Vacation rentals in Jamaica with a pool

Explore 23 vacation rentals, homes, and villas with pools in Jamaica for your next getaway or business trip. Step outside to your own private or shared pool and into a home filled with premium amenities such as Air Condition Homes, Homes with Free Parking and Best Affordable Homes. Throughout your stay, unwind poolside, soak up the sun, and enjoy an outdoor space designed for relaxation. With options starting as low as $91 per night and homes offering up to bedrooms and bathrooms, it's easy to book a comfortable, personalized stay. You'll also have access to high-speed Wi-Fi and 24/7 local support, creating a more secure, connected atmosphere for your trip. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, so each trip's more rewarding than the last. Book your next poolside escape with Homes & Villas by Marriott.

23 Homes with Pools in Jamaica

Luxury 5BR Oceanfront Villa in Ocho Rios

Plantation Village, St. Ann Parish, JM
5 Bedrooms 10 Guests
Aug 18 - 21
$2,025 night

Brown Shuggah is a refined five-bedroom oceanfront villa on Jamaica’s North Coast, ideally positioned between Ocho Rios and Runaway Bay. Set on 7,500 square feet of private waterfront grounds, the villa blends Caribbean charm with elegant comfort, featuring a heated infinity-edge pool, tropical gardens, expansive outdoor living areas, and a private beach cove for a stay that feels both secluded and experience-rich. Brown Shuggah is designed for easy indoor-outdoor living, with large glass folding doors, a spacious covered verandah, and inviting interiors that open beautifully to the sea. Surrounded by tropical gardens and perched above the coastline, the villa offers a setting that feels private, breezy, and deeply relaxing from the moment you arrive. The villa includes five bedrooms and five bathrooms, accommodating up to ten guests. Bedroom layouts include a mix of king, queen, and two-queen arrangements, with sea views featured in several rooms. The home also offers thoughtful comforts such as air conditioning in the bedrooms, Wi-Fi, a heated pool, outdoor dining, a dedicated workspace, gym equipment, and beach access. Beyond the main living spaces, Brown Shuggah offers a private beach set within a naturally protected cove, ideal for calm-water swimming, along with dramatic nearby coastal scenery around Chukka Cove and Chukka Bay. For slower moments at home, guests can unwind beside the heated pool, gather on the verandah, or enjoy relaxed al fresco meals with sea views. Guests enjoy exclusive access to the villa and its private grounds, including the indoor living areas, covered verandah, heated infinity-edge pool, tropical gardens, and beach access. The setting offers privacy and a strong sense of escape while still being close to the North Coast’s resort towns and attractions. Your stay is supported by a dedicated on-site team that includes a butler, private chef, housekeeping, laundry service, and gardener, allowing for a seamless villa experience throughout your time at Brown Shuggah. Grocery planning and ordering support is also available through the chef, with groceries delivered and paid for at the house for added ease. Whether you want the freedom of a rental car or prefer to arrive in comfort with a private driver, our team is happy to assist with car rentals and driver arrangements. Airport transfers and personalized transportation can be easily coordinated through our team and our guest app, Privé by CVE, ensuring thoughtful support is always within reach as your plans take shape. Brown Shuggah includes a dedicated on-site team to support your stay, ensuring comfort, privacy, and a seamless experience throughout. Please note that certain features, amenities, natural conditions, and access to nearby beaches and coastal areas may be subject to availability, seasonal changes, and local conditions. Staff gratuity is customary and should be prepared in cash at the villa. One listing source specifies a recommended gratuity of 15% of the gross rental rate to be divided among staff members. Grocery costs are additional and are not included in the villa rate. Beyond just a stay, Brown Shuggah offers a warm yet elevated Caribbean escape where ocean views, personalized service, and relaxed coastal living come together beautifully.

Luxury Villa Discovery Bay: Luxurious Resort Experience

Discovery Bay, St. Ann Parish, JM
5 Bedrooms 10 Guests
Aug 18 - 21
$2,000 night

An Ultra-Luxurious Resort Style Villa: Get Ready To Be Wowed! Fully Staffed - Butler, Private Chef, Daily Housekeepers, Concierge! Amazing Ocean Views - World Class Customer Service!!! We also offer a state of the art recording studio for those in the music business and are looking for a working vacation. The Mimosa is a fragrant tropical plant, a favorite cocktail, and your welcome drink when you arrive at the ultra- luxurious Villa in Discovery Bay, Jamaica. Take your first refreshing sips in paradise as you explore this majestic retreat for 10 guests, comprising over 20,000 square feet of private vacation bliss. Pause to take in the panoramic views of the Caribbean Sea from nearly every suite. Dip a toe in the private infinity pool with waterfall spa—both facing that soul-expanding view of the sea. Gather for a satisfying feast: whether an intimate dinner with family or a fully catered special event. The resort elegance begins when you cross the stair bridge over a vibrant koi pond and approach the ten-foot double doors that open into an expansive foyer. Look up: an enchanting mural of the galaxy—a work of art titled "On Earth as it is in Heaven"—sparkles on the ceiling above the foyer’s staircase. The knowledgeable staff will spoil you! Throughout the home, you will find a unique blend of antique furniture, primarily from Jamaica and accentuated with pieces from Italy and France. These more traditional selections are offset by modern, clean lines and top-of-the-line appliances and features. Interior spaces are flooded with sunlight from the sky-high windows. To ensure the windows and sea views take center stage, much of the home’s artwork can be found on its ceilings! Families with older kids and teens will especially appreciate the Villa’s forthcoming gaming center—called "The Vent" opening September 2023 with its XBOX, PS4, retro arcade machines like Pac-Man, flight and drive simulators, projectors and TVs on the walls, a pool table, other table games, and comfy seating for those who prefer to sit back and watch! This beautiful Villa features 5 bedrooms and 5 en-suite bathrooms plus 3 half bathrooms in the main house. Suite Dreams: · Main master bedroom suite (only offered with 5 bedroom rental). · King bed · Large master bath with separate rain shower, Whirlpool tub, dual sinks · Large front and side balconies with views of the ocean, pool and mountain · Extra-large two-story lofted closet with dressing room and make-up area · Vaulted ceilings in bedroom, bathroom and closet · In-room speaker with individual control · In-room safe · Wet bar in bathroom o Mini fridge · Sitting area with loveseat and coffee table · Flatscreen TV · A/C Airy Suite: · Mini-master ocean view bedroom · King bed · Fabulous balcony with a direct ocean and pool view · En-suite bathroom with separate rain shower and Whirlpool tub · Walk-in closet and dressing room · Sitting area with loveseat and coffee table · In-room safe · Flat-screen TV · A/C Sidorma: · Direct ocean and pool view · Queen bed · En-suite bathroom with rain shower · Vaulted ceiling · Walk-in closet · In-room safe · Flatscreen TV · A/C The Garnett: · Ocean and garden view · King bed · Ocean and mountain-view balcony · En-suite bathroom with rain shower · Sitting area with loveseat and coffee table Dabrielle: · Garden-view bedroom · Two full-size beds · En-suite bathroom with rain shower · Balcony · In-room safe · Flatscreen TV · A/C Outdoor Features: Panoramic ocean views • 35 x 16 Infinity swimming pool with bar stools - Beach Access - Puerto Seco Beach • Hot Tub (heated upon request) • Ocean, mountain and garden views • Large pool terrace • Spa cabana • Cool Breeze Outdoor Bar and Grill with sitting area adjacent the pool • Entertainment Deck & Pool Cabana o Male/Female powder rooms on the pool deck o Outdoor shower on the pool deck o Television • Koi pond • Sun loungers • Half basketball court • Balconies • Alfresco dining • Badminton • Complementary Puerto Seco Beach Club access included Staff & Services: • Some members of staff live on site in staff apartments • Butler or House Manager • Concierge (welcomes you then works remotely except for weddings and events) • Private chef (food & beverage is provided by guests, we will help you to pre-stock) • Wait Staff • Housekeeper • Laundress • Security (6:00 PM to 6 AM) • Houseman • Gardener The attentive staff will welcome you home. You will also be given a temporary door code for your stay. Villa Pre-Stocking - We offer optional villa pre-stocking services so you can start your vacation the moment you arrive • Grocery Delivery Service - The local super market will deliver groceries directly to the villa; you pay cash or with your credit card on delivery • Hair Salon – please note the Villa will be equipped with an in-home hair salon as of December 2023, please request services in advance • Spa Services – Available by appointment only. We are happy to schedule your spa services after your reservation is secured and prior to your arrival. • Tours – Your concierge will be happy to assist you plan your vacation activities and book local tours • Transportation – Airport transfer • Nanny – Prior notification required • Wellness Activities – Prior notification required . Recording Studio - State of art recording studio with engineer We also have our stunning yacht. It is now available for excursions from the Montego Bay Yacht Club. Ours is a fully staffed villa, it comes with chefs, butlers and housekeepers who cater to you every day. In Jamaica and in villas in general, tipping 15% to the staff is customary.

Orchids & Palms Luxury Villa Pool, Chef, Hot Tub, Airport Pickup!

