Vacation rentals in North Side, Cayman Islands with free parking

Explore 226 vacation rentals, homes, and villas with free parking in North Side for your next getaway or business trip. With on-site parking included in your stay, enjoy the comfort and privacy of a home filled with premium amenities such as Air Condition Homes, Homes with Pools and Best Affordable Homes. Throughout your stay, come and go with ease, knowing parking is always convenient and close at hand. With options starting as low as $30 per night and homes offering up to 12 bedrooms and 14 bathrooms, it's easy to book a personalized stay designed for your comfort. With 24/7 local support and high-speed Wi-Fi, you can also stay connected and protected throughout your trip. Plus, Marriott Bonvoy members earn points on every stay, making each trip more rewarding than the last. Book your next stay with ease and enjoy the convenience of free parking.

226 Homes with Free Parking in North Side

Maravilla

North Side, KY
4 Bedrooms 9 Guests
Aug 21 - 26
$489 night

***PROPERTY DESCRIPTION*** Welcome to Maravilla, a bright and inviting 4-bedroom, two-story oceanfront villa located on the tranquil North Side. With direct beach access and spacious interiors, Maravilla is designed for families and groups seeking a peaceful coastal getaway. Outside, the villa’s oceanfront setting delivers stunning panoramic ocean views and refreshing sea breezes. Step down to the beach for sunbathing, reef-protected snorkeling, or quiet morning walks along the shoreline. Mature trees provide shade along the beach. Guests can also take refuge from the island sun under the elevated pergola with sun loungers overlooking the ocean. Step inside to an airy, open-concept layout filled with natural light and dazzling ocean views. Soft neutrals, modern lighting, and tasteful décor create a warm and comfortable atmosphere throughout the home. The main living area features an oversized sectional sofa and a large HD cable television—perfect for movie nights after a day in the sand. For added entertainment, there’s a convertible pool & ping-pong table, giving guests the perfect spot to unwind and enjoy friendly competition. The villa’s expansive foyer and great room offer soaring ceilings, elegant columns, and polished travertine flooring that enhances the modern ambiance. A sleek staircase leads to the upper level, where you’ll find additional living spaces and bedrooms, giving your group plenty of room to spread out. ***Sleeping Arrangements*** (Sleeps 9 guests total, 8 adults max) -- Bedroom 1: upper-level, king bed, ocean views, private sunroom, shares adjacent bathroom with double vanity, and shower bath. -- Bedroom 2: upper-level, king bed, ocean views, private sunroom, shares adjacent bathroom with double vanity, and shower bath. -- Bedroom 3: upper-level, queen bed, shares hall bathroom with shower. -- Bedroom 4: upper-level, twin beds, shares hall bathroom with shower. -- Additional bedding: lower-level daybed suitable for one child. -- Additional bath: lower-level full bath with shower. Maravilla’s fully equipped kitchen features crisp white cabinetry, granite countertops, an oven, microwave, and ample workspace—ideal for preparing anything from quick breakfasts to island-inspired dinners. Whether you choose to cook or hire a private chef, this kitchen is built for convenience and style. For nights out on the town, you’re only a short drive away from food + drinks at the Rum Point Club and Kaibo. A small grocery store, Chisholm’s, is also just a short walk away. Whether you’re seeking serenity, family time, or a picture-perfect Caribbean retreat, Maravilla offers the ideal setting to create unforgettable island memories. Note: Cruiser bicycles and kayaks are available at discounted rental rates with free delivery. A signed waiver is required. ***NEARBY ATTRACTIONS*** -- Short walk to the nearest grocery, Chisholm’s Grocery. -- 5-minute drive east to Over the Edge restaurant and Cayman Crystal Caves -- 4 miles from our Grand Cayman Villas & Condos Welcome Center -- 5 miles west to the Rum Point Club and Bioluminescent Bay -- 6 miles to the Kaibo Beach Bar & Grill & Starfish Point -- 8 miles to the nearest supermarket, Foster’s Express -- 10 miles to Tukka East Restaurant & Bar and the Cayman Parrot Sanctuary -- 11 miles to La Casita Taco & Tequilla Bar -- 21 miles (40-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, Marshalls, or Hertz. ***RATE DETAILS*** -- 13% Occupancy tax added to rates. -- 10% Guest Service Fee added to rates. -- Accidental Damage Protection added to 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. ***GCVC GUEST SERVICES*** The following perks are provided during your stay! Member Benefits -- Free snorkel gear for all members of your group -- Free pack-n-plays, booster seats, & baby gates -- Free Bluetooth speakers, beach coolers, Apple TVs, and more convenience items to enhance your stay. -- 10% Advance Booking Discount towards a private charter to Stingray City -- On-island Welcome Center with guest-only private gym (18+ yrs.) and business hub (computers, printer, scanner, & FedEx/DHL supplies) -- Guest Benefit card for 10% discounts at select restaurants and businesses -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Referral to preferred vendors, guest services desk assistance At-Villa Benefits -- Complimentary early check-in, if no check out on the same day -- Day-after-arrival guest services follow-up -- Hotel-grade bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- Tandem/Single kayaks available for discounted rental; signed waiver required. *** 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.

Beautiful 3 Bd Beachfront Home North Side Sleeps 7

North Side, Grand Cayman, KY
3 Bedrooms 7 Guests
Aug 29 - Sep 1
$205 night

Welcome to Azure Breeze #6, a recently renovated beachfront property. This stunning 3-bedroom, 2-bathroom home, nestled within a small 6-unit complex, invites you to embark on an unforgettable vacation in the Cayman Islands. Located on the northern coast of Grand Cayman, Azure Breeze offers convenient proximity to Crystal Caves, Rum Point, and Cayman Kai, ensuring access to a variety of exciting adventures. With comfortable accommodations for up to 7 guests, including a king, queen, and a full bed with an overhead single bunk, this spacious two-story retreat is thoughtfully designed for both relaxation and family fun. Step outside onto the secluded beach and sway in a hammock beneath the coconut trees, as gentle sea breezes embrace you. Watch as children joyfully play on the shore or venture into the crystal-clear waters for snorkeling and kayaking adventures. Inside, every detail of this exquisite villa exudes elegance. Revel in breathtaking views from multiple windows, capturing the essence of the coastal paradise. Upstairs, sliding doors invite refreshing breezes and illuminate the main living room, which offers a tranquil space to unwind. The patio on the main floor is perfect for entertainment and relaxation, and features a beachside BBQ area with a provided propane grill. On the ground floor, a cozy bedroom with a queen-sized bed and a bathroom with a shower await. The recently renovated kitchen showcases modern appliances and utensils, ensuring a seamless culinary experience. While Azure Breeze #6 provides a private sanctuary, it remains conveniently close to a local grocery store, attractions, and restaurants, ensuring your needs and desires are effortlessly fulfilled. Indulge in the allure of this coastal oasis, where the pristine beach, stylish accommodations, and proximity to local treasures converge to create an unforgettable vacation experience. To fully embrace the serene ambiance of North Side, we suggest renting a car for convenient transportation, as public options may be limited. With George Town approximately 50 minutes away, having a car will grant you the freedom to explore the area’s hidden treasures and embrace the picturesque beauty at your own leisurely pace. A 2-seater kayak with lifejackets and snorkeling gears are available at the property. If the booking website does not collect it directly, a refundable security deposit of US$750.00 will be collected by the property prior to your stay. We reserve the right to substitute equal or better accommodation in the event of a double booking or if the rental is unavailable for any reason, including but not limited to sale or repair.

