Browse 195 Villas

From $2597.43 Per Night

Tryall - Haystack, Montego Bay

Haystack is the only eight-bedroom villa at the posh Tryall Club. Completed in 2008, it is also among the newest. 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. Distinctive at Haystack is the wonderful ...

Jamaica, Hillside, Montego Bay
8 Bedrooms , 8 Bathrooms
Maximum Occupancy: 16


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From $2337.71 Per Night

Tryall - Hummingbird House, Tryall

Hummingbird House has recently undergone a two year renovation and expansion, becoming one of the finest properties within the Tryall Club! Premier 7 bedroom private villa on 4 acres of meticulously landscaped grounds magnificent views of the Caribbean Sea heated infinity edge pool staff of 5: butler, chef, gardener, housekeeper, laundress WiFi throughout 70'' HD flat screen TV in living room 2 complimentary golf carts Tryall Club Temporary Membership Fee ...

Jamaica, Hillside, Tryall
7 Bedrooms , 7 Bathrooms , 1 Half Bathrooms
Maximum Occupancy: 14


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From $1948.00 Per Night

Tryall - Karma Bay Villa, Tryall Resort

Karma Bay Villa at Tryall is s 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.BEAUTIFULLY RENOVATED in 2013! 6-bedroom private villa at the famous Tryall Club rated Premier (highest luxury category) full staff: butler, cook, housekeeper, laundress, gardener printer and fax machine wireless internet throughout board games iPod ...

Jamaica, Waterfront with small beach, Tryall Resort
6 Bedrooms , 6 Bathrooms


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From $3052.00 Per Night

Tryall - L'Dor V'Dor, Tryall Resort

Tucked away on a hill overlooking the majestic Tryall Club and providing 360 degree panoramic views of Montego Bay and Hanover, L’Dor V’Dor is a haven waiting to be discovered. The largest villa on the property; it has great flexibility to meet the needs of the most discriminating adult or large families with children. 9 bedrooms, 9 en-suite bathrooms, 3 powder rooms rated Premier (highest luxury category) heated private pool ...

Jamaica, Hillside waterview, Tryall Resort
9 Bedrooms , 9 Bathrooms


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From $2077.86 Per Night

Tryall - Phoenix on the Beach, 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. Architecturally distinctive, the rooms of Phoenix encompass 2,000 square feet and wrap around the 35-foot circular swimming ...

Jamaica, Beachfront, Montego Bay
7 Bedrooms , 7 Bathrooms
Maximum Occupancy: 14


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From $1948.00 Per Night

Tryall - Rose Cottage, Montego Bay

Rose Cottage is a large and lavish new 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. While nestled in the chic Tryall Club among other upscale homes, Rose Cottage is situated on a large plot of beautifully landscaped grounds and is quite private. Unique is ...

Jamaica, Hillside, Montego Bay
6 Bedrooms , 7 Bathrooms , 2 Half Bathrooms
Maximum Occupancy: 12


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From $1948.00 Per Night

Tryall - Viviana Villa , Montego Bay

Enter a quarter-mile driveway, beautifully landscaped with brilliant bougainvillea on all sides. Then see the Travertine-paved Italianate courtyard which is the dramatic entrance to Viviana. You're home. On a remarkable six private acres on a plum site at the prestigious Tryall Club, Viviana is distinguished by the top rank of Premier. Uniquely private, the feeling is being in a world of your own, wonderfully quiet and tranquil while just minutes ...

Jamaica, Golf Course, Montego Bay
6 Bedrooms , 7 Bathrooms , 1 Half Bathrooms
Maximum Occupancy: 17


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From $2192.86 Per Night

Turtle Breeze Villa, Grace Bay, Providenciales

Turtle Breeze villa is a brand new, 6-bedroom, luxury villa on the World Famous Grace Bay Beach where you have excellent snorkel right out your door on Smith's Reef Passing through the iron gate, you will be amazed at the architectural beauty against the aqua waters. Built on two levels, Turtle Breeze is unique in design and features separate pods for each of the five bedrooms with en-suite bathrooms, air-conditioning, ...

