Caribbean Wedding Villas

Caribbean Wedding Villas


There is nothing like having a villa wedding in the Caribbean. While hotels and resorts can often be crowded, private Caribbean villas provide the perfect backdrop for your ideal tropical wedding. Our Caribbean villa experts have been helping plan Caribbean weddings for years. We know which villas will accommodate weddings, provide all-inclusive wedding packages and even on-site coordinators to make your day a stress free experience. Check out a few of our favorites below or simply give us a call for expert advice on the best Caribbean villas for weddings!


Luxurious, private island with a full staff, six beaches, and every activity you could ask for. 20 BR rate available. Calivigny Island is located just south of Woburn Bay, Grenada

Grenada

Beachfront | Pool | AC

from Call for rates
This totally private island will make you feel like royalty. 15 BR rate available.
Has specials.
The Beach pool at Necker Island

Necker Island, BVI, British Virgin Islands

Beachfront | Pool | AC

from $77500/Nt
Private island resort with rustic, eco-friendly design and every activity under the sun. Thatch Caye photo

Belize

Near Beach

from $9785/Nt
Totally secluded private island with luxurious amenities and a full staff. 6 BR rate available. Over Yonder Cay is a spectacular exclusive private island south of Nassau in the Bahamas

Exuma and Cays, Bahamas

Beachfront | Pool | AC

from Call for rates
Luxurious private estate with resort amenities, professional service, and 10 huge Master Suites. 10 BR rate available.
Has specials.
Ani Villa Estate in The Dominican Republic has an amazing infinity edge pool with Caribbean views

Cabrera, Dominican Republic

Pool

from $10025/Nt
Elegance inside and out at this 11-bedroom villa, Mes Amis - Bring your friends! 4, 5, 6, 7, 8, 9, 10, 11, 12 & 13 BR rates available.
Has specials.
The stunning infinity pool at Mes Amis Villa overlooks the beauty of Baie Rouge

Terres Basses (French side), St. Martin

Pool

from $1357/Nt
A quietly luxurious, All-Inclusive Hideaway 8 BR rate available. Three Bees at Harbour Island photo

Harbour Island, Bahamas

Beachfront | Pool | AC

from Call for rates
This European-inspired villa is perfectly sized for family reunions, group get-togethers, and weddings. 4, 5, 6, 7, 8, 9, 10 & 11 BR rates available.
Has specials.
La Bella Casa overlooks Baie Longue Beach and is near La Samanna

Terres Basses (French side), St. Martin

Pool

from $1071/Nt
Six acre estate with beachfront access to coral reefs, on-site sports courts, and two freshwater pools. 7, 8, 9, 10 & 11 BR rates available.
Has specials.
Lounge by the pool at Golden Clouds

Ocho Rios, Jamaica

Pool

from $1571/Nt
2, 3, 4, 5, 6, 7 & 8 BR rates available. Enjoy relaxing by the pool and spectacular views of the Sir Francis Drake Channel beyond

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

from $5000/Nt
Sophisticated, three-story home perfect for family vacation or getaway with friends. The Beach House at Calivigny Island

Grenada

Beachfront | Pool | AC

from Call for rates
Luxurious, expansive mansion in a tropical oasis. The amazing infinity edge pool at Vista Chavon 7 overlooks the Chavon River and the ocean beyond

Casa de Campo, Dominican Republic

Pool

from $6500/Nt
Waterfront gem with secluded location, full staff, and a spacious layout. 5 & 8 BR rates available. Indigo Villa is located right on Little Harbor and has its on little piece of sandy beach

Anguilla

Beachfront | Pool | AC

from $6860/Nt
Sun, sand, and sea are in ample abundance at this luxurious Plum Bay Beach estate. 6 & 9 BR rates available.
Has specials.
Le Chateau des Palmiers is located along a beautiful stretch of Plum Bay Beach

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $5000/Nt
Park yourself right on the beach in Jamaica's 10 bedroom jewel, Flor de Cabrera Villa Has specials. The luxurious resort like pool is just steps away from the ocean at Flor de Cabrera

Cabrera, Dominican Republic

Beachfront | Pool | AC

from $2900/Nt
Stunning 10-bedroom vacation villa with privacy, onsite staff, and access to Sandy Lane Beach facilities. 6 & 8 BR rates available.
Has specials.
Elsewhere Villa is located in the prestigious Sandy Lane Club area

Barbados

Pool

from $4500/Nt
Oceanfront villa with 10 acres and 11 bedrooms. Lazy Heart Villa is located just along the Playa Caleton Paquena

Cabrera, Dominican Republic

Near Beach | Pool

from $1500/Nt
High-end, modern elegance with two pools, two beaches, and two and a half acres. Le Bleu Villa its on 2.5 acres of beachfront in Little Harbor

Anguilla

Beachfront | Pool | AC

from $8600/Nt
An impressive pool and terrace winds throughout this luxury villa. 5, 6 & 9 BR rates available. Aerial View of Silent Waters

Montego Bay, Jamaica

Pool

from $2482/Nt
Huge luxury estate features two separate villas, a full staff, and incredible ocean views. 8 BR rate available.
Has specials.
Ani Estate Anguilla - North and South

Anguilla

Pool

from $7500/Nt
Large beachfront estate with two pools that's ideal for family and friends alike. 4, 5, 6, 7, 8 & 9 BR rates available.
Has specials.
Casa Sunshine photo