Montego Bay, St. James Parish, JM
6 Bedrooms 14 Guests
Aug 17 - 20
$1,093 night

Rated 5 stars by 100+ guests for cleanliness, location, and hospitality! Discover a five-star villa experience where every detail is designed with your comfort and celebration in mind. Perfect for birthdays, anniversaries, or relaxing group getaways, this luxury villa offers daily included chef-prepared breakfast. We have an on site driver and airport transfers can be arranged, excursions, and more! Orchids & Palms Villa offers the perfect mix of luxury, privacy, and authentic Jamaican hospitality, just 10 minutes from the Montego Bay airport. Your Stay Includes: • Daily Chef-Prepared Breakfast Enjoy freshly made breakfast daily from our talented on-site chef. No cooking or groceries needed our à la carte restaurant-style menu is available for lunch and dinner, with pricing starting at $15USD and up per meal. • Hot Tub Access Included Daily Relax in the heated jacuzzi with 2 complimentary hours per day. Want more time? Additional use is $50 USD per hour or $120 USD for 3 hours. On-Site Services for Ultimate Relaxation • Chef (included for breakfast, available for additional meals) • Villa Attendants to ensure your stay is effortless and relaxing • Driver & vehicle (airport transfers/trips/excursions at the best rates) • Massage therapy & yacht rentals available upon request Spacious Comfort for Families & Groups The villa offers 5 spacious bedrooms, each with: • En-suite bathroom • Air conditioning • Smart TV • Mini refrigerator & safety box Bedroom Configuration: • 3 bedrooms with king beds (Bedroom 3, 5 & 6) • 1 bedroom with a queen + single bed (Bedroom 1) • 1 bedroom with 2 double beds (Bedroom 4) Optional Suite Upgrade: Upgrade to our premium Master Suite (Bedroom 2 in photos) for a nominal fee. This luxurious space features a private balcony, soaking tub, and personal bar area perfect for honeymoons or special occasions. (Added after booking confirmation.) ⸻ Premium Amenities: • Private Pool with Waterfall Feature • Heated Jacuzzi (included 2 hrs daily) • Fully Equipped Kitchen • Indoor & Outdoor Dining Spaces • Two Family Lounge Areas • High-Speed Wi-Fi Throughout • Private Gym • Tropical Gardens & Relaxation Areas ⸻ Dining Your Way: Enjoy the flexibility of restaurant-style dining without leaving the villa. All meals are freshly prepared to order. Our à la carte menu is shared 3 weeks before arrival and includes local favorites and international dishes. No grocery shopping needed! • Breakfast – Included • Lunch & Dinner – Optional, à la carte ($15+ per meal) • Special Buffet Packages Option – Pre-booked, 1 week in advance Message us anytime we’re happy to help plan your dream Jamaica getaway! Guests have exclusive access to the entire villa, pool, hot tub, gym, gardens, and lounge areas. Private chef and driver are on-site for your convenience. Stress-free arrival: We provide hassle-free airport transfers with our own transportation, getting you to your vacation quickly. Let us take care of your transportation needs with our convenient on-site vehicle. Please note additional guest fee applies for over 4 guests. Select correct number of guests to see the total License number: 251506

Santosha - 10BR Luxury Villa, Fully Staffed

Whitehouse, JM
10 Bedrooms 20 Guests
Aug 16 - 19
$2,150 night

Imagine yourself surrounded by stunning oceanfront property, with your own private white-sand beach and secluded swimming cove. Your stay includes the dedicated service of a private chef, attentive butlers, and discreet housekeepers, ensuring every detail of your vacation is cared for with effortless luxury. This undiscovered paradise is where Jamaica’s true charm comes to life, away from the crowds. Immerse yourself in the pristine turquoise waters of the Caribbean, perfect for swimming, snorkeling, paddleboarding, and kayaking right from the villa’s shores. An exquisite 12,000-square-foot luxury villa nestled along the breathtaking South Coast of Jamaica. This modern, architecturally designed retreat offers the perfect blend of sophistication, tranquility, and natural beauty, making it your ultimate island escape. Whether you’re basking in the golden sun, exploring the coastline, or unwinding with a sunset cocktail, every moment here is pure bliss. The villa’s ideal location in the West Bay development of Whitehouse, just minutes from the world-renowned Sandals Whitehouse resort, makes it the perfect destination for those seeking serenity, adventure, or a bit of both. Getting to Santosha Jamaica is effortless and scenic, with a drive through lush mountains and along Jamaica’s captivating coastline. Donald Sangster International Airport offers multiple daily flights from around the world, ensuring your arrival is smooth and stress-free. From its stunning natural beauty to its luxurious comfort and exclusivity, Santosha Jamaica is more than a villa – it’s an unforgettable experience. Whether you’re seeking relaxation, adventure, or a mix of both, this is the place where cherished memories are made. Host Your Special Event Santosha Jamaica also offers the perfect setting for your special event. With prior approval from the owner, events are permitted at the villa, subject to a separate event fee. Our event policy includes: - Event fees range from $750 to $2,500, depending on the number of guests - Additional kitchen usage fee of $500 for caterers - Event timing restrictions, with a 15% service charge applied to all event fees *Please Note the below Important Booking Information:* A mandatory Security Damage Fee of USD $65 will be applied to all bookings, covering damages up to USD $3000 during your stay. Some properties may also require an additional refundable damage deposit, which will be held against your form of payment.

Forever Summer | Gorgeous 4BDR Villa w/ Pool - Panoramic Views

Runaway Bay, JM
4 Bedrooms 12 Guests
Aug 16 - 19
$864 night

Occupancy # 12 Guests (Adults & kids) *Kindly note: The standard rate includes up to 8 guests. For groups larger than 8, an additional fee of $80 per guest per night will apply. This ensures the property is adequately prepared to accommodate all guests comfortably. Discover the true beauty of Jamaica at Forever Summer Villa, a gorgeous 4-bedroom, fully private villa. Relax by the private pool or take in the stunning scenery from the patio with pool views. Escape to your own private paradise at Forever Summer Villa in the serene, upscale community of Cardiff Hall, just above Runaway Bay. With 4 spacious ensuite bedrooms, a private pool, and all the amenities you need, this villa is the ultimate getaway for relaxation or adventure in a tropical Jamaican paradise. The tranquil atmosphere, beautiful gardens, and stunning pool views are a perfect backdrop for unforgettable family memories and quality time with friends. Bask in the warm Caribbean sun, sip a refreshing drink by the sparkling blue pool, and savour delicious meals prepared just for you, as you enjoy views of the Caribbean Sea, golf course and tropical greenery. This will quickly become your favourite spot - and our warm, friendly and professional villa team will ensure you’re pampered throughout your stay! This air-conditioned villa boasts a vast pool deck with lounge chairs and outdoor dining table, private pool, well-stocked outdoor bar, lush gardens and an on-site tennis court. With free WiFi, you can also stay connected while enjoying your stay. Your family or group will enjoy four spacious bedrooms, each with their own private bathroom, comfortable bed linens, and fresh towels. Unwind in the comfortable living room, watch your favorite shows on the flat-screen TV with cable channels in the living room. Each bedroom also features a TV for your relaxation. Enjoy a meal in the dining area, prepared to your preferences by your private chef. The fully equipped kitchen also offers everything else you may need during your vacation; although please note; no cooking is allowed by guests, since the villa team handles that for you! With the vibrant resort town of Ocho Rios just a stone’s throw away, you’ll have endless opportunities to explore, shop, dine, and make unforgettable memories. Forever Summer Villa is also within easy reach of many attractions on Jamaica’s North Coast. Free private parking is available on site. Other important details: - On-site tennis court - Smiley’s outdoor bar on pool deck - Outdoor dining table with umbrella - Sun loungers / shady and sun areas The closest international airport is Sangster International Airport in Montego Bay, about an hour’s drive. We will recommend a transport provider who can help you with all your transportation needs. Book your getaway today! **NOTE** - Fully Staffed Private Villa Services Included/Excluded | Rental includes: utilities, internet, cable, and Villa Team Services. Private Chef service and housekeeping are mandatory and included. Not included are groceries for included meal preparation; tours or transportation; any personal services outside of the Villa Team Services, and staff gratuities. External services are to be paid directly to providers. Most groceries can be covered by credit card, however, cash may be required for some fresh produce or specialty items. The villa owner recommends purchasing alcoholic beverages duty-free, but they can also be purchased for you if you prefer. Please plan on paying a gratuity to the staff in cash (USD or JMD) at the end of your stay; 15% of the total rental price is recommended, customary, and expected, if service is to your satisfaction. Estimated budget for 3 meals per day - breakfast, lunch, dinner, dessert and non-alcoholic beverages is US$80 - $100 per day. The Villa Team will work with you to plan meals in advance and looks forward to pampering you during your stay! ​​​​​​​*The Villa has expansive outdoor space which can also accommodate special events/celebrations or weddings. Separate fees and policies apply to events and these must be pre authorized by the villa owner. All Special Event arrangements are coordinated directly with the Owner/Villa Team. Feel free to inquire and we can send you this information separately. Book your getaway today!