Willow Beach

North Side, KY
4 Bedrooms 12 Guests
Aug 21 - 26
$799 night

*** PROPERTY OVERVIEW *** On the quiet North Side of Grand Cayman, you will find this newly built and freshly decorated bespoke villa. Welcome to Willow Beach! This spacious 4-bedroom, 4-bath villa sits on an elevated ridge overlooking a sandy beachfront with amazing backyard snorkeling. Water entry requires fins or pool shoes, as there are rocky ironshore areas along the waterline. Overlooking the ocean, the villa’s freshwater pool and tiled deck are elevated for enhanced privacy. Ample deck furniture, an outdoor shower, artificial grass terraces, plus an outdoor kitchen with a propane grill make for easy island living. The spacious open-concept great room links the living, dining, and kitchen areas with mesmerizing ocean views throughout. Quality furnishings and decor have been used throughout the property for an elegant and contemporary feel. The living area is furnished with a plush sectional sofa and high-definition Samsung Frame television with Cable programming & Sonos soundbar. Folding glass doors provide seamless indoor/outdoor living, allowing you to fill the great room with unobstructed oceanfront views. Each master suite has a vaulted ceiling, a king bed, and a large bathroom with ocean views! The gourmet kitchen comes equipped with modern appliances and everything needed to prep and serve a homemade meal. The formal dining table seats 10 guests easily, while the veranda dining table seats 6. The owner also provides a beachfront picnic table for seaside meals, with your toes in the sand. The villa’s 4-bedroom suites are separated by the great room, with 2 bedrooms on opposite ends of the home. **Sleeping Arrangements** (Licensed to sleep 12 guests or 8 adults max.) -- East Suite: oceanfront views, king bed, walkout access to the beach, vaulted ceilings, dual nightstands, ensuite with dual vanity, soaking tub, plus an open shower with water wand. -- Bunk Suite #1: queen bed + 2 upper twin bunk beds, island views, ensuite with shower. -- Bunk Suite #2: queen bed + 2 upper twin bunk beds, island views, ensuite with shower. -- West Suite: oceanfront views, king bed, walkout access to the beach, vaulted ceilings, dual nightstands, ensuite with dual vanity, soaking tub, plus an open shower with water wand. -- Bunk beds are suitable for children only. Willow Beach is equipped with high-speed internet for work-from-home professionals and multiple streaming devices. Only 10 minutes from the Rum Point Club to the west, Willow Beach is very convenient to a small grocery store, a handful of restaurants, and our Guest Services Welcome Center with a private fitness center. Click the Map tab for other nearby attractions. With its private pool, modern interiors, and central location on North Side, Willow Beach is an ideal home-away-from-home in the Caribbean, with plenty of style. *Note: Single and tandem kayaks 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 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 during your stay -- Complimentary pack-n-plays, booster seats, & baby gates -- 10% Advance Booking Discount towards a private charter -- Guest discount card for 10% savings with local vendors. -- Complimentary early check-in, if no check out on same day -- 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 -- Referral to preferred vendors, guest services desk assistance -- Single or tandem kayaks available at discounted rates; signed waiver required. ================= ***Nearby Points of Interest*** -- 2-minute drive west to the nearest grocer, Chisholm’s Grocery -- 2-minute drive east to Over the Edge restaurant and Cayman Crystal Caves -- 3.5 miles from our Guest Services Welcome Center, plus Jacques Scott Wine & Spirits -- 6 miles west to the Rum Point Club and the Bioluminescent Bay -- 6.5 miles to the Kaibo Beach Bar & Grill & Starfish Point -- 7 miles east to the nearest supermarket, Foster’s Express, plus The Italian Kitchen, and two beach resorts, Morritt’s and The Reef. -- 9.5 miles to Tukka East Restaurant & Bar and the Cayman Parrot Sanctuary -- 10 miles to La Casita Taco & Tequilla Bar -- 21 miles (39-minute drive) to 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 harmless floating seaweed that has increased in frequency during the summer. Our owners make efforts to remove heavy sargassum and will have the beach raked prior to 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.

Coastal Charm

North Side, KY
3 Bedrooms 9 Guests
Aug 21 - 26
$604 night

***Property Description*** Welcome to Coastal Charm, a newly constructed 3-bedroom home nestled along Grand Cayman’s tranquil North Side. Thoughtfully designed with modern coastal elegance, this inviting retreat offers the perfect blend of comfort, style, and island serenity—ideal for families or small groups seeking a relaxing Caribbean escape. Step inside to an airy open-concept living space where floor-to-ceiling glass doors frame sweeping ocean views, filling the home with natural light. The seamless flow between the living area, dining area, and gourmet kitchen creates a welcoming gathering space. The kitchen features high-end appliances, a spacious island with seating, and everything needed to prepare meals with ease—whether you’re enjoying a casual breakfast indoors or an island cookout at sunset. The living area is designed for both comfort and style, with plush seating, warm natural textures, and calming neutral tones that reflect the beauty of the surrounding coastline. The home is equipped with central air conditioning, fiber optic wifi, and cable SmartTVs to keep you cool and connected during your stay. Just beyond, the tropical outdoors invites you to unwind, with a private pool, lounge seating, and reef-protected snorkeling in the crystal-clear Caribbean waters—perfect for swimming, kayaking, or simply soaking in the view. Coastal Charm offers three well-appointed bedroom suites designed for cloud-nine comfort. Each room provides a peaceful retreat after a day in the sun, with quality furnishings and a soothing coastal aesthetic. **Sleeping Arrangements** (Sleeps 9 guests, 6 adults max) -- Bedroom 1: lower level, ocean view, king bed, HD TV, walk-out access to pool deck, ensuite with double vanity and shower. -- Bedroom 2: upper level, ocean view, king bed, HD TV, ensuite with shower. -- Bedroom 3: upper level, ocean view, twin over queen bunk bed, HD TV, ensuite with shower. -- Additional Bedding: sleeper sofa in upper den, suitable for 2 children only. Located in the peaceful North Side, Coastal Charm offers a more secluded island experience while still being within easy driving distance of local attractions, dining, and adventure. Spend your days at the Rum Point Club snorkeling along the pier, dining with your toes in the sand, or staying in for a relaxing day in your oceanfront oasis. Whether you’re seeking quiet mornings by the water, memorable family antics, or a stylish island getaway, Coastal Charm delivers a refined yet laid-back Caribbean experience you won’t forget. *Notes: 1) Housekeeping can be added after booking; 2) Cruiser bikes for adults and kids, plus kayaks, are available for discounted rental. A signed waiver is required. =================== ***NEARBY ATTRACTIONS*** -- 2-minute drive east to the nearest grocery, Chisholm’s Grocery. -- 6-minute drive east to Over the Edge restaurant and Cayman Crystal Caves -- 7-minute drive west to Rum Point Beach and Bioluminescent Bay -- 9-minute drive west to the Kaibo Beach Bar & Grill & Starfish Point -- 10-minute drive from our Welcome Center -- 15-minute drive to the nearest supermarket, Foster’s Express -- 19-minute drive to Tukka East Restaurant & Bar and the Cayman Parrot Sanctuary -- 21-minute drive to La Casita Taco & Tequilla Bar -- 45-minute drive from Owen Roberts Airport (GCM) ***GETTING AROUND*** The entire island is only 22 miles wide, so you are never too far from anywhere on Grand Cayman. However, a rental car is highly recommended. Taxis are unreliable and expensive beyond Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Avis, or Marshalls. We’ll provide a 20% promo code for any rentals at Budget Cayman after booking. You can also rent kids’ or adult bikes to cruise the shoreline. Helmets and locks provided. ***RATE DETAILS*** -- 13% Occupancy Tax added to rates. -- 10% Guest Service Fee added to rates. -- Accidental Damage Protection added to 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. ***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 will be coordinated with your property manager on arrival. ***BEACH NOTES*** All beaches in Grand Cayman are technically public since the Crown owns up to the high-water mark. The shoreline quality behind your property may vary slightly from the images on our website due to shifting tides and weather patterns. The beach next door is also always available for your use. The homes on the oceanfront in Rum Point offer great reef-protected snorkeling. The beaches usually have plenty of white sand, but can also have spots of rocky “ironshore”. We recommend wearing pool shoes or fins for foot protection. The big draw to this area is the Rum Point Club, a public beachfront destination with beach service, food + drinks, a gift shop, excursions, and snorkeling. Also nearby is the Kaibo, another seaside dining spot with a cafe, beach bar & grill, and a fine dining restaurant. ***OCEAN DEBRIS & SARGASSUM*** Beaches in Grand Cayman may experience floating ocean debris and sargassum. Sargassum is a harmless seaweed that has increased due to warming waters. 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. We try our best to work around Mother Nature.