Guana Bay (Dutch Side), St. Martin

Beachfront | Pool | AC

from $1143/Nt
The ultimate in luxury, this 10-bedroom estate sits on the best part of Grace Bay beach. 5, 6 & 8 BR rates available. The Hawksbill Villa Estate

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $7100/Nt
Pool area for Arrecife Villas

Punta Cana, Dominican Republic

Pool

from $2790/Nt
Fully-equipped villa with easy beach access and great amenities. One Perfect Day Villa is located on the Peterborg Peninsula overlooking Magens Bay

St. Thomas, USVI

Near Beach | Pool

from $5500/Nt
Opulent beachfront villa with maximum luxury and a full staff. 5, 6 & 8 BR rates available. Nevaeh is located on a beautiful stretch of Long Bay Beach

Anguilla

Beachfront | Pool | AC

from $6800/Nt
A former embassy, this sprawling property is set up for big groups. The villa has a full staff and a fantastically creative manager. Its also walkable to a beach which is hard to find in St Lucia. 5, 6, 7 & 8 BR rates available. Capri Villa photo

Cap Estate, St. Lucia

Near Beach | Pool

from $850/Nt
An opulent, gated estate with everything a large group could need, including a sport court and massive pool. 6 BR rate available. Luxurious private swimming pool at Casa Varnishkes

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $2218/Nt
This nine-bedroom villa is luxurious inside and out, with grandiose interiors and lush gardens. 5, 6, 7 & 8 BR rates available.
Has specials.
Aliseo is located near Colony Club and has access to Sandy Lane Beach Club

Barbados

Pool

from $2200/Nt
Ultra private, beachfront estate! 5, 6, 7 & 8 BR rates available. Santosha is located along a beautiful stretch of Long Bay Beach

Anguilla

Beachfront | Pool | AC

from $5000/Nt
This luxury villa offers a multilevel pool, golf simulator, tennis/basketball court, and signing privileges at nearby resorts. 5, 6 & 8 BR rates available. Nevaeh is located on a beautiful stretch of Long Bay Beach

Anguilla

Beachfront | Pool | AC

from $5000/Nt
Luxury oceanfront property with seven bedrooms, water-sports equipment, and access to Seven Mile Beach. Has specials. Coconut Walk Villa at twilight

Grand Cayman, Cayman

Beachfront | Pool | AC

from $4000/Nt
Private beach access, full equipment, and beautiful living spaces set this villa apart. 4, 5, 6 & 7 BR rates available. The pool is nestled in a tropical landscape at Enea villa

Lorient, St. Barts

Near Beach | Pool

from $2857/Nt
Luxurious private villa with resort amenities, professional service, and a personal sandy beach area. 5 BR rate available.
Has specials.
The swimming pool at the Larimar Villa overlooks the Caribbean

Cabrera, Dominican Republic

Pool

from $5200/Nt
Oceanfront villa with outdoor amenities, spacious design, and wedding capability. Has specials. Villa Del Mare is in an ideal oceanfront location near Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2500/Nt
This secluded villa has access to Sandy Lane Beach, a large pool, and a staff. 2 & 6 BR rates available.
Has specials.
Bluff House and Cottage are located very near by Sandy Lane Bay

Barbados

Near Beach | Pool

from $500/Nt
Villa Castellamonte del Mare: Tuscan living on the northern coast of the Dominican Republic. Villa Castellamonte del Mare photo

Cabrera, Dominican Republic

Near Beach | Pool

from $2200/Nt
Large beachfront home can accommodate up to 16 and has a child-friendly gated pool. 5 BR rate available.
Has specials.
View of the villa and private pool

Barbados

Near Beach | Pool

from $625/Nt
Beachfront architectural masterpiece with butler, sports courts, and full entertainment system. Has specials. African Sapphire Villa is just one of the -jewels- of the Villas at Altamer

Anguilla

Beachfront | Pool | AC

from Call for rates
Elegant luxury combines with intense privacy at Casa Kimball Casa Kimball photo

Cabrera, Dominican Republic

Near Beach | Pool

from $3250/Nt
Exciting extras like a private cabana and a Mastercraft make this converted sugar mill a real treasure for discerning guests 4 & 6 BR rates available.
Has specials.
There is a beautiful ridge side pool at Mullins Mill

Barbados

Pool

from $1960/Nt
Privacy and luxury for large groups on a two acre, beachfront tropical haven. Sunrise Villa photo

Cabrera, Dominican Republic

Beachfront | Pool | AC

from $1600/Nt
Sprawling estate with a panoramic view that's perfect for weddings, corporate retreats, and more. 1 & 5 BR rates available.
Has specials.
The pool and ocean views from Eco Serendib!

Rendezvous Bay, St. John

Pool

from $1843/Nt
Ultra modern and fully staffed villa with regal amenities. The Beach House features an amazing pool and outdoor area

Anguilla

Beachfront | Pool | AC

from $10714/Nt
Enjoy a mini golf-course and five separate units at this oceanfront beauty. 3, 4 & 5 BR rates available. Lounge on a balcony patio over looking the ocean from Anguillitta Villa

Anguilla

Near Beach | Pool

from $1150/Nt
Large, modern and completely luxurious, this impressive estate is the ultimate beachfront hideaway. Beautiful stretch of Long Bay Beach

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $7600/Nt
Bring your laptop if you must; Sea Star has a wireless connection that will allow you to hop online from any place on the property 5 & 6 BR rates available. Sea Star Villa  is located on Cabrita Point

