Villa search results


Cliffside Nl

Cliffside Cottage

Caribbean Villa

from $643 /night
up to 10 guests

Cliffside Cottage

5 bedroom 5 bath Jamaica villa in Montego Bay

Dramatically perched on a lush green hillside above the sea, Cliffside Cottage commands stunning views of the deep blue Caribbean Sea by day and romantic lights that glisten across Montego Bay after sunset. Sunrise and sunset vistas from this vantage point are mesmerizing.

ES+pool+

Endless Summer

Caribbean Villa

from $1429 /night
up to 14 guests

Endless Summer

7 bedroom 7 bath Jamaica villa in Montego Bay

One of the most glamorous villas in Jamaica, Endless Summer is a turreted mansion with breathtaking views of the Caribbean Sea.

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Everything Nice by the Sea

Caribbean Villa

from $2200 /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 water front property on Emerald Quay. Nestled in between the Breathless & Secrets Hotels & within walking distance to the Montego Bay Yacht Club.

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Fairway Manor

Caribbean Villa

from $1815 /night
up to 14 guests

Fairway Manor

7 bedroom 9 bath Jamaica villa in Montego Bay

Stunning for its massive renovation and outstanding new features. 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.

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Hidden Bay by the Sea

Caribbean 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.

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Hummingbird House at the Tryall Club

Caribbean Villa

from $2714 /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!

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Jus Paradise at Rose Hall

Caribbean Villa

from $743 /night
up to 6 guests

Jus Paradise at Rose Hall

3 bedroom 6 bath Jamaica villa in Montego Bay

JUS' PARADISE is an charming private villa located in a gated residential area of upscale homes in the lush hills of Rose Hall. This well-located home sits between two renowned golf courses: the challenging White Witch and championship Cinnamon Hill course. Five minutes west is the famous Half Moon course.

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Karma Bay at the Tryall Club

Caribbean Villa

from $1500 /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.

Slide

Lime Acre on the Beach

Caribbean Villa

from $1360 /night
up to 10 guests

Lime Acre on the Beach

5 bedroom 6 bath Jamaica villa in Whitehouse

Take a step back in time. Welcome to Lime-Acre Villa, a 5 bedroom villa that sits on the South Coast among the untouched beauty of the Jamaica of years gone by.

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Ma Moura at the Tryall Club

Caribbean Villa

from $1571 /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.

Out of the Blue on the Beach

Caribbean Villa

from $750 /night
up to 8 guests

Out of the Blue on the Beach

4 bedroom 4 bath Jamaica villa in Treasure Beach

Out of the Blue is an oxymoron: a contemporary home in Old Jamaica. And what a home it is! The villa sits on the longest uninterrupted expanse of sea view at beach level of any other beach property in this group.

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Pavilion

Caribbean Villa

from $1200 /night
up to 10 guests

Pavilion

5 bedroom 6 bath Jamaica villa in Montego Bay

Pavilion is an exquisite villa privately located at the end of a cul-de-sac with magnificent views of the Caribbean Sea to the north and a tranquil 10-mile view of the mountains to the south. It is spacious, quiet, peaceful and beautiful.

Phoenix+swimming+pool

Phoenix on the Beach at the Tryall Club

Caribbean Villa

from $2357 /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.

Round House 3

Round House at the Tryall Club

Caribbean Villa

from $1339 /night
up to 14 guests

Round House at the Tryall Club

7 bedroom 10 bath Jamaica villa in Montego Bay

From the moment one approaches its colorful entrance, the eponymous architecture of Round House is intriguing. Spiral stairways and balconies connect multiple living, dining and sleeping areas in this eight-bedroom staffed villa at the Tryall Club.

Pool

Scotch on the Rocks

Caribbean Villa

from $1140 /night
up to 10 guests

Scotch on the Rocks

5 bedroom 5 bath Jamaica villa in Ocho Rios

SCOTCH ON THE ROCKS is a charming turquoise villa overlooking the Caribbean Sea.

Sea Grapes on the Beach

Caribbean Villa

from $1000 /night
up to 12 guests

Sea Grapes on the Beach

6 bedroom 6 bath Jamaica villa in Discovery Bay

On its own sugary white sand beach lapped by the clear turquoise waters of Discovery Bay sits the charming home Sea Grapes. The translucent azure waters here are excellent for swimming and kayaking. Surrounding the swimming pool is a spacious grassy lawn, wonderful for children and games.

