Caribbean Luxury Villas

Caribbean Luxury Villas


Our luxury villa collection offers the ultimate in lavish appointments. These hand-selected villas meet our ultimate standards based on their level of excellence, attention to detail, customer satisfaction, and aesthetic appeal. They go above and beyond with unparalleled staff, impeccable design, and every indulgence. Expect superior, personal attention from our dedicated luxury villa experts with over 20 years of expertise. They will plan and execute every aspect of your luxury villa experience with one focus… perfection.


There's really no island quite like Calivigny. This gem was purchased in 2000 by a couple who wanted to create a ... 20 BR rate available. Calivigny Island is located just south of Woburn Bay, Grenada

Grenada

Beachfront | Pool | AC

from $132000/Nt
Necker Island is the place to go if you want the ultimate privacy, luxury, and pampering. You can rent out ... The Beach pool at Necker Island

Necker Island, BVI, British Virgin Islands

Beachfront | Pool | AC

from $87500/Nt
Over Yonder Cay is the pinnacle of luxury. It's a private island in the Bahamas with a full staff of ... 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
Ani Villa Estate - Dominican Republic is a property that doesn't skimp on luxury. There's pools with massive water slides, ... 10 BR rate available. Ani Villa Estate in The Dominican Republic has an amazing infinity edge pool with Caribbean views

Cabrera, Dominican Republic

Pool

from $10500/Nt
Seaclusion Estate combines two gorgeous properties into one luxurious villa rental. The villas sit on the world’s most beloved ... Has specials. Seaclusion Villa and Seascape Villa combined comprise the Seaclusion Estate in Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $12700/Nt
Combining the words, "Luxurious" and "All-Inclusive" can almost sound paradoxical. But at Three Bees at Harbour Island, Bahamas these two ... 8 BR rate available. Three Bees is located on Harbour Island Bahamas

Harbour Island, Bahamas

Beachfront | Pool | AC

from Call for rates
Casa Bahia is luxurious, exclusive, and elegant. It has full chef services, two infinity pools, and a full home gym… ... Casa Bahia is located in Casa de Campo directly on Minitas Beach

Casa de Campo, Dominican Republic

Beachfront | Pool | AC

from $11800/Nt
Located in the Exuma Islands, Musha Cay at Copperfield Bay has five luxurious homes you can choose from, from the 10,000... 6, 7, 8, 9, 10 & 11 BR rates available. Musha Cay at Copperfield Bay photo

Musha Cay, Bahamas

Beachfront | Pool | AC

from $42000/Nt
This estate is the perfect place for a big group vacation. Whether you’re traveling with extended family or friends ... Palmier Royal Estate is located in Mont Jean with amazing views of Marigot Bay

Mont Jean, St. Barts

Pool

from $18571/Nt
If you've always wanted to spend a week or two in a home with interiors designed by Donna Karan including ... 3 BR rate available.
Has specials.
Private luxury at The Sanctuary at Parrot Cay

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $14000/Nt
The Beach House is the biggest and most impressive accommodation on the island. If you want to vacation in style, ... The Beach House at Calivigny Island

Grenada

Beachfront | Pool | AC

from $57000/Nt
This beachfront estate combines two villas into one luxurious rental. The St. James Estate enjoys an oceanfront location on Paynes ... The St. James Estate is located on Paynes Bay Beach and is comprised of The One and The Villa

Barbados

Beachfront | Pool | AC

from $3000/Nt
This beachfront vacation rental is a tranquil, luxurious place to take your family, friends, or wedding party. With ten bedrooms, ... Aerial views of the Samsara property and surrounding area

North Shore, Turks and Caicos

Beachfront | Pool | AC

from $6050/Nt
If you want a lot of room to roam around in, water access, a full staff, and luxury accommodations, Indigo ... 5 & 7 BR rates available.
Has specials.
Indigo Villa is located right on Little Harbor and has its on little piece of sandy beach

Anguilla

Beachfront | Pool | AC

from $6590/Nt
Cove Spring offers its guests every amenity they could possibly need or imagine. Guests can give their full attention to ... Has specials. Cove Spring photo

Barbados

Beachfront | Pool | AC

from $20000/Nt
If you do things with an all or nothing attitude, you'll flip over Le Bleu Villa. It's hard to think ... 5, 7 & 9 BR rates available.
Has specials.
Le Bleu Villa its on 2.5 acres of beachfront in Little Harbor

Anguilla

Beachfront | Pool | AC

from $6750/Nt
The cove on which Crystal Springs Villa rests is like a clip out of a castaway movie. It is private ... 7 & 8 BR rates available.
Has specials.
Crystal Springs is a beautiful Estate located right on the beach

Barbados

Beachfront | Pool | AC

from $8150/Nt
For large groups wanting extreme luxury, the oceanfront Ani Villa Estate is a perfect choice. There are two separate villas, ... 8 BR rate available. Ani Estate Anguilla - North and South

