a taste of easy-island living at its finest with watersport rentals, beach service, plus a delectable new restaurant and open-air beach bar. A little further to the south is the Kaibo, where you can enjoy casual beachfront dining, tasty takeaway pizza, or refined gourmet dining along the upper veranda. For early risers, Kaibo Espresso serves premium coffees, tea, pastries, and breakfast paninis. Wight Away has been meticulously designed and constructed to ensure your vacation is as comfortable and enjoyable as possible. It truly is a slice of paradise! *Note: Bicycles, tandem kayaks, and stand-up paddleboards (SUPs) are available for discounted rental. A signed waiver is required. ======= ***RATE DETAILS*** -- 13% Occupancy Tax added to all rates. -- A 10% Guest Service Fee is added to all rates. -- Accidental Damage Protection added to all rates. -- A Departure Cleaning Fee is required for all stays. ***BOOKING RULES*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays are welcome but subject to a higher cleaning fee. Please inquire to book. -- Must be 25 years or older to book and must occupy the property during the entire stay. *** GUEST SERVICES *** The Service Fee includes your Guest Services Membership. Member Benefits -- Complimentary use of snorkel equipment throughout your stay. -- Complimentary convenience items to enhance your stay: Apple TVs, Bluetooth speakers, coolers, Kuerigs, etc. -- 10% Advance Booking Discount towards a private charter. -- Guest Benefit Card offering 10% discounts with local restaurants and vendors. -- Centralized on-island guest services desk & welcome center. -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies. -- Jacques Scott Wine & Spirits pre-order & hold for check-in. -- Referral to preferred vendors, guest services desk assistance. At-Villa Benefits -- Complimentary pack-n-plays, booster seats, & baby gates -- Complimentary early check-in, if no check-out on the same day -- Day-after-arrival guest services follow-up -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- Kayaks and stand-up paddleboards (SUPs) available for discounted rental* *Signed waiver required. ================= ***Nearby Points of Interest*** -- The home is adjacent to the island’s Bioluminescent Bay -- Short walk to the Rum Point Club for food, drinks, and watersport rentals. -- 10-minute walk to the Kaibo Beach Bar & Grill. -- 1.0 mile south to Starfish Point. -- 5.0 miles to the nearest general store, Chisholm’s Grocery. -- 6.9 miles east to Over the Edge restaurant. -- 7.4 miles east to Cayman Crystal Caves. -- 9.4 miles from Grand Cayman Villas & Condos Welcome Center. -- 13.2 miles to the nearest supermarket, Foster’s Market. -- 26.2 miles (51-minute drive) from Owen Roberts Airport (GCM). ***Getting Around*** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Avis, Marshalls, or Hertz. ***Beach Notes*** All beaches in Grand Cayman are technically public, since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. The water behind Wight Away is on a canal, providing easy launching of kayaks and paddleboards, as well as dockside service for charters. The backyard beach does not extend into the water. For a true beachfront experience, guests can walk 5 minutes to the Rum Point Club. This public beach spot features a white sandy beach with complimentary beach service, a restaurant with an open-air bar, plus watersport rentals, public changing rooms, and beach volleyball. Guests will find excellent snorkeling under the dock and along the coral heads to the right of the dock. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. The water behind Wight Away is rarely ever affected by Sargassum, as it is protected.