The Mastic Cana Cottage | 2BR w/ Private Pool on 11 Acre North Side Estate

North Side, Grand Cayman, KY
2 Bedrooms 6 Guests
Oct 31 - Nov 3
$409 night

The Mastic Cana Luxury Cottage is a ground floor, 2 bedroom, 2 bath retreat set on an 11 acre private estate along the Cayman Mastic Trail on Grand Cayman’s North Side. This thoughtfully designed cottage combines modern amenities with Caribbean inspired architecture, high ceilings, and a synthetic thatch roof for a truly tropical feel. Surrounded by lush vegetation and featuring its own screened in private pool, it’s a tranquil, immersive escape—perfect for two couples or families seeking nature, privacy, and comfort. 2 Bedrooms | 2 Bathrooms | Sleeps 6 EXPERIENCE. EXPLORE. ESCAPE. The Mastic Cana Luxury Cottage at Mastic Cottages offers a warm and welcoming 2 bedroom layout that blends modern comforts with relaxed Caribbean design. High ceilings, a synthetic thatch roof, and lush landscaping create a tropical, indoor–outdoor vibe, while the layout works beautifully on its own or in combination with the nearby Mastic estate cottages for larger groups. MAIN COTTAGE ACCOMMODATION The main building is designed as a comfortable hub for cooking, dining, and relaxing. • Spacious open concept living area • Primary bedroom with king size bed and ensuite bathroom with large walk in shower • Fully equipped kitchen with modern stainless steel appliances • Dining area and cozy seating area with sofa and chaise lounge • Large flat screen smart TV with Netflix and Apple TV • Wi Fi available throughout the property SEPARATE SUITE ACCOMMODATION A covered breezeway connects the main cottage to a separate guest suite, adding privacy and flexibility. • Second bedroom with king size bed • Sitting area with queen sleeper sofa • Ensuite bathroom with spacious walk in shower • Flat screen TV in this suite as well This setup makes Cana Cottage ideal for two couples traveling together or families with older children who appreciate their own space. POOL, OUTDOOR LIVING & ENTERTAINMENT One of the highlights of Mastic Cana Cottage is its private screened in pool area and outdoor living spaces. • Screened in private pool (max depth 4 feet), reserved exclusively for Cana Cottage guests • Beach style entry for easy, relaxed use • Poolside bar and dining area for casual meals and evening cocktails • BBQ grill for outdoor cooking • Large covered palapa with comfortable seating and a hammock • Screened in porch offering a tranquil spot to unwind and enjoy the sounds of nature Inside, entertainment is easy: • Smart TVs in the living room and bedrooms with Netflix and Apple TV • Reliable Wi Fi to stay connected • Central air conditioning for comfort throughout INCLUSIONS & SERVICES Cana Cottage is stocked with practical comforts so guests can settle in quickly. • All linens provided, including bath towels and beach towels • Bathroom toiletries: shampoo, conditioner, and soap • Complimentary mid stay cleaning service for stays of seven nights or more • Complimentary bikes for guest use • Pack ’n play and high chair available on request for little ones • Parties and weddings require prior consent; please share details and obtain approval before planning events WHO THIS SUITS The Mastic Cana Luxury Cottage is especially well suited to: • Two couples who want separate sleeping spaces (main cottage + connected suite) and shared pool and living areas • Families with older children or teens who enjoy having a semi private suite connected by a breezeway • Nature lovers who want to be surrounded by greenery and close to the Mastic Trail rather than in a busy resort area • Guests seeking a quiet, character rich base that can be combined with other Mastic estate cottages for larger group stays LARGER GROUPS – ESTATE OPTIONS Have a bigger group or planning a family gathering? The connected Mastic estate properties can be combined to create flexible setups with both togetherness and privacy: • 5 bedrooms (up to 10 guests): Combine Sunnyhill Cottage (3BR) with either Mastic Chapel or Mastic Cana Cottage • 7 bedrooms (up to 14 guests): Reserve all three Mastic properties for the ultimate group retreat DINING & NEARBY AREA – NORTH SIDE & RUM POINT Old Man Bay and the North Side offer a laid back, local dining scene with some very popular spots within a short drive. VERY CLOSE (OLD MAN BAY / NORTH SIDE) • Over the Edge – Long time North Side favorite right on the water with Caribbean dishes, seafood, and a casual bar atmosphere. • The Caboose – Well reviewed local spot in Old Man Bay known for Caribbean flavors and easy, relaxed vibes. • Other local stands and cafes – Small, authentic stops for Caymanian bites along the North Side and into East End. RUM POINT & CAYMAN KAI (ABOUT 10–15 MINUTES) • Rum Point Club – Casual beachfront restaurant and bar with pizzas, beach fare, and the island famous Mudslide. • Kaibo Beach Restaurant & Upstairs Restaurant – Beachfront dining downstairs and a more refined experience upstairs, popular for sunset dinners and cocktails. You’re also within an easy drive of water based activities at Rum Point and Cayman Kai, including boat charters, snorkeling trips, and sandbar excursions. GETTING THERE Northside is roughly 30 km from Owen Roberts International Airport, typically about 30–40 minutes by car depending on traffic and stops along the way. GROCERIES, SUNDAY CLOSURES & PRACTICAL DETAILS Nearby grocery options such as Foster’s Express and Chisholm’s Grocery are about 10 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. 10 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 Northside, having a car offers the greatest convenience and flexibility. ACCESSIBILITY & PARKING • Accessibility: Ground floor condo • Parking: Complex parking available. PROMOTIONS Automatic discounts may apply based on travel dates, including 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. TRAVEL INSURANCE Travel insurance is recommended, especially during hurricane season from August through October, to help protect against trip interruptions and weather-related disruptions. Mastic Chapel Cottages https://my.matterport.com/show/?m=c1fsEyHe8ZK&help=1&brand=0&nt=tab&title=0&guides=0&play=1 License number: CC-019