Anguilla

Pool

from $8425/Nt
This estate is perfect for family reunions or staff retreats. The sheer size of it all makes you feel like ... 5, 6 & 8 BR rates available. The Hawksbill Villa Estate

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $7500/Nt
Yarari Royale is one of a kind when it comes to luxury. You'll be spoiled by daily housekeeping, full butler ... 5, 6, 7 & 8 BR rates available. Yarari Royale is a beautiful home located in Cap Cana

Cap Cana, Dominican Republic

Pool

from $2430/Nt
La Dolce Vita is super luxurious and spacious. There's seven different lounges inside the villa and tons around the property's ... Has specials. La Dolce Vita sits beachfront on a beautiful stretch of Long Bay Beach

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $17000/Nt
One Perfect Day is a well-equipped, charming villa. It has a five-star kitchen with tons of appliances, massive outdoor space, ... One Perfect Day Villa is located on the Peterborg Peninsula overlooking Magens Bay

St. Thomas, USVI

Near Beach | Pool

from $5500/Nt
This villa may be painted pink, but it has all the luxury and amenities you'd expect in a five-star Caribbean ... La Palmeraie is located on Harbour Island in the Bahamas

Harbour Island, Bahamas

Beachfront | Pool | AC

from Call for rates
Nirvana and Mirador are lovely on their own, but even better together. Both properties are ideal for couples getaways or ... Has specials. Nirvana and Mirador ar the located in Fitts Village on and amazing stretch of sandy beach

Barbados

Beachfront | Pool | AC

from $3375/Nt
This ultra-modern villa is a great choice for any multi-generational family vacation. It's golf course location keeps kids a few ... 5, 6, 7 & 8 BR rates available. Arrecife Royale is located in the renowned Punta Cana Resort on the golf course

Punta Cana, Dominican Republic

Pool

from $2430/Nt
If you’re looking for luxury, Nevaeh has it in abundance. Not only does it sit on a gorgeous, private ... 5, 6, 7 & 8 BR rates available.
Has specials.
Nevaeh is located on a beautiful stretch of Long Bay Beach

Anguilla

Beachfront | Pool | AC

from $6800/Nt
Located on picture-perfect Grace Bay Beach, Seaclusion epitomizes luxury island lifestyle. The design is ultra-modern, with sleek finishes, cutting-edge technology, ... Has specials. Seaclusion photo

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $8800/Nt
Kiko has a great location that truly can't be beat. It's in Paynes Bay on Barbados's Platinum Coast, which is ... 6 & 8 BR rates available. Villa Kiko is located on Payne's Bay

Barbados

Beachfront | Pool | AC

from $7500/Nt
"Cerulean" means "heaven," and this private resort attends to all the details of your stay to create your personal heaven. ... Has specials. The beautiful Cerulean Villa on Barnes Bay in Anguilla

Anguilla

Beachfront | Pool | AC

from $14286/Nt
Sitting directly on Long Bay Beach, Casa Varnishkes is an opulent, gated estate perfect for families or larger group gatherings. ... 6 BR rate available.
Has specials.
Luxurious private swimming pool at Casa Varnishkes

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $1970/Nt
Santosha sits right on Long Bay Beach and is perfect for beach weddings, anniversaries, and any special event. You can't ... 5, 6, 7 & 8 BR rates available.
Has specials.
Santosha is located along a beautiful stretch of Long Bay Beach

Anguilla

Beachfront | Pool | AC

from $5000/Nt
“Nevaeh” is “heaven” backwards, and the villa's golf simulator, movie theater, media room, and gym are just a few of ... 5, 6, 7 & 8 BR rates available.
Has specials.
Nevaeh is located on a beautiful stretch of Long Bay Beach

Anguilla

Beachfront | Pool | AC

from $5000/Nt
Ani Villas - Larimar is ideal for any group of travelers who wants the full luxury experience. There’s a ... 4, 5 & 6 BR rates available. The swimming pool at the Larimar Villa overlooks the Caribbean

Cabrera, Dominican Republic

Pool

from $4925/Nt
Tartaruga is the place to be for a luxurious vacation. Guests have full access to Punta Cana Resort amenities, including ... Tartaruga photo

Punta Cana, Dominican Republic

Pool

from $8670/Nt
If you want to breathe in the ocean air and relax, Arrecife 17 is an excellent choice for your next vacation. ... 6 BR rate available.
Has specials.
Arrecife 17 is located in Punta Cana with beautiful Caribbean views

Punta Cana, Dominican Republic

Pool

from $3000/Nt
Emerald Cay combines natural beauty with state-of-the-art technology for the ideal modern getaway. The master suite is a great example ... Aerial views of Emerald Cay

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $30000/Nt
If you’re traveling with a large group and want plenty of space to spread out and relax, English Harbour #46 ... 7 BR rate available. English Harbour #46 is located on a hillside above Windward Bay and English Harbour