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Serenity on the Beach

Caribbean Villa

from $1021 /night
up to 8 guests

Serenity on the Beach

4 bedroom 4 bath Jamaica villa in Montego Bay

SERENITY is one of the most beloved and often revisited villas on Jamaica's beautiful north coast. Its prize location is a waterfront acre 8 miles west of Montego Bay. Grounds include a shared tennis court and basketball hoop and a heated pool.

Seven Seas Jamaica Villas

Seven Seas on the Beach

Caribbean Villa

from $1071 /night
up to 8 guests

Seven Seas on the Beach

4 bedroom 4 bath Jamaica villa in Ocho Rios

The morning sun has turned the sea and the dew on the palm trees to silver. The non-stop trade winds waft through the rooms of the villa and the aroma of fresh-baked bread works its way from the kitchen to my bedroom window.

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Sugar Bay on the Beach

Caribbean Villa

from $1786 /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!

Sunset Tryall Nl

Sunset on the Beach at the Tryall Club

Caribbean Villa

from $2000 /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.

Pool

Windsong

Caribbean Villa

from $643 /night
up to 8 guests

Windsong

4 bedroom 4 bath Jamaica villa in Montego Bay

Windsong is an exquisite and very private home just minutes from Round Hill. Designed by noted architect Kasimir Coribut, the site benefits from spectacular views day and night and the most favorable tradewinds. The east view captures the sunrise and Montego Bay ... the west view is an equally lovely vista of Round Hill, the sea and the sunset.

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Yellowbird at the Tryall Club

Caribbean Villa

from $786 /night
up to 8 guests

Yellowbird at the Tryall Club

4 bedroom 4 bath Jamaica villa in Montego Bay

Yellowbird is an excellent family home on a large, lovely landscaped site overlooking the Tryall golf course and the Caribbean Sea. The tradewinds are delightful; the view is wonderful.

Calypso Shores

Caribbean Villa

from $950 /night
up to 8 guests

Calypso Shores

4 bedroom 4 bath Jamaica villa in Montego Bay

Calypso Shores is located in a lovely California-style residential neighborhood named Lagoons. Its prize location is a waterfront acre on a calm lagoon. Lovers of water sports will revel in this location.

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Eight Rivers at Prospect Estate

Caribbean Villa

from $996 /night
up to 8 guests

Eight Rivers at Prospect Estate

4 bedroom 4.5 bath Jamaica villa in Ocho Rios

Set within one and a half acres of tropical gardens, populated by mature indigenous trees, plants and flowers, the Eight Rivers villa has a magnificent swimming pool and sun terrace overlooking a gazebo and the sea beyond.

Linga Awile Nl

Linga-Awile Cottage on the Beach

Caribbean Villa

from $471 /night
up to 6 guests

Linga-Awile Cottage on the Beach

3 bedroom 4 bath Jamaica villa in Discovery Bay

This 3-bedroom casual cottage shares a delightful waterfront site with its sister property, Coral Cove Villa, on the clear waters of Discovery Bay. Linga-Awile sits on a lovely, long, large lawn. Beyond the lawn and swimming pool is its sugary white sand beach with two thatched roof umbrellas for shade.

Sea Haven Sea

Sea Haven on Discovery Bay

Caribbean Villa

from $500 /night
up to 8 guests

Sea Haven on Discovery Bay

4 bedroom 4 bath Jamaica villa in Discovery Bay

Located on a private waterfront acre, Sea Haven is a traditional West Indian cottage dressed in charming periwinkle blue. It sits directly on the edge of beautiful Discovery Bay.

Seaside Nl Sharpenai Standard

Seaside Villa at Round Hill

Caribbean Villa

from $3572 /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.

Sentosa

Caribbean Villa

from $15000 /night
up to 16 guests

Sentosa

8 bedroom 8 bath Turks & Caicos villa in Providenciales

Sentosa (Peace and Tranquility) Villa is a beautiful contemporary style home on 1.5 acres of land on the number 1 rated beach in the world.

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Summertime at Silver Sands

Caribbean Villa

from $500 /night
up to 8 guests

Summertime at Silver Sands

4 bedroom 4 bath Jamaica villa in Montego Bay

Summertime at Silver Sands has a wonderful beach vibe, it benefits from cool sea breezes and is a relaxed and unfussy villa located on the renowned Silver Sands Beach Club, a collection of privately owned villas all overlooking the Caribbean sea.