St. Thomas, USVI

Beachfront | Pool | AC

from $1399/Nt
Style and elegance abound at La Josephine Villa, home to an impressive infinity pool and 7 bedrooms. 2, 3, 4, 5 & 6 BR rates available.
Has specials.
La Josephine Villa is located near La Samanna and overlooks Baie Longue

Terres Basses (French side), St. Martin

Near Beach | Pool

from $414/Nt
The private tennis court is just the beginning of this stunning estate perched right above the beach. 3, 4, 5 & 6 BR rates available. Zenaida Beach & Tennis Estate is located just above Sandy Hill Beach

Anguilla

Beachfront | Pool | AC

from $950/Nt
Warm, open interiors and stunning views combine in this oceanfront villa. 3, 4 & 5 BR rates available. Paradise Villa is located near Blowing Point

Anguilla

Pool

from $1200/Nt
Moroccan-inspired beachfront villa with a guest house, private pool, and access to Sapodilla Bay. 6 BR rate available. La Koubba Villa sits on the white sands of Sapodilla Bay

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $1786/Nt
Big groups will love this waterfront villa. 5 BR rate available. Private pool deck at Vieux Caribe Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1225/Nt
St. Lucia's Tamarind Villa is made for guests who don't want to wait until the kids leave the nest to start seeing the world 3 & 4 BR rates available.
Has specials.
Tamarind Villa photo

Cap Estate, St. Lucia

Pool

from $575/Nt
Extravagant gardens envelop this luxurious 18th century villa. Has specials. Amazing private swimming pool at Fustic House

Barbados

Near Beach | Pool

from $4030/Nt
This attractive getaway is perfect for couples or families who want privacy and tranquility. 1, 2, 3, 4, 5 & 6 BR rates available. Monte Bay Villa sits atop a hillside just above Monte Bay

Klein Bay, St. John

Near Beach | Pool

from $750/Nt
Outdoor living reigns supreme at this lush garden estate. 5 & 6 BR rates available.
Has specials.
Resort like pool at Sandyline Villa

Terres Basses (French side), St. Martin

Near Beach | Pool

from $4429/Nt
Six bedroom oceanfront property with a protective coral reef Has specials. Twin Palms Villa - the namesake beautiful palm trees

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1250/Nt
18-guest villa with oceanfront privacy, 75-foot pool, and space for everyone. Has specials. Villa Mora is located beachfront in South Sound

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1650/Nt
Oceanfront villa with private beach access, total seclusion, and unique architecture. Has specials. Spectacular views, infinity edge pool and oceanfront lounging await at Cayman Castle

Grand Cayman, Cayman

Near Beach | Pool

from $1295/Nt
Oceanfront villa right on Seven Mile Beach, with accommodations for 17 guests. Seascape Villa

Grand Cayman, Cayman

Beachfront | AC

from $2500/Nt
A spacious, open, two-story house comfortable for large groups. 3, 4, 5 & 6 BR rates available.
Has specials.
Private resort style pool and outdoor entertainment area at Jamoon

Barbados

Pool

from $1290/Nt
Spacious split-level villa with gorgeous sunset views and luxurious amenities. 5 BR rate available.
Has specials.
La Maison Michelle is located in Westmoreland near the golf course

Barbados

Pool

from $2300/Nt
A luxuriously modern 5-bedroom beachfront villa. Mandalay Villa photo

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from Call for rates
Large beachfront villa with wraparound ocean views and lots of room for decompressing! Expansive living area has endless views of the ocean

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $3571/Nt
Fully-equipped large group villa with several family-friendly suites and lots of outdoor space. Has specials. Beachfront pool at Oceanus Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2139/Nt
Stunning, all-inclusive property dripping with luxury. 4 BR rate available.
Has specials.
Enjoy amazing sunsets from the beach at the Amber Villa

Cabrera, Dominican Republic

Pool

from $4400/Nt
One-acre beachfront villa in the popular West End. Has specials. Kandara Villa is located on Anguilla's West End

Anguilla

Near Beach | Pool

from $3900/Nt
Waterfront villa with a game room, guest house, and outdoor space. Salacia Villa in Grace Bay offers amazing amenities

Grace Bay, Turks and Caicos

Near Beach | Pool

from $6000/Nt
Multiple couples and families can enjoy paradise at this gated community villa. The Harmon Estate Villa is located in the Eco Golf Community

Costa Rica

Pool

from $1500/Nt
Modern amenities and luxurious service combine at this oceanfront villa on the northern end of Grace Bay beach. Footprints villa is located on a beautiful stretch of Grace Bay Beach

Grace Bay, Turks and Caicos

Pool

from $3500/Nt
Escape to pure luxury on this huge 4.5-acre estate that is just minutes from beaches, restaurants, and shops 3, 4 & 5 BR rates available. Chateau Margot Villa photo

Bordeaux, St. John

Pool

from $857/Nt
Choose between two beaches and a large private pool for your stay in paradise, or, have them all. 4 & 5 BR rates available.
Has specials.
La Salamandre is located in Terres Basses with views of Simpson Bay

Terres Basses (French side), St. Martin

Near Beach | Pool

from $1414/Nt
Wonderful architectural design suited for anyone with an artist's tastes, this property dates back to 1791 3, 4 & 5 BR rates available. Enjoy relaxing poolside at Estate Belvedere

St. Croix, USVI

Pool

from $860/Nt
Encore Villa will have you wanting to visit over and over, and over, again. 4 & 5 BR rates available.
Has specials.
Encore Villa is located in Terres Basses and is nestled amongst beautiful tropical foliage

