Caribbean Honeymoon Villas

Caribbean Honeymoon Villas


Private, quiet and intimate, these villas are perfect for a honeymoon or any romantic celebration. Imagine a private chef-prepared dinner for two under the stars with no one else around but the two of you. Or perhaps, lounge by the ocean side at your private beach or private island villa. Away from the crowded hotels, resorts and cruise ships, a villa provides the ultimate romantic getaway.


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 Call for rates
Necker Island is the place to go if you want the ultimate privacy, luxury, and pampering. You can rent out ... 15 BR rate available.
Has specials.
The Beach pool at Necker Island

Necker Island, BVI, British Virgin Islands

Beachfront | Pool | AC

from $77500/Nt
This private island resort is perfect for a casual, relaxing vacation for any group of travelers. Every activity you can ... Thatch Caye photo

Belize

Near Beach

from $9785/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 Call for rates
Silent Waters Villa is a sprawling villa just outside of Montego Bay that offers everything you could possibly need for ... 5, 6 & 9 BR rates available. Aerial View