Caribe Sun

Rum Point, KY
5 Bedrooms 10 Guests
Aug 23 - 28
$914 night

***PROPERTY DESCRIPTION*** Welcome to Caribe Sun, a newly constructed 5-bedroom, 4-bathroom villa in the serene Cayman Kai neighborhood. Designed with a calming blue color scheme, this modern retreat offers a seamless blend of luxury and island charm, accommodating up to 10 guests. The outdoor spaces at Caribe Sun are a highlight of the villa. The private pool is the centerpiece, offering a refreshing retreat surrounded by lush tropical landscaping. Relax in the sun on the pool deck, take a leisurely swim, or gather for alfresco dining on the wraparound veranda. Optional pool heat is available for the full duration of your stay for $25 per day. The villa also boasts a Trex private boat dock, ideal for water enthusiasts to launch kayaks or paddleboards to explore the waterways. The dock is also ideal for boat charter pickups to Stingray City, the island’s top attraction! Step into the spacious living room, where a comfy sectional sofa and a large SmartTV create the perfect space to relax and unwind after a day of exploration. The gourmet kitchen, outfitted with modern appliances, a large island, and sleek quartz countertops, is perfect for preparing meals and gathering with loved ones. Adjacent to the high-end kitchen, the formal dining area comfortably seats 10+ guests. The screened porch also features an outdoor dining table seating 10 for alfresco meals during peaceful Cayman evenings. The home’s five bedrooms provide plenty of space and privacy, with 4-bedroom suites in the main villa and an apartment suite above the detached garage. ***Sleeping Arrangements*** (Licensed to sleeps 10 guests max.) -- Bedroom 1: primary suite, lower level, king bed, television, walk-out access to the pool deck, sitting area, walk-in closet, ensuite with double vanity, soaking bathtub, and separate shower. -- Bedroom 2: upper-level, king bed, television, private furnished balcony, ensuite with double vanity and shower. -- Bedroom 3: upper-level, king bed, television, private furnished balcony, shares adjacent bathroom equipped with a shower. -- Bedroom 4: upper-level, two twin beds, television, shares adjacent bathroom equipped with a shower. -- Bedroom 5: apartment suite, upper-level, queen bed, television, full kitchen, living area, in-unit washer & dryer, ensuite with shower. Caribe Sun is within short walking distance of The Kaibo and the Rum Point Club, where you can enjoy watersport rentals plus food + drinks in a laid-back beachfront setting. Ferry service from the Kaibo Marina to Camana Bay/Seven Mile Beach makes it easy to experience first-class shopping, dining, and entertainment without sitting in traffic. For those seeking other fun adventures, explore nearby attractions like the Cayman Crystal Caves or the Queen Elizabeth II Royal Botanic Park. To discover more of the island’s natural beauty, book an EcoBike tour of the North Side, or a kayak tour of the Bioluminescent Bay. A scenic 15-minute drive will bring you to the North Side and then the East End, where you’ll find local grocery stores, dive shops, and restaurants. This villa was also built for the unforeseen, with hurricane windows/doors (quiet), and a backup generator, providing power during any (rare) local power outages. Whether lounging by the private pool, savoring the water views from the balconies and porches, or setting off on an island adventure, Caribe Sun promises an unforgettable Grand Cayman vacation experience for the whole family. *Note: A Cleaning Fee is included due to enhanced cleaning, sanitation, and inspection protocols. **Additional tandem kayaks and stand-up paddleboards (SUPs) are available for discounted rental. A signed waiver is required. ======= ***RATE DETAILS*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service Fee is added to all rates. -- Accidental Damage Protection added to all rates. -- A Departure Cleaning Fee is added for all stays. ***BOOKING RULES*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates prior to booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 years or older to book and must occupy the property during the entire stay. *** GUEST SERVICES *** The Service Fee includes the following Guest Services perks. Member Benefits -- Complimentary use of snorkel equipment (mask, fins, and snorkel) during your stay -- Complimentary pack-n-plays, booster seats, & baby gates -- Complimentary early check-in, if no check out on same day -- 10% Advance Booking Discount towards a private snorkel charter -- 10% Discount Card for savings with our preferred partner restaurants, watersports, and more -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Referral to preferred vendors, guest services desk assistance -- Single/tandem kayaks & paddleboards available for discounted rental* ================= ***Nearby Points of Interest*** -- Villa is located across the street from Cayman’s Bioluminescent Bay -- 13-minute walk to the Rum Point Club & the Kaibo Beach Bar & Grill -- 20-minute walk to Starfish Point -- 5 miles to the nearest grocery store, Chisholm’s Grocery -- 6.7 miles to Over the Edge restaurant -- 7.2 miles to Cayman Crystal Caves -- 9.2 miles to our Guest Services Welcome Center -- 13 miles to the nearest supermarket, Foster’s Express -- 26.5 miles (50 min drive) from Owen Roberts Airport (GCM) ***Getting Around*** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Avis, or Marshalls. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks.

