Jamaica Villa Rentals


Sweet Spot Master Nl Copy

Sweet Spot on the Beach

Runaway Bay Villa

from $1921 /night
up to 12 guests

Sweet Spot on the Beach

6 bedroom 6.5 bath Jamaica villa in Runaway Bay

Located on a wide sandy beach, Sweet Spot is like a pretty jewel box next to the sea. Its remarkable location is the best of all worlds ... a 6,000-square-foot private home with a huge lawn and beach.

Hidden Bay Nl Copy

Hidden Bay by the Sea

Runaway Bay Villa

from $1929 /night
up to 12 guests

Hidden Bay by the Sea

6 bedroom 6 bath Jamaica villa in Runaway Bay

HIDDEN BAY by the SEA perches dramatically on a cliffside and is one of the most remarkable sites on Jamaica’s renowned North Coast.

Ma+Moura NL +copy

Ma Moura at the Tryall Club

Montego Bay Villa

from $1929 /night
up to 8 guests

Ma Moura at the Tryall Club

4 bedroom 4.5 bath Jamaica villa in Montego Bay

Built and owned by the same family for over forty years, Ma’Moura’s unique setting sits high on a hill overlooking the 17th green and the Caribbean Sea. Enjoying cool breezes and unobstructed views, this villa provides one of the most private yet outdoor experiences at Tryall.

Ee Dji

Everything Nice by the Sea

Montego Bay Villa

from $1950 /night
up to 10 guests

Everything Nice by the Sea

5 bedroom 5.5 bath Jamaica villa in Montego Bay

Everything Nice is a lovely waterfront property on Emerald Quay sitting on the edge of the Bogue Lagoon. Nestled in between the Breathless & Secrets Hotels & within walking distance of the Montego Bay Yacht Club.

Sugar Bay Nl Copy

Sugar Bay on the Beach

Discovery Bay Villa

from $1964 /night
up to 10 guests

Sugar Bay on the Beach

5 bedroom 5.5 bath Jamaica villa in Discovery Bay

On its own sugary white sand beach lapped by the turquoise waters of Discovery Bay sits the exquisite home Sugar Bay. Interiors have just been refreshed throughout and are distinguished by elegant custom-designed furniture, gleaming breadnut floors, and fascinating objets d`art from around the world. There has also been an addition of a brand new air conditioned Gym!

Casuarina

Casuarina at the Tryall Club

Montego Bay Villa

from $1964 /night
up to 8 guests

Casuarina at the Tryall Club

4 bedroom 4 bath Jamaica villa in Montego Bay

Casuarina is a hidden gem and one of the loveliest villas at Tryall. The ocean views are breathtaking while inside there is a magical charm created by a very clever combination of flower-filled gardens, and furniture designed for total comfort.

Viviana Nl

Sea Glass at Tryall Club

Montego Bay Villa

from $1995 /night
up to 12 guests

Sea Glass at Tryall Club

6 bedroom 8 bath Jamaica villa in Montego Bay

Formerly named Annabella, Sea Glass sits on a remarkable six private acres on a plum site at the prestigious Tryall Club. Uniquely private, the feeling is being in a world of your own, wonderfully quiet and tranquil while just minutes away by complimentary golf cart are the amenities that have defined the Tryall Club as one of the finest private clubs in the world.

Cielo Nl Lr 1

Cielo at the Tryall Club

Montego Bay Villa

from $2000 /night
up to 10 guests

Cielo at the Tryall Club

5 bedroom 6 bath Jamaica villa in Montego Bay

Cielo means "sky" and "heaven" and the name tells a lot about living in this wonderful villa on a hill. Add the all-day panorama of blue Caribbean Sea at every glance and "heaven" gets even better!

Sugar Hill 6 Pool Nl

Sugar Hill at the Tryall Club

Montego Bay Villa

from $2000 /night
up to 16 guests

Sugar Hill at the Tryall Club

8 bedroom 8 bath Jamaica villa in Montego Bay

Sugar Hill is a luxurious eight-bedroom villa perched atop a lush three-acre property with breathtaking views over the Tryall Club to the Caribbean Sea and horizon. This glamorous home is ideal for golf and tennis buffs, couples, large groups and families. Children welcome!

Villa Rosa

Montego Bay Villa

from $2000 /night
up to 10 guests

Villa Rosa

5 bedroom 6 bath Jamaica villa in Montego Bay

Villa Rosa is our newest villa in Montego Bay's Spring Farm neighborhood. It is a stunning, modern villa, brilliantly designed for an extraordinary indoor-outdoor lifestyle with a full complement of impressive luxuries for the upscale traveler.