The Mastic Chapel Cottage | 2BR w/ Private Pool on 11 Acre North Side Estate

North Side, Grand Cayman, KY
2 Bedrooms 4 Guests
Oct 31 - Nov 3
$473 night

The Mastic Chapel Cottage is a unique 2 bedroom, 2 bath ground floor retreat set on an 11 acre private estate along the Cayman Mastic Trail on Grand Cayman’s North Side. This historic style chapel cottage blends modern comforts with old world charm—think vaulted ceilings, stained glass arched windows, and natural stone from the property itself. With its own private beach entry pool, lush surroundings, and access to nearby sister cottages, it’s an intimate, nature immersed escape ideal for two couples or families with older children. 2 Bedrooms | 2 Bathrooms | Sleeps 4 EXPERIENCE. EXPLORE. ESCAPE. Chapel Cottage at Mastic Cottages offers a one of a kind stay that combines history, design, and nature. Vaulted ceilings, natural stone, and historic stained glass from Keokuk, Iowa (crafted by Kokomo Glass in the late 1800s) give the space a distinctive character, while modern amenities keep it comfortable and easy to live in. A highlight of the property is the private sand entry pool, with a maximum depth of 4 feet, creating a shallow, beach like oasis just outside your door. MAIN COTTAGE ACCOMMODATION The main ground floor cottage is designed for relaxed, open concept living with easy flow between social spaces. • Spacious open plan living, dining, and kitchen area • Large primary suite with king size bed and generous ensuite bathroom • Living room with two sofas and a smart projection TV—perfect for movie nights • Modern, fully equipped kitchen with stainless steel appliances and a wine cooler SEPARATE COTTAGE ACCOMMODATION Just beside the main cottage, a smaller detached cottage adds privacy and flexibility. • Queen size bed • Flat screen smart TV • Ensuite bathroom with large walk in shower • Located next to the pool (better suited to couples or older children; not ideal for very small children who need constant supervision) The overall layout is fantastic for two couples who want both privacy and shared spaces, or families with older kids who enjoy having their own “mini cottage.” ENTERTAINMENT & COMFORT Mastic Chapel Cottage is set up for comfort, connection, and unplugging in nature—without giving up modern tech. • TVs in the living room and bedrooms with Netflix and Apple TV • Central air conditioning throughout the cottages • Wi Fi available across the property • Private sand bottom swimming pool with gentle beach style entry (exclusive to Chapel Cottage guests) • Outdoor BBQ and lounge area surrounded by native trees and greenery • Complimentary bikes for exploring the surrounding area INCLUSIONS & SERVICES You’ll arrive to a well prepared cottage with thoughtful essentials already in place. • All linens provided, including bath towels and beach towels • Bathroom toiletries: shampoo, conditioner, and soap • Pack ’n play and high chair available on request for little ones • Complimentary mid stay cleaning service for stays of seven nights or more • Parties and weddings are possible with prior consent—please share details and obtain approval before planning events Chapel Cottage offers a serene, private experience, making it ideal for guests who want a peaceful, nature focused stay rather than a traditional resort environment. WHO THIS SUITS The Mastic Chapel Cottage is especially well suited to: • Two couples who want separate sleeping spaces (main cottage + chapel cottage) and a shared pool and living area • Families with older children or teens who enjoy a bit of independence and unique spaces (separate cottage by the pool) • Nature lovers and hikers who want to be immersed in greenery, birdlife, and the Mastic Trail area rather than on a busy beach strip • Guests seeking a quiet, private, and character rich base for exploring North Side, East End, and the more untouched side of Grand Cayman LARGER GROUPS – ESTATE OPTIONS Have a bigger group or planning a family gathering? The connected Mastic estate properties can be combined to create flexible setups with both togetherness and privacy: • 5 bedrooms (up to 10 guests): Combine Sunnyhill Cottage (3BR) with either Mastic Chapel or Mastic Cana Cottage • 7 bedrooms (up to 14 guests): Reserve all three Mastic properties for the ultimate group retreat DINING & NEARBY AREA – NORTH SIDE & RUM POINT Old Man Bay and the North Side offer a laid back, local dining scene with some very popular spots within a short drive. VERY CLOSE (OLD MAN BAY / NORTH SIDE) • Over the Edge – Long time North Side favorite right on the water with Caribbean dishes, seafood, and a casual bar atmosphere. • The Caboose – Well reviewed local spot in Old Man Bay known for Caribbean flavors and easy, relaxed vibes. • Other local stands and cafes – Small, authentic stops for Caymanian bites along the North Side and into East End. RUM POINT & CAYMAN KAI (ABOUT 10–15 MINUTES) • Rum Point Club – Casual beachfront restaurant and bar with pizzas, beach fare, and the island famous Mudslide. • Kaibo Beach Restaurant & Upstairs Restaurant – Beachfront dining downstairs and a more refined experience upstairs, popular for sunset dinners and cocktails. You’re also within an easy drive of water based activities at Rum Point and Cayman Kai, including boat charters, snorkeling trips, and sandbar excursions. GETTING THERE North Side is roughly 30 km from Owen Roberts International Airport, typically about 30–40 minutes by car depending on traffic and stops along the way. GROCERIES, SUNDAY CLOSURES & PRACTICAL DETAILS Nearby grocery options such as Foster’s Express and Chisholm’s Grocery are about 10 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 North Side, and is open 7 days a week, and is well stocked with food, supplies, beer, wine & liquor. 10 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 North Side, having a car offers the greatest convenience and flexibility. ACCESSIBILITY & PARKING • Accessibility: Ground floor condo • Parking: Complex parking available. PROMOTIONS Automatic discounts may apply based on travel dates, including 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. TRAVEL INSURANCE Travel insurance is recommended, especially during hurricane season from August through October, to help protect against trip interruptions and weather-related disruptions. Mastic Chapel Cottages https://my.matterport.com/show/?m=c1fsEyHe8ZK&help=1&brand=0&nt=tab&title=0&guides=0&play=1 License number: CC-019

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.

Penthouse 2 Bd/Bth Beachfront Condo w/ Heated Pool

North Side, North Side, KY
2 Bedrooms 6 Guests
Aug 24 - 26
$199 night

Experience the Ultimate Beachfront Getaway and truley find your Happy Place at On the Bay # 312. Discover unparalleled luxury and serenity at this expansive 2-bedroom, 2-bathroom beachfront condo, nestled within the prestigious On the Bay complex in Old Man Bay, North Side, Grand Cayman. Renowned for its immaculate tropical landscaping and pristine white sand beach, On the Bay stands as one of the premier condo developments along the northern coastline. Experience the Ultimate Beachfront Getaway and truely find your Happy Place at On the Bay, Grand Cayman Discover unparalleled luxury and serenity at this expansive 2-bedroom, 2-bathroom beachfront condo, nestled within the prestigious On the Bay complex in North Side, Grand Cayman. Renowned for its immaculate tropical landscaping and pristine white sand beach, On the Bay stands as one of the premier condo developments along the northern coastline. Tropical Paradise Awaits Set within a sheltered cove, guests can effortlessly transition from lush gardens to the crystal-clear waters teeming with vibrant marine life. Ideal for snorkeling enthusiasts, the warm Caribbean Sea offers an underwater world waiting to be explored. After a day of adventure, relax at the sprawling complex pool, a serene oasis perfect for unwinding amidst gentle tropical breezes under the shade of swaying coconut palms. Luxurious Living Spaces Inside, the condo features two generously sized bedrooms, each with a spacious ensuite bathroom, ensuring privacy and convenience. With over 1,685 square feet of living space, including a sizeable balcony offering uninterrupted views of the Caribbean Sea, this unit provides ample room for relaxation and enjoyment. The fully equipped kitchen, complete with stunning ocean vistas, inspires culinary adventures, making home-cooked meals a delightful experience. Elegant Comfort The expansive Master bedroom boasts a plush king-size bed, complemented by nightstands, a desk, chest of drawers, and a lavish ensuite bathroom with a jet tub, shower, toilet, and walk-in closet—everything needed for a stress-free vacation. The second bedroom offers two full beds, ensuring comfortable accommodations for additional guests, with an adjoining ensuite bathroom featuring a jetted jacuzzi tub for added luxury. Prime Location for Island Exploration Conveniently located just 10 minutes from Cayman Kai and Rum Point, as well as various restaurants, attractions, and amenities in East End and Bodden Town, Old Man Bay serves as an ideal base for exploring the island’s treasures. Within a short drive, guests can visit the Botanical Gardens, Crystal Caves, and the Mastic Trail, immersing themselves in the island’s natural splendor. With George Town and the airport a pleasant 45-minute drive away, a rental car is highly recommended for ease of access and exploration. Your Dream Vacation Awaits Immerse yourself in the beauty and tranquility of Grand Cayman. Book your stay at On the Bay, where luxury, adventure, and relaxation converge to create the perfect beachfront getaway. The entire condo, pool, beach and grounds. If the booking website does not collect it directly, a refundable security deposit of US$500 will be collected by the property prior to your stay. We reserve the right to substitute equal or better accommodation in the event of a double booking or if the rental is unavailable for any reason, including but not limited to sale or repair.