English Harbour, Antigua

Pool

from $5700/Nt
Mango Bay is a large estate featuring seven bedrooms, a full on-site staff, and easy access to some of Barbados ... 6 & 7 BR rates available.
Has specials.
Mango Bay's patio sits right on the beach

Barbados

Beachfront | Pool | AC

from $5200/Nt
Located on Flamands Beach, St. Bart's, Villa ELA is an ideal retreat for families with older children or large groups. ... 4 & 6 BR rates available. ELA Villa is located on a beautiful stretch of Flamands Beach

Flamands, St. Barts

Beachfront | Pool | AC

from $5714/Nt
The Beach House's high-class architecture and contemporary style is enough to make you want to stay forever, but that's not ... 3 & 5 BR rates available.
Has specials.
The Beach House features an amazing pool and outdoor area

Anguilla

Beachfront | Pool | AC

from $8900/Nt
Sentosa Villa is the perfect vacation rental if you want a luxurious getaway on Grace Bay Beach with resort amenities. ... Sentosa is located along a beautiful stretch of Grace Bay Beach

Providenciales, Turks and Caicos

Beachfront | Pool | AC

from $15000/Nt
Pearl East will make you feel like royalty. I love this villa for large family reunions and get-togethers with all ... 5, 6 & 7 BR rates available.
Has specials.
Aerial view of Pearl East

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $5500/Nt
Tucked behind the pristine sand dunes of Long Bay Beach, Triton Villa has set a new standard for luxury in ... Has specials. Beautiful stretch of Long Bay Beach

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $8000/Nt
Impulse is honestly one of a kind. There's sculptures and statues throughout the space, waves of colored lights in the ... 6 BR rate available. Expansive living area has endless views of the ocean

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $3571/Nt
Offering king-size beds and an en-suite bathroom for each of the five bedrooms, La Plage is a villa conveniently located ... 5 BR rate available. Luxurious Lorient Bay beachside pool deck at La Plage

Lorient, St. Barts

Beachfront | Pool | AC

from $5714/Nt
Fustic House is a legendary vacation destination. The villa was built in the 18th century, but it’s been extremely ... Has specials. Amazing private swimming pool at Fustic House

Barbados

Near Beach | Pool

from $4030/Nt
If you are looking for a completely stunning location for your family getaway, Coral House might just be it. With ... 5 BR rate available.
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 $5500/Nt
This villa is literally right on the beach, with the most gorgeous view from the back patio. Kids can swim ... 4 & 5 BR rates available. Loungers by the beachfront pool at Aqua Villa

Grand Cul de Sac, St. Barts

Beachfront | Pool | AC

from $4714/Nt
Bleu's pool runs the length of the house, and sits right on the beach. 6 bedrooms leaves room for every family ... 4 & 5 BR rates available. The beachfront lap pool at Bleu Villa

Grand Cul de Sac, St. Barts

Beachfront | Pool | AC

from $4714/Nt
Wake Up is super modern, well-equipped, and gorgeously designed. There's tons of space to relax outside by the pool or ... Wake Up Villa is located on the beautiful Flamands Beach

Flamands, St. Barts

Beachfront | Pool | AC

from $12143/Nt
If you want a fully-staffed villa that has activities for everyone, then Villa Corales 114 is perfect for you. There's a 72 ... Villa Corales 114 has a decadent lawn and pool area

Punta Cana, Dominican Republic

Near Beach | Pool

from $2211/Nt
I love this villa because it's secluded, designed with tons of windows, and has private beach access. Willoughby Bay is ... 3, 4 & 5 BR rates available. Villa Liene at Daniel Bay is situated in Willoughby Bay

English Harbour, Antigua

Beachfront | Pool | AC

from $1161/Nt
Oceanus is the perfect place to host your next family reunion, corporate retreat, or special event. This villa rental is ... Beachfront pool at Oceanus Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2139/Nt
Ani Villas - Amber is a beachfront resort property that doesn't skimp on luxury. There’s not one, but two ... 4 & 5 BR rates available. Enjoy amazing sunsets from the beach at the Amber Villa

Cabrera, Dominican Republic

Pool

from $4925/Nt
Kandara is great if you're looking for space and privacy. The villa has 8,000 square feet of space, an acre of ... Has specials. Kandara Villa is located on Anguilla's West End

Anguilla

Near Beach | Pool

from $2330/Nt
Seaclusion will make you feel like royalty. There's more chandeliers and ocean views that I can count, and the exterior ... 4 & 5 BR rates available.
Has specials.
Seaclusion is located just steps away from an amazing white sand beach

Barbados

Beachfront | Pool | AC

from $3750/Nt
These resort villas are perfect for any group that wants to vacation in style. The villas range from three to ... 5 BR rate available.
Has specials.
The elegant Shore Club Villas feature private swimming pools

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $6000/Nt
Kempa Kai is luxurious, gorgeous, and unforgettable. Its modern design is both beautiful and practical, while the exterior is packed ... Kempa Kai villa is located on a nature preserve near Rum Point