Kailypso

Rum Point, KY
3 Bedrooms 8 Guests
Aug 23 - 28
$719 night

***Property Overview*** Welcome to Kailypso, a newly renovated 3-bedroom beachfront villa in Cayman Kai located on Bio Bay. Measuring over 2,800 square feet with spectacular outdoor spaces, renovated interiors, and a secluded beach, this popular villa is the perfect destination for family vacations and group getaways. Nestled among tall palm trees and lush tropical plants, Kailypso’s waterfront pool and patio create a tropical oasis. Plenty of loungers dot the pool deck for sunbathers to kick back and work on their tans. After hours under the sun, cool off with a refreshing dip in the pool or seek shade on the screened-in porch. A concrete pathway leads you down from the pool deck onto a soft sandy beach with a private boat dock. Beach lovers will love this slice of paradise. Take full advantage of the villa’s private dock by booking a charter to Stingray City. Request to be picked up and dropped off right on your dock for the ultimate charter experience! Two single kayaks are provided during your stay. During the day, launch from the dock and explore the calm surrounding waters of Cayman Kai. Then, on moonless nights, take the kayaks out and watch the water glow with light as you paddle. Bio Bay is one of the few bioluminescent bays in the world making it an unforgettable experience. Kailypso’s three bedrooms include a primary suite with an ensuite bathroom and two additional bedrooms with a shared bathroom between them. ***Sleeping Arrangements*** (Sleeps 8 guests total, 6 adults max) -- Bedroom 1: primary suite, king bed, waterfront views, television, walk-out access to the screened porch, ensuite with double vanity and shower. -- Bedroom 2: king bed, waterfront views, television, walk-out access to the screened porch, shares hall bathroom furnished with shower. -- Bedroom 3: queen bed + bunk bed for kids (not pictured), garden views, shares hall bathroom furnished with shower. Kailypso’s interiors feature an open-concept great room with living and dining areas furnished in light tropical decor. The formal dining table seats 6 and is adjacent to the kitchen with waterfront views. A galley kitchen comes equipped with modern appliances including a microwave and dishwasher, plus cookware, dishes, glassware, and cutlery. A full-width screened porch sits off the great room leading out to the pool deck. The porch is furnished with comfortable seating areas and a patio dining table with seating for 8. A propane grill and outdoor dining table, with seating for 6, sit on the pool deck and are perfect for island cookouts under the stars. Finally, Kailypso’s location puts it at the center of all the best that Cayman Kai has to offer, minus the crowds. Guests can walk to the Rum Point Club, The Kaibo, or Starfish Point. With a great location and fabulous outdoor amenities, it’s easy to see why guests love Kailypso! ***IMPORTANT NOTES*** -- The boat photographed at the dock is not included with the villa, however, a boat rental can be arranged. -- A Cleaning Fee is required due to enhanced cleaning and sanitation protocols. -- Additional kayaks and stand-up paddleboards (SUPs) are available for discounted rental. Signed waiver required. ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service added to all rates. -- Accidental Damage Protection added to all rates. -- A Departure Cleaning Fee is added to all stays. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 or older to book and must occupy the property during the entire stay. ***Grand Cayman Villas & Condos Guest Services*** The 10% Guest Service Fee includes your Guest Services Membership. Member Benefits -- Free snorkel equipment (mask, fins, & snorkel) during your stay -- Complimentary pack-n-plays, booster seats, & baby gates -- 10% Advance Booking Discount towards a private Stingray City snorkel charter -- Guest Benefit Card for 10% discounts at local restaurants, bars, watersports providers, and more! -- Complimentary early check-in, if no check-out on the same day -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Referral to preferred vendors, guest services desk assistance -- Additional kayaks and stand-up paddleboards (SUPs) available for discounted rental* *Signed waiver required. =================== **Nearby Attractions*** -- Villa is located on Cayman’s Bioluminescent Bay -- 13-minute walk to beachfront dining at the Rum Point Club or The Kaibo Beach Bar & Grill -- 20-minute walk to Starfish Point -- 5 miles to the nearest grocery store, Chisholm’s Grocery -- 6 miles to Over the Edge restaurant -- 7 miles to Cayman Crystal Caves -- 9 miles to our Grand Cayman Villas & Condos Welcome Center -- 13 miles to the nearest supermarket, Foster’s Express -- 26.5 miles (50 min drive) from Owen Roberts Airport (GCM) ***Getting Around*** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Avis, or Marshalls. ***Day Tripping*** Cayman Ferries operates daily water taxis departing from the Kaibo Marina to Camana Bay. Perfect for day trips to Seven Mile Beach or shopping excursions at Camana Bay. Download their app to purchase your tickets in advance. Just be sure to make it back for the return voyage across the sound! ***Villa Cleaning & Sanitation*** All villas are cleaned and sanitized before each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked before your arrival. Should sargassum be extremely heavy behind your property, we will reach out to the owner for alternative solutions which may include a partial refund or relocation. We try our best to work around Mother Nature.

Rum Point Resort #407

Rum Point, KY
2 Bedrooms 6 Guests
Aug 24 - 27
$514 night

*** PROPERTY DESCRIPTION *** 4th Floor Condo | 1,250 sq. ft. Welcome to Rum Point Resort #407! All Rum Point Resort condos feature sleek finishes, designer decor, and an open-concept layout maximizing space, natural light, and stunning ocean views. All the comforts of home are included in this 1-bedroom + den condo, totaling 1,250 sq. ft., including gourmet kitchen appliances, quartz countertops, SmartTVs for streaming, and a private oceanfront balcony. All condos strike the perfect balance of modern luxury and seamless indoor/outdoor island living. Central air conditioning and high-speed wifi will keep you cool and connected during your stay. Beyond the entryway foyer, the home flows into a spacious open-concept great room encompassing the living, dining, and kitchen areas. Forever blue ocean views from the great room and primary suite will leave you breathless. Crisp coastal decor throughout accentuates the island scenery. The living area includes a comfy sofa, a large SmartTV, and stunning ocean views. Walk out from the living area onto the private open-air balcony overlooking the oceanfront. The gourmet kitchen features a suite of Thermador appliances, plus countertop appliances. Cookware, dishware, glassware, and cutlery also come provided. An outdoor dining table is furnished on the private balcony for meals with sweeping oceanfront views. An indoor dining table is also furnished just off the kitchen area. The Rum Point Resort fits all condos with blackout window shades, the finest Egyptian cotton bedding, hypoallergenic pillows, duvets, and sumptuous robes. ***Sleeping Arrangements*** (Sleeps 6 guests; 4 adults max.) -- Primary Suite: king bed, ocean views, walk-out access to the balcony, SmartTV, ensuite with shower. -- Bunk Den: full-over-full bunk beds, SmartTV, ensuite with shower. There is also a rarely used 5th-floor open-air owner’s terrace with dining tables and seating for sunset dinners with 270-degree island views of Cayman Kai, North Sound, and George Town in the distance. The terrace is also a serene setting for a quiet read with elevated island views. Trade the crowds of Seven Mile Beach for an escape to Cayman’s quieter side where life is easy and not so fast. ***Additional Resort Amenities*** -- 500 feet of beachfront with daily beach umbrella, chair, and towel service. -- Resort pool deck with heated infinity pool. -- Resort dock with cabana and ladder for gentle water entry for snorkeling and swimming. -- Our new on-resort restaurant, Blue Flame, is open from 11:00 a.m. to 11:00 p.m. for lunch and dinner service. -- Private chef dining options available*. -- Front desk staff for local recommendations, pre-arrival grocery stocking, chartered excursions, and more*. -- Access to the 5th-floor Owner’s Terrace for group events or sunset dinners*. -- On-site fitness center (18+ and over). -- On-site wellness suite for spa treatments or massage*. -- Xbox Gaming Console or DVD Player Available at the Front Desk+. -- Complimentary snorkel equipment provided during your stay+. -- Complimentary bike share for cruising the Cayman Kai neighborhood+. Discover why the Rum Point Resort is Cayman’s hidden 5-star gem! Resort Amenities Notes: * Pre-arrival reservations are required; additional fees apply. + Provided on a first-come, first-served basis. Cannot be reserved before arrival. *** RATE DETAILS *** -- 13% Occupancy Tax added to all rates. -- 10% Resort Fee is added to all rates. -- Accidental Damage Protection added to all rates. *** BOOKING RULES *** -- Christmas & New Year’s are split into two separate rental periods. Please inquire about your dates before booking for the holidays. -- Guests must be 25 years or older to book and must occupy the unit during the entire stay. -- Check-in: 4:00 pm. -- Check-out: 11:00 am. *** NEARBY POINTS OF INTEREST *** -- The resort is next door to the Rum Point Club for food + drinks, snorkeling, watersport rentals, and Stingray City excursions. -- The resort is adjacent to Cayman’s Bioluminescent Bay for nighttime kayak tours. -- 1.2 miles to the Kaibo Beach Bar & Grill and The Kaibo Marina. -- 1.7 miles south to Starfish Point -- 4.4 miles to the nearest market, Chisholm’s Grocery. -- 6.2 miles east to Over the Edge restaurant -- 6.7 miles to Cayman Crystal Caves -- 12.5 miles to the nearest supermarket, Foster’s Market -- 26 miles (49-minute drive) from Owen Roberts Airport (GCM) *** GETTING AROUND *** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget, Avis, Marshalls, or Hertz. *** DAY TRIPPING *** Cayman Ferries operates daily water taxis departing from the Kaibo Marina to Camana Bay. Perfect for day trips to Seven Mile Beach or shopping excursions at Camana Bay. Download their app to purchase your tickets in advance. Just be sure to make it back for the return voyage across the sound!