Afimi Beach 4BDR Villa | Impressive Montego Bay Ocean View

Montego Bay, JM
4 Bedrooms 8 Guests
Aug 14 - 17
$1,157 night

Occupancy # 10 Guests (Adults & kids) AFIMI Beach House is a beachfront villa in the Lagoons, an upscale gated community in Freeport. This spectacular villa with its own private white sand beach and infinity edge swimming pool is only a 10-minute drive from the Airport. The community sits on a thin peninsula surrounded by the ocean on both sides and has 24-hour security, two tennis courts with a tennis pro, a large main pool, and a gym. The villa itself has four large bedrooms, each with ocean views and en-suite bathrooms. Three of the bedrooms are upstairs, while the fourth is downstairs. All upstairs bedrooms have Teak hardwood floors with split air-conditioning and 50" HD LCD televisions. The villa is beautifully decorated with a mix of elegant new pieces, authentic Jamaican antiques, and original artwork. All bathrooms, which are finished in natural stone, marble, or granite, have walk-in showers. Relax in the large master suite, complete with a luxurious marble tiled bathroom with an eight-foot-wide shower enclosure with a skylight and spa-like soaking tub while watching your favorite movie on a wall-mounted flat-screen television. This suite opens unto a spacious upstairs patio where one can enjoy the breathtaking sunrise in the morning or have afternoon tea while viewing the birds of the Marine Park’s lagoon with city lights as a backdrop. Dine as a group at different locations at the villa, on the balcony, in the gardens, or experience the romantic Beach Grill night, where we grill your favorite meal right on our beach while you dine by candlelight surrounded by tiki torches. AFIMI is a free-standing villa, complete with an air-conditioned TV/family room with BOSE surround sound and 65" SmartTV. It also has a restaurant-equipped kitchen that produces exceptional meals. The villa rental includes a full complement of staff, your personal butler, a full-time chef, housekeepers, and a gardener to attend to all your needs. Relax in your own private beach cabana or have a drink by the pool or at our outdoor tiki bar. Other amenities for your exclusive use include a Hobie Cat sailboat, Kayaks, paddle boards, snorkeling equipment, a computer with printer, a tablet to control WIFI, internet radio, home automation, and built-in Sonos whole-house stereo, and an automatic standby generator. Our villa subscribes to the green initiative and is equipped with a solar photovoltaic system. There is playing cards, darts, ping pong, dominoes, and board games for your entertainment. You should visit the world-famous Doctor’s Cave Beach or Harmony Beach on the ’Hip Strip’. While there, enjoy several restaurants and bars, including Margaritaville and the Bobsled Cafe. Only a two-minute drive from the villa in one direction is the charming Houseboat restaurant and the Yacht Club in the other direction. AFIMI is also within minutes from 3 major golf courses at Tryall, Cinnamon Hill, and White Witch.

Contemporary 6BR Villa | Sea Views, Infinity Pool & Resort Access

Montego Bay, St. James Parish, JM
6 Bedrooms 12 Guests
Aug 16 - 20
$2,927 night

BougainVilla is a contemporary six-bedroom villa perched in the gated Spring Farm community of Montego Bay, Jamaica. With panoramic Caribbean sea views from every angle, striking modern design, and generous indoor-outdoor living spaces, this villa is ideal for families and groups seeking both comfort and style. Staffed with a full professional team and offering thoughtful amenities and resort benefits, BougainVilla provides a relaxed Caribbean escape just minutes from beaches, golf, and local culture. BougainVilla’s design celebrates light, space, and seamless flow. Floor-to-ceiling windows and open living areas welcome sea breezes throughout the villa, while sun-soaked terraces and outdoor seating areas create inviting spots for morning coffee, sunset cocktails, and alfresco meals. The villa features six well-appointed bedrooms, each with ensuite bathrooms, comfortably accommodating up to 10 guests. Neutral modern interiors and carefully chosen furnishings create a sense of calm and understated elegance. Several bedrooms open directly to terraces or balconies with garden and ocean views, reinforcing the indoor-outdoor connection. The extra-large terrace across the front of the villa includes multiple seating areas, a night-lit bar, and outdoor dining spaces that are perfect for shared meals and sunset evenings. Throughout the property, landscaped garden spaces and bougainvillea blooms add color and serenity. Guests enjoy exclusive access to BougainVilla and its private grounds, including indoor living areas, outdoor terraces, infinity edge heated swimming pool, wellness spaces, and garden seating areas with fire pit and outdoor entertaining zones. As part of your stay, guests also enjoy complimentary resort membership benefits at the Half Moon Resort, subject to availability and resort policies. Included access features Eclipse Beach, Jacuzzi, tennis courts, fitness center, croquet lawn, and a miniature putting green. The Half Moon membership includes unlimited complimentary green fees at the Half Moon Golf Course plus practice facilities, with 25 percent discounts on optional cart rentals, instructional services, and pro shop purchases. Members also receive access to additional resort amenities. Additional services, such as spa treatments, watersports, dining, and tennis instruction, may be arranged through the resort for a fee and are subject to availability. Please note that access to resort facilities and services is governed by resort policies and availability. On occasion, facilities or guest services may be unavailable due to private events. Half Moon Resort reserves the right to modify or update its membership benefits without prior notice. Whether you prefer the freedom of a rental car or the comfort of a private driver, our team is happy to assist with arranging car rentals and driver services. Airport transfers and tailored transportation can be easily coordinated through our team and our guest app, Privé by CVE, ensuring thoughtful support is always available as your plans take shape. Please note that complimentary driver service with a 12 or 14-seater van is included on seven-night reservations, with fuel and gratuities at the guest’s expense. BougainVilla includes a dedicated on-site team to support your stay, ensuring comfort, privacy, and a seamless experience throughout. Please note that certain features, amenities, natural conditions, and access to nearby resort amenities and beach facilities may be subject to availability, seasonal changes, and local policies. Gratuity for the villa staff is customary and appreciated. Recommended staff gratuity at the end of your stay is 10 percent of the villa rental rate during High Season and 15 percent during Low Season, divided among staff members in accordance with the Gratuity Guide in your villa’s Welcome Book. It is considered standard in the villa industry to observe these guidelines. Gratuities and grocery funds are best prepared in cash, in US dollars. Tips are typically given on the day of departure or may be prepaid at the time of booking. A handwritten thank-you note is a thoughtful personal touch and is always warmly received by the villa team. Beyond just a stay, BougainVilla offers a relaxed Caribbean escape where every detail is designed for comfort, beauty, and unforgettable moments.

Luxury 6BR Villa With Sea Views & Private Pool

Hopewell, Hanover Parish, JM
6 Bedrooms 16 Guests
Aug 14 - 17
$2,171 night

Bambu is an elegant, fully staffed hillside villa overlooking perhaps the most glorious view of sea and sky on Jamaica’s renowned North Coast. Elegantly perched atop eight and a half acres, this expansive private estate features six well-appointed bedrooms in the main villa, along with a separate hillside cottage offering two additional bedrooms with a shared bathroom. Designed for relaxed gatherings and meaningful moments, Bambu blends refined comfort with natural beauty in a setting that feels elevated in every sense. Set high above the coastline, Bambu is thoughtfully designed to embrace its extraordinary surroundings. Open, airy interiors flow seamlessly to expansive terraces and outdoor living areas, framing uninterrupted views of the Caribbean Sea and the ever-changing sky. The main villa features six well-appointed bedrooms, each designed for comfort, privacy, and understated luxury. A separate hillside cottage provides two additional bedrooms with a shared bathroom, offering an ideal option for extended family members, guests seeking added privacy, or staff accommodations. Generous social spaces invite gathering and relaxation, from elegant indoor lounges to outdoor terraces perfect for sunset cocktails, quiet mornings, and evenings under the stars. Lush gardens and curated design details enhance the calm, resort-like atmosphere while preserving the intimacy of a private estate. Guests enjoy exclusive access to the main villa and its grounds, including indoor living areas, outdoor terraces, gardens, pool, and gym. Bambu is a private retreat designed solely for your group’s enjoyment. The separate hillside cottage is available for use at an additional fee and is not included in the base villa rate unless specifically reserved. Guests may also have the option to enjoy select Tryall Club amenities through temporary membership, subject to club policies and availability. Whether you want the freedom of a rental car or prefer to arrive in comfort with a private driver, our team is happy to assist with car rentals and driver arrangements. Airport transfers and personalized transportation can be easily coordinated through our team and our guest app, Privé by CVE, ensuring thoughtful support is always within reach as your plans take shape. Bambu includes a dedicated on-site team to support your stay, ensuring comfort, privacy, and a seamless experience throughout. Please note that certain features, amenities, natural conditions, and access to nearby resort amenities and beach facilities may be subject to availability, seasonal changes, and local policies. Guests who wish to enjoy Tryall Club amenities during their stay may do so through optional temporary membership. These fees are separate from the villa rate and only apply to guests who choose to access the club. Temporary membership may include access to select Tryall Club amenities such as the Tryall Beach Club with beach access and a beachfront infinity pool, non-motorized watersports, tennis courts, fitness center, jogging trails, Hummingbird Kids Club, Great House afternoon tea, the Manager’s Cocktail Party, select special events, and the Usain Bolt Games Room, subject to current club policies and availability. Current temporary membership fees are US$45 per person, per day for guests aged 16 and over, US$25 per person, per day for guests aged 13 to 15, and complimentary for children 12 and under. Temporary membership fees are subject to change without prior notice and are governed by current Tryall Club policies. Gratuity for the villa staff is customary and greatly appreciated. Recommended staff gratuity at the end of your stay is 10% of the villa rental rate during High Season and 15% during Low Season, divided among staff members in accordance with the Gratuity Guide provided in your villa’s Welcome Book. It is standard within the villa industry to observe these guidelines. Gratuities and grocery funds are best prepared in cash, in US dollars. Tips are typically given on the day of departure or may be prepaid at the time of booking. A handwritten thank-you note is a thoughtful personal touch and is always warmly received by the villa team. Beyond just a stay, Bambu offers a refined Caribbean escape where every detail is designed for comfort, beauty, and unforgettable moments.

Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

Tower Isle, St. Mary Parish, JM
6 Bedrooms 12 Guests
Aug 14 - 17
$2,478 night

Breathtaking Oceanfront Luxury Villa – | Home Theatre | Event Ready Welcome to your private cliffside paradise – a luxury 6-bedroom oceanfront villa perched majestically above the Caribbean Sea in Tower Isle, Jamaica. Designed for the discerning traveler, this fully staffed villa offers an unmatched blend of seclusion, sophistication, and service. ✨ Why You’ll Love It - At the right time you might spot dolphins! - Home movie theatre - Destination weddings, birthday, private retreats Whether you’re sipping cocktails by the pool, enjoying a candlelit dinner prepared by your private chef, or hosting a memorable celebration, this villa delivers an unforgettable Caribbean experience. Privacy Meets Paradise Tucked away in a secure, tranquil enclave, the villa offers total privacy while being just minutes from local attractions. It’s the ultimate sanctuary for couples, families, or groups seeking luxury, comfort, and stunning natural beauty. Perfect For: Destination weddings & intimate events Family vacations or friends’ getaways Luxury retreats in a serene, scenic setting ****************************** ️ Bedrooms & Bathrooms (5) ✔︎ Bedrooms are elegant sanctuaries featuring cozy bedding and ample storage. ✔︎ Sleek ensuite bathrooms ~ Enjoy your private space ✔︎ Air Conditioned, featuringTVs Bonus Bedroom (1) ✔︎ Two Queen beds without an ensuite bathroom, great for extra space for visiting family/friends or children. Living/Dining Space Central Air-Condition to keep your temperature regulated throughout your stay, Open concept with 12+ seater dining room table. Movie Theatre Inviting Patio Space: ✔︎ Enjoy your morning coffee or an evening cocktail on your bedroom private patio or covered pool deck as you watch the sun go down. It’s the perfect spot for alfresco dining or simply soaking in the serene surroundings. POOL & JACUZZI ACCESS ️ Pool Access~ 24hr access Jacuzzi - 4pm - 9pm daily Gourmet Service Kitchen: ✔︎ Enjoy the best meals prepared by our Chef ALL DAY LONG using only high-end appliances ✔︎ Dishwasher ✔︎ Blender, Toaster, ✔︎ Coffee Maker ✔︎ Microwave oven ✔︎ Wall mounted Oven ✔︎ Cook top and extractor ✔︎ Double door refrigerator ✔︎ Wine & Champagne Glass etc BEACHES ✔︎ Enjoy great local beaches at every corner - Swim in crystal-clear waters, or savor beachside dining – all just a short drive away ✔︎ Sugar Pot Beach 4 mins drive ✔︎ Mahogany Beach 10 mins drive ✔︎ Ocho Rios Bay Beach 12 mins drive ✔︎ Rio Nuevo Beach 6 mins drive Just to name a few Book Your Escape Today! Your island paradise awaits! GUEST ACCESS Property is exclusively for the the guests staying OTHER DETAILS TO NOTE Important 1. There are 5 bedrooms with ensuite bathrooms 2. We have a 6th bonus bedroom without an ensuite 3. While Chef services are included you are required to cover costs of groceries which we are happy to pre-stock for you. 4. While we allow events and parties please enquire about out event fees and policies Security Deposit of USD1500 to be collected upon arrival.

Luxury Staffed 7BR Villa | Pool, Gym & Sea Views

Montego Bay, St. James Parish, JM
7 Bedrooms 16 Guests
Aug 14 - 18
$2,622 night

Endless Summer is a grand seven-bedroom villa perched hillside in the prestigious Spring Farm area of Montego Bay. Set high above the coastline, this expansive private estate offers sweeping views across the championship Half Moon Golf Course and the Caribbean Sea beyond. Designed for relaxed luxury and effortless entertaining, Endless Summer is ideal for multi-generational families, group getaways, and special celebrations seeking space, privacy, and exceptional service. Endless Summer spans approximately 11,000 square feet and welcomes guests through a dramatic entrance into elegant, light-filled living spaces. Formal and casual lounges flow seamlessly onto deep verandas and outdoor terraces, creating a natural connection between indoor comfort and the surrounding landscape. The villa features seven well-appointed bedrooms, each with an ensuite bathroom, comfortably accommodating up to fourteen guests. Bedrooms are thoughtfully arranged to provide privacy while maintaining easy access to shared living areas, making the home well-suited for both large gatherings and quiet moments of retreat. Outdoor living is a highlight, with a generous pool and terrace overlooking the golf course and sea beyond. Lush gardens, open lawns, and multiple seating areas create inviting spaces for morning coffee, sunset cocktails, and evenings under the stars. Guests enjoy exclusive access to Endless Summer and its grounds, including indoor living areas, wraparound verandas, outdoor terraces, landscaped gardens, and the private pool and hot tub. As part of your stay, guests also enjoy complimentary access to The Shore by CVE, our private white sand beach club experience located on Montego Bay’s vibrant Hip Strip. Guests can relax by the sea, soak up the Caribbean sunshine, and enjoy the on-site restaurant and bar, creating the perfect setting for a laid-back beach day during your stay. Select beach club experiences such as spa services, watersports, private excursions, dining experiences, and other curated island activities may also be arranged at The Shore by CVE, subject to availability and applicable fees. Please note that food and beverages are not permitted to be brought onto the club property, and towel service is not provided for members at the beach. Access to The Shore by CVE is subject to venue policies, special events, weather conditions, and occasional closures. On occasion, facilities and guest services may be unavailable. Amenities, services, and operating hours may be modified without prior notice. Half Moon Beach Club * Half Moon Day Pass for Resort Amenities Day Pass - Relax for the day at Half Moon for US$125 per person, including tax and service charge (US$100.00 + 25% tax), which includes a $50 credit toward food and beverages. | Children ages 4–12: $62.50 per child, which includes a $25 credit toward food and beverages. Includes access to Sunrise Beach with a shower/bathroom area Includes access to the Fitness Center Includes a US$50 food & beverage credit redeemable at North Pointe and Spice Hammock Bar Includes use of resort bicycles Applicable from 10 am to 6 pm The names of all persons in the party are required for our security team’s awareness. All persons in the party will be required to visit the front office located at the Eclipse Lobby to open an account for any accumulated charges (such as Food and Beverage purchases) and receive a brief property orientation. Photos ID’s must be presented for everyone Blackout dates: December 23, 2026 - January 03,27 | Other restrictions may apply Whether you want the freedom of a rental car or prefer to arrive in comfort with a private driver, our team is happy to assist with car rentals and driver arrangements. Airport transfers and personalized transportation can be easily coordinated through our team and our guest app, Privé by CVE, ensuring thoughtful support is always within reach as your plans take shape. Endless Summer includes a dedicated on-site team to support your stay, ensuring comfort, privacy, and a seamless experience throughout. Please note that certain features, amenities, natural conditions, and access to nearby resort amenities and beach facilities may be subject to availability, seasonal changes, and local policies. Gratuity for the villa staff is customary and greatly appreciated. Recommended staff gratuity at the end of your stay is 10% of the villa rental rate during High Season and 15% during Low Season, divided among staff members in accordance with the Gratuity Guide provided in your villa’s Welcome Book. It is standard within the villa industry to observe these guidelines. Gratuities and grocery funds are best prepared in cash, in US dollars. Tips are typically given on the day of departure or may be prepaid at the time of booking. A handwritten thank-you note is a thoughtful personal touch and is always warmly received by the villa team. Beyond just a stay, Endless Summer offers a refined Caribbean escape where every detail is designed for comfort, beauty, and unforgettable moments.

