Caribbean Villa Rentals


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Sol e Luna

St. Martin, St. Martin (French)

from $572 /night
up to 6 guests

Sol e Luna

3 bedroom 3.5 bath St. Martin villa in St. Martin (French)

Sol e Luna is a very pretty, French Creole style villa that blends Caribbean charm with a contemporary attitude.

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Smuggler’s Nest

St. Lucia, Gros Islet

from $575 /night
up to 4 guests

Smuggler’s Nest

2 bedroom 2.5 bath St. Lucia villa in Gros Islet

This magnificent two-bedroom home is one of the finest in the whole Caribbean and was extensively described in one of the issues of Architectural Digest.

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Skyline at Tryall

Jamaica, Montego Bay

from $571 /night
up to 2 guests

Skyline at Tryall

1 bedroom 2 bath Jamaica villa in Montego Bay

Stella Marina is a very smart and well-presented one-bedroom villa with stunning ocean and golf course views.

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Sky Villa

Anguilla, Long Bay Village

from $4500 /night
up to 10 guests

Sky Villa

5 bedroom 4 bath Anguilla villa in Long Bay Village

Inspired by cloudless skies, Sky Villa offers an elevated slice of island life.

Sky Blue

St. Martin, Sint Maarten

from $608 /night
up to 11 guests

Sky Blue

5 bedroom 5.5 bath St. Martin villa in Sint Maarten

Sky Blue is a luxurious, five-bedroom, ocean-view villa where you will see all the hues of the blue sky and ocean, located in the exclusive gated community of Dawn Beach Estates on St. Maarten.

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Skrutten

St. Barthélemy, Pointe Milou

from $750 /night
up to 8 guests

Skrutten

4 bedroom 4 bath St. Barthélemy villa in Pointe Milou

The vacation villa rental Skrutten is a property located on the heights of Pointe-Milou.

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Sirena

Dominican Republic, Punta Cana

from $2860 /night
up to 14 guests

Sirena

6 bedroom 6.5 bath Dominican Republic villa in Punta Cana

Sirena is located in the exclusive gated community of Punta Cana Resort and Club, a 26-square mile paradise that is blessed with a temperate year-round climate, light rainfall, and soft breezes.

Sirena Blue

Dominican Republic, Punta Cana

from $6430 /night
up to 14 guests

Sirena Blue

5 bedroom 5 bath Dominican Republic villa in Punta Cana

The villa of a globetrotter!

Silver Sands

Silver Sands

Turks & Caicos, Thompson Cove

from $5800 /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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Silent Waters

Jamaica, Montego Bay

from $2853 /night
up to 16 guests

Silent Waters

8 bedroom 6 bath Jamaica villa in Montego Bay

Silent Waters is one of the most glamorous private homes in the Caribbean. It is distinguished by world-class architecture and design, breathtaking location, and exquisite accommodations and service.

Seven Seas

Seven Seas on the Beach

Jamaica, Ocho Rios

from $1243 /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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Serenity on the Beach

Jamaica, Montego Bay

from $1093 /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.

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Serendipity

British Virgin Islands, Virgin Gorda

from $768 /night
up to 6 guests

Serendipity

3 bedroom 2 bath BVI villa in Virgin Gorda

Secluded Oceanfront Caribbean Vacation Villa on Leverick Bay.

Serena

St. Martin, St. Martin (French)

from $1643 /night
up to 10 guests

Serena

5 bedroom 5.5 bath St. Martin villa in St. Martin (French)

This elegant, beachfront, villa is truly exceptional.

Sentosa

Turks & Caicos, Providenciales

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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Secret Garden

Barbados, St. James

from $530 /night
up to 6 guests

Secret Garden

3 bedroom 3 bath Barbados villa in St. James

Secret Garden at Merlin Bay is a lovely three bedroom fully air-conditioned villa with a private plunge pool set on two floors.

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Secret Bay - Zabuco Honeymoon Villas II I

Dominica, Secret Bay

from $2043 /night
up to 2 guests

Secret Bay - Zabuco Honeymoon Villas II I

1 bedroom 1 bath Dominica villa in Secret Bay

Secret Bay’s Zabuco Villas are the most beautiful Honeymoon villas in the Caribbean.

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Secret Bay - Zabuco Honeymoon Villa I

Dominica, Secret Bay

from $2708 /night
up to 2 guests

Secret Bay - Zabuco Honeymoon Villa I

1 bedroom 1 bath Dominica villa in Secret Bay

Secret Bay’s original Zabuco Villa is where the beautiful dream of Secret Bay began.