Spacious 3-Bedroom 3-Bathroom Beachfront Condo with Heated Pool

North Side, North Side, KY
3 Bedrooms 6 Guests
Feb 6 - 12
$525 night

Tranquility in the Tropics, relax by the pool or dig your toes into the white sand beach catching some rays! This is what you’ll find greeting you at On the Bay! Enjoy our comfortable slice of heaven on Cayman’s lush North Side. The view from your balcony is priceless, the sound of the waves waking you up in the morning is surreal. This 3-bedroom beachfront condominium located in Old Man Bay on the North Side of Grand Cayman exudes the charm of traditional Caribbean architecture. The interiors are adorned with rustic wooden furnishings and artisanal decor that creates a cozy and inviting atmosphere. Each bedroom is furnished with plush beds and premium linens that offer ultimate comfort, while the living area boasts stunning ocean views and plush seating. Each bedroom in this house comes equipped with its own bathroom for added convenience. As you enter the master bedroom, you’ll be greeted by a spacious and elegant room with a king-sized bed. Connected to the master bedroom is a private bathroom that boasts a jetted tub. You can indulge in a soothing soak after a long day, as the tub is designed to provide an exquisite spa-like experience. Moving on to the second bedroom, you’ll find a comfortable queen-sized bed awaiting you. Adjacent to the second bedroom is its dedicated bathroom, ensuring privacy and convenience for its occupants. In the third bedroom of this house, you’ll find a cozy double bed, perfect for a comfortable night’s sleep. The room also has its own dedicated bathroom. The fully equipped kitchen features modern appliances and all the essential cookware and utensils for preparing delicious meals, while the spacious balcony offers breathtaking views of the turquoise waters and gentle sea breeze. Entire condo, shared heated pool and beach. To fully embrace the serene ambiance of the North Side, we recommend renting a car for convenient transportation, as public options may be limited. With George Town approximately 50 minutes away, having a car will grant you the freedom to explore the area’s hidden treasures and embrace the picturesque beauty at your own leisurely pace. A restaurant, bar, liquor store and gas station are within walking distance. If the booking website does not collect it directly, a refundable security deposit of US$500 will be collected by the property prior to your stay. We reserve the right to substitute equal or better accommodation in the event of a double booking or if the rental is unavailable for any reason, including but not limited to sale or repair.

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!

Spacious 3 Bd Beachfront Ground Flr Condo w/ Pool

North Side, North Side, KY
3 Bedrooms 6 Guests
Aug 21 - 26
$525 night

Welcome to On The Bay #101. This serene and luxurious 3-bedroom, 3-bath ground-floor condo is set directly on the beachfront. Step from your screened patio to hammocks waiting just outside, stroll onto soft white sand, or relax at the beachfront pool overlooking the cove. On The Bay’s protected cove makes swimming and water access easy and calm, perfect for families and snorkelers. Located on Cayman’s tranquil North Side, enjoy sweeping ocean views and island-style comforts. This upgraded 3-bedroom, 3-bath beachfront condo at On The Bay #101 sits directly on the sands of Old Man Bay on Grand Cayman’s North Side. While the exterior showcases classic Caribbean charm, the owners have transformed the interior with modern amenities and elegant finishes. The open living area features plush seating, a custom bar, and sweeping ocean views, creating an inviting space to unwind. Each bedroom includes its own private bathroom for added comfort. The master suite offers a spacious retreat with a king bed and a luxurious spa-style bath complete with a large freestanding soaking tub. The second bedroom features a queen bed with an en-suite bathroom, while the third bedroom provides a cozy double bed and its own private bath. The fully equipped kitchen includes modern appliances and all essentials for easy meal prep. Step onto the screened-in patio and enjoy plush outdoor seating, a perfect spot for morning coffee or sunset cocktails. Just beyond the patio, hammocks sway in the breeze, the beachfront pool awaits, and a protected cove offers calm, easy access to the water, ideal for swimming and snorkeling. Unit #101 blends modern comfort with serene coastal living, offering a beautifully updated beachfront escape in one of Cayman’s most peaceful locations. Entire condo, shared heated pool and beach. To fully embrace the serene ambiance of the North Side, we recommend renting a car for convenient transportation, as public options may be limited. With George Town approximately 50 minutes away, having a car will grant you the freedom to explore the area’s hidden treasures and embrace the picturesque beauty at your own leisurely pace. If the booking website does not collect it directly, a refundable security deposit of US$500 will be collected by the property prior to your stay. Please note that the owners of this rental live on the property in a separate unit for approximately six months each year. During this time, we will continue to provide full management of the rental; however, the owners will be onsite and available to assist in the event of an emergency. This property is not suitable for children under the age of 12 years old. We reserve the right to substitute equal or better accommodation in the event of a double booking or if the rental is unavailable for any reason, including but not limited to sale or repair.