Modern 4BR Hillside Villa Pool & Beach Club Access

Montego Bay, St. James Parish, JM
4 Bedrooms 12 Guests
Aug 14 - 18
$1,800 night

The Vacation Haven is a sophisticated four-bedroom villa nestled in the tranquil hills of Rose Hall, Montego Bay, Jamaica. Surrounded by lush greenery and ocean views, this private villa blends open-plan living with vibrant Jamaican design, offering sun-soaked terraces, panoramic views of both sea and mountains, and an inviting pool deck with a bar and grill area. Ideal for families, groups, or celebrations, The Vacation Haven delivers a flexible, tailored Caribbean escape with space for up to 12 guests. Designed around open living and seamless indoor-outdoor flow, The Vacation Haven’s contemporary spaces capture breezes and views at every turn. The spacious living and dining area opens to the outdoors with expansive sea views, creating a relaxed yet vibrant atmosphere for gathering and entertaining. The villa accommodates four very spacious bedrooms, each with its own ensuite bathroom and generous views of the ocean or surrounding mountains. Comfortable layouts and thoughtful furnishings ensure privacy and rest for every guest, while the large pool deck, outdoor bar, grill area, and pool chaises make the exterior just as inviting as the interior. Guests enjoy exclusive access to The Vacation Haven and its grounds, including indoor living spaces, outdoor terraces, gardens, and the private pool with bar and grill area. As part of your stay, guests also enjoy complimentary resort membership benefits at the Rose Hall Beach Club, subject to availability and club policies. This includes access to the beach, pool facilities, and shared amenities at the beachfront club. Additional services and experiences such as watersports, spa treatments, food and beverage offerings, and tennis may be available through the club for a fee and are subject to availability and club terms. Please note that access to beach club amenities and services is governed by club policies and availability. On occasion, facilities and guest services may be unavailable due to private events. The Rose Hall Beach Club reserves the right to modify or update its membership benefits without prior notice. Whether you want the freedom of a rental car or prefer to arrive in comfort with a private driver, our team is happy to assist with car rentals and driver arrangements. Airport transfers and personalized transportation can be easily coordinated through our team and our guest app, Privé by CVE, ensuring thoughtful support is always within reach as your plans take shape. The Vacation Haven includes a dedicated on-site team to support your stay, ensuring comfort, privacy, and a seamless experience throughout. Please note that certain features, amenities, natural conditions, and access to nearby resort amenities and beach facilities may be subject to availability, seasonal changes, and local policies. Gratuity for the villa staff is customary and greatly appreciated. Recommended staff gratuity at the end of your stay is 10% of the villa rental rate during High Season and 15% during Low Season, divided among staff members in accordance with the Gratuity Guide provided in your villa’s Welcome Book. It is standard within the villa industry to observe these guidelines. Gratuities and grocery funds are best prepared in cash, in US dollars. Tips are typically given on the day of departure or may be prepaid at the time of booking. A handwritten thank-you note is a thoughtful personal touch and is always warmly received by the villa team. Beyond just a stay, The Vacation Haven offers a refined Caribbean escape where every detail is designed for comfort, beauty, and unforgettable moments.

Windward - 5BR Ocean Front Villa w/ Staff

White House, JM
5 Bedrooms 10 Guests
Aug 14 - 17
$1,075 night

This luxurious villa is designed to offer the ultimate blend of elegance and tranquillity, making it your perfect escape. Your stay includes the dedicated service of a private chef, attentive butlers, and discreet housekeepers, ensuring every detail of your vacation is cared for with effortless luxury The W boasts a magnificent main house with four opulent bedrooms, each featuring a king-sized bed and a lavish en-suite bath. Additionally, a chic 1-bedroom apartment provides extra space and privacy. With accommodations for up to 10 guests, The W ensures that every detail is tailored to your comfort and indulgence. Immerse yourself in relaxation as you float in the sparkling private pool or savor expertly crafted cocktails at the stylish pool bar. Delight in gourmet meals prepared in the outdoor kitchen, where every meal becomes a culinary celebration against the backdrop of Jamaica’s natural beauty. At The W, your every desire is met with grace and sophistication, offering an unparalleled retreat experience on one of the island’s most picturesque coasts. **Please Note the below Important Booking Information:** A mandatory Security Damage Fee of USD $65 will be applied to all bookings, covering damages up to USD $3000 during your stay. Some properties may also require an additional refundable damage deposit, which will be held against your form of payment. Licence number: CCTWV0001

Expansive 6BR Estate | Panoramic Sea Views, Pool & Resort Access

Montego Bay, St. James Parish, JM
6 Bedrooms 17 Guests
Aug 14 - 18
$3,544 night

Flower Hill is an exceptional six-bedroom villa located in the prestigious Spring Farm neighborhood of Montego Bay, Jamaica. Set on beautifully landscaped grounds overlooking the Half Moon Resort and Golf Club, this grand residence offers panoramic sea and mountain views, generously proportioned living spaces, and a host of notable amenities on site. Designed to accommodate families, groups of friends, and multi-generational gatherings with ease, Flower Hill combines impressive scale with relaxed Caribbean style. Flower Hill encompasses approximately 19,000 square feet of elegant living space set amid lush tropical gardens and manicured grounds spanning several acres. The villa’s architecture and layout create a sense of spaciousness and flow, inviting guests to enjoy wide verandas, expansive terraces, and scenic views that extend toward the Caribbean Sea. There are six well-appointed bedroom suites, each with king-size beds and ensuite bathrooms, comfortably accommodating up to 12 guests with options to expand for larger groups if needed. Many of the suites feature adjacent sitting areas, private patios, or views that reinforce the villa’s connection to its setting. Indoor gathering spaces include a variety of elegant lounges and social areas, bars, and media spaces. Flower Hill also offers a large games room with ping-pong, foosball, shuffleboard, and a projection theater, providing entertainment for all ages. A private gym and spa area add to the sense of retreat and wellness within the villa. Outdoor living highlights include a dramatic heated infinity pool and hot tub, wide sun decks with loungers and seating areas, and multiple verandas for al fresco dining and relaxation. The villa’s generous outdoor footprint offers many peaceful spots to take in the views or enjoy a sunset cocktail. Guests enjoy exclusive access to Flower Hill and its private grounds, including indoor living areas, outdoor terraces, the heated infinity pool and hot tub, gardens, games room, gym, spa area, and all villa amenities. As part of your stay, guests also enjoy complimentary resort membership benefits at the Half Moon Resort, subject to availability and resort policies. Included access features Eclipse Beach, the Jacuzzi, tennis courts, fitness center, croquet lawn, and a miniature putting green. The Half Moon membership includes unlimited green fees at the Half Moon Golf Course along with discounted green fees and cart rental, and preferred rates for instructional services and pro shop purchases. Additional services such as spa treatments, watersports, food and beverage offerings, and tennis instruction may be arranged through the resort for a fee and are subject to availability. Please note that access to resort facilities and services is governed by resort policies and availability. On occasion, facilities or guest services may be unavailable due to private events. Half Moon Resort reserves the right to modify or update its membership benefits without prior notice. Whether you prefer the freedom of a rental car or the ease of chauffeured transportation, we are happy to assist with arranging car rentals and private drivers. Airport transfers and personalized transportation can be coordinated through our team and our guest app, Privé by CVE, ensuring thoughtful support is always within reach as your plans take shape. Please note that complimentary driver service with a 12 or 14-seater van is included on seven-night reservations, with fuel and gratuities at the guest’s expense. Flower Hill includes a dedicated on-site team to support your stay, ensuring comfort, privacy, and a seamless experience. Please note that certain features, amenities, shared facilities, natural conditions, and access to nearby resort amenities may be subject to availability, seasonal changes, and local policies. Gratuity for the villa staff is customary and greatly appreciated. Recommended staff gratuity at the end of your stay is 10 percent of the villa rental rate during High Season and 15 percent during Low Season, divided among staff members in accordance with the Gratuity Guide provided in your villa’s Welcome Book. It is standard within the villa industry to observe these guidelines. Gratuities and grocery funds are best prepared in cash, in US dollars. Tips are typically given on the day of departure or may be prepaid at the time of booking. A handwritten thank-you note is a thoughtful personal touch and is always warmly received by the villa team. Beyond just a stay, Flower Hill offers a refined Caribbean escape where every detail is designed for comfort, beauty, and unforgettable moments.