Grand Cayman, Cayman

Beachfront | AC

from $2395/Nt
Corales 50 is ideal for a family or couples who want a resort experience without sacrificing privacy. It's near the beach, ... Corales 50 is situated in Punta Cana on the golf course only several hundred yards from the ocean

Punta Cana, Dominican Republic

Pool

from $1800/Nt
Blue Dragon is dramatic, luxurious, and spacious. It's minutes from Gouverneur's shops and activities, and a short hike from the ... Blue Dragon sits on the hillside above Gouverneur

Gouverneur, St. Barts

Pool

from $10000/Nt
CieloMar is one of the most stunning villas in the Caribbean. It has everything you could want in a vacation ... CieloMar is perched on the hillside above Peninsula Papagayo in a gated community

Costa Rica

Pool

from $7143/Nt
Footprints villa offers an amazing location on the most envied coast on Turks & Caicos: Grace Bay. Its modern technology, air-conditioning, ... Footprints villa is located on a beautiful stretch of Grace Bay Beach

Grace Bay, Turks and Caicos

Pool

from $3500/Nt
Ammonite is an amazing villa for your next vacation with family or friends. Not only does it have a full ... Ammonite Villa is located in Punta Cana on the golf course just a short distance away from the ocean

Punta Cana, Dominican Republic

Pool

from $6000/Nt
Gorgeous doesn’t do this villa justice. It’s been expertly designed so every space has a Wow Factor - ... Architect's Estate is located in Casa de Campo Resort between Minitas Beach and Altos de Chavón

Casa de Campo, Dominican Republic

Pool

from $2500/Nt
Villa de Agua has all the amenities of a classic Caribbean rental, and the design is magazine-worthy. If you love ... Villa de Agua is located in Punta Cana on the ocean ans just moments from Corales Beach

Punta Cana, Dominican Republic

Pool

from $4500/Nt
Cabuya is one of the most gorgeous villas on Providenciales's eastern coast. This villa has it all: a beachfront location, ... 5 BR rate available. Cabuya Villa is located in Leeward on a beautiful stretch of white sand beach

Leeward, Turks and Caicos

Beachfront | Pool | AC

from $4300/Nt
If you want to get away from it all and relax, Pearns Bay House is an excellent choice. It’s ... 3 BR rate available.
Has specials.
Pearns Bay House is located in a luxury community

Pearns Point, Antigua

Beachfront | Pool | AC

from $5000/Nt
Elegant, convenient, private. Haven House is beautiful inside and out, with magazine-worthy decor and a tranquil beachfront location on one ... Has specials. Haven House is located on shores of Long Bay on the south east coast of Providenciales

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $7000/Nt
Paradis Sur Mer is an inarguably beautiful villa, but the real advantage is its beachfront location. The beach has sugar ... Paradis Sur Mer is located on a quiet residential road in Cayman Kai

Grand Cayman, Cayman

Beachfront | Pool | AC

from $4150/Nt
This is a great place to combine work and play. There's every amenity you could want, from a fully equipped ... 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
This Happy Bay hideaway has plenty of space for everybody to relax - especially several couples traveling together. Ocean 5 is ... 4 & 5 BR rates available. Ocean 5 Villa sits on a Hillside in Mt. Choisy

Happy Bay (French Side), St. Martin

Near Beach | Pool

from $829/Nt
Located in Saline, Dunes Villa is an ideal selection for families with young children or four couples. With 6 bedrooms (2 king ... Amazing pool at Dunes Villa

Saline, St. Barts

Near Beach | Pool

from $8571/Nt
With three secluded villas offering accommodations for up to 12, an on-site chef, and a chapel, Little Whale Cay is a ... 3 BR rate available. Little Whale Cay private island retreat in the Berry Islands

Berry Islands, Bahamas

Pool

from $16250/Nt
Antilles Pearl is a super luxurious, fully staffed, beachfront villa in one of the best spots on Anguilla. There's a 50... 5 BR rate available.
Has specials.
Antilles Pearl is located on Shoal Bay Beach

Anguilla

Beachfront | Pool | AC

from $3200/Nt
Sandyline Villa is one of the most luxurious estates on St. Martin. The exterior amenities are endless, and the villa’... 5 BR rate available.
Has specials.
Plenty of loungers surround the swimming pool

Terres Basses (French side), St. Martin

Near Beach | Pool

from $4429/Nt
Book Ani Villa South if you need a family friendly, wheelchair accessible vacation rental. This 6-bedroom villa is ultra modern ... Ani Villa South in Anguilla is an excellent destination in the Caribbean

Anguilla

Pool

from $6775/Nt
With a billiards table, fitness area, an outdoor covered terrace, a heated swimming pool, and nearby tennis courts, this property ... 4 BR rate available.
Has specials.
Tropical ambiance surrounds Casa del Mar Villa

Petit Cul de Sac, St. Barts

Near Beach | Pool

from $4286/Nt
When you arrive at Bon Temps Villa, the first thing to do is stake out your chaise lounge. While everyone ... 4 & 5 BR rates available.
Has specials.
Bon Temps is located on the west side of Pointe Milou looking out into the Caribbean