Terres Basses (French side), St. Martin

Pool

from $979/Nt
Beautiful villa on Plum Bay has spectacular sunset views over the water and tons of privacy for guests 4 & 5 BR rates available.
Has specials.
Cascades Villa photo

Terres Basses (French side), St. Martin

Near Beach | Pool

from $714/Nt
Two-building home near St. Lucia's Petit Piton, rainforest, botanical gardens, and dive sites. 2 & 4 BR rates available.
Has specials.
Colibri Cottage sits on a hill above Soufriere Bay

Soufriere, St. Lucia

Near Beach | Pool

from $415/Nt
Large groups or families will love this luxury villa just minutes away from Baie Rouge Beach. 4 & 5 BR rates available.
Has specials.
Maison de Reve is located on a hillside in the Terres Basses area

Terres Basses (French side), St. Martin

Near Beach | Pool

from $857/Nt
Families or active couples will find every need met at Mare Blu Villa on Rendezvous Bay 3, 4 & 5 BR rates available. Mare Blu Villa photo

Rendezvous Bay, St. John

Pool

from $1571/Nt
Bright, modern and private villa situated on Providenciales' coveted Long Bay Beach. 3 & 5 BR rates available.
Has specials.
Long Bay Beach House Villa is located on a beautiful stretch of beach

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $1200/Nt
Little Whale Cay offers three secluded villas for maximum privacy and pleasure, accommodating up to 12 persons. 3 BR rate available. Little Whale Cay private island retreat in the Berry Islands

Berry Islands, Bahamas

Pool

from $14760/Nt
Vintage charm, private cottages and a great beachfront location. 4 & 5 BR rates available.
Has specials.
From Nelson Gay House the view of the ocean within its tropical garden for privacy

Barbados

Beachfront | Pool | AC

from $2200/Nt
A gated community, resort amenities, and luxurious design make this six-bedroom villa irresistible. 4 BR rate available.
Has specials.
Go Easy Vill at Sugar hills offers a beautiful pool area

Barbados

Pool

from $1695/Nt
This sleek, modern, private property is just above Little Bay on Anguilla. Has specials. Ani Villa South in Anguilla is an excellent destination in the Caribbean

Anguilla

Pool

from $6400/Nt
Sprawling six-bedroom villa situated among tropical gardens and a huge private pool. Has specials. Vistamar features a poolside gazebo and an ample sundeck

Barbados

Pool

from $1800/Nt
Exclusive private island rental with full staff, all-inclusive rates, and endless activity. 5 BR rate available.
Has specials.
Royal Belize Private Island

Belize

Beachfront | AC

from $6200/Nt
Family-friendly villa with a bunk room, huge Great Room, outdoor amenities, and an ideal location in Rum Point. Has specials. The perfect image for Sun Salutations Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2499/Nt
Relax like royalty with stunning views and regal architecture. 2 & 4 BR rates available. Villa Hall sits on the tropical hillside over Gros Islet

Cap Estate, St. Lucia

Near Beach | Pool

from $1000/Nt
With a media room that doubles as a children's suite, this villa is perfect for multi-family vacations. 5 BR rate available. Deja View photo

Gift Hill, St. John

from $1507/Nt
Tons of room, seating, entertainment, and nothing can beat this hilltop scenery! 1, 2, 3, 4 & 5 BR rates available. Clairmont Overlook photo

St. Croix, USVI

Pool

from $629/Nt
This villa's full staff and beach access eliminates any potential stressors for your Caribbean vacation. 4 BR rate available. Kishti Villa East on Meads Bay offers relaxing outdoor spaces

Anguilla

Beachfront | Pool | AC

from $4200/Nt
Modern beachside villa with sound system, expansive outdoor space, and a gourmet kitchen. Has specials. C'est La Vie Villa photo

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $4714/Nt
A private Grand Cayman estate with tranquil design and a Master Suite that feels like a spa. Has specials. Tranquility Cove Villa has a luxurious infinity edge pool

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2139/Nt
Two story, beachfront villa with spacious rooms and a large balcony. Has specials. Amarone Villa is a luxurious home on the South Coast

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1300/Nt
Tortuga Bay C-17 photo

Punta Cana, Dominican Republic

Near Beach | Pool

from $2000/Nt
Breathtaking views and beach proximity set this villa apart. 2 & 4 BR rates available. Trou Rolland Villa photo

Marigot Bay, St. Lucia

Near Beach | Pool

from $517/Nt
South Sound Beach villa with five star amenities and no shortage of entertainment. Has specials. Point of View Villa is located on a picturesque Caribbean beachfront

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2859/Nt
The ultimate in modern beachfront luxury, with sleek design and privacy. Eos is a beachfront villa that is located directly on Long Bay

Eos

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $3000/Nt
Modern villa luxury with amenities. Helios Villa on Long Bay Beach

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $3000/Nt
Amenities and privacy - a hard combination to find. Hyperion is flanked by two sister villas ideally located on Long Bay Beach

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $3000/Nt
Privacy and luxury within a secluded beach hideaway. 3 & 4 BR rates available.
Has specials.
The pool and view of the ocean from Beach Enclave Ocean View Villas

North Shore, Turks and Caicos

Beachfront | Pool | AC

from $3100/Nt
Beach lovers and adventurers will love this villa's private beach access and nearness to Kaibo Yacht Club and Rum Point Club. Has specials. Crystal Waters Villa sits beach front near the popular Water Cay and Kaibo Yacht Club

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1000/Nt
Enjoy total tranquility in a main house and guest cottage set amongst the lush hillside. 2, 3 & 4 BR rates available. Darcini Villa is located in Fish Bay with a south facing view of rolling hills