Vision Beach

Caribbean Villa

from $7700 /night
up to 10 guests

Vision Beach

5 bedroom 7 bath Turks & Caicos villa in Providenciales

Vision Beach is a modern beach house located on the exclusive Prince of Wales Drive along a quiet stretch of Grace Bay Beach, one of the best beaches in the world.

Blue+Heaven NL

Blue Heaven

Caribbean Villa

from $643 /night
up to 6 guests

Blue Heaven

3 bedroom 2.5 bath Jamaica villa in Montego Bay

This lovely villa and grounds sit on a hilltop overlooking Montego Bay and beyond. Perfectly situated only 20 minutes from the airport and 15 minutes from the Tryall Club. Blue Heaven also comes with a complimentary driver on 7-night reservations.

Coach House B Fin

Coach House at Good Hope

Caribbean Villa

from $800 /night
up to 14 guests

Coach House at Good Hope

7 bedroom 8 bath Jamaica villa in Montego Bay

The Coach House at Good Hope is a fantastic informal gathering place for families, retreats, and friends - with space for togetherness, space for discovering nature, space for alone time. Like travelling through a time warp, to visit Jamaica's countryside is to experience another Jamaica of 30 years ago. The pace is slow, the lifestyle uncomplicated, the people are kind and calm, service is relaxed and meals are served family style. For larger groups The Coach House villa & The Great House villa can be rented together to offer 14 bedrooms, accommodating 28 guests.

Property+with+Kayaks+and+Chairs

Sandcastle Beach House

Caribbean Villa

from $2200 /night
up to 8 guests

Sandcastle Beach House

4 bedroom 4.5 bath Anguilla villa in Limestone Bay

Welcome to Anguilla’s newest rental property, Sandcastle Beach House! We offer a one of a kind experience for couples, families, or private events.

Silver Sands

Silver Sands

Caribbean Villa

from $6900 /night
up to 16 guests

Silver Sands

8 bedroom 7.5 bath Turks & Caicos villa in Thompson Cove

This spectacular, spacious 8 bedroom family home has been extended and renovated with love, a European design flare and imagination.

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Spanish Cove

Caribbean Villa

from $957 /night
up to 8 guests

Spanish Cove

4 bedroom 4 bath Jamaica villa in Runaway Bay

Located on Runaway Bay, Spanish Cove is perched on a beautiful sandy beach nearby the heart of town. Runaway Bay is known for beautiful beaches, coral reefs, excellent scuba diving as well as the well-known Green Grotto Caves. It is also conveniently located and within easy reach of Ocho Rios for restaurants, excursions, and shopping.

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Seawards

Caribbean Villa

from $575 /night
up to 6 guests

Seawards

3 bedroom 4 bath Barbados villa in St. James

Seawards is a lovely three-bedroom vacation rental property sitting on the edge of a lovely quiet beach on the west coast of Barbados.

Bee Happy Nl

Bee Happy at the Tryall Club

Caribbean Villa

from $629 /night
up to 4 guests

Bee Happy at the Tryall Club

2 bedroom 3 bath Jamaica villa in Montego Bay

Bee Happy, newly renovated and newly named! The home owners have done a masterful job. This staffed two-bedroom villa at the legendary Tryall Great House is sumptuous. The villa is distinguished by beautiful Jamaican crafted artisan work, including dramatic new ceilings in the entrance and living areas, bespoke furnishings and artwork, breathtaking views of sea, sky and mountain from its comfy furnished veranda and spacious interiors, top that with a private plunge pool and you may never need to leave!

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Mirador at the Tryall Club

Caribbean Villa

from $357 /night
up to 2 guests

Mirador at the Tryall Club

1 bedroom 2 bath Jamaica villa in Montego Bay

Mirador is a stylish one-bedroom apartment at the posh Tryall Club. Its prize location provides both proximity to the elegant Tryall Club Great House and a breathtaking view over the deep blue Caribbean Sea and the manicured championship golf course.

Sailrock Resort South Caicos Horizon 1

1 BR Beachfront Villa at Sailrock Resort

Caribbean Villa

from $1950 /night
up to 3 guests

1 BR Beachfront Villa at Sailrock Resort

1 bedroom 1 bath Turks & Caicos villa in South Caicos Island

Wake up to the sounds of the ocean washing ashore

Amanyara Two Bedroom Pool Villa High Res

2 Bedroom Pool Villa at Amanyara

Caribbean Villa

rates on request
up to 4 guests

2 Bedroom Pool Villa at Amanyara

2 bedroom 2.5 bath Turks & Caicos villa in Providenciales

Perfect for families the two-bedroom Pool Villa offers a large living and dining room, two bedrooms, private fitness room, a nanny’s room and open up onto an expansive sun deck with private lap pool.