On the Bay #103 | Oceanfront 3BR Condo | Old Man Bay, North Side

North Side, North Side, KY
3 Bedrooms 6 Guests
Aug 21 - 24
$296 night

On the Bay #103 is a bright, ground floor 3 bedroom, 3 bath condo set in a lush, tropical beachfront resort in Old Man Bay on Grand Cayman’s North Side. With views of the gardens and sea, a private patio, direct access to the resort pool, and a protected swimming cove just steps away, it offers a peaceful alternative to Seven Mile Beach while still being within about 10 minutes of Rum Point and nearby dining. It’s ideal for families or small groups looking for island tranquility, snorkeling, and easy access to North Side and Rum Point attractions. 3 Bedrooms | 3 Bathrooms | Sleeps 6 LIVING AREA & INTERIOR FEATURES The condo has a relaxed, coastal feel with everything you need for a comfortable stay. • Newly furnished interior with an open plan layout • Fully equipped kitchen with stainless steel appliances • Drip coffee maker and complete cookware/utensils for home cooked meals • Spacious living area with a large flat panel HDTV and comfortable seating • Sliding doors leading to a breezy garden level patio with views of the pool and ocean • In unit washer and dryer for added convenience BEDROOMS & BATHROOMS On the Bay #103 comfortably sleeps up to 6 guests across three well appointed bedrooms and three full bathrooms. • Primary bedroom: king size bed, ensuite bathroom, flat screen TV • Second bedroom: queen size bed • Third bedroom: two twin beds, ideal for kids or friends • Fresh linens and ample closet space in each room STARTER ESSENTIALS Guests are welcomed with a comprehensive starter pack including dishwashing liquid, dishwasher detergent, laundry detergent, shampoo, conditioner, hand soap, toilet paper, paper towels, and coffee filters. Linens, bath towels, beach towels, a blow dryer, and an iron with board are also provided, along with charcoal bags and utensils for the BBQ. BEACH & OUTDOOR AMENITIES This small resort is designed for relaxed days by the water, with a natural, North Side feel. • Large oceanfront freshwater pool with loungers and a shaded gazebo • Beachfront area with a natural cove offering calm water for swimming and snorkeling, especially good for children • Rocky shoreline in places—water shoes are recommended for comfort and footing • Communal charcoal BBQ grill near the pool/beach for casual outdoor cooking The protected cove and reef offshore make this a great spot for those who enjoy snorkeling, floating, and simply unwinding by the sea away from the busier areas of the island. BEACH CONDITIONS Properties on the North Side and East End of Grand Cayman may occasionally see sargassum (seaweed) wash ashore, mostly between May and August. This is a natural, seasonal occurrence throughout the Caribbean, and conditions can vary day to day. Grand Cayman offers gorgeous beaches, great snorkeling, and plenty to enjoy island-wide, so we don’t anticipate it impacting your trip, just a heads-up in case you notice it during your visit. DINING & NEARBY AREA – NORTH SIDE & RUM POINT Old Man Bay and the North Side offer a laid back, local dining scene with some very popular spots within a short drive. VERY CLOSE (OLD MAN BAY / NORTH SIDE) • Over the Edge – Long time North Side favorite right on the water with Caribbean dishes, seafood, and a casual bar atmosphere. • The Caboose – Well reviewed local spot in Old Man Bay known for Caribbean flavors and easy, relaxed vibes. • Other local stands and cafes – Small, authentic stops for Caymanian bites along the North Side and into East End. RUM POINT & CAYMAN KAI (ABOUT 10–15 MINUTES) • Rum Point Club – Casual beachfront restaurant and bar with pizzas, beach fare, and the island famous Mudslide. • Kaibo Beach Restaurant & Upstairs Restaurant – Beachfront dining downstairs and a more refined experience upstairs, popular for sunset dinners and cocktails. You’re also within an easy drive of water based activities at Rum Point and Cayman Kai, including boat charters, snorkeling trips, and sandbar excursions. GETTING THERE Old Man Bay is roughly 30 km from Owen Roberts International Airport, typically about 30–40 minutes by car depending on traffic and stops along the way. WHO THIS SUITS On the Bay #103 is a great match for guests who want a quieter, more natural setting without being far from well known North Side attractions. • Families with children who will appreciate the ground floor access, pool, and protected swimming cove. • Snorkelers and ocean lovers who prefer a reefy, more natural shoreline over a fully manicured resort beach. • Couples or small groups looking for a calm alternative to Seven Mile Beach, while staying within a short drive of Rum Point and Cayman Kai. • Guests planning longer stays who value a full kitchen, in unit laundry, and a laid back residential resort feel. GROCERIES, SUNDAY CLOSURES & PRACTICAL DETAILS Nearby grocery options such as Foster’s Express and Chisholm’s Grocery are about 10 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. 10 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 Northside, having a car offers the greatest convenience and flexibility. ACCESSIBILITY & PARKING • Accessibility: Ground floor condo • Parking: Complex parking available. PROMOTIONS Automatic discounts may apply based on travel dates, including seasonal Stay 7, Pay 6 offers from May 1 to November 1, 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. TRAVEL INSURANCE Travel insurance is recommended, especially during hurricane season from August through October, to help protect against trip interruptions and weather-related disruptions. Stay 7 Pay 6 On the Bay License number: GH-167

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 22 - 25
$615 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!

Luxury 3bd Beach View, # 2 Peach, Stunning Views

North Side, Grand Cayman, KY
3 Bedrooms 9 Guests
Aug 23 - 25
$252 night

Perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations and is conveniently located near renowned Stingray City, Rum Point and Kaibo’s restaurants, beaches and water sport activities. Bask on the white sand beach, enjoy the pool, swim and snorkel with a myriad of sea life, or simply lounge in your hammock snoozing away the day. This 3-bedroom, 3-bathroom charming retreat combines the natural beauty of the seaside with a warm and cozy atmosphere. The decor is simple, yet elegant, with a focus on comfort and relaxation. Large windows provide an abundance of natural light and breathtaking views of the ocean. Each one of the five homes at this intimate enclave at Ocean Paradise is characterized by a unique color and Peach offers its own unique charm. The fully equipped kitchen features high-end appliances, ample counter space, and all the necessary cookware and utensils to whip up a culinary masterpiece. The living area is spacious and cozy, featuring plush sofas and chairs, a large coffee table, and tasteful decor that creates a warm and inviting atmosphere for relaxation and entertainment. An outdoor terrace offers the perfect spot to relax and soak up the salty sea breeze with stunning ocean views. The home is the ideal setting for a couple, family or group of friends getaway. Entire Home. To fully embrace the serene ambiance of North Side, we suggest renting a car for convenient transportation, as public options may be limited. With George Town approximately 50 minutes away, having a car will grant you the freedom to explore the area’s hidden treasures and embrace the picturesque beauty at your own leisurely pace. Upon booking, you will receive a key code for the keyless entry system, allowing for a seamless and convenient self-check-in process at this exquisite property. While it may not be necessary for everyone, we recommend bringing sea shoes. If the booking website does not collect it directly, a refundable security deposit of US$500 will be collected by the property prior to your stay. We reserve the right to substitute equal or better accommodation in the event of a double booking or if the rental is unavailable for any reason, including but not limited to sale or repair.

Rum Point Resort #307

Rum Point, KY
1 Bedrooms 2 Guests
Aug 21 - 24
$559 night

==> PROPERTY DESCRIPTION <== ***Third 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 1,250 sq. ft. condo including gourmet kitchen appliances, quartz countertops, SmartTVs throughout, 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 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 pool deck and beachfront. The gourmet kitchen comes equipped with 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 2 guests) -- Primary Suite: king bed, ocean views, walk-out access to a private balcony, SmartTV, walk-in closet, oversized in-room soaking tub, walk-thru ensuite bath with walk-in 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 prior to 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 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 located next door to the Rum Point Club for lunch, dinner, and drinks, plus snorkeling, watersport rentals, Stingray City excursions, and beach volleyball. -- 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 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!

Hidden Treasure & Guesthouse

East End, KY
6 Bedrooms 18 Guests
Aug 21 - 26
$913 night

***Property Overview*** Welcome to Hidden Treasure + Little Treasure, centrally located on the quiet southern coast. With over 5,500 sq. ft., this stately oceanfront villa features a private infinity pool, beach fire pit, spacious interiors, and a screened dining balcony. This 6-bedroom beachfront villa sits on over 100 feet of sandy beach and iron shore with convenient backyard snorkeling and breathtaking sunrise views. A newly installed private dock + hammock cabana provide gentle water entry or simply lounging above the waves. The main villa can sleep 12 guests across five spacious bedrooms, three of which are oceanfront. The 1-bedroom guest house sleeps an additional 2 adults, plus 2 small children on a sleeper sofa. The gourmet kitchen features modern appliances, granite countertops, and breakfast bar seating for four. The formal dining area provides seating for 10. The screened dining balcony seats 12 for meals with sweeping ocean views. Hire a chef for a night of gourmet dining or start your day with brunch service on the dining balcony. This listing includes both the 5-bedroom villa and 1-bedroom guest house sleeping 18 guests total or 16 adults max. ***Sleeping Arrangements*** (Sleeps 18 guests total, 14 adults max) -- Bedroom 1: lower-level, queen bed, ocean views, walk-out access to the pool deck, closet, ensuite bath with soaking tub, and separate shower. -- Bedroom 2: primary suite, upper-level, king bed, ocean views, walk-out access to a shared oceanfront balcony, television, closet, office with desk + chair, ensuite with dual vanity, soaking tub, and separate shower. -- Bedroom 3: upper-level, queen bed, ocean views, walk-out access to a shared oceanfront balcony, closet, desk + chair, shares a jack-and-jill bathroom with shower bath. -- Bedroom 4: upper-level, two twin beds, closet, shares a jack-and-jill bathroom with shower bath. -- Bedroom 5: upper-level, four twin-over-twin bunks + two trundle beds, closet, and ensuite with shower. -- Bedroom 6: full bed, garden views, television, ensuite with shower bath; sleeper sofa in the living room. ***Hidden Treasure’s Notable Features*** -- High-speed fiber optic internet for streaming devices and work-from-home professionals. -- Air-conditioned throughout. -- Home office on the second floor with workstation, private balcony, and oversized recliner. There is no sleeping option in the office. -- Propane grill for island cookouts. -- Propane fire pit for late-night hangouts on the beach. -- Dock with hammock cabana for gentle water entry or siestas above the waves. Daily housekeeping is optional and can be arranged for guests in addition to a private chef, massage therapist, personal trainer, or yoga instructor. Hidden Treasure is conveniently located 30 minutes east of the airport. The villa is only 15 minutes from the supermarket, 10 minutes from Ocean Frontiers, one of Cayman’s premier dive operators and 5 minutes from both our private fitness center and Cayman Health City. ***IMPORTANT NOTES*** -- A Cleaning Fee is included due to enhanced cleaning and sanitation protocols. -- Tandem or single kayaks 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. ***Booking Rules*** -- Christmas & New Year’s are split into two rental periods. Please inquire about your travel dates before booking. -- Must be 25 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 -- 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 -- Tandem kayaks available for discounted rental* *Signed waiver required. =============== ***Nearby Points of Interest*** -- 33 minutes from Owen Roberts Int’l Airport (GCM) -- 4 minutes from our Welcome Center -- 5 minutes to The Blowholes -- 10 minutes to La Casita restaurant and Ocean Frontiers Dive Shop -- 13 minutes to Tukka East restaurant and the Cayman Parrot Sanctuary -- 15 minutes to The Italian Kitchen restaurant and Tortuga Divers -- 17 minutes to the nearest supermarket, Foster’s Countryside -- 18 minutes to Spotts Public Beach -- 19 minutes to the Rum Point Club -- 22 minutes to the Kaibo Beach Bar & Grill and Starfish Point -- 35 minutes to Seven Mile Beach ***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. All 3 have pickup locations at the airport. ***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. ***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 is largely seasonal in summer months. 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. ***Beach Notes*** The entire island is only 22 miles wide from west to east, so you are never too far from anywhere on Grand Cayman. The villas in the Cottage District on the southeast coast offer great reef-protected snorkeling with calm waters plus proximity to the island’s best dive operators--Ocean Frontiers and Tortuga Divers. 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.