Fish Bay, St. John

Pool

from $514/Nt
Has specials. Magens Hideaway photo

St. Thomas, USVI

Pool

from $1125/Nt
Private boat dock, beach, and panoramic ocean views at this fully air-conditioned villa. The Beach House photo

St. Thomas, USVI

Beachfront | AC

from $1200/Nt
Elegant, refined villa with beachfront access, luxurious amenities, and an open layout. The luxury pool at Coral Pavilion Villa sits just a few yard from the beautiful Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4950/Nt
Well-decorated villa with ocean views and snorkeling access. Three Dolphins sits in a beautiful location with great ocean views

Anguilla

Beachfront | Pool | AC

from $1850/Nt
A party-sized outdoor space combines with an ideal location for the perfect special event villa. 2, 3 & 4 BR rates available. Alicia photo

Tortola, BVI, British Virgin Islands

Pool

from $550/Nt
Has specials. Emerald Pavilion Villa is located on Emerald Point beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $5500/Nt
Resort villa with eco-friendly amenities, five king suites, and beach club privileges. 3 BR rate available. Dunes 2 by Grace Bay Resorts photo

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4800/Nt
Beachfront, resort community with eco-friendly features and Grace Bay location. 4 BR rate available.
Has specials.
The Residences are located directly on Grace Bay Beachfront and each have private infinity pools

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $5100/Nt
This beachfront villa enjoys resort amenities, eco-friendly features, and Grace Bay access. 4 BR rate available.
Has specials.
The Residences are located directly on Grace Bay Beachfront and each have private infinity pools

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $5100/Nt
An expansive sun-drenched deck and beautifully decorated interiors guarantee luxury. 2, 3 & 4 BR rates available. Casa Bougainvillea Villa has a beautiful private pool

St. Thomas, USVI

Beachfront | Pool | AC

from $853/Nt
Entertaining is a joy at Silk Cotton Villa onSt. Thomas with ample space for lively group conversation 2, 3 & 4 BR rates available. Silk Cotton Villa photo

St. Thomas, USVI

Pool

from $600/Nt
A vibrant, yet tranquil villa owned by artist Peter Max. 2, 3 & 4 BR rates available. At Caribe Villa you can lounge on the sundeck and enjoy views of Rendezvous Bay

Rendezvous Bay, St. John

Pool

from $700/Nt
St. Lucia's gorgeous Wild Orchid Villa has entertainment features for kids and grown ups alike 1, 2 & 3 BR rates available. Wild Orchid Villa photo

Cap Estate, St. Lucia

Near Beach | Pool

from $400/Nt
A separate guest cottage makes this location ideal for several travelers who want to dwell independently. Luxurious resort style pool in a lush tropical setting at Sol y Sombra

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

from $2075/Nt
Enjoy sunset views over the ocean from Mer Soleil, a charming villa set on the hillside 3 & 4 BR rates available.
Has specials.
Mer Soleil sits on a hillside in Terres Basses

Terres Basses (French side), St. Martin

Pool

from $743/Nt
This villa has five spacious suites with sea view terraces. Sea Villa is situated facing the beach with amazing unobscured ocean views

Anguilla

Beachfront | Pool | AC

from $3300/Nt
Enjoy easy beach access and spacious bedrooms. The luxurious Sand Villa at Long Bay

Anguilla

Beachfront | Pool | AC

from $3100/Nt
Relax and unwind at La Siesta Villa, a residence offering panoramic ocean views and comfortable accommodations. 3 & 4 BR rates available.
Has specials.
Amazing Caribbean views from the pool area at La Siesta

Terres Basses (French side), St. Martin

Near Beach | Pool

from $543/Nt
Elegant, spacious villa with a luxurious exterior and gorgeous gardens. 3 & 4 BR rates available.
Has specials.
Dene Court Villa is located in the prestigious Sandy Lane on the Old Nine Golf Course

Barbados

Pool

from $800/Nt
A child friendly villa with a uniquely open design near the beach. 3 & 4 BR rates available.
Has specials.
Lounge by the pool and enjoy views of the ocean in the distance at San Flamingo Villa

Barbados

Pool

from $635/Nt
This Maria Bluff villa enjoys 360-degree sunrise and sunset views. A aerial view of the beautiful Villa Kismet property

Chocolate Hole, St. John

Pool

from $2000/Nt
Private beach, lots of space and gorgeous waters Has specials. Aerial view of Two Rainbows

Grand Cayman, Cayman

Beachfront | Pool | AC

from $900/Nt
This villa's unique design revolves around the pool and sunbathing area in the center of the house. 3 & 4 BR rates available.
Has specials.
Luxurious pool and courtyard at Buttsbury House

Barbados

Pool

from $650/Nt
Named for its views, this villa is a paradise for weddings, couples retreats, or glamorous getaways. 3 & 4 BR rates available.
Has specials.
Point of View Villa has an extremely large pool and surround to enjoy the Caribbean sun

Barbados

Near Beach | Pool

from $2643/Nt
Newly remodeled and freshly redecorated, this hillside villa is ideal for family gatherings 3 & 4 BR rates available.
Has specials.
Belle Fontaine is located above Baie Rouge in the Terres Basses hillside

Terres Basses (French side), St. Martin

Pool

from $700/Nt
Set up high for fantastic pool views and a beachfront location on Taylor Bay. 4 BR rate available. Alizee Villa is located just a short distance away from Taylor Bay Beach