Bumpers Nest Nl Copy

Bumper’s Nest at the Tryall Club

Montego Bay Villa

from $2006 /night
up to 12 guests

Bumper’s Nest at the Tryall Club

6 bedroom 6 bath Jamaica villa in Montego Bay

On three acres of land with a commanding view of the Caribbean Sea, lush green mountains, and a golf course, Bumper's Nest was designed by distinguished architect Kasimir Korybut in 1995. A brilliant renovation has recreated one of the most glamorous homes at the Tryall Club. Here is an extraordinary private home with simply the best of everything.

Reef House Pool To House Late Afternoon

Reef House at Tryall

Montego Bay Villa

from $2006 /night
up to 8 guests

Reef House at Tryall

4 bedroom 4 bath Jamaica villa in Montego Bay

Reef House is the embodiment of oceanfront cottage living. This gorgeous home brings the outside in, bathing the rooms with soft natural light and the irresistible blues of the ocean beyond.

House Whole W Pool Copy

Hanover Grange at Tryall

Montego Bay Villa

from $2025 /night
up to 18 guests

Hanover Grange at Tryall

9 bedroom 9.5 bath Jamaica villa in Montego Bay

Hanover Grange has become one of the highest profile, privately owned villas in the Caribbean, welcoming a succession of international celebrities, politicians and business leaders as guests.

Villa Christina

Montego Bay Villa

from $2071 /night
up to 10 guests

Villa Christina

5 bedroom 6.5 bath Jamaica villa in Montego Bay

Set on the historic Rose Hall Estate, Villa Christina welcomes couples, families, and friends to Caribbean luxury in a remarkable 10,000 sq. ft. well-appointed Tuscan style villa located in the Greens at Rose Hall - a private gated-community on the Cinnamon Hill Golf Course.

+Fairway+Manor NL +copy

Fairway Manor

Montego Bay Villa

from $2090 /night
up to 14 guests

Fairway Manor

7 bedroom 9 bath Jamaica villa in Montego Bay

Today’s Fairway Manor is a stylish multi-faceted 10,000-square-foot private home. Its rooms feature cool marble floors and overlook the famous Half Moon 18-hole Robert Trent Jones golf course and a dramatic panorama of the Caribbean Sea.

A Summer Place Nl

A Summer Place on the Beach

Discovery Bay Villa

from $2100 /night
up to 14 guests

A Summer Place on the Beach

7 bedroom 9 bath Jamaica villa in Discovery Bay

Nestled on its own sandy beach by the blue waters of Discovery Bay, A Summer Place is a spacious and playful family home. The design is of typical Caribbean gingerbread style with hand-carved fretwork trimming the length of the house.

Bougainvillea 7

Bougainvillea at the Tryall Club

Montego Bay Villa

from $2209 /night
up to 10 guests

Bougainvillea at the Tryall Club

5 bedroom 6 bath Jamaica villa in Montego Bay

Bougainvillea is one of the most stylish homes in this collection. Brilliant architecture and design have resulted in a luxurious state-of-the-art vacation home that is elegant but not daunting.

Rose Cottage Nl

Hyde Park at the Tryall Club

Montego Bay Villa

from $2251 /night
up to 14 guests

Hyde Park at the Tryall Club

6 bedroom 8 bath Jamaica villa in Montego Bay

Hyde Park is a large and lavish home with glorious views of the lush Jamaican mountains and the deep blue Caribbean Sea. Its design is a stylish blend of Jamaican, Asian, and European elements with an emphasis on extraordinary comfort.

Following Seas Mix Nl

Following Seas at the Tryall Club

Montego Bay Villa

from $2286 /night
up to 12 guests

Following Seas at the Tryall Club

6 bedroom 7 bath Jamaica villa in Montego Bay

Following Seas is a marvelous private villa with the top rating of Premier. It is tastefully renovated with thoughtful comforts, amenities and stylish bathrooms throughout.

Tradewinds Nl Copy

Tradewinds on the Sea at the Tryall Club

Montego Bay Villa

from $2286 /night
up to 8 guests

Tradewinds on the Sea at the Tryall Club

4 bedroom 4 bath Jamaica villa in Montego Bay

This amazing seafront property sits on two acres at the famous Tryall Club – directly on the Caribbean Sea. 300 feet of waterfront from the north perimeter of the property, and it is one of the newest premier villas at The Tryall Club.