Luxury 3bd Beach Front, # 4 Green, Stunning Views

North Side, Grand Cayman, KY
3 Bedrooms 8 Guests
Aug 21 - 23
$283 night

Perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations and is conveniently located near renowned Stingray City, Rum Point and Kaibo’s restaurants, beaches and water sport activities. Bask on the white sand beach, enjoy the pool, swim and snorkel with a myriad of sea life, or simply lounge in your hammock snoozing away the day. Each one of the five homes at this intimate enclave at Ocean Paradise is characterized by a unique color and Green blends in perfectly with its lush tropical surroundings. The three-bedroom, three-bathroom oasis features spacious accommodations and breathtaking Caribbean views that will leave you speechless. Enjoy a fully equipped kitchen complete with modern appliances and ample seating for you and your guests. The spacious living area features comfortable seating, high-end electronics, and tasteful decor to create a relaxing and inviting atmosphere. Each of the three bedrooms is beautifully designed with plush bedding and comfortable furnishings, ensuring a peaceful night’s sleep. Whether you’re lounging on the private balcony, taking a dip in the nearby pool, or exploring the local area, this vacation rental is the perfect retreat for your next getaway. Home #4 at Ocean Paradise is one of our two premier beachfront homes with spectacular views of Grand Cayman’s northern coastline from almost every room in the house. Entire Home. To fully embrace the serene ambiance of the North Side, we recommend renting a car for convenient transportation, as public options may be limited. With George Town approximately 50 minutes away, having a car will grant you the freedom to explore the area’s hidden treasures and embrace the picturesque beauty at your own leisurely pace. Upon booking, you will receive a key code for the keyless entry system, allowing for a seamless and convenient self-check-in process at this exquisite property. While it may not be necessary for everyone, we recommend bringing sea shoes. If the booking website does not collect it directly, a refundable security deposit of US$500 will be collected by the property prior to your stay. We reserve the right to substitute equal or better accommodation in the event of a double booking or if the rental is unavailable for any reason, including but not limited to sale or repair.

SunRays Villa

Rum Point, KY
8 Bedrooms 22 Guests
Sep 21 - 26
$3,393 night

===> PROPERTY OVERVIEW <=== Welcome to SunRays, a newly built, luxury oceanfront estate located directly on a barefoot beach with calm waters and sunset views. This magnificent new villa lacks nothing and checks just about every box imaginable for a sumptuous island vacation. The vacation experience for our Luxury Platinum Collection villas begins with a group airport greeting by a professional chauffeur and a 28-seat mini-coach (7-day min stay). Our on-island hospitality team can coordinate the delivery of your rental vehicles to the villa in advance. The villa’s driveway has plenty of off-street and covered parking for 4-5 vehicles. Located in the resort neighborhood of Cayman Kai, guests can expect very light vehicle traffic and short walking distances to the Rum Point Club, and the Kaibo. A luxe beach dining destination, Kaibo provides casual beachfront dining or elegant fine dining across two restaurants. Kaibo also features watersport rentals and ferry service to Camana Bay for day trips. Pre-stocking the villa with groceries and beverages is also a popular choice by our guests, as is having our team coordinate in-villa dining with a private chef, or family-style cook, for a few nights. Brunch service can also be arranged. SunRays is a three-story villa measuring 7,200 square feet indoors with another 5,000 square feet of outdoor living and entertaining areas. The oceanfront lanai overlooks the pool and white-sandy beachfront with a private dock and putting green. Hone your chipping and putting game amid sunny oceanfront views. The outdoor kitchen and dining area are screened. The pool and spa areas are elevated to offer privacy from any passersby on the beach as well as amazing sunset views at cocktail hour while sitting on the submerged bench seats in the pool or spa (the spa is heated Nov 15 - Apr 15). SunRays offers privacy, luxury amenities, and convenience as well as a quintessential barefoot swimming beach and private dock all with on-island hospitality support. ***Sleeping Arrangements*** (Licensed to sleep 22 Guests; 18 Adults max.) -- Bedroom Suite #1 - lower level, ocean views, king bed, SmartTV, walk-out access to the pool deck, walk-in closet, grand ensuite with double vanity, walk-in tiled shower, soaking tub, and walk-out stone-walled outdoor shower. -- Bedroom Suite #2 - lower-level, island views, two queen beds, SmartTV, closet, ensuite with single vanity, and walk-in shower with shower wand and rainfall shower head; sleeps 4. -- Bedroom Suite #3 - upper-level, elevated ocean views, king bed, walk-out access to a shared balcony, SmartTV, walk-in closet, guest safe, grand ensuite bathroom with double vanity, walk-in tiled shower with rainfall shower head, and soaking tub. -- Bedroom Suite #4 - upper-level, elevated ocean views, king bed, walk-out access to a shared balcony, walk-in closet, SmartTV, grand ensuite bathroom with double vanity, walk-in tiled shower, and soaking tub. -- Bedroom Suite #5 - upper-level, island views, king bed, double closets, SmartTV, ensuite bath with single vanity, and large shower/tub combo. -- Bedroom Suite #6 - upper-level, island views, queen bed, walk-in closet, SmartTV, ensuite bath with single vanity, and shower. -- Bedroom Suite #7 - upper-level, island views, two sets of full-over-full bunks, dresser, closet, SmartTV, beanbag chairs, ensuite bath with single vanity, and tiled shower; ideal for 6 children or 2 adults max. -- Bedroom Suite #8 - loft level via a private staircase, elevated ocean views, king bed, walk-out access to a private balcony, SmartTV, desk with chair, small coffee and beverage station, ensuite with double vanity, and tiled shower. ***INCLUDED SERVICES*** -- Airport greeting, baggage assistance, and group transportation by motorcoach upon arrival and departure (7-night stay required) -- At-villa property manager greeting day of arrival -- Mid-week light housekeeping (7-day stay min), linen-change weekly -- Silver Thatch services for pre-planning and concierge items -- Access to a private fitness center at Silver Thatch (Guests and Owners only) -- On-island manager for any maintenance or equipment operating questions -- In-villa chefs, cooks, servers, masseuses, and yoga instructors are available for private hire. ***IMPORTANT NOTES*** -- 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. -- 12.90% Service Fee added to all rates. -- 3.50% Admin Fee added to all rates. -- A Departure Cleaning Fee is added to all rates. -- Owner requires a $2,500 refundable excess cleaning and damage deposit. -- The refundable deposit will be processed 30 days prior to arrival and released back to the card provided 7 days after departure pending any damages. ==> 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 <=== -- Across the street from the island’s Bioluminescent Bay -- Short walk up the road to Rum Point Club -- 1.1 miles south to the Kaibo Beach Bar & Grill -- 1.6 miles south to Starfish Point -- 4.4 miles to the nearest general store, Chisholm’s Grocery -- 6.2 miles east to Over the Edge restaurant -- 9 miles from Grand Cayman Villas & Condos Welcome Center -- 12.6 miles to the nearest supermarket, Foster’s Market -- 26 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, 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! ==> 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.