Rum Point Resort #408

Rum Point, KY
2 Bedrooms 4 Guests
Aug 23 - 26
$575 night

*** PROPERTY DESCRIPTION *** Fourth Floor Condo | 1,350 sq. ft. All Rum Point Resort condos feature sleek finishes, designer decor, and an open-concept layout maximizing space, natural light, and stunning ocean views. All the comforts of home are included in this 1-bedroom + den condo, totaling 1,350 sq. ft., including gourmet kitchen appliances, quartz countertops, SmartTVs for streaming, and a private oceanfront balcony. All condos strike the perfect balance of modern luxury and seamless indoor/outdoor island living. Central air conditioning and high-speed wifi will keep you cool and connected during your stay. Beyond the entryway foyer, the home flows into a spacious open-concept great room encompassing the living, dining, and kitchen areas. Forever blue ocean views from the great room and primary suite will leave you breathless. Crisp coastal decor throughout accentuates the island scenery. The living area includes a comfy sofa, a large SmartTV, and stunning ocean views. Walk out from the living area onto the private open-air balcony overlooking the oceanfront. The gourmet kitchen features a suite of Thermador appliances, plus countertop appliances. Cookware, dishware, glassware, and cutlery also come provided. An outdoor dining table is furnished on the private balcony for meals with sweeping oceanfront views. An indoor dining table is also furnished just off the kitchen area. The Rum Point Resort fits all condos with blackout window shades, the finest Egyptian cotton bedding, hypoallergenic pillows, duvets, and sumptuous robes. ***Sleeping Arrangements*** (Sleeps 6 guests; 4 adults max.) -- Primary Suite: king bed, ocean views, walk-out access to the balcony, SmartTV, ensuite with soaking tub and shower. -- Bunk Den: full-over-full bunk beds, SmartTV, ensuite with shower. There is also a rarely used 5th-floor open-air owner’s terrace with dining tables and seating for sunset dinners with 270-degree island views of Cayman Kai, North Sound, and George Town in the distance. The terrace is also a serene setting for a quiet read with elevated island views. Trade the crowds of Seven Mile Beach for an escape to Cayman’s quieter side where life is easy and not so fast. ***Additional Resort Amenities*** -- 500 feet of beachfront with daily beach umbrella, chair, and towel service. -- Resort pool deck with heated infinity pool. -- Resort dock with cabana and ladder for gentle water entry for snorkeling and swimming. -- Our new on-resort restaurant, Blue Flame, is open from 11:00 a.m. to 11:00 p.m. for lunch and dinner service. -- Private chef dining options available*. -- Front desk staff for local recommendations, pre-arrival grocery stocking, chartered excursions, and more*. -- Access to the 5th-floor Owner’s Terrace for group events or sunset dinners*. -- On-site fitness center (18+ and over). -- On-site wellness suite for spa treatments or massage*. -- Xbox Gaming Console or DVD Player Available at the Front Desk+. -- Complimentary snorkel equipment provided during your stay+. -- Complimentary bike share for cruising the Cayman Kai neighborhood+. Discover why the Rum Point Resort is Cayman’s hidden 5-star gem! Resort Amenities Notes: * Pre-arrival reservations are required; additional fees apply. + Provided on a first-come, first-served basis. Cannot be reserved before arrival. *** RATE DETAILS *** -- 13% Occupancy Tax added to all rates. -- 10% Resort Fee is added to all rates. -- Accidental Damage Protection added to all rates. *** BOOKING RULES *** -- Christmas & New Year’s are split into two separate rental periods. Please inquire about your dates before booking for the holidays. -- Guests must be 25 years or older to book and occupy the unit during the entire stay. -- Check-in: 4:00 pm. -- Check-out: 11:00 am. *** NEARBY POINTS OF INTEREST *** -- The resort is next door to the Rum Point Club for food + drinks, snorkeling, watersport rentals, and Stingray City excursions. -- The resort is adjacent to Cayman’s Bioluminescent Bay for nighttime kayak tours. -- 1.2 miles to the Kaibo Beach Bar & Grill and The Kaibo Marina. -- 1.7 miles south to Starfish Point -- 4.4 miles to the nearest market, Chisholm’s Grocery. -- 6.2 miles east to Over the Edge restaurant -- 6.7 miles to Cayman Crystal Caves -- 12.5 miles to the nearest supermarket, Foster’s Market -- 26 miles (49-minute drive) from Owen Roberts Airport (GCM) *** GETTING AROUND *** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget, Avis, Marshalls, or Hertz. *** DAY TRIPPING *** Cayman Ferries operates daily water taxis departing from the Kaibo Marina to Camana Bay. Perfect for day trips to Seven Mile Beach or shopping excursions at Camana Bay. Download their app to purchase your tickets in advance. Just be sure to make it back for the return voyage across the sound!