Pointe Milou, St. Barts

Pool

from $3143/Nt
Le Manoir de Lurin Villa is not your typical rental. Of course, it is larger than most with its 6 bedrooms ... 1, 2, 3 & 5 BR rates available. Le Manoir de Lurin Villa photo

Lurin, St. Barts

Pool

from $2143/Nt
Perched on the coast, Sun Salutations Villa has spacious, modern interiors and stunning views that make it an ideal spot ... The perfect image for Sun Salutations Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2499/Nt
There's no need to fight the crowds at a large beach resort when you can stay at Gardenia Villa and ... 4 BR rate available.
Has specials.
Tropical luxury surrounds the pool area and views of the ocean at Gardenia Villa

Barbados

Beachfront | Pool | AC

from $2900/Nt
Kishti Villa on Meads East is a spacious and extravagant beachfront property on one of the best beaches in the ... 4 BR rate available. Kishti Villa East on Meads Bay offers relaxing outdoor spaces

Anguilla

Beachfront | Pool | AC

from $4200/Nt
Awa’s unique pool with a dark mosaic floor keeps the water extra cool and makes for a beautiful focal ... Awa Villa photo

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $6900/Nt
Maison Blanc Bleu is breathtaking. The pool is huge, and the deck leaves plenty of room if you use the ... 4 & 5 BR rates available. Maison Blanc Bleu Villa photo

Lurin, St. Barts

Pool

from $5000/Nt
Tip of the Tail is so private, you'll feel like you have the island all to yourself. It has an ... Tip of the Tail Villa sits on the peninsula for which it is named

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $4800/Nt
Belle Etoile's pool is the selling point for me. The view of the island and ocean is amazing, and the ... 3 & 4 BR rates available. Ocean views from the terrace at Belle Etoile

Vitet, St. Barts

Pool

from $2500/Nt
I think Godings is simply breathtaking. The indoors and outdoors blend together beautifully, and I can't say enough about the ... Godings Beach House photo

Barbados

Beachfront | Pool | AC

from $5000/Nt
Coral Pavilion is chic and elegant, the perfect vacation rental if you want to feel like royalty. You’ll love ... 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
The Five Bedroom Beach Level residences are perfect for families or four couples to share. They're right on Grace Bay ... 4 BR rate available.
Has specials.
The Grace Bay Club Estate

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $3840/Nt
Casa de la Playa is perfect for two families who want to vacation on St. Martin's glamorous west coast. It ... Has specials. Casa de la Playa Villa is located on Baie Longue in Terres Basses

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $3614/Nt
Nirvana is ideal for couples who want to vacation on the beach in style. The pool isn't massive, but who ... 4 BR rate available.
Has specials.
Nirvana's pool deck and lounges

Barbados

Beachfront | Pool | AC

from $1500/Nt
This luxury rental sits right on Paynes Bay and is the only unit in the complex to have a private ... 3 & 4 BR rates available.
Has specials.
The Villa at the St. James is located beachfront on Paynes Bay Beach

Barbados

Beachfront | Pool | AC

from $1300/Nt
This beachfront villa is ideal for anyone who wants the security of a resort and the spaciousness of a private ... 3 & 4 BR rates available.
Has specials.
The One at St. James is located on Paynes Bay Beach

Barbados

Beachfront | AC

from $1100/Nt
Zazen is an ultra-modern beachfront villa that doesn't sacrifice any privacy. It's on Cattlewash Beach, a little-known but gorgeous part ... Has specials. Zazen Villa is located on Cattlewash Beach

Barbados

Beachfront | Pool | AC

from $3000/Nt
Windfall is an amazing family vacation destination for any age group. It has three king suites, one queen, and two ... Has specials. Windfall Villa's open-air pool with retractable canopy

Barbados

Pool

from $1750/Nt
Emerald Pavilion is the place to stay for a luxurious, beachfront vacation. This villa was designed by Paul Duesing Partners ... Has specials. Emerald Pavilion Villa is located on Emerald Point beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $6000/Nt
Vision Beach is a gorgeous, luxurious villa on Turks and Caicos’s most envied location: Grace Bay Beach. Not only ... Hot tub with-in the pool

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $6500/Nt
Seascape is the perfect place for five couples to experience the best part of Turks and Caicos. This chic five-bedroom ... Has specials. Seascape Villa is located on a beautiful stretch of Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $3900/Nt
Dunes 2 by Grace Bay Resorts is an easy, breezy way to relax in luxury in Turks and Caicos. This villa ... Has specials. Dunes 2 on Grace Bay

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $3600/Nt
Residence 2 lets you enjoy the convenience of a resort community and the comforts of home, in one villa. The villa ... 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 $3800/Nt
Residence 3 enjoys luxurious design inside and out, from the open exterior to the elegant living area. The kitchen is well-designed ... Has specials. Residence 3 photo