Silver Reef 1 Luxury 2BR Beachfront Retreat with Pool

Old Man Bay, North Side, KY
2 Bedrooms 4 Guests
Aug 24 - 26
$190 night

Welcome to Silver Reef #1, a tranquil ground-floor end unit on Grand Cayman’s North Side. This newly built 2BR/2BA beachfront condo blends modern comfort with soothing ocean views, ideal for guests seeking relaxation, privacy, and a stylish base to explore the island. Within the gated Silver Reef Residences, this corner unit offers abundant natural light, added privacy, easy access to on-site amenities, and a private patio to enjoy sea breezes. Book your stay and experience true North Side calm. Welcome to Silver Reef #1, a peaceful ground-floor end unit tucked along the quiet, natural coastline of Grand Cayman’s North Side. From the moment you arrive, the calm of the sea and the ease of the space invite you to slow down and settle into island life. This newly built two-bedroom, two-bathroom beachfront retreat blends contemporary design with the soothing rhythm of the ocean, ideal for travelers seeking tranquility, open views, and a luxurious home base for exploring Grand Cayman. As part of the intimate, gated Silver Reef Residences, this corner unit offers added privacy, beautiful natural light, and seamless access to the community’s amenities. Inside, the condo unfolds into an airy, open-plan layout crafted for effortless island living. The fully equipped kitchen features European-style cabinetry, quartz countertops, and modern stainless-steel appliances, giving you everything you need to prepare a simple breakfast or a full dinner after a day on the water. The living area flows naturally toward the private patio, where ocean breezes and the sound of the shoreline create the perfect backdrop for coffee at sunrise or a glass of wine at dusk. The bedrooms are designed with relaxation in mind. The primary suite offers a king bed, ample storage, and a spa-inspired en-suite bathroom. The guest bedroom features a queen bed with its own full bathroom just steps away. Plush linens, soft towels, and thoughtful essentials make settling in effortless. As a ground-floor end unit, Silver Reef #1 offers a quieter, more private outdoor experience. Guests can enjoy direct access to the complex’s heated 40’ saltwater pool, complete with a spacious sundeck and shaded cabanas. A short walk brings you to the peaceful, uncrowded coastline of the North Side, perfect for sunbathing, strolling, or simply listening to the waves. The secure gated community and on-site parking add convenience and peace of mind. To help you get settled, we provide a generous starter pack of essentials including dish soap or dishwasher tabs, salt, pepper, and coffee filters. Bathrooms include shampoo, conditioner, hand soap, toilet paper, and fresh towels. Laundry detergent, a blow dryer, an iron and ironing board, high-speed Wi-Fi, cable TV, and beach towels are also provided for your convenience. The entire condo, pool, beach and grounds. To fully embrace the serene ambiance of the North Side, we recommend renting a car for convenient transportation, as public options may be limited. With George Town approximately 50 minutes away, having a car will grant you the freedom to explore the area’s hidden treasures and embrace the picturesque beauty at your own leisurely pace. To help you enjoy the beautiful ocean right in front of the property, we suggest bringing water shoes for easier and more comfortable entry. There is no cable but guests may log in to their own streaming accounts (Netflix etc.) to watch TV. If the booking website does not collect it directly, a refundable security deposit of US$500 will be collected by the property prior to your stay. We reserve the right to substitute equal or better accommodation in the event of a double booking or if the rental is unavailable for any reason, including but not limited to sale or repair.

Rum Point Resort Penthouse #501

Rum Point, KY
4 Bedrooms 10 Guests
Aug 25 - 28
$1,083 night

*** PROPERTY DESCRIPTION *** 5th Floor Corner Penthouse | 3,800 sq. ft. All Rum Point Resort condos feature sleek finishes, designer decor, and an open-concept layout maximizing space, natural light, and elevated ocean views. All the comforts of home are included in this 4-bedroom corner penthouse condo, totaling 3,800 sq. ft., including gourmet kitchen appliances, quartz countertops, SmartTVs throughout, and a sprawling open-air balcony. All condos strike the perfect harmony 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 both primary suites will leave you breathless. Vaulted ceilings and crisp coastal decor throughout accentuate the views. The living area includes a plush sectional sofa, a large SmartTV, a tray ceiling with a ceiling fan, and coastal decor. Walk out from the living area onto the private open-air balcony overlooking the resort’s pool deck and beachfront. The balcony stretches the full width of the home, providing ample outdoor living space. Furnished with an alfresco dining table, outdoor lounge seating, and sun loungers, you will love the sky-high panoramic views. The balcony is also equipped with a retractable sunshade above an aluminum pergola, providing relief from the island sun. The gourmet kitchen comes equipped with a suite of Thermador appliances, plus countertop appliances and a kitchen island with breakfast bar seating. Cookware, dishware, glassware, and cutlery are also provided. The outdoor dining table seats 8 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 10 guests, 8 adults max.) -- Primary Suite #1: king bed, ocean views, walk-out access to the open-air balcony, SmartTV, walk-in closet, ensuite with soaking tub, and shower. -- Primary Suite #2: king bed, ocean views, walk-out access to the open-air balcony, SmartTV, walk-in closet, ensuite with shower bath. -- Guest Suite: king bed, SmartTV, ensuite with shower. -- Guest Suite #2: queen bed, SmartTV, ensuite with shower. -- Additional bedding: sleeper sofa suitable for 2 children; crib or pack-n-play provided upon request. 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! 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, 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 #404

Rum Point, KY
2 Bedrooms 6 Guests
Aug 21 - 24
$740 night

*** PROPERTY DESCRIPTION *** ***Fourth Floor Condo | 2,087 sq. ft.*** Welcome to Rum Point Resort #404! 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-bedroom condo, totaling 2,087 sq. ft., including gourmet kitchen appliances, quartz countertops, SmartTVs throughout, 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. 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 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. An outdoor dining table with seating for 4 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 6 guests; 4 adults max.) -- Primary Suite: king bed, ocean views, walk-out access to a private roofed balcony, SmartTV, walk-in closet, ensuite with oversized soaking tub, and shower. -- Guest Suite: queen bed, SmartTV, ensuite with shower. -- Additional bedding: sleeper sofa in the living room suitable for 2 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 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 #105

Rum Point, KY
2 Bedrooms 6 Guests
Aug 22 - 25
$554 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 North Side by Amenities & Features

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Vacation Rentals Near North Side

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