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Secret Bay - Ylang Ylang Villa

Dominica, Secret Bay

from $1291 /night
up to 2 guests

Secret Bay - Ylang Ylang Villa

1 bedroom 1 bath Dominica villa in Secret Bay

Rising up from the ground from a single stem, the Ylang Ylang Villas are the latest stunning creation at Secret Bay.

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Secret Bay - Ti-Fey` Villa I

Dominica, Secret Bay

from $1575 /night
up to 2 guests

Secret Bay - Ti-Fey` Villa I

1 bedroom 2 bath Dominica villa in Secret Bay

A six-star all-villa rainforest resort experience, featuring secluded clifftop residential-style villas with private plunge pools, dedicated villa hosts, on-call concierge, chefs and guides, secret beaches, and transformative experiences curated just for you.

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Seaside Villa at Round Hill

Jamaica, Montego Bay

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.

Seascape

Turks & Caicos, Providenciales

from $4320 /night
up to 10 guests

Seascape

5 bedroom 5.5 bath Turks & Caicos villa in Providenciales

Located on the tranquil shores of Grace Bay, Seascape epitomizes luxury island lifestyles.

Seagrace Villa

Turks & Caicos, Providenciales

from $1500 /night
up to 10 guests

Seagrace Villa

5 bedroom 4 bath Turks & Caicos villa in Providenciales

Seagrace Villa is nestled on the canal in the gated community of Leeward, just moments away from Salt Bar and Grill.

Seaduced at Royal Westmoreland

Barbados, St. James

from $1850 /night
up to 10 guests

Seaduced at Royal Westmoreland

5 bedroom 5 bath Barbados villa in St. James

Seaduced is one of the few contemporary architect designed holiday villas available for rent in Royal Westmoreland, home to one of the finest golf courses in the Caribbean.

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Seacove

United States Virgin Islands, St. John

from $2451 /night
up to 10 guests

Seacove

5 bedroom 5.5 bath USVI villa in St. John

Overlooking sublime views of Peter Bay and beyond, Seacove is one of the most beautifully-detailed homes we offer, set within lush landscaping replete with bananas, lime, papayas, citrus, coconut palms, and a soothing garden waterfall.

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Seaclusion

Turks & Caicos, Providenciales

from $10400 /night
up to 16 guests

Seaclusion

8 bedroom 9.5 bath Turks & Caicos villa in Providenciales

Located on the tranquil shores of Grace Bay Beach, Seaclusion epitomizes luxury island lifestyles.

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Seacliff

Turks & Caicos, Providenciales

from $1575 /night
up to 10 guests

Seacliff

5 bedroom 5.5 bath Turks & Caicos villa in Providenciales

Set high atop the cliff in scenic Chalk Sound, Villa Seacliff is a striking luxury villa with incredible 180-degree oceanfront panoramas.

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Sea Villa

Anguilla, Long Bay Village

from $5200 /night
up to 11 guests

Sea Villa

6 bedroom 5 bath Anguilla villa in Long Bay Village

Perched overlooking the azure water, Sea Villa offers unrivaled Caribbean views and private stairs leading to our secluded stretch of sand.

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Sea Horse Harbour Jumby Bay

Antigua, Jumby Bay Island

from $6900 /night
up to 6 guests

Sea Horse Harbour Jumby Bay

3 bedroom 3 bath Antigua villa in Jumby Bay Island

At Sea Horse, guests indulge in a tropical luxury escape.

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Sea Haven on Discovery Bay

Jamaica, Discovery Bay

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 and sitting directly on the edge of beautiful Discovery Bay.

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Sea Hare Harbour at Jumby Bay

Antigua, Jumby Bay Island

from $6900 /night
up to 6 guests

Sea Hare Harbour at Jumby Bay

3 bedroom 3 bath Antigua villa in Jumby Bay Island

Resting serenely along the shore of Harbour Beach, Sea Hare boasts an impressive strip of secluded private beach within arm’s reach of its cerulean-tiled infinity-edge pool.

Sea Grapes on the Beach

Jamaica, Discovery Bay

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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Sea Glass at Tryall Club

Jamaica, Montego Bay

from $1500 /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.

Sea Forever

United States Virgin Islands, St. John

from $1587 /night
up to 10 guests

Sea Forever

5 bedroom 5.5 bath USVI villa in St. John

This villa’s name has layers of meaning – not only can you can see forever from its vantage point above St. John’s southwestern shore, but you could also, happily, spend forever gazing at that incomparable panorama.

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Sea Breeze at Old Trees

Barbados, St. James

from $1050 /night
up to 6 guests

Sea Breeze at Old Trees

3 bedroom 3 bath Barbados villa in St. James

Sea Breeze at Old Trees is a luxury beachfront Barbados apartment offering exquisite panoramic views of the Caribbean Sea.