Rum Point Resort #206

Rum Point, KY
3 Bedrooms 8 Guests
Aug 23 - 26
$672 night

*** PROPERTY DESCRIPTION *** Second Floor Condo | 2,250 sq. ft. Welcome to Rum Point Resort #206! All Rum Point Resort condos feature sleek finishes, designer decor, and an open-concept layout maximizing space, natural light, and stunning ocean views. All the comforts of home are included in this 2,250 sq. ft. condo including gourmet kitchen appliances, quartz countertops, SmartTVs, and a private oceanfront balcony. All condos strike the perfect balance of modern luxury and seamless indoor/outdoor island living. Central air conditioning and high-speed wifi will keep you cool and connected during your stay. Beyond the entryway foyer, the home flows into a spacious open-concept great room encompassing the living, dining, and kitchen areas. Forever blue ocean views from the great room and primary suite will leave you breathless. Crisp coastal decor throughout accentuates the island scenery. The living area includes comfy sofa seating, a large SmartTV, a tray ceiling with ceiling fans, and stunning ocean views. Walk out from the living area onto the private roofed balcony overlooking the resort’s pool deck and beachfront. The gourmet kitchen features a suite of Thermador appliances, plus countertop appliances and a kitchen island with breakfast bar seating. Cookware, dishware, glassware, and cutlery also come provided. A formal indoor dining table just off the kitchen seats 6. For meals with sweeping oceanfront views, an outdoor dining table on the balcony seats 6 as well. The Rum Point Resort fits all condos with blackout window shades, the finest Egyptian cotton bedding, hypoallergenic pillows, duvets, and sumptuous robes. ***Sleeping Arrangements*** (Sleeps 6 guests) -- Primary Suite: king bed, ocean views, walk-out access to a private roofed balcony, SmartTV, walk-in closet, ensuite with dual vanity, soaking tub, and shower. -- Guest Suite: king bed, ensuite with shower. -- Guest Suite #2: queen bed, SmartTV, walk-in closet, ensuite with shower bath. -- Additional bedding: Crib or pack-n-play provided upon request; children under 2 do not count towards occupancy. There is also a rarely used 5th-floor open-air owner’s terrace with dining tables and seating for sunset dinners with 270-degree island views of Cayman Kai, North Sound, and George Town in the distance. The terrace is also a serene setting for a quiet read with elevated island views. Trade the crowds of Seven Mile Beach for an escape to Cayman’s quieter side where life is easy and not so fast. ***Additional Resort Amenities*** -- 500 feet of beachfront with daily beach umbrella, chair, and towel service. -- Resort pool deck with heated infinity pool. -- Resort dock with cabana and ladder for gentle water entry for snorkeling and swimming. -- Our new on-resort restaurant, Blue Flame, is open from 11:00 a.m. to 11:00 p.m. for lunch and dinner service. -- Private chef dining options available*. -- Front desk staff for local recommendations, pre-arrival grocery stocking, chartered excursions, and more*. -- Access to the 5th-floor Owner’s Terrace for group events or sunset dinners*. -- On-site fitness center (18+ and over). -- On-site wellness suite for spa treatments or massage*. -- Xbox Gaming Console or DVD Player Available at the Front Desk+. -- Complimentary snorkel equipment provided during your stay+. -- Complimentary bike share for cruising the Cayman Kai neighborhood+. Discover why the Rum Point Resort is Cayman’s hidden 5-star gem! Resort Amenities Notes: * Pre-arrival reservations are required; additional fees apply. + Provided on a first-come, first-served basis. Cannot be reserved before arrival. *** RATE DETAILS *** -- 13% Occupancy Tax added to all rates. -- 10% Resort Fee is added to all rates. -- Accidental Damage Protection added to all rates. *** BOOKING RULES *** -- Christmas & New Year’s are split into two separate rental periods. Please inquire about your dates before booking for the holidays. -- Guests must be 25 years or older to book and occupy the unit during the entire stay. -- Check-in: 4:00 pm. -- Check-out: 11:00 am. *** NEARBY POINTS OF INTEREST *** -- The resort is next door to the Rum Point Club for food + drinks, snorkeling, watersport rentals, and Stingray City excursions. -- The resort is adjacent to Cayman’s Bioluminescent Bay for nighttime kayak tours. -- 1.2 miles to the Kaibo Beach Bar & Grill and The Kaibo Marina. -- 1.7 miles south to Starfish Point -- 4.4 miles to the nearest market, Chisholm’s Grocery. -- 6.2 miles east to Over the Edge restaurant -- 6.7 miles to Cayman Crystal Caves -- 12.5 miles to the nearest supermarket, Foster’s Market -- 26 miles (49-minute drive) from Owen Roberts Airport (GCM) *** GETTING AROUND *** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget, Avis, Marshalls, or Hertz. *** DAY TRIPPING *** Cayman Ferries operates daily water taxis departing from the Kaibo Marina to Camana Bay. Perfect for day trips to Seven Mile Beach or shopping excursions at Camana Bay. Download their app to purchase your tickets in advance. Just be sure to make it back for the return voyage across the sound!