Turks and Caicos, Beachfront, Grace Bay, Providenciales
6 Bedrooms , 6 Bathrooms
Maximum Occupancy: 12


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From $1857.00 Per Night

VI Friendship Villa, Estate Contant, Great Cruz Bay

This beautifully-rendered oasis of 'the good life,' built in 2008, has been wowwing lucky guests who spend their sun-kissed vacation at unique VI Friendship Villa. All the key elements of a superb vacation villa are right here: six equally-sized, air-conditioned queen bedroom/bath suites with individual private balconies, a sand bulkhead 'beach,' pool and hot tub, a stunning waterfront location right over silvery ocean waves, and an expansive view of Great ...

St. John, Oceanfront, Estate Contant, Great Cruz Bay
6 Bedrooms , 7 Bathrooms , 2 Half Bathrooms
Maximum Occupancy: 12


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From $1440.00 Per Night

Vieux Caribe, Providenciales

Vieux Caribe Completed in the year 2000 has 5 master bedrooms, each with en-suite bathrooms. There is also an optional separate two-bedroom suite available in the event you need more than 5 bedrooms. Each bedroom opens onto a covered deck affording spectacular views of the Caribbean sea,stunning sunsets and the villas pool. The outdoor dining area is a great place to enjoy your dinner and take in the beauty of ...

Turks and Caicos, Waterfront, Providenciales
7 Bedrooms , 7 Bathrooms , 1 Half Bathrooms
Maximum Occupancy: 14


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From $550.00 Per Night

Villa Motts, Signal Hill, Southeast

Perched on a hillside and enjoying the cool sea breezes, Villa Motts looks across Rockley Bay to Scarborough. The brand new villa is of a high quality and spacious enough to accommodate 2 or 3 families, but also suitable for smaller groups. On the ground floor is the open-plan living and dining, kitchen, three bedrooms and a veranda across the front of the villa. The veranda overlooks the large swimming ...

Tobago, Hillside, Signal Hill, Southeast
6 Bedrooms , 6 Bathrooms , 1 Half Bathrooms
Maximum Occupancy: 12


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From $2700.00 Per Night

Villa Oasis, Grace Bay Beach, Providenciales

Appropriately named, Villa Oasis is located on Grace Bay on the north shore of the island. The beach is one of the most exceptional beaches in the Caribbean and offers extraordinary swimming and snorkeling. Extremely private, the home is pure beach bliss. It is set so close to the water that guests can enjoy the soothing sounds of waves lapping. The interiors are comfortably furnished. The Great Room has tall ...

Turks and Caicos, Beachfront, Grace Bay Beach, Providenciales
7 Bedrooms , 6 Bathrooms
Maximum Occupancy: 14


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From $1800.00 Per Night

Villa Paradise, near Sandy Point

This 6/7 bedroom gated 7,000 square foot property with large oceanfront freshwater pool sits on a 3.5 acre landscaped Estate situated right on the Caribbean Sea with the mountains of St. Martin/St. Maarten beyond The villa's protected harbor with boat dock and small private cove are located directly in front of the Villa. The adjacent coral reef offers some of the best snorkeling opportunities in Anguilla. There is a small boat ...

Anguilla, Beachfront, near Sandy Point
6 Bedrooms , 6 Bathrooms
Maximum Occupancy: 14


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From $1571.00 Per Night

Villa St. John, Chocolate Hole

Come and enjoy this one of a kind, palatial, Mediterranean-style retreat, perched on a beautifully landscaped bluff overlooking a secluded bay on the island paradise of St. John, U.S. Virgin Islands. A dream come true, this stunning villa welcomes you with gentle tropical breezes, warm and delicious sunlight to bathe in, sweet floral scents of the tropics and the soothing music of waves caressing the white-sand beach below. A rare ...