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4400/Nt
The owners of La Vita are long-time St. Johnians, and you can tell they love the island. The villa is ... La Vita Villa is located on a hillside above Peter Bay Beach

Peter Bay, St. John

Pool

from $2571/Nt
Bajan Heights is a luxurious villa with five-star amenities, daily housekeeping, and a private chef. The villa is in a ... Bajan Heights is located in Royal Westmoreland

Barbados

Pool

from $1500/Nt
Vivero 39 offers an ideal location within the Casa de Campo Resort Community. Casa de Campo’s tennis courts, country club, ... Vivero 39 is located in Casa de Campo and is just a short distance from the golf course

Casa de Campo, Dominican Republic

Pool

from $2580/Nt
Akim is absolutely stunning. It’s super open and modern, there are cement walls and marble pillars, and glass windows ... Pool

Cap Cana, Dominican Republic

Pool

from $3600/Nt
Cool Wind is a gorgeous, well-designed villa for your next family vacation. It's spacious, elegant, and near tons of activities ... Cool Wind is located the Westland Heights neighborhood of Westmoreland

Barbados

Pool

from $2800/Nt
Tolumnia is a beautiful, spacious villa for group vacations. There’s tons of lounging space outside around the pool and ... 2, 3 & 4 BR rates available. Tolumnia is located on an acre of national park overlooking the bay of Willoughby

English Harbour, Antigua

Pool

from $627/Nt
If you want the resort experience without the crowds, Beach Enclave at Grace Bay is for you. Each villa enjoys ... Has specials. Beach Enclave Beach Front at Grace Bay photo

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $7600/Nt
If you want to be pampered, come to Sea Villa. In addition to its stunning common areas, you have access ... Has specials. Sea Villa is situated facing the beach with amazing unobscured ocean views

Anguilla

Beachfront | Pool | AC

from $3300/Nt
At Long Bay Villas, you can expect to be relaxed and pampered. There's a full staff, water sports, four king ... Has specials. The luxurious Sand Villa at Long Bay

Anguilla

Beachfront | Pool | AC

from $3100/Nt
Moon Reach combines privacy, luxury, and convenience perfectly. Lush gardens and a wrought iron gate are all that stands between ... Has specials. The ocean is just steps away from the pool at Moon Reach

Barbados

Beachfront | Pool | AC

from $3200/Nt
Great for a family, Indian Song Villa is in a private gated community, with beachfront access and plenty of space ... 2, 3 & 4 BR rates available. Beautiful infinity edge pool over looking Petit cul de sac

Petit Cul de Sac, St. Barts

Beachfront | Pool | AC

from $2429/Nt
If you want true pampering, come to Sky Villa. Things like daily housekeeping service are par for the course. Speaking ... Has specials. Sky Villa is the most private of the Long Bay Villas located just off the beach

Anguilla

Near Beach | Pool

from $2900/Nt
If you have ever dreamed about the perfect family beach vacation or getaway for several couples, St. Bernard's Hill House ... St. Bernard's Hill House sit on a tropical hillside overlooking Belmont

Tortola, BVI, British Virgin Islands

from $3643/Nt
When staying at this villa, you will be privy to a one-of-a-kind island deck with deck chairs located just above ... 4 BR rate available. The pool at Palm Beach is just steps away from the beach

Lorient, St. Barts

Near Beach

from $3571/Nt
Located on a private cove with a sandy beach, Arushi Villa is one of Anguilla's premier villas. With over 5,300 square ... 1, 2, 3 & 4 BR rates available. Arushi Villa is located on the western end of Rendezvous Bay

Anguilla

Beachfront | Pool | AC

from $2800/Nt
Palm Springs Villa is in Gouverneur minutes away from the beach and Gustavia. Every room opens to the sundeck and ... 2, 3 & 4 BR rates available. Palm Springs Villa is located on a hillside in Gouverneur

Gouverneur, St. Barts

Pool

from $2857/Nt
Featuring 9,000-square-feet of living space, five spacious bedrooms, and over 600 feet of the sugary sands of Grace Bay beach, Amazing ... The pool area at Amazing Grace Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $5500/Nt
Five spacious bedrooms and five bathrooms make up Nirvana Villa, whose name fits perfectly with the home's zen vibe. Everything ... 2, 3 & 4 BR rates available.
Has specials.
The beautiful pool and tropical landscaping at Nirvana Villa

Lurin, St. Barts

Pool

from $2843/Nt
At La Danse Des Etoiles Villa in the Pointe Milou area of St. Barts, guests are invited to experience relaxation ... 3 BR rate available. La Danse Des Etoiles Villa photo

Pointe Milou, St. Barts

Pool

from $4800/Nt
Vue De Reve Villa is a uniquely designed private estate with upscale furnishings and tons of privacy. The main house ... Amazing views of the bay and the Caribbean beyond

Saint Jean, St. Barts

Pool

from $7071/Nt
The Dream is a luxurious beachfront villa with ocean views, open floor plans, outdoor living areas, and a gorgeous pool. ... Has specials. Luxurious pool just steps away from the beach at The Dream Villa