Rum Point Resort #207

Rum Point, KY
2 Bedrooms 4 Guests
Aug 23 - 26
$514 night

*** PROPERTY DESCRIPTION *** Second Floor Condo | 1,250 sq. ft. All Rum Point Resort condos feature sleek finishes, designer decor, and an open-concept layout maximizing space, natural light, and stunning ocean views. All the comforts of home are included in this 1-bedroom + den condo, totaling 1,250 sq. ft., including gourmet kitchen appliances, quartz countertops, SmartTVs for streaming, and a private oceanfront balcony. All condos strike the perfect balance of modern luxury and seamless indoor/outdoor island living. Central air conditioning and high-speed wifi will keep you cool and connected during your stay. Beyond the entryway foyer, the home flows into a spacious open-concept great room encompassing the living, dining, and kitchen areas. Forever blue ocean views from the great room and primary suite will leave you breathless. Crisp coastal decor throughout accentuates the island scenery. The living area includes a comfy sofa, a large SmartTV, and stunning ocean views. Walk out from the living area onto the private roofed balcony overlooking the resort’s beachfront. A private staircase provides convenient walk-out access to the resort’s beach and pool deck. The gourmet kitchen features a suite of Thermador appliances, plus countertop appliances. Cookware, dishware, glassware, and cutlery also come provided. An outdoor dining table is furnished on the private balcony for meals with sweeping oceanfront views. An indoor dining table is also furnished just off the kitchen area. The Rum Point Resort fits all condos with blackout window shades, the finest Egyptian cotton bedding, hypoallergenic pillows, duvets, and sumptuous robes. ***Sleeping Arrangements*** (Sleeps 6 guests; 4 adults max.) -- Primary Suite: king bed, ocean views, walk-out access to the private roofed balcony, SmartTV, ensuite bath with shower. (2 adults) -- Bunk Den: full-over-full bunk beds, SmartTV, ensuite bathroom with shower. (2 adults or 4 children) There is also a rarely used 5th-floor open-air owner’s terrace with dining tables and seating for sunset dinners with 270-degree island views of Cayman Kai, North Sound, and George Town in the distance. The terrace is also a serene setting for a quiet read with elevated island views. Trade the crowds of Seven Mile Beach for an escape to Cayman’s quieter side where life is easy and not so fast. ***Additional Resort Amenities*** -- 500 feet of beachfront with daily beach umbrella, chair, and towel service. -- Resort pool deck with heated infinity pool. -- Resort dock with cabana and ladder for gentle water entry for snorkeling and swimming. -- Our new on-resort restaurant, Blue Flame, is open from 11:00 a.m. to 11:00 p.m. for lunch and dinner service. -- Private chef dining options available*. -- Front desk staff for local recommendations, pre-arrival grocery stocking, chartered excursions, and more*. -- Access to the 5th-floor Owner’s Terrace for group events or sunset dinners*. -- On-site fitness center (18+ and over). -- On-site wellness suite for spa treatments or massage*. -- Xbox Gaming Console or DVD Player Available at the Front Desk+. -- Complimentary snorkel equipment provided during your stay+. -- Complimentary bike share for cruising the Cayman Kai neighborhood+. Discover why the Rum Point Resort is Cayman’s hidden 5-star gem! Resort Amenities Notes: * Pre-arrival reservations are required; additional fees apply. + Provided on a first-come, first-served basis. Cannot be reserved before arrival. *** RATE DETAILS *** -- 13% Occupancy Tax added to all rates. -- 10% Resort Fee is added to all rates. -- Accidental Damage Protection added to all rates. *** BOOKING RULES *** -- Christmas & New Year’s are split into two separate rental periods. Please inquire about your dates before booking for the holidays. -- Guests must be 25 years or older to book and must occupy the unit during the entire stay. -- Check-in: 4:00 pm. -- Check-out: 11:00 am. *** NEARBY POINTS OF INTEREST *** -- The resort is next door to the Rum Point Club for food + drinks, snorkeling, watersport rentals, and Stingray City excursions. -- The resort is adjacent to Cayman’s Bioluminescent Bay for nighttime kayak tours. -- 1.7 miles south to Starfish Point -- 4.4 miles to the nearest market, Chisholm’s Grocery. -- 6.2 miles east to Over the Edge restaurant -- 6.7 miles to Cayman Crystal Caves -- 12.5 miles to the nearest supermarket, Foster’s Market -- 26 miles (49-minute drive) from Owen Roberts Airport (GCM) *** GETTING AROUND *** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Marshalls, or Hertz. *** DAY TRIPPING *** Cayman Ferries operates daily water taxis departing from the Kaibo Marina to Camana Bay. Perfect for day trips to Seven Mile Beach or shopping excursions at Camana Bay. Download their app to purchase your tickets in advance. Just be sure to make it back for the return voyage across the sound!