Sailrock Resort South Caicos Horizon 1

2 BR Beachfront Premier Villa at Sailrock Resort

Caribbean Villa

from $2780 /night
up to 4 guests

2 BR Beachfront Premier Villa at Sailrock Resort

2 bedroom 2 bath Turks & Caicos villa in South Caicos Island

Wake up to the sounds of the ocean washing ashore

B Peter Bay Beach Villa Pool

2B at Peter Bay

Caribbean Villa

from $2064 /night
up to 8 guests

2B at Peter Bay

4 bedroom 4.5 bath USVI villa in St. John

Besides the amazing 2B Peter Bay Beach Villa being just steps above a sandy clear water North Shore beach within the stunning Virgin Islands National Park, this home boasts 4 master bedroom suites, a pool and a hot tub built and designed at the highest quality letting in the big multi blue views that could rival any global destination.

Villa Exterior Living Dining Pavilion

3 Bedroom Tranquility Villa at Amanyara

Caribbean Villa

rates on request
up to 8 guests

3 Bedroom Tranquility Villa at Amanyara

3 bedroom 3 bath Turks & Caicos villa in Providenciales

A nature lover's paradise, Amanyara sits on a promontory on the western shore of Providenciales.

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3 Bedroom Villa at Ambergris Cay All Inclusive Resort

Caribbean Villa

from $6100 /night
up to 8 guests

3 Bedroom Villa at Ambergris Cay All Inclusive Resort

3 bedroom 3.5 bath Turks & Caicos villa in Ambergris Cay

Spacious 2-story villa with 3 bedrooms and 3 ½ bathrooms and stunning sunrise views.

Paradise Beach 3 Bed Rgb

3 Bedroom Villa at Paradise Beach

Caribbean Villa

from $2065 /night
up to 6 guests

3 Bedroom Villa at Paradise Beach

3 bedroom 3.5 bath Nevis villa in Paradise Beach

Located only footsteps from the sandy beaches of the Caribbean ocean, these Villas are a split-level design with the upstairs king suite opening to a balcony with gorgeous panoramic views of the ocean.

Sailrock Resort Great House Infinity Pool

3 BR Beachfront Villa at Sailrock Resort

Caribbean Villa

from $3880 /night
up to 8 guests

3 BR Beachfront Villa at Sailrock Resort

3 bedroom 3 bath Turks & Caicos villa in South Caicos Island

Wake up to the sounds of the ocean washing ashore

Villa 4 Infinity Pool

4 Bedroom Beach Sala Villa at Amanyara

Caribbean Villa

rates on request
up to 10 guests

4 Bedroom Beach Sala Villa at Amanyara

4 bedroom 4 bath Turks & Caicos villa in Providenciales

A nature lover's paradise, Amanyara sits on a promontory on the western shore of Providenciales.

Villa 1 Terrace

4 Bedroom Beach Villa at Amanyara

Caribbean Villa

rates on request
up to 10 guests

4 Bedroom Beach Villa at Amanyara

4 bedroom 4 bath Turks & Caicos villa in Providenciales

A nature lover's paradise, Amanyara sits on a promontory on the western shore of Providenciales.

Paradise Beach 4 Bed O Rgb

4 Bedroom Beach Villa at Paradise Beach

Caribbean Villa

from $2595 /night
up to 8 guests

4 Bedroom Beach Villa at Paradise Beach

4 bedroom 4.5 bath Nevis villa in Paradise Beach

Located only steps from the sandy beaches of the Caribbean ocean, the Beachfront Villas have private patios, thatched cabana for outdoor dining, and plunge pools, all with panoramic views of the ocean and the towering Mount Nevis.

Paradise Beach 4 Bed G Rgb

4 Bedroom Garden Villa at Paradise Beach

Caribbean Villa

from $2550 /night
up to 8 guests

4 Bedroom Garden Villa at Paradise Beach

4 bedroom 4.5 bath Nevis villa in Paradise Beach

Located in mature, lush tropical gardens only a short walk to the Caribbean ocean, the Garden Villas have private patios, a thatched cabana for outdoor dining, and plunge pools, all within private lush tropical gardens.

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