Little Hill Pool With Stairs To South Garden

Little Hill at Tryall

Montego Bay Villa

from $2286 /night
up to 8 guests

Little Hill at Tryall

4 bedroom 4 bath Jamaica villa in Montego Bay

Little Hill was built in 1959 by an architect Robert Hartley. It was the first villa to be built at The Tryall Club in the Classic West Indies style around a circular 30 foot diameter swimming pool with extensive covered terraces throughout.

Keela Wee Nl

Keela Wee on the Beach

Discovery Bay Villa

from $2357 /night
up to 12 guests

Keela Wee on the Beach

6 bedroom 6 bath Jamaica villa in Discovery Bay

Located on a private coral cove, this pretty yellow stone villa overlooks one of Jamaica's loveliest bodies of water ~ Discovery Bay. On its own private coral cove, this newest property can be rented alone ~ or in combination with its neighboring sister villa – Whispering Waters..

Sunset Tryall Nl

Sunset on the Beach at the Tryall Club

Montego Bay Villa

from $2357 /night
up to 10 guests

Sunset on the Beach at the Tryall Club

5 bedroom 5 bath Jamaica villa in Montego Bay

Sunset is a beautiful five-bedroom villa that sits on the edge of the Caribbean Sea with a private beach offering the perfect escape for all those who love waterside living.

Entrance O

Flower Hill

Montego Bay Villa

from $2450 /night
up to 12 guests

Flower Hill

6 bedroom 12 bath Jamaica villa in Montego Bay

Flower Hill is one of the most luxurious villas in Montego Bay's, Spring Farm neighborhood. This Premier 19,000-sq-ft villa sits on 4 beautifully landscaped acres overlooking the Half Moon Beach Resort and Golf Club.

Create Abundance Nl

Villa Amana at Tryall

Montego Bay Villa

from $2464 /night
up to 20 guests

Villa Amana at Tryall

10 bedroom 13 bath Jamaica villa in Montego Bay

With an ocean panorama that is nothing short of awe-inspiring, this grand ten-bedroom villa is the largest at Tryall. With large airy rooms exuding sophisticated style, a terrific infinity pool, a cascading garden waterfall, a children’s playground and the choice of outdoor or indoor air-conditioned living make this a one-of-a-kind villa

Quint Nl

Celestial Villa at Tryall

Montego Bay Villa

from $2550 /night
up to 10 guests

Celestial Villa at Tryall

5 bedroom 5 bath Jamaica villa in Montego Bay

Offering what is undoubtedly the most magnificent ocean view in Tryall from a commanding position atop Garden Hill; Celestial Villa is one of the finest private homes in Jamaica where meticulous attention to detail and designers flourish resulting in the epitome of sophisticated living without compromise.

Phoenix+swimming+pool

Phoenix on the Beach at the Tryall Club

Montego Bay Villa

from $2571 /night
up to 14 guests

Phoenix on the Beach at the Tryall Club

7 bedroom 8 bath Jamaica villa in Montego Bay

Phoenix sits on a spectacular seascape on Jamaica's lush North Coast at the luxurious Tryall Club 12 miles west of Montego Bay. The beach club, pro shop, first tee and driving range are within walking distance of the Phoenix front door. Nine laykold tennis courts are just a golf cart ride up the hill.

Trinity

Trinity at Tryall

Montego Bay Villa

from $2643 /night
up to 10 guests

Trinity at Tryall

5 bedroom 5 bath Jamaica villa in Montego Bay

Trinity is a recently renovated luxury villa that boasts breathtaking views, features two expansive swimming pools, offers opulent furnishings and accessories, incorporates a Sonos music system throughout, and is staffed by a team of professionally trained individuals dedicated to ensuring your vacation is unforgettable.

Infinity Nl

Infinity at the Tryall Club

Montego Bay Villa

from $2657 /night
up to 12 guests

Infinity at the Tryall Club

6 bedroom 5.5 bath Jamaica villa in Montego Bay

A Premier villa at the renowned Tryall Club, Infinity is a halcyon haven overlooking the Caribbean Sea. Its rooms are large and tastefully furnished -- some traditional, some eclectic -- with a designer’s eye to comfort throughout. Named for its seemingly endless private pool, Infinity is a vacationer’s paradise for golf and tennis enthusiasts, spa weeks, family reunions or merely relaxing into the good life for a week or more.

Ind

Villa Indigo

Montego Bay Villa

from $2750 /night
up to 10 guests

Villa Indigo

5 bedroom 5.5 bath Jamaica villa in Montego Bay

Villa Indigo at HALF MOON is one of the undisputed finest private homes in this collection.