Rum Point Resort #308

Rum Point, KY
2 Bedrooms 4 Guests
Aug 23 - 26
$575 night

*** PROPERTY DESCRIPTION *** 3rd Floor Condo | 1,350 sq. ft. All Rum Point Resort condos feature sleek finishes, designer decor, and an open-concept layout maximizing space, natural light, and stunning ocean views. All the comforts of home are included in this 1,350 sq. ft. 1-bedroom + den premium condo including gourmet kitchen appliances, quartz countertops, SmartTVs for streaming, and a private oceanfront balcony. All condos strike the perfect balance of modern luxury and seamless indoor/outdoor island living. Central air conditioning and high-speed wifi will keep you cool and connected during your stay. Beyond the entryway foyer, the home flows into a spacious open-concept great room encompassing the living, dining, and kitchen areas. Forever blue ocean views from the great room and primary suite will leave you breathless. Crisp coastal decor throughout accentuates the island scenery. The living area includes a plush sectional sofa, a large SmartTV, a tray ceiling with a ceiling fan, and stunning ocean views. Walk out from the living area onto the private roofed balcony overlooking the resort’s beachfront. The gourmet kitchen features a suite of Thermador appliances, and countertop appliances, plus a kitchen island with breakfast bar seating. Cookware, dishware, glassware, and cutlery also come provided. An outdoor dining table is furnished on the private balcony for meals with sweeping oceanfront views. An indoor dining table is also furnished just off the kitchen. The Rum Point Resort fits all condos with blackout window shades, the finest Egyptian cotton bedding, hypoallergenic pillows, duvets, and sumptuous robes. ***Sleeping Arrangements*** (Sleeps 6 guests; 4 adults max.) -- Primary Suite: king bed, ocean views, walk-out access to the ocean balcony, SmartTV, walk-in closet, ensuite with oversized soaking tub, and shower. -- Bunk Suite: full-over-full bunk beds, SmartTV, ensuite with shower. There is also a rarely used 5th-floor open-air owner’s terrace with dining tables and seating for sunset dinners with 270-degree island views of Cayman Kai, North Sound, and George Town in the distance. The terrace is also a serene setting for a quiet read with elevated island views. Trade the crowds of Seven Mile Beach for an escape to Cayman’s quieter side where life is easy and not so fast. ***Additional Resort Amenities*** -- 500 feet of beachfront with daily beach umbrella, chair, and towel service. -- Resort pool deck with heated infinity pool. -- Resort dock with cabana and ladder for gentle water entry for snorkeling and swimming. -- Our new on-resort restaurant, Blue Flame, is open from 11:00 a.m. to 11:00 p.m. for lunch and dinner service. -- Private chef dining options available*. -- Front desk staff for local recommendations, pre-arrival grocery stocking, chartered excursions, and more*. -- Access to the 5th-floor Owner’s Terrace for group events or sunset dinners*. -- On-site fitness center (18+ and over). -- On-site wellness suite for spa treatments or massage*. -- Xbox Gaming Console or DVD Player Available at the Front Desk+. -- Complimentary snorkel equipment provided during your stay+. -- Complimentary bike share for cruising the Cayman Kai neighborhood+. Discover why the Rum Point Resort is Cayman’s hidden 5-star gem! Resort Amenities Notes: * Pre-arrival reservations are required; additional fees apply. + Provided on a first-come, first-served basis. Cannot be reserved before arrival. *** RATE DETAILS *** -- 13% Occupancy Tax added to all rates. -- 10% Resort Fee is added to all rates. -- Accidental Damage Protection added to all rates. *** BOOKING RULES *** -- Christmas & New Year’s are split into two separate rental periods. Please inquire about your dates before booking for the holidays. -- Guests must be 25 years or older to book and occupy the unit during the entire stay. -- Check-in: 4:00 pm. -- Check-out: 11:00 am. *** NEARBY POINTS OF INTEREST *** -- The resort is next door to the Rum Point Club for food + drinks, snorkeling, watersport rentals, and Stingray City excursions. -- The resort is adjacent to Cayman’s Bioluminescent Bay for nighttime kayak tours. -- 1.2 miles to the Kaibo Beach Bar & Grill and The Kaibo Marina. -- 1.7 miles south to Starfish Point -- 4.4 miles to the nearest market, Chisholm’s Grocery. -- 6.2 miles east to Over the Edge restaurant -- 6.7 miles to Cayman Crystal Caves -- 12.5 miles to the nearest supermarket, Foster’s Market -- 26 miles (49-minute drive) from Owen Roberts Airport (GCM) *** GETTING AROUND *** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Marshalls, or Hertz. *** DAY TRIPPING *** Cayman Ferries operates daily water taxis departing from the Kaibo Marina to Camana Bay. Perfect for day trips to Seven Mile Beach or shopping excursions at Camana Bay. Download their app to purchase your tickets in advance. Just be sure to make it back for the return voyage across the sound!