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $1143/Nt
With a 40 ft pool right on Long Bay Beach, this villa is a water-lover's dream. Shambhala Villa is located on a beautiful stretch of Long bay Beach

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $1271/Nt
Saramanda Villa is close to Holetown, tennis, golf, and beaches along the Platinum Coast. Has specials. Saramanda Villa is located in Sandy Lane near golf and tennis facilities

Barbados

Pool

from $2000/Nt
Ashiana Villa overlooks Marigot Bay and offers complete privacy and modern luxury. Its also relatively easy to get to Soufriere and enjoy the beauty of that location. 1, 2, 3 & 4 BR rates available.
Has specials.
Ashiana Villa photo

Marigot Bay, St. Lucia

Pool

from $420/Nt
Spacious, with an amphitheater and built-in seating; the expansive Coco de Mer is great for a wedding 2, 3 & 4 BR rates available. Coco de Mer at Peter Bay photo

Peter Bay, St. John

Near Beach | Pool

from $1400/Nt
The quintessential villa for the active, sports-loving family, the 5 bedroom Decaj Villa is full of wonderful suprises 1, 2, 3 & 4 BR rates available.
Has specials.
Decaj Villa is located in Cap Estate with views of the ocean in the distance

Cap Estate, St. Lucia

Pool

from $400/Nt
Relax in this villa's infinity pool, beach cabana and hammock and enjoy the close proximity to George Town Has specials. Lounge poolside on the beach at Pease Bay House

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1495/Nt
Perfect for a large group that wants to spend time in the gardens and sunshine. 4 BR rate available.
Has specials.
Stanford House photo

Barbados

Pool

from $1500/Nt
The Beach House is an adventure destination perfect for the outdoor person in tune with nature Lounge and enjoy views of the Caribbean from the deck at The Beach House

St. Thomas, USVI

Beachfront | AC

from $650/Nt
Unparalleled luxury and access to the only golf course on Anguilla. Sky Villa is the most private of the Long Bay Villas located just off the beach

Anguilla

Near Beach | Pool

from $2900/Nt
Ultra-modern upscale Anguilla villa with glass walls that face the sea. Champagne Shores villa sits on a secluded beach near Pelican Bay

Anguilla

Near Beach | Pool

from $1700/Nt
Large enough for five couples or a small business retreat, Tom Tom Villa is located in a secure gated community Has specials. Tom Tom Villa is located in the heart of Royal Westmoreland and features an infinity edge pool

Barbados

Pool

from $1700/Nt
Kalorama villa has a unique Great Room, but with views like these, you're likely to spend most of your time on the spacious deck. 1, 2, 3 & 4 BR rates available. From the upper deck looking down on the pool area at Kalorama Villa

Virgin Grand Estates, St. John

Pool

from $860/Nt
Striking four-story villa beachfront villa with ocean views and a private tennis court. Has specials. Antilles Pearl Villa is located on Shoal Bay Beach at the Altamer Villas

Anguilla

Beachfront | Pool | AC

from $3214/Nt
Chic, plantation-style estate with full staff. Has specials. Coral House sits on a beautiful stretch of the world famous Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4310/Nt
The self-contained, detached guest house offers a wonderful private getaway for newlyweds or couples wanting to spend some time on their own. 2, 3 & 4 BR rates available. Lush tropical greenery surrounds Sade Villa

Tortola, BVI, British Virgin Islands

Near Beach | Pool

from $600/Nt
Classically Caribbean villa with an impressive pool and gorgeous mountain views. 3 BR rate available.
Has specials.
Arc En Ciel Villa photo

Soufriere, St. Lucia

Near Beach | Pool

from $1900/Nt
Huge beachfront villa with housekeeping, five bedrooms, and 18 acres of land. The pool area at Amazing Grace Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4950/Nt
Super modern, upscale villa with glass walls and a spacious design. Lounge by the pool and enjoy amazing ocean views at Beaches Edge East Villa

Anguilla

Near Beach | Pool

from $1400/Nt
Palatial, secluded oceanfront mansion near great snorkeling. 2, 3 & 4 BR rates available. Miramar Villa has amazing ocean views

St. Croix, USVI

Near Beach | Pool

from $2441/Nt
Private beachfront villa great for families, with scuba diving at the Cayman Wall. Has specials. Literally steps to the beach at Cayman Sands Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $625/Nt
Beachfront island home with plenty of room for family getaways Has specials. The pool and this cabana are located right on the beach at Reef Romance Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $825/Nt
Tropical island elegance, Cayman style Has specials. Blue Water is located on Rum Point with a beautiful stretch of beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $900/Nt
This secluded, luxury beach house boasts fantastic amenities on over four tropical acres. Turtle Tail Estate is located on the southern tip of Turtle Tail

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $10000/Nt
The Sanskrit word for “Paradise” is Nandana, and this villa fits the name perfectly through its outstanding accommodations, amenities, and unbeatable location. 3 BR rate available. Nandana Villa in the Bahamas

Grand Bahama Island, Bahamas

Pool

from $10500/Nt
A luxurious five-bedroom retreat with a full staff, entertainment system, and Meads Bay location. 4 BR rate available. Relax in the pool and hot tub during your stay at Kishti Villa West

Anguilla

Beachfront | Pool | AC

from $4200/Nt
Enjoy the private beachfront villa experience with the comforts of a five-star resort. 4 BR rate available.
Has specials.
The Residences are located directly on Grace Bay Beachfront and each have private infinity pools