Tranquil 4BR Villa | Pool, Spa & Resort Access

Montego Bay, St. James Parish, JM
4 Bedrooms 6 Guests
Aug 14 - 18
$1,913 night

Abacus Villa is a luxury, fully staffed hillside retreat overlooking the shimmering waters of Half Moon Bay in Montego Bay, Jamaica. With open-concept indoor-outdoor spaces that capture refreshing ocean breezes and lush tropical gardens that frame panoramic views, Abacus harmonizes modern Caribbean style with effortless comfort. Whether you’re gathering by the pool, dining beneath the stars, or unwinding in serene living spaces, this villa delivers warmth, privacy, and an unforgettable Jamaican escape. Perched atop a gentle hill in the exquisite gated community of Spring Farm Estates, Abacus Villa features a beautifully renovated design with living and social spaces that flow into one another and out to sun-drenched terraces. The villa offers three air-conditioned bedrooms with ensuite bathrooms, and it can be configured to include a fourth guest room in the media space for flexibility. Each room is well-appointed with flat-screen TVs, premium sound systems, plush bathrobes, and premium toiletries. Social spaces include an open living and dining area, a fully equipped chef’s kitchen, and covered outdoor dining terrace. The pool deck with heated pool and Jacuzzi, BBQ area, fire pit, and expansive lawn are perfect for relaxing, playing, or entertaining against the backdrop of sea views. Guests have full access to Abacus Villa and its grounds, including the heated pool, Jacuzzi, outdoor dining and lounge areas, and beautifully landscaped garden. High-speed Wi-Fi, SONOS sound system, and complimentary telephone calls to the US, UK, and Canada are included. Whether you want the freedom of a rental car or prefer to arrive in comfort with a private driver, our team is happy to assist with car rentals and driver arrangements. Airport transfers and personalized transportation can be easily coordinated through our team and our guest app, Privé by CVE, ensuring thoughtful support is always within reach as your plans take shape. Abacus Villa includes a dedicated on-site team to support your stay, ensuring comfort, privacy, and a seamless experience throughout. Please note that certain features, amenities, natural conditions, and access to nearby resort amenities and beach facilities may be subject to availability, seasonal changes, and local policies. Gratuity for the villa staff is customary and greatly appreciated. Recommended staff gratuity at the end of your stay is 10% of the villa rental rate during High Season and 15% during Low Season, divided among staff members in accordance with the Gratuity Guide provided in your villa’s Welcome Book. It is standard within the villa industry to observe these guidelines. Gratuities and grocery funds are best prepared in cash, in US dollars. Tips are typically given on the day of departure or may be prepaid at the time of booking. A handwritten thank-you note is a thoughtful personal touch and is always warmly received by the villa team. Beyond just a stay, Abacus Villa offers a refined Caribbean escape where every detail is designed for comfort, beauty, and unforgettable moments.

Canoe Cove 7BDR Villa | Awe-Inspiring Caribbean Views

Ocho Rios, JM
7 Bedrooms 14 Guests
Aug 14 - 19
$6,613 night

Occupancy # 14 Guests (Adults & kids) Escape to your own private slice of paradise. Canoe Cove sits on 3 acres of land in Old Fort Bay, St. Ann, and boasts 180 feet of unspoiled oceanfront with a white sand beach. This beautiful landscape forms the backdrop for the magnificent open air-villa. ​​​​​​​You can choose to soak up the sun down on the beach or by the 3-lane 75-foot junior Olympic-sized pool. Watch the sun set spectacularly over the Caribbean Sea as you savour your evening meal under the thatch-covered gazebo. There is so much to offer at this luxurious vacation spot. Earth tones and materials blend indoors and outdoors seamlessly, while high-end appliances in the kitchen and modern finishes throughout the house create an ambiance of grandeur. No experience of luxury is complete without a full-service staff, and Canoe Cove offers a brilliant 11-person staff complement including; Professional Chefs, Butlers, Housekeeping/Laundress, and Groundsmen. There’s never a dull moment at Canoe Cove. You don’t have to leave the property to find fun things to do. Canoe Cove offers the facilities and equipment for some well-loved outdoor activities, as well as board games for indoor play. **NOTE Services Included/Excluded Canoe Cove rental prices include: utilities, cable, internet, Villa Staff Services (Chef, Butler, Housekeeping & Grounds), paper & soap products and 24hr security. Not included are additional staff other than noted e.g. nannies, food & beverage and most incidental personal services. Also, specifically excluded from the rental price are damage deposit, car & chauffeur, airport greeting & transfers, rental cars, massage & spa treatments, tennis pro, sightseeing tours, water sports and private boat excursions. If such services are required, they are payable directly to the person/s providing those services. Most groceries can be paid via Visa or MasterCard, however, you may be required to use cash for some of your fresh produce or specialty items. In addition, plan to pay your gratuity monies in cash (US or Jamaican dollars). Staff Gratuity at the end of your stay is a recommended 10% of the Villa Rental in High Season and 15% in Low Season. We welcome you with open arms!

Private 4BR Open-Air Villa With Sea Views & Pool

Hopewell, Hanover Parish, JM
4 Bedrooms 10 Guests
Aug 14 - 17
$1,419 night

Windsong is an exquisite and very private four-bedroom villa nestled on three acres in the low foothills overlooking Montego Bay’s western coastline. Designed by noted architect Kasimir Coribut, this open-air estate is perfectly positioned to capture Jamaica’s most favorable trade winds along with breathtaking panoramic views to both the east and west. From sunrise over Montego Bay to glowing sunsets stretching toward Negril and the lush hills of Hanover, Windsong offers a truly elevated Caribbean experience defined by serenity, space, and natural beauty. Windsong is a thoughtfully designed open-air villa that blends the beauty of its natural surroundings into every living space. Airy rooms, soothing water features, and seamless indoor-outdoor flow create an immediate sense of calm from the moment you arrive. The experience begins at the circular driveway, shaded by a majestic banyan tree adorned with hanging orchids, and continues through a welcoming courtyard filled with tropical plants and gentle fountains. Throughout the estate, lush gardens, rolling lawns, and fruit trees surround the villa, with seasonal produce often finding its way to the breakfast table. The villa features a 20’ x 40’ private tiled swimming pool with a poolside bar, expansive verandahs for al fresco dining, and inviting gathering spaces for relaxed afternoons and candlelit evenings. Music flows easily throughout the home, both indoors and out, setting the tone for laid-back Caribbean living. Guests enjoy exclusive access to Windsong and its grounds, including indoor living areas, expansive verandahs, landscaped gardens, the private pool, and poolside bar. As part of your stay, guests also enjoy complimentary resort membership benefits at the The Tryall Club, subject to availability and club policies. Included access features the beach, non-motorized water sports, tennis courts, a well-equipped fitness center, the Hummingbird Kids Club, Great House afternoon tea, the Manager’s Cocktail Party, and a variety of special events throughout the year. Additional services and experiences may be arranged for a fee and are subject to availability. These may include bar and restaurant dining, spa services, grocery purchases, golf, motorized water sports, tennis shop services, ball boys, and nanny services. Please note that access to club amenities and services is governed by club policies and availability. On occasion, facilities and guest services may be unavailable due to private events. The Tryall Club reserves the right to modify or update its membership benefits without prior notice. Whether you want the freedom of a rental car or prefer to arrive in comfort with a private driver, our team is happy to assist with car rentals and driver arrangements. Airport transfers and personalized transportation can be easily coordinated through our team and our guest app, Privé by CVE, ensuring thoughtful support is always within reach as your plans take shape. Please note that complimentary driver service with a 10-seater van is included on seven-night reservations, with fuel and gratuities at the guest’s expense. Full house reservations are required. Windsong includes a dedicated on-site team to support your stay, ensuring comfort, privacy, and a seamless experience throughout. Please note that certain features, amenities, natural conditions, and access to nearby resort amenities and beach facilities may be subject to availability, seasonal changes, and local policies. Gratuity for the villa staff is customary and greatly appreciated. Recommended staff gratuity at the end of your stay is 10% of the villa rental rate during High Season and 15% during Low Season, divided among staff members in accordance with the Gratuity Guide provided in your villa’s Welcome Book. It is standard within the villa industry to observe these guidelines. Gratuities and grocery funds are best prepared in cash, in US dollars. Tips are typically given on the day of departure or may be prepaid at the time of booking. A handwritten thank-you note is a thoughtful personal touch and is always warmly received by the villa team. Beyond just a stay, Windsong offers a refined Caribbean escape where every detail is designed for comfort, beauty, and unforgettable moments.

Exquisite Buttonwood Reef 6BDR Villa | Ocho Rios

Ocho Rios, JM
6 Bedrooms 12 Guests
Aug 14 - 19
$5,713 night

Occupancy # 12 Guests (Adults & kids) Located in the Heart Beat of Ocho Rios, St. Ann is a brand-new Luxury 6 Bedroom, 6.5 Bathroom Villa right on the water’s edge that was completed in March 2020. Entry to the villa is through the private Boutique Resort of Hermosa Cove Villa Resorts and Suites. Its location boasts stunning views of the crystal clear blue waters that Ocho Rios, also known as “Ochi,” is well-known for. You enter the Villa through the dramatic Jequitiba wood ceiling and eclectic light fixtures designed by Clayton Korver. Then, transition through the oversized pivot door, and your eyes meet the Caribbean Sea. Coupled with our luxury cottage Sea Biscuit, these two Villas offer an incredible experience at the water’s edge in Paradise! This incredible luxury villa sits right on the ocean’s edge, providing a stunning 180-degree view of the pristine coastal landscape. Buttonwood Reef is conducive to outside living and offers a shallow entry, infinity-edge pool that has a Baja ledge with sun shelves and an adjacent hot tub. Of course, the experience is made complete with our friendly, attentive, and trustworthy Staff of 7 persons, which includes: Chef, Butlers, Housekeeping & Laundresses, and a Pool & Watersports Attendant. Clear Caribbean water laps at the shores of these two properties which can be reserved as one large estate to host your multi-generation family. The oldest Buttonwood Tree in Jamaica (hence the main Villa name) shades both the thatch-roofed gazebo and a newly built sea deck of Sea Biscuit. With bedroom doors that open to the sea, you can enjoy a peaceful breakfast in your own private gazebo or explore the intricate and joyful artistry of Sea Biscuit. **NOTE Services Included/Excluded Canoe Cove rental prices include: utilities, cable, internet, Villa Staff Services (Chef, Butler, Housekeeping & Grounds), paper & soap products and 24hr security. Not included are additional staff other than noted e.g. nannies, food & beverage and most incidental personal services. Also, specifically excluded from the rental price are damage deposit, car & chauffeur, airport greeting & transfers, rental cars, massage & spa treatments, tennis pro, sightseeing tours, water sports and private boat excursions. If such services are required, they are payable directly to the person/s providing those services. Most groceries can be paid via Visa or MasterCard, however, you may be required to use cash for some of your fresh produce or specialty items. In addition, plan to pay your gratuity monies in cash (US or Jamaican dollars). Staff Gratuity at the end of your stay is a recommended 10% of the Villa Rental in High Season and 15% in Low Season. We welcome you with open arms!