Barbados

Beachfront | Pool | AC

from $3500/Nt
Taking a family vacation is exciting, and the best ones happen when you choose a place that the whole family ... Vitti Villa photo

Lurin, St. Barts

Near Beach | Pool

from $4571/Nt
The sunsets at Kishti Villa on Blackgarden are truly incomparable. In fact, the sunset-obsessed owner of the villa gave his ... Kishti Villa on Blackgarden is situated to enjoy amazing ocean views

Anguilla

Near Beach | Pool

from $3500/Nt
La Petite Sereine is definitely luxurious. The decor is beautiful, the view is beautiful, the outdoor space is beautiful. I ... Pool at La Petite Sereine overlooking the ocean

Pointe Milou, St. Barts

Pool

from $7143/Nt
Turtle Tail is for any large group that wants it all. The activities you can do are limitless inside and ... Turtle Tail Estate is located on the southern tip of Turtle Tail

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $10000/Nt
Whatever you’re looking for in an island getaway, Nandana’s got it. You have ultimate privacy, luxurious everything, and ... 3 BR rate available. Nandana Villa in the Bahamas

Grand Bahama Island, Bahamas

Pool

from $10500/Nt
If you want an oceanfront property that is as deluxe as it is spacious, then Kishti Villa on Meads Bay ... 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
This villa's name and decor was inspired by Sinatra's "I Did It My Way", and the luxurious, unique design certainly ... 3 & 4 BR rates available. My Way Villa sits on a hillside looking over the Flamands Bay

Flamands, St. Barts

Pool

from $3571/Nt
This villa manages to be luxurious and family friendly at the same time. Four bedrooms plus a bungalow make the ... BOM Villa is located on the beach in St. Jean Bay

Saint Jean, St. Barts

Beachfront | Pool | AC

from $8421/Nt
This villa is great for a family. Most of the bedrooms are upstairs, and there's terraces on both levels so ... 4 BR rate available. Saving Grace Villa is located on the far northeast end of Grace Bay

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2300/Nt
The Dunes 1 is perfect for any traveler who wants five-star resort amenities on picturesque Grace Bay. Stroll along the beach ... Has specials. The interior pool and dining palapa at the Dunes 1 Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $3600/Nt
This villa's outdoor space almost reminds me of a James Bond movie. The open view is sure to induce heavy ... 3 & 4 BR rates available. Castle Rock Villa photo

Camaruche, St. Barts

Pool

from $4000/Nt
Besides this villa's spectacular view, it has one of the most complete private wine inventories on island that guests can ... 3 & 4 BR rates available. Legends B Villa is located in Lurin above Shell Beach with views of Gustavia

Lurin, St. Barts

Pool

from $2857/Nt
I can't get over this villa's decor and layout. It feels like a zen retreat, but is still fairly convenient ... 3 BR rate available. Ixfalia photo

Saint Jean, St. Barts

Pool

from $3571/Nt
Axel Rocks is great for many reasons, and one of those is its location. A short drive will take you ... 2 & 3 BR rates available. Amazing Caribbean views from Axel Rocks Villa

Gustavia, St. Barts

Pool

from $3571/Nt
Villa B53 at Tortuga Bay

Punta Cana, Dominican Republic

Pool

from $960/Nt
Olympus is a modern, beachfront villa with full air-conditioning and an enviable location near Rum Point Beach. Rum Point is ... Has specials. An aerial view of Olympus Villa and the beautiful beachfront

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1500/Nt
The Penthouse Suite in the Villas at Grace Bay Club is perfect for travelers who want to be as close ... Has specials. Grace Bay Club Resort pool

Grace Bay, Turks and Caicos

Beachfront | AC

from $4270/Nt
If you're traveling to Costa Rica with your friends or extended family, you'll love La Perla. There's three suites in ... Has specials. La Perla Villa is located in Altamira, just above the Marina in Los Suenos

Costa Rica

Pool

from $1600/Nt
The Four Bedroom Beachfront Collection at Sugar Beach is the place to go for a luxury experience. Each villa provides ... The Beachfront Luxury Collection is located on the white sands of Sugar Beach in St. Lucia

Soufriere, St. Lucia

Beachfront | Pool | AC

from $5985/Nt
Bristol Bliss is the perfect villa for a quiet vacation with your favorite couples. It's on Turtle Tail, which is ... The pool at Bristol Bliss sits beachside overlooking the azure waters so famous in Turks and Caicos

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $2100/Nt
Emeraude feels like a private resort, it’s so gorgeous. The pool deck is super luxurious, and there’s so ... 3 BR rate available.
Has specials.
Villa Emeraude is located in Indigo Bay

Indigo Bay (Dutch Side), St. Martin

Pool

from $929/Nt
Beach House is all about location, location, location. It’s on Taylor Bay, which is one of my absolute favorites ... The Beach House Villa is located within walking distance of Taylor Bay Beach