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $5100/Nt
Perfect family and friends beachfront villa with sunset views. 4 BR rate available.
Has specials.
Caribbean Blue Villa photo

Pelican Key (Dutch side), St. Martin

Beachfront | Pool | AC

from $743/Nt
Fully air-conditioned beachfront villa with sunset views and a massive Master Suite. Has specials. The Caribbean view from the balcony at Cos Kai Villa

Grand Cayman, Cayman

Beachfront | AC

from $950/Nt
This eco-friendly villa enjoys a beachfront location and resort amenities. 3 BR rate available.
Has specials.
The interior pool and dining palapa at the Dunes Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4800/Nt
Swanky waterfront villa with resort-like amenities and a boat dock. Has specials. The Reef Villa photo

Simpson Bay (Dutch side), St. Martin

Pool

from $1300/Nt
Luxuriously modern resort villa with stunning ocean views and private beach access. 3 & 4 BR rates available.
Has specials.
Beach Enclave Beachfront Villas offer amazing ocean views

North Shore, Turks and Caicos

Beachfront | Pool | AC

from $3800/Nt
Chic, modern villa with an ideal location near all of Grace Bay's amenities. Aerial view of the Turquoise Villa property

Grace Bay, Turks and Caicos

Near Beach | Pool

from $1300/Nt
Super private beachfront villa with water sports, a home theater, and ocean views. Has specials. Stepping Stone Villa is located along a beautiful beach at the East End of Grand Cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1719/Nt
Modern, private beachfront villa with a stylish rooftop deck. Has specials. An aerial view of Olympus Villa and the beautiful beachfront

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1500/Nt
Three pools, the ocean, and the beach will keep guests entertained. Has specials. The Estate pools

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4800/Nt
Luxurious resort property with full service and amenities. Has specials. Grace Bay Club Resort pool

Grace Bay, Turks and Caicos

Beachfront | AC

from $5330/Nt
Child-friendly beachfront villa with 10,000 sq. feet of Tuscan architecture. 3 BR rate available.
Has specials.
Pool with view of ocean

Anguilla

Beachfront | Pool | AC

from $1600/Nt
Stunning Long Bay Beach villa with panoramic ocean views and spacious, modern design. 2 & 3 BR rates available.
Has specials.
Lounge by the pool with amazing ocean views

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $929/Nt
Cadasse Villa is a unique property, recently renovated and sitting on a hilltop in Cap Estate, the views from the fantastic outside space are wonderful. The best part of this villa is the amazing staff, they cook meals you will talk about for years. 1, 2 & 3 BR rates available. Cadasse Villa has beautiful views and fun area for swimming and relaxing

Cap Estate, St. Lucia

Pool

from $315/Nt
Impressive historical estate with first-class gardens and a private beach. 2 & 3 BR rates available. Morne Trulah photo

Rodney Bay, St. Lucia

Near Beach | Pool

from $900/Nt
Bright, spacious decor, an expansive lawn with tons of lounging space, and direct beach access. Has specials. Take a dip in the pool at High Trees Villa

Barbados

Beachfront | Pool | AC

from $1180/Nt
Four-bedroom resort villa right on Grace Bay beach. Has specials. The West Bay Club by night

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2020/Nt
Kayaks, hammocks, screened porches, and a boat dock makes this fully air-conditioned villa perfect for sun-lovers. Has specials. Great Escape Villa is very close to the beautiful beach

Grand Cayman, Cayman

Near Beach | Pool

from $645/Nt
A huge pool deck and several gazebos provides the ultimate relaxation with a view. 2 & 3 BR rates available.
Has specials.
Ambiance is located in the heart of Terres Basses with access to beautiful beaches nearby

Terres Basses (French side), St. Martin

Pool

from $857/Nt
Set between Taylor Bay and Sapodilla Bay, this house has a modern vibe and amazing ocean views. Has specials. Lounge by the ocean front pool at La Percha

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1500/Nt
Art lovers will adore the villa's modern architecture and island views. 2 & 3 BR rates available. Sunspot Villa photo

Peter Bay, St. John

Near Beach | Pool

from $1453/Nt
This ultra modern villa has a private concierge and take your breath away sunsets. Has specials. Ani Villa North is a beautiful location for a Caribbean getaway

Anguilla

Pool

from $5100/Nt
If tennis is your game, you'll love having a court right on the premises-you'll just have to provide the partner. 2 & 3 BR rates available.
Has specials.
La Pinta is located in the heart of Terres Basses

Terres Basses (French side), St. Martin

Pool

from $486/Nt
Breathtaking ocean views engulf this ultra-chic, spacious villa. 2 & 3 BR rates available.
Has specials.
Terrasse de Mer Villa photo

Terres Basses (French side), St. Martin

Pool

from $814/Nt
Tropical luxury on Sandy Hill Beach. 1, 2 & 3 BR rates available.
Has specials.
The beautiful Bird of Paradise Villa

Anguilla

Near Beach | Pool

from $1850/Nt
A formal, modern villa located in the privacy of Estate Shoys with all the amenities a gated community offers Mango Hill is located on the eastern end of St. Croix

St. Croix, USVI

Pool

from $843/Nt
Handicap accessible vila with an elevator and a dumbwaiter. Has specials. Beautiful views from the balcony at Illusion Villa

Barbados

Pool

from $2250/Nt
Soak in the sun in one of the two pools! 2 & 3 BR rates available.
Has specials.
Grand Bleu is located on the hillside of Terres Basses