Luxurious 5BR Villa Christina | Tuscan Charm + Golf Course

Montego Bay, JM
5 Bedrooms 10 Guests
Aug 14 - 19
$2,910 night

Occupancy # 10 Guests (Adults & kids) 5BR Luxury Villa, Tuscan Charm + Golf Course Views Welcome to the breathtaking Tuscan estate of Villa Christina, where 5 luxurious bedrooms offer stunning views of the Caribbean Sea and mountains. Relax and enjoy all the best of a Caribbean vacation retreat in the billiards room, wellness center, 2 Jacuzzis, salt-water infinity pool, and more. Each spacious room features the finest details and comforts, including HD TVs and walk-in closets. Our gracious staff of butlers, chefs, housekeepers, laundresses, and caretakers will provide tailored hospitality to ensure your stay is unparalleled. Experience the charm of a European country estate amidst the picturesque Caribbean scenery at Villa Christina, overlooking the renowned Cinnamon Hill golf course. This luxurious vacation rental boasts Tuscan-inspired architecture, spanning 10,000 square feet with five bedrooms and ample living space for up to ten guests. Located in a private gated community near Montego Bay, Villa Christina offers easy access to the beach, golf, and other nearby attractions. Relax in style while your personal chef, housekeeper, and villa manager take care of your needs. Take a dip in the saltwater infinity pool, unwind in the hot tub, or entertain outdoors in the barbecue and al-fresco dining area. Indoors, enjoy the bar room, pool table, cable TV, and Wi-Fi. Villa Christina also features a spa and exercise room. Despite its impressive lofty ceilings, stately columns, and bays of windows, Villa Christina offers a casual, chic atmosphere. Gather with loved ones in the open-concept living and dining room or enjoy an intimate meal in the breakfast nook. Although chef service is included, you have full access to the well-equipped kitchen. This exquisite estate includes a master bedroom with a king bed, en-suite bathroom, honeymoon-suite-worthy jetted tub, and an outdoor plunge pool. There are two additional bedrooms with queen beds and en-suite bathrooms, a bedroom with a king bed and shared hall bathroom, and a fifth bedroom with two twin beds, one trundle bed, an en-suite bathroom, and its own kitchenette. With Villa Christina, you’ll have less than a 10-minute drive to some of the top golf courses in Jamaica and the Rose Hall Beach Club. The Half Moon Resort is also only 8 minutes away, and your stay includes complimentary membership. Please note the following other amenities: *Chef service is included in your stay, but also a fully equipped kitchen with a breakfast bar *Formal dining area with seating for 10 • Outdoor dining for 10 • Media Room • Sonos sound system • Bar room • Spa room • Pool table • Kids’ lounge *Extra cost (advance notice may be required): • Chef service • Villa pre-stocking • Airport transfer • Activities and excursions *On Cinnamon Hill Golf Course. Half Moon Beach Club Membership: Guests must pay a resort entry fee per day if staying for less than 7 nights. Rose Hall Golf Membership *Available on request at an extra charge: crib, high chair. Book your getaway today!

Upful Villa | Modern-Rustic 4BDR w/ Pool

Treasure Beach, JM
4 Bedrooms 10 Guests
Aug 14 - 17
$952 night

Occupancy # 10 Guests (Adults & kids) Airy, bright, spacious, and modern-rustic family-friendly villa in Treasure Beach, St. Elizabeth, Jamaica Ideal for a family or friends vacationing together, our staffed two-level four-bedroom home is spacious with lots of cozy spaces to gather, hang out, and reconnect. Designed for relaxation in nature, Upful is light, airy, modern, and homey. Green architecture and design for quintessential indoor-outdoor living. With the Caribbean Sea behind us to the south + the pristine Old Wharf beach just across the road, the brisk sea breezes make Upful one of the coolest spots in Treasure Beach. Book your getaway today! **NOTE** - Fully Staffed Villa Services Included/Excluded | Rental includes: utilities, internet, cable, and Villa Team Services. Private Chef service and housekeeping are mandatory and included. Not included are groceries for included meal preparation; tours or transportation; any personal services outside of the Villa Team Services, and staff gratuities. External services are to be paid directly to providers. Most groceries can be covered by credit card, however, cash may be required for some fresh produce or specialty items. Please plan on paying a gratuity to the staff in cash (USD or JMD) at the end of your stay; 15% of the total rental price is recommended, customary, and expected, if service is to your satisfaction. ​​​​​​​Please estimate between US$40 - $50 per person for two meals a day, including fruits, cold and hot soft beverages. The Villa Team will work with you to plan meals in advance and looks forward to pampering you during your stay!

Hidden 4BR Gem | Pool & Nature Escape in the Hills of Port Antonio

Fairy Hill, Portland Parish, JM
4 Bedrooms 8 Guests
Aug 14 - 18
$1,092 night

Villa Helliconia is a hidden four bedroom retreat tucked into the lush hills near Port Antonio, offering a peaceful escape surrounded by rainforest greenery and tropical gardens. Designed to harmonize with nature, the villa blends relaxed Caribbean living with thoughtful design, creating a tranquil setting ideal for rest, reflection, and reconnection. Named for the vibrant heliconia flowers that flourish throughout the property, this serene hideaway invites guests to slow down and fully embrace the beauty of Jamaica’s northeast coast. Villa Helliconia unfolds across thoughtfully designed indoor and outdoor living spaces that open seamlessly to the surrounding landscape. Large windows, garden views, and open terraces invite natural light and cool breezes throughout the villa, reinforcing its calm, nature driven atmosphere. The villa features four individually styled bedrooms, each inspired by one of the classical elements Air, Earth, Water, and Fire. Every bedroom includes an en suite bathroom and is designed to offer a restful, grounding experience for guests. The décor incorporates natural textures, warm tones, and subtle artistic details that reflect the villa’s connection to its environment. Outdoor living centers around a private swimming pool set within a lush garden courtyard, ideal for quiet afternoons, morning swims, or evening relaxation. Additional spaces support wellness focused stays, with areas suited for yoga, meditation, or simply enjoying the surrounding birdlife and tropical scenery. Guests enjoy exclusive access to Villa Helliconia and its grounds, including all indoor living areas, outdoor terraces, garden spaces, and the private pool. The villa is designed for both shared moments and personal retreat, offering flexibility for couples, families, or small groups. Optional services such as private chef experiences, massage treatments, yoga sessions, and guided wellness activities may be arranged upon request and are subject to availability and additional cost. Whether you prefer the freedom of a rental car or the ease of a private driver, our team is happy to assist with car rentals and driver arrangements. Airport transfers and personalized transportation can be coordinated through our team and our guest app, Privé by CVE, ensuring thoughtful support as your plans take shape. Villa Helliconia includes a dedicated on site team to support your stay, ensuring comfort, privacy, and a seamless experience throughout. Please note that certain features, amenities, and natural conditions may be subject to availability, seasonal changes, and local policies. Gratuity for the villa staff is customary and greatly appreciated. Recommended staff gratuity at the end of your stay is 10 percent of the villa rental rate during High Season and 15 percent during Low Season, divided among staff members in accordance with the Gratuity Guide provided in your villa’s Welcome Book. It is standard within the villa industry to observe these guidelines. Gratuities and grocery funds are best prepared in cash, in US dollars. Tips are typically given on the day of departure or may be prepaid at the time of booking. A handwritten thank you note is a thoughtful personal touch and is always warmly received by the villa team. Beyond just a stay, Villa Helliconia offers a nature immersed escape where every detail is designed for comfort, balance, and unforgettable moments.