Rum Point Resort #105

Rum Point, KY
2 Bedrooms 6 Guests
Aug 23 - 26
$514 night

*** PROPERTY DESCRIPTION *** Ground Floor Condo | 1,292 sq. ft. All Rum Point Resort condos feature sleek finishes, designer decor, and an open-concept layout maximizing space, natural light, and stunning ocean views. All the comforts of home are included in this 1-bedroom + bunkroom condo, totaling 1,292 sq. ft., including gourmet kitchen appliances, SmartTVs for streaming, and a private oceanfront veranda with walkout beach access. All condos strike the perfect balance of modern luxury and seamless indoor/outdoor island living. Central air conditioning and high-speed wifi will keep you cool and connected during your stay. Beyond the entry foyer, the condo reveals a spacious oceanfront great room encompassing the living, dining, and kitchen areas. 20 feet of sliding glass ocean views from the great room and primary suite will leave you breathless. The crisp coastal decor throughout accentuates the island scenery. The living area includes a comfy sofa, a large SmartTV, and stunning ocean views. Walk out from the living area onto the private roofed veranda that opens directly to a gently sloping ramp to the sandy beach, dock, and pool access. The gourmet kitchen features a suite of Thermador appliances, plus bespoke countertop appliances. Cookware, dishware, glassware, and cutlery are also provided. A private outdoor dining table and chairs are on the shaded verandah. The Rum Point Resort fits all condos with blackout window shades, the finest Egyptian cotton bedding, hypoallergenic pillows, duvets, and sumptuous robes. *** Sleeping Arrangements *** (Sleeps 6 guests; 4 adults max.) -- Primary Suite: king bed, ocean views, walk-out access to the private roofed balcony, SmartTV, ensuite with shower. -- Bunk Suite: full-over-full bunk beds, SmartTV, ensuite with shower; sleeps 2 adults or 4 children. #105 may be rented along with #106 immediately next door as a connecting 4-bedroom Family Suite. There is also a rarely used 5th-floor open-air owner’s terrace with dining tables and seating for sunset dinners with 270-degree island views of Cayman Kai, North Sound, and George Town in the distance. The terrace is also a serene setting for a quiet read with elevated island views. Trade the crowds of Seven Mile Beach for an escape to Cayman’s quieter side where life is easy and not so fast. ***Additional Resort Amenities*** -- 500 feet of beachfront with daily beach umbrella, chair, and towel service. -- Resort pool deck with heated infinity pool. -- Resort dock with cabana and ladder for gentle water entry for snorkeling and swimming. -- Our new on-resort restaurant, Blue Flame, is open from 11:00 a.m. to 11:00 p.m. for lunch and dinner service. -- Private chef dining options available*. -- Front desk staff for local recommendations, pre-arrival grocery stocking, chartered excursions, and more*. -- Access to the 5th-floor Owner’s Terrace for group events or sunset dinners*. -- On-site fitness center (18+ and over). -- On-site wellness suite for spa treatments or massage*. -- Xbox Gaming Console or DVD Player Available at the Front Desk+. -- Complimentary snorkel equipment provided during your stay+. -- Complimentary bike share for cruising the Cayman Kai neighborhood+. Discover why the Rum Point Resort is Cayman’s hidden 5-star gem! Resort Notes: * Pre-arrival reservations are required; additional fees apply. + Provided on a first-come, first-served basis. Cannot be reserved before arrival. *** RATE DETAILS *** -- 13% Occupancy Tax added to all rates. -- 10% Resort Fee is added to all rates. -- Accidental Damage Protection added to all rates. *** BOOKING RULES *** -- Christmas & New Year’s are split into two separate rental periods. Please inquire about your dates before booking for the holidays. -- Guests must be 25 years or older to book and must occupy the unit during the entire stay. -- Check-in: 4:00 pm. -- Check-out: 11:00 am. *** NEARBY POINTS OF INTEREST *** -- The resort is next door to the Rum Point Club for food + drinks, snorkeling, watersport rentals, and Stingray City excursions. -- The resort is adjacent to Cayman’s Bioluminescent Bay for nighttime kayak tours. -- 1.2 miles to the Kaibo Beach Bar & Grill. Ferry service to Camana Bay/Seven Mile Beach departs from the Kaibo Marina. -- 1.7 miles south to Starfish Point -- 4.4 miles to the nearest market, Chisholm’s Grocery. -- 6.2 miles east to Over the Edge restaurant -- 6.7 miles to Cayman Crystal Caves -- 12.5 miles to the nearest supermarket, Foster’s Express -- 12-15 miles to the Italian Kitchen, Tukka West, and La Casita for food and drinks. -- 26 miles (49-minute drive) from Owen Roberts Airport (GCM) *** GETTING AROUND *** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Avis, or Marshalls. *** DAY TRIPPING *** Cayman Ferries operates daily water taxis departing from the Kaibo Marina to Camana Bay. Perfect for day trips to Seven Mile Beach or shopping excursions at Camana Bay. Download their app to purchase your tickets in advance. Just be sure to make it back for the return voyage across the sound!

Vacation Rentals in Rum Point by Amenities & Features

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Vacation Rentals Near Rum Point

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