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $1750/Nt
Olympus has it all: a beachfront location, modern design, and tons of space to lounge. Whether you want to relax ... Olympus is located on the beach front in Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1500/Nt
Gorgeous sunsets, modern interiors, and resort amenities make this villa special. Elysium is right on the beach, so the views ... Elysium is located in the Jolly Harbour community

Jolly Harbour, Antigua

Beachfront | Pool | AC

from $3990/Nt
If you're looking for something super modern, you've come to the right place. Ani Villa North is a 4-bedroom, 4-bath ... Ani Villa North is a beautiful location for a Caribbean getaway

Anguilla

Pool

from $5225/Nt
When ISLANDS magazine names you 'One of the Top 20 villas in the World', it's always a good sign. It has ... 1, 2 & 3 BR rates available.
Has specials.
The beautiful Bird of Paradise Villa

Anguilla

Near Beach | Pool

from $1850/Nt
With a unique layout, Olive Villa offers its guests a private hillside escape from which to enjoy all that St. ... 1, 2 & 3 BR rates available. Olive Villa is  located in Gouverneur with a panoramic view of the bay

Gouverneur, St. Barts

Pool

from $2571/Nt
Good News Villa has much to offer potential guests. This 4-bedroom property not only has the vast, quiet spaces that ... Good News Villa is located in Petit Cul De Sac overlooking Petites Anses  into the Caribbean

Petit Cul de Sac, St. Barts

Pool

from $2714/Nt
This villa is definitely striking! Two steel wings cap the roof, and the pool flows over the top deck to ... 2 & 3 BR rates available. Enjoy your private pool perched hillside in St. Jean with views of St. Jean Bay

Saint Jean, St. Barts

Pool

from $2286/Nt
Located off the white sands of Malcolm beach, the Amanyara Resort is great for the nature-focused traveler who wants to ... Amanyara Beach Villa photo

Providenciales, Turks and Caicos

Beachfront | Pool | AC

from Call for rates
Sienna has a gorgeous terrace and views of the golf course. The terrace can be closed off to the pool ... Has specials. Sienna Villa

Barbados

Pool

from $950/Nt
Skyline is absolutely gorgeous. Its so modern, so chic, and so luxurious! I love how much glass is in the ... Has specials. Skyline photo

North Shore, Turks and Caicos

Pool

from $2300/Nt
If you’re looking for an Anguilla beachfront rental, this resort villa is worth a look. It’s right on ... Tranquility Beach - Beachfront Penthouse Villa is located on Meads Bay Beach

Anguilla

Beachfront | AC

from $1500/Nt
Modern design, beach access, and three bedrooms make this penthouse the perfect rental for your next vacation. It’s right ... Tranquility Beach - Penthouse photo

Anguilla

Beachfront | AC

from $1050/Nt
Villa Lam offers families of older children, or up to three couples who want to vacation together, a pleasant way ... Amazing infinity edge pool at Lam Villa

Gustavia, St. Barts

Pool

from $3286/Nt
Your friends and family will love this beachfront rental on Meads Bay. It combines two units into one villa, so ... Tranquility Beach - Two Bedroom Beachfront Villa is located on Meads Bay Beach

Anguilla

Beachfront | AC

from $950/Nt
Your friends and family will love staying in this Meads Bay villa. It combines two units into one, so everyone ... Tranquility Beach Anguilla is located on Meads Bay Beach

Anguilla

Beachfront | AC

from $675/Nt
It doesn't get better than this! Tranquility Beach sits directly on one of the most beautiful beaches in the Caribbean...... Tranquility Beach - One Bedroom Beachfront Villa is located on Meads Bay Beach

Anguilla

Beachfront | AC

from $500/Nt
Meads Bay is one of the Caribbean’s most gorgeous white sand beaches, and Tranquility Beach sits right in the ... Tranquility Beach - One Bedroom Premium Beachfront Villa is located on Meads Bay Beach

Anguilla

Beachfront | AC

from $600/Nt
Tranquility Beach’s Beachfront 1 Bedroom Suite is a stress-free choice for a honeymoon or romantic getaway. You can catch ocean ... Tranquility Beach - One Bedroom Suite Beachfront Villa is located on Meads Bay Beach

Anguilla

Beachfront | AC

from $500/Nt
The 1 Bedroom Premium unit is a great place to stay if you want beach access, resort facilities, and one modern ... Tranquility Beach - 1 Bedroom Premium photo

Anguilla

Beachfront | AC

from $395/Nt
Tranquility Beach has one of the best locations on the island. It’s in the center of Meads Bay near ... Tranquility Beach - 1 Bedroom Suite photo

Anguilla

Beachfront | AC

from $350/Nt
Meads Bay is one of the Caribbean’s most gorgeous white sand beaches, and Tranquility Beach sits front and center. ... Tranquility Beach Anguilla is located on Meads Bay Beach

Anguilla

Beachfront | AC

from $350/Nt

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