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Sea Breeze at Jumby Bay

Antigua, Jumby Bay Island

from $9800 /night
up to 8 guests

Sea Breeze at Jumby Bay

4 bedroom 4.5 bath Antigua villa in Jumby Bay Island

Dramatic views of the Caribbean Sea greet guests each morning at this comfortable four-bedroom retreat.

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Scotch on the Rocks

Jamaica, Ocho Rios

from $1380 /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.

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Schooner Bay 207 - Innisfree

Barbados, Speightstown

from $645 /night
up to 6 guests

Schooner Bay 207 - Innisfree

3 bedroom 3.5 bath Barbados villa in Speightstown

Schooner Bay 207 "Innisfree" is an elegant, three-bedroom residence located on the first floor of the Schooner Bay complex.

Schooner Bay 112

Barbados, Speightstown

from $285 /night
up to 2 guests

Schooner Bay 112

1 bedroom 1.5 bath Barbados villa in Speightstown

Escape the hustle and bustle of the world in your own private holiday home hideaway at the exclusive Schooner Bay on the serene Platinum coast of Barbados.

Saving Grace

Turks & Caicos, Providenciales

from $3600 /night
up to 8 guests

Saving Grace

5 bedroom 3.5 bath Turks & Caicos villa in Providenciales

Located in a residential area on Grace Bay Beach, Saving Grace Villa Providenciales is a 4,000+ square foot, two-story, L-shaped Colonial style villa nestled discreetly into a sunset-facing cove on this world-famous beach.

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Saramanda

Barbados, St. James

from $2200 /night
up to 10 guests

Saramanda

5 bedroom 5.5 bath Barbados villa in St. James

Saramanda is a luxurious and spacious five-bedroom villa with a large swimming pool located in the heart of the prestigious Sandy Lane Estate in St. James on the West Coast of Barbados.

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Sapphire Beach 211

Barbados, Christ Church

from $460 /night
up to 6 guests

Sapphire Beach 211

3 bedroom 3 bath Barbados villa in Christ Church

Sapphire Beach 211 is a popular holiday rental choice for those seeking a home-away-from-home experience.

Sapphire Beach 116

Barbados, Dover Beach

from $350 /night
up to 4 guests

Sapphire Beach 116

2 bedroom 2 bath Barbados villa in Dover Beach

This lovely condo is situated in the modern gated community of Sapphire Beach and offers South Coast luxury with lots of island charm.

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Sanzaru

Barbados, St. James

from $13750 /night
up to 22 guests

Sanzaru

11 bedroom 11.5 bath Barbados villa in St. James

This impeccable luxury Caribbean villa with five-star amenities exceeds all expectations for the ultimate luxury family holiday.

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Santosha

Anguilla, Long Bay Village

from $7500 /night
up to 22 guests

Santosha

9 bedroom 11 bath Anguilla villa in Long Bay Village

Surrender to the pull of island life at our exclusive beachfront estate.

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Sandyline

St. Martin, Terres Basses

from $4214 /night
up to 14 guests

Sandyline

7 bedroom 8 bath St. Martin villa in Terres Basses

Though the Villa Sandyline on St. Martin is just a short distance from the Caribbean Sea, which it overlooks from its elite Terres Basses location, visitors may find themselves loathe leaving the exquisite estate grounds.

Sandy Shore

Sandy Shore Villa

Turks & Caicos, Providenciales

from $2249 /night
up to 8 guests

Sandy Shore Villa

4 bedroom 4 bath Turks & Caicos villa in Providenciales

Sandy Shores is a 4 bedrooms all-suite beachfront villa located on the Southside of Providenciales in the Turtle Tail region.

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Sandy Cove at Jumby Bay

Antigua, Jumby Bay Island

from $9800 /night
up to 8 guests

Sandy Cove at Jumby Bay

4 bedroom 4 bath Antigua villa in Jumby Bay Island

Sandy Cove is a delightful beachfront retreat that makes any Caribbean dream vacation a reality.

Sandy Bottom

Sandy Bottom

Turks & Caicos, Providenciales

from $2500 /night
up to 8 guests

Sandy Bottom

4 bedroom 4 bath Turks & Caicos villa in Providenciales

Welcome to this cool, new, modern and contemporary property that sits on the South shores of Providenciales overlooking the turquoise Caicos Banks.

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Sandcastle Villa

Anguilla, Limestone Bay

from $2600 /night
up to 10 guests

Sandcastle Villa

5 bedroom 5 bath Anguilla villa in Limestone Bay

A secluded beachside Tuscan inspired 10,000 sq. ft. 5 bedroom villa on the North Shore of Anguilla with magnificent views of the ever changing shades of blue of the Atlantic Ocean.

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