Terres Basses (French side), St. Martin

Near Beach

from $786/Nt
Let Unforgettable Views Define Your Next Holiday At Ana Capri Estate 1, 2 & 3 BR rates available. Ana Capri Estate photo

Tortola, BVI, British Virgin Islands

Pool

from $572/Nt
Modern, crescent-shaped villa with panoramic views from every room. Has specials. Lounge in luxury,  poolside at Marsh Mellow Villa

Barbados

Pool

from $1035/Nt
Eco-friendly beachfront villa conveniently located near Rum Point Club. Has specials. Kai Vista photo

Grand Cayman, Cayman

Beachfront | Pool | AC

from $745/Nt
A private, beachfront villa that offers comfort and ease on beautiful Grace Bay. Saving Grace Villa photo

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2300/Nt
Grace Bay villa with chic accommodations, a freshwater pool, and direct access to the best part of the beach. 3 BR rate available. Beach side deck at Sunsara Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2025/Nt
Oceanfront villa near snorkeling reefs, Seven Mile Beach, and marine life. Has specials. Deck and patio area

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1139/Nt
This tropical escape has an Italian design and spans two acres of wild Caribbean fauna. Gwynt A Mor Villa has a beautiful resort like pool

North Shore, Turks and Caicos

Pool

from $1214/Nt
This penthouse villa has completely amazing views: miles of sand and blue sea. Has specials. Penthouse at The Venetian photo

Grace Bay, Turks and Caicos

Beachfront | AC

from $1425/Nt
Enjoy easy access to Grace Bay and luxurious service from the resort. Has specials. The Estate at Grace Bay Club

Grace Bay, Turks and Caicos

Beachfront | AC

from $3700/Nt
Luxury beachfront villa with endless amenities and event-friendly design. Has specials. The Sandcastle Beach House is located on a beautiful beach in Limestone Bay

Anguilla

Beachfront | Pool | AC

from $1250/Nt
Saline Reef: Two pools and a waterfall will tempt you to stay home and skip all of the nearby activities 2 BR rate available.
Has specials.
Saline Reef sits on the northernmost end of St. Lucia and has a beautiful pool and patio

Cap Estate, St. Lucia

Near Beach | Pool

from $580/Nt
The drinks never stop flowing at this stunning, modern home with breathtaking ocean views. 1 & 2 BR rates available.
Has specials.
Lounge poolside with amazing views of the ocean

Anguilla

Near Beach | Pool

from $990/Nt
Beachfront luxury on the best part of Grace Bay Beach, with fantastic outdoor space and privacy. Poolside views of the Caribbean from Villa del Sol

Leeward, Turks and Caicos

Beachfront | Pool | AC

from $1750/Nt
Classic yet chic beachfront villa on Gibbes Bay. Has specials. Plunge pool and gardens leading to the beach at Waverly Villa

Barbados

Beachfront | Pool | AC

from $600/Nt
Get in touch with nature by taking advantage of the outdoor shower and private, au natural swimming pool. 1 & 2 BR rates available.
Has specials.
Sol e Luna is located in the desirable Terres Basses

Terres Basses (French side), St. Martin

Pool

from $521/Nt
Waterfall Villa: A waterfall infinty pool is the centerpiece of this gorgeous estate property 1 & 2 BR rates available.
Has specials.
Waterfall Villa is located on a tropical hillside over looking the Caribbean

Rendezvous Bay, St. John

Pool

from $479/Nt
Small, quiet, luxurious resort with ocean views from every room and five-star amenities. 1 & 2 BR rates available.
Has specials.
The Tuscany Resort is located on East Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $775/Nt
Each villa has a balcony overlooking Grace Bay at this luxury resort complex. 1 & 2 BR rates available.
Has specials.
The Venetian photo

Grace Bay, Turks and Caicos

Beachfront | AC

from $875/Nt
Stunning beachfront resort villa has spectacular views, access to Grace Bay Beach, and includes resort amenities of the West Bay Club. Has specials. The West Bay Club from Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1680/Nt
Fully staffed Sea Pearl Villa by Smuggler's Cove Beach is for water lovers and their families. The private pool and gardens are perfect for small groups, yet its just minutes from Rodney Bay. 1 BR rate available.
Has specials.
Sea Pearl Villa photo

Cap Estate, St. Lucia

Near Beach | Pool

from $415/Nt
Your very own exotic, secluded paradise with an earthy, open feel Perfect pool - Walk out the door and take a dip!!

Cap Estate, St. Lucia

Pool

from $300/Nt
Bamboo Villa sounds like a place you'd like to stay on a tropical island, doesn't it? 1 BR rate available.
Has specials.
Bamboo Villa is located less than a mile from Long Bay

Terres Basses (French side), St. Martin

Pool

from $545/Nt
Within exclusive Estate Shoys, Royal Palms Villa is close to golf and tennis activities, as well as the beach. 1 BR rate available. Royal Palms Villa photo

St. Croix, USVI

Pool

from $525/Nt
A gorgeous 2-bedroom resort villa on famous Grace Bay Beach - West Bay Club has a restaurant, beach bar and staff to attend to your vacation needs. Has specials. Grace Bay Beach along the West Bay Club

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1020/Nt
A Wyndham Resort stay with a beachfront location and tons of activity options! Rio Mar Beach Resort Luxury Ocean Villa photo

Northeast Coast, Puerto Rico

Beachfront | Pool | AC

from $450/Nt
This 1 bedroom resort villa is luxurious and comfortable, and right on the beach Has specials. The West Bay Club has a beautiful pool

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $630/Nt

Where To Stay

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