St. John, Beachfront, Chocolate Hole
6 Bedrooms , 6 Bathrooms , 2 Half Bathrooms
Maximum Occupancy: 16


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From $2000.00 Per Night

Vistamar, Sandy Lane Estate

Stylish and spacious, Vistamar has 6 bedrooms and sits on 2 acres of beautifully landscaped tropical gardens in a quiet cul-de-sac within the exclusive Sandy Lane Estate on the west coast of Barbados. With all the benefits of luxury villa living, Vistamar features a stunning partially covered veranda which leads to the pool deck and covered poolside gazebo along with a two-bedroom self-contained cottage, just a stones’ throw away from the ...

Barbados, Neighborhood, Sandy Lane Estate
6 Bedrooms , 6 Bathrooms
Maximum Occupancy: 12


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From $1115.00 Per Night

Vittoria, Simpson Bay Beach

This lovely 6 bedroom villa is located on the 2+ mile crystal clear and sandy beach of Simpson Bay. Just a few minutes from restaurants, bars, grocery store, and the vibrant nightlife of St. Maarten.Vittoria is a 3,500 square meter plus private gated property containing a variety of plants as well as a pool and Jacuzzi, a large outdoor dining area facing the beach, and a sun deck and umbrellas ...

St. Martin, Beachfront, Simpson Bay Beach
6 Bedrooms , 5 Bathrooms
Maximum Occupancy: 12


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From $2278.57 Per Night

Whispering Waters, Discovery Bay

Whispering Waters, on Discovery Bay,completed November 2006 - brand new ultimate in luxury, 7 bedrooms, 7 ensuite bathrooms - all bedrooms air conditioned. This deluxe Villa is located right beside sister villa Keela Wee.There are 7 bedrooms with 5 king-size beds upstairs and 2 bedrooms downstairs, each with twin double beds, all with ensuite bathrooms and closets, wooden floors throughout. Interiors are luxuriously designed with beautiful silks and original art. ...

Jamaica, Beachfront, Discovery Bay
7 Bedrooms , 7 Bathrooms
Maximum Occupancy: 14


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From $2285.71 Per Night

Whispering Waters on Discovery Bay, Discovery Bay

From the homeowner who created the wonderful villa Keela Wee comes its new sister house, Whispering Waters. Located side by side, these neighboring villas combine to offer 13 bedrooms, 2 swimming pools, 2 private beaches and 2 tennis courts lit for night play. Each villa has its own private coral cove and sandy beach. Both villas overlook one of Jamaica’s loveliest crystal clear bodies of water, Discovery Bay. They can ...

Jamaica, Waterfront, Discovery Bay
7 Bedrooms , 7 Bathrooms
Maximum Occupancy: 14


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From $1800.00 Per Night

Witenblauw Estate , Pelican Key

Located in Pelican Key on the southern shores of Dutch Sint Maarten, the Witenblauw vacation rental home is truly a vacationer’s paradise Witenblauw Estate is a magnificent, sprawling 6 bedroom paradise built for entertaining and relaxation! If a picture is worth a thousand words then Witenblauw speaks volumes when it comes to making memories of a lifetime. This ocean side retreat redefines the traditional get-a-way vacation experience... you'll enjoy the ...

St. Martin, Beachfront, Pelican Key
6 Bedrooms , 6 Bathrooms
Maximum Occupancy: 12


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From $2400.00 Per Night

Zenaida Beach & Tennis Estate,

Zenaida Beach and Tennis Estate is nestled on three acres of lush tropical gardens with sweeping views of the Caribbean Sea, and the mountains of St Martin and St Barths beyond. Luxuriate in the white powdery sands of our deserted beach. Enjoy ultimate privacy in a three-, four-, or seven-bedroom pavilion with pool. For tennis players we provide the only Har-Tru soft court in the Leeward Islands lit for playing ...

Anguilla, Beachfront
7 Bedrooms , 7 Bathrooms
Maximum Occupancy: 14


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