Zion Hill Nl

Zion Hill at Tryall

Montego Bay Villa

from $2751 /night
up to 14 guests

Zion Hill at Tryall

7 bedroom 7 bath Jamaica villa in Montego Bay

From its splendid location 300 ft above sea level, this luxurious five bedroom villa offers bewitching, unobstructed views of the ocean, its own private spa and Turkish bath and a cinema.

Silent Waters 9 Pool Sundeck Mobay Daytime

Silent Waters

Montego Bay Villa

from $2853 /night
up to 16 guests

Silent Waters

8 bedroom 6 bath Jamaica villa in Montego Bay

Set atop one of the highest mountaintops overlooking Montego Bay and the Caribbean Sea, Silent Waters Villa offers a secluded retreat just 4.6 miles west of Montego Bay. This breathtaking 16.5-acre estate combines world-class architecture and design with unparalleled luxury, making it an ideal destination for family gatherings, weddings, retreats, and milestone celebrations.

Ww

Whispering Waters on the Beach

Discovery Bay Villa

from $2857 /night
up to 14 guests

Whispering Waters on the Beach

7 bedroom 7 bath Jamaica villa in Discovery Bay

Whispering Waters offers seven bedrooms and en-suite bathrooms. Overlooking one of Jamaica’s loveliest crystal clear bodies of water, Discovery Bay. On its own private coral cove, this newest property can be rented alone ~ or in combination with its neighboring sister villa – Keela Wee.

Point Of View O

Point of View at the Tryall Club

Montego Bay Villa

from $2877 /night
up to 10 guests

Point of View at the Tryall Club

5 bedroom 5 bath Jamaica villa in Montego Bay

Located on the highest point at the renowned Tryall Club, Point of View sits on one of the most spectacular sites in the Caribbean … indeed, in the world. From its unique vantage point, a sweeping panorama stretches down the mountain and across the 18-hole championship golf course to the deep blue Caribbean and distant horizon. Breathtaking at every turn.

Pool 1 O

Hummingbird House at the Tryall Club

Montego Bay Villa

from $2986 /night
up to 14 guests

Hummingbird House at the Tryall Club

7 bedroom 8 bath Jamaica villa in Montego Bay

Hummingbird House is one of the finest properties within the Tryall Club!

Dragonfly Nl

Dragonfly at Tryall

Montego Bay Villa

from $3000 /night
up to 14 guests

Dragonfly at Tryall

7 bedroom 7 bath Jamaica villa in Montego Bay

Occupying a commanding position on Garden Hill, this sensational new villa is a dramatic new addition to the Tryall Club.

Karma Bay Nl Copy

Karma Bay at the Tryall Club

Montego Bay Villa

from $3045 /night
up to 12 guests

Karma Bay at the Tryall Club

6 bedroom 6 bath Jamaica villa in Montego Bay

A sprawling double lot directly on the Caribbean Sea is among the most stunning waterfront locations in all Jamaica. This is the rarefied site of the private villa named Karma Bay.

Pineapple House

Pineapple House at Tryall

Montego Bay Villa

from $3071 /night
up to 10 guests

Pineapple House at Tryall

5 bedroom 5.5 bath Jamaica villa in Montego Bay

Pineapple House is a spacious villa located on Copper Ridge with a magnificent 180 degree view of the Caribbean Sea located on Jamaica’s exclusive North Shore

Am

Amanoka on the Beach

Discovery Bay Villa

from $3142 /night
up to 14 guests

Amanoka on the Beach

7 bedroom 8 bath Jamaica villa in Discovery Bay

Located on beautiful Discovery Bay, Amanoka is one of the most stunning villas in this collection. From the spacious verandah and pool, a barefoot stroll leads down a soft lawn to the 70’ white sand beach, clear turquoise water, and waterfront gazebo with suspended canvas swings.

Fortlands Point Nl

Fortlands Point on the Beach

Discovery Bay Villa

from $3143 /night
up to 18 guests

Fortlands Point on the Beach

9 bedroom 9 bath Jamaica villa in Discovery Bay

On a stunning promontory, once the site of an old stone fort, sits a remarkable home named Fortlands Point. From its breathtaking location on the tip of the peninsula, the commanding view encompasses the turquoise water of Discovery Bay on one side and the deep blue Caribbean Sea on the other.

Makana

Makana on the Beach

Discovery Bay Villa

from $3286 /night
up to 14 guests

Makana on the Beach

7 bedroom 7 bath Jamaica villa in Discovery Bay

Makana is one of the most glamorous private villas on the precious strip of land that borders Discovery Bay. The site itself is remarkable: a spacious villa with private tennis court and swimming pool on a sugary white sand beach bordering translucent swimming and kayaking water.

Dji

Aqua Bay at the Tryall Club

Montego Bay Villa

from $3358 /night
up to 8 guests

Aqua Bay at the Tryall Club

4 bedroom 6 bath Jamaica villa in Montego Bay

Aqua Bay is an amazing seafront property and is one of the premier villas at The Tryall Club.

Harmony Hill 4 Nl

Harmony Hill at Tryall

Montego Bay Villa

from $3499 /night
up to 14 guests

Harmony Hill at Tryall

7 bedroom 7.5 bath Jamaica villa in Montego Bay

Harmony Hill is a private oasis offering the finest in Caribbean living, combining Jamaica’s rich architectural tradition with today’s modern amenities and service.

Buttonwood Master Nl Copy

Buttonwood Reef

Ocho Rios Villa

from $3600 /night
up to 12 guests

Buttonwood Reef

6 bedroom 6.5 bath Jamaica villa in Ocho Rios

This stunning 6- bedroom villa is located right on the water’s edge, overlooking the crystal clear blue waters that Ocho Rios is well-known for. Entry to the villa is through the private compound of Hermosa Cove Boutique Resort.

Promiseas

Ocho Rios Villa

from $4000 /night
up to 16 guests

Promiseas

8 bedroom 8 bath Jamaica villa in Ocho Rios

Promiseas Villas are located on a fabulous private sandy cove which are newly completed and exceptional in every way imaginable.

Seaside Nl Sharpenai Standard

Seaside Villa at Round Hill

Montego Bay Villa

from $4400 /night
up to 8 guests

Seaside Villa at Round Hill

4 bedroom 4 bath Jamaica villa in Montego Bay

Seaside was completely renovated & refurbished in 2018. This amazing sea front property is one of the newest premier villas at Round Hill.

Canoe Cove Nl

Canoe Cove on the Beach

Ocho Rios Villa

from $4600 /night
up to 14 guests

Canoe Cove on the Beach

7 bedroom 8 bath Jamaica villa in Ocho Rios

In the 1950’s, Kingston attorney Clinton Hart happened onto this remarkable 3-acre waterfront location, bought it and built a simple beach cottage for his family. Through four generations, Canoe Cove has been a beloved family home, virtually unembellished. In 2015, Hart’s grandson replaced the worn cottage with a new sort of architecture, straightforward, uncomplicated and loaded with thoughtful comforts and essentials to redefine luxury in a beachy, barefoot lifestyle.

Dji

Haystack at the Tryall Club

Montego Bay Villa

from $4714 /night
up to 20 guests

Haystack at the Tryall Club

10 bedroom 10 bath Jamaica villa in Montego Bay

Its remarkable architecture defines spacious bedroom suites, a long furnished verandah, a striking inside dining room and large family play room ~ all enhanced by overviews of the long private pool and acres of landscaped lawns and breathtaking views of the deep blue Caribbean Sea.

Malatai NL +copy

Malatai on the Beach

Ocho Rios Villa

from $5000 /night
up to 16 guests

Malatai on the Beach

8 bedroom 8.5 bath Jamaica villa in Ocho Rios

MALATAI is a fabulous contemporary home with modern updated bedrooms and noteworthy bathrooms nestled on a wide beachfront on the beautiful Old Fort Bay Beach. While privately located, Malatai is only minutes from Dolphin Cove, famous Dunn‘s River Falls, and lively Ocho Rios with its wide selection of duty-free shopping, excursions, and music.

Frankfort on the Beach

Ocho Rios Villa

from $5500 /night
up to 12 guests

Frankfort on the Beach

6 bedroom 7 bath Jamaica villa in Ocho Rios

17th Century fortress restored as a remarkable private home on a perfect private Caribbean beach.

Find Jamaica Villas


Travel Dates
Travel Dates


Villa Size
Villa Size

Default minimum and maximum values represent the current range of villas in Jamaica.

Price Range
Price Range (per night)

Prices represent the starting per-night rate for matched villas. Default minimum and maximum prices represent the current range of villas in Jamaica.

Amenities
Amenities
Collections
Collections
Locations
Locations

If none are checked then all destinations are included.

Villa Destinations


Find Jamaica Villas