Secluded 3BR Garden Villa | Pool & Ocean Views

Unity Hall, St. James Parish, JM
3 Bedrooms 8 Guests
Aug 14 - 17
$1,069 night

Villa Sorrento is a beautifully appointed three-bedroom villa nestled in the lush hills of the prestigious Great River Private community in Montego Bay, Jamaica. Surrounded by vibrant tropical gardens, blooming palms, and serene outdoor spaces, this retreat offers a blend of relaxed Caribbean charm and refined comfort for families or groups seeking a tranquil escape. Set against spectacular Caribbean Sea views, Villa Sorrento features three air-conditioned bedrooms, each with an ensuite bathroom, and generous living spaces designed for comfort and connection. An open living room and dining area invite gatherings, while the fully equipped kitchen accommodates shared meals and casual breakfasts. Outdoor living is a highlight here. The villa opens to a spacious verandah and back patio with a water feature, creating relaxing spots to enjoy morning coffee or evening sunsets. The private pool and heated outdoor Jacuzzi offer refreshing escapes beneath lush foliage, and a unique outdoor shower under a majestic banyan tree adds charm to everyday moments. Guests have exclusive access to the entire villa and grounds, including the pool, outdoor Jacuzzi, verandah, and garden areas. High-speed Wi-Fi and fully outfitted living spaces provide all the comforts you need for an effortless stay. Whether you want the freedom of a rental car or prefer to arrive in comfort with a private driver, our team is happy to assist with car rentals and driver arrangements. Airport transfers and personalized transportation can be easily coordinated through our team and our guest app, Privé by CVE, ensuring thoughtful support is always within reach as your plans take shape. Villa Sorrento includes a dedicated on-site team to support your stay, ensuring comfort, privacy, and a seamless experience throughout. Please note that certain features, amenities, natural conditions, and access to nearby resort amenities and beach facilities may be subject to availability, seasonal changes, and local policies. Gratuity for the villa staff is customary and greatly appreciated. Recommended staff gratuity at the end of your stay is 10% of the villa rental rate during High Season and 15% during Low Season, divided among staff members in accordance with the Gratuity Guide provided in your villa’s Welcome Book. It is standard within the villa industry to observe these guidelines. Gratuities and grocery funds are best prepared in cash, in US dollars. Tips are typically given on the day of departure or may be prepaid at the time of booking. A handwritten thank-you note is a thoughtful personal touch and is always warmly received by the villa team. Beyond just a stay, Villa Sorrento offers a refined Caribbean escape where every detail is designed for comfort, beauty, and unforgettable moments.

Tropical-Inspired 5BR Modern Seafront Villa | Infinity Pool & Direct Sea Access

Boscobel, St. Mary Parish, JM
5 Bedrooms 10 Guests
Aug 14 - 19
$2,738 night

Timbuktu By The Sea is a striking five bedroom seafront villa located in Boscobel, Jamaica, just east of Ocho Rios and near Ian Fleming International Airport. Blending globally inspired design with relaxed Caribbean living, the villa offers uninterrupted ocean views, direct sea access, and thoughtfully curated spaces designed for connection and retreat. Supported by a dedicated on site team, this villa delivers an immersive coastal escape shaped by beauty, comfort, and a strong sense of place. Timbuktu By The Sea spans multiple levels of beautifully finished living spaces, each designed to embrace the surrounding sea and sky. Interiors feature handcrafted details, natural textures, and large windows that frame the Caribbean horizon from nearly every angle. The villa includes five well appointed bedrooms, each with an ensuite bathroom and private terrace or balcony overlooking the ocean. Several bedrooms feature outdoor showers, adding to the indoor and outdoor living experience. Upper level suites offer elevated views and a sense of privacy, making them ideal for longer stays or multi generational groups. Outdoor living is a defining feature of the villa. A heated infinity pool overlooks the sea, complemented by multiple lounging and dining areas, a barbecue space, and a lawn suitable for yoga or sunset gatherings. A private jetty provides direct ocean access for swimming, snorkeling, and water activities, with a nearby dive site easily reached from shore. Additional amenities include a private gym, games areas, fire pit seating, and kayaks for exploring the coastline. Guests enjoy exclusive access to Timbuktu By The Sea and its grounds, including all indoor living areas, outdoor terraces and patios, the infinity pool, lawn and garden seating areas, wellness spaces, gym, games areas, and direct ocean access via the private jetty. Housekeeping and chef services are provided to ensure a comfortable and seamless stay. Meals and services can be personalized to your preferences, and spa or wellness treatments may be arranged through the villa team. Whether you prefer the freedom of a rental car or the comfort of a private driver, our team is happy to assist with arranging car rentals and driver services. Airport transfers and tailored transportation can be easily coordinated through our team and our guest app, Privé by CVE, ensuring thoughtful support is always available as your plans take shape. Timbuktu By The Sea includes a dedicated on site team to support your stay, ensuring comfort, privacy, and a seamless experience throughout. Please note that certain features, amenities, and natural conditions may be subject to availability, seasonal changes, and local policies. Gratuity for the villa staff is customary and greatly appreciated. Recommended staff gratuity at the end of your stay is 10 percent of the villa rental rate during High Season and 15 percent during Low Season, divided among staff members in accordance with the Gratuity Guide provided in your villa’s Welcome Book. It is standard within the villa industry to observe these guidelines. Gratuities and grocery funds are best prepared in cash, in US dollars. Tips are typically given on the day of departure or may be prepaid at the time of booking. A handwritten thank you note is a thoughtful personal touch and is always warmly received by the villa team. Beyond just a stay, Timbuktu By The Sea offers a refined Caribbean escape where every detail is designed for comfort, beauty, and unforgettable moments.

Nature-Inspired 4BR Modern Villa | Pool & Resort Access

Montego Bay, St. James Parish, JM
4 Bedrooms 10 Guests
Sep 1 - 5
$2,700 night

Villa Rosa is a stylish and thoughtfully designed villa located in the gated Spring Farm community of Montego Bay, Jamaica. With four spacious bedrooms and a flexible media room, expansive living spaces, and sweeping garden and sea views, this residence offers a refined Caribbean lifestyle. Thoughtful design, premium amenities, and a professional on site team create a retreat that is both serene and generous in scale, ideal for families and groups seeking comfort and ease. Villa Rosa is designed for seamless indoor and outdoor living, with clean lines and floor to ceiling glass that invite natural light and tropical surroundings into every space. The main living areas flow effortlessly into social and dining spaces, creating a relaxed yet polished environment for gathering and entertaining. The villa features four well appointed bedrooms, each with king size beds, ensuite bathrooms, and private terraces or balconies with garden or sea views. A media room provides additional sleeping flexibility with a convertible sofa that can accommodate additional guests, making the villa well suited for larger groups. Outdoor living is a highlight at Villa Rosa, with a private swimming pool, sun decks, and multiple spaces for lounging and dining. A dedicated fitness and wellness pavilion with gym and yoga space adds to the sense of a complete private retreat. Guests enjoy exclusive access to Villa Rosa and its private grounds, including indoor living areas, outdoor terraces, landscaped gardens, the private pool, sun deck, media room, and fitness pavilion. As part of your stay, guests also enjoy complimentary resort membership benefits at the Half Moon Resort, subject to availability and resort policies. Included access features Eclipse Beach, the Jacuzzi, tennis courts, fitness center, croquet lawn, and a miniature putting green. The Half Moon membership also includes unlimited complimentary green fees at the Half Moon Golf Course, along with discounted green fees at the White Witch and Cinnamon Hill golf courses at Rose Hall. The Tryall Club is located across town and offers additional championship golf options. Additional services such as spa treatments, watersports, dining, and tennis instruction may be arranged on the day of service and are subject to availability and applicable fees. Please note that access to resort amenities and services is governed by resort policies and availability. On occasion, facilities or guest services may be unavailable due to private events. Half Moon Resort reserves the right to modify or update its membership benefits without prior notice. Whether you prefer the freedom of a rental car or the ease of chauffeured transportation, we are happy to assist with arranging car rentals and private drivers. Airport transfers and personalized transportation can be coordinated through our team and our guest app, Privé by CVE, ensuring thoughtful support is always within reach as your plans take shape. Please note that complimentary driver service with a 12 or 14-seater van is included on seven-night reservations, with fuel and gratuities at the guest’s expense. Villa Rosa includes a dedicated on site team to support your stay, ensuring comfort, privacy, and a seamless experience throughout. Please note that certain features, amenities, natural conditions, and access to nearby resort amenities and beach facilities may be subject to availability, seasonal changes, and local policies. Gratuity for the villa staff is customary and greatly appreciated. Recommended staff gratuity at the end of your stay is 10 percent of the villa rental rate during High Season and 15 percent during Low Season, divided among staff members in accordance with the Gratuity Guide provided in your villa’s Welcome Book. It is standard within the villa industry to observe these guidelines. Gratuities and grocery funds are best prepared in cash, in US dollars. Tips are typically given on the day of departure or may be prepaid at the time of booking. A handwritten thank you note is a thoughtful personal touch and is always warmly received by the villa team. Beyond just a stay, Villa Rosa offers a refined Caribbean escape where every detail is designed for comfort, beauty, and unforgettable moments.

Vacation Rentals in Jamaica by Amenities & Features

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Vacation Rentals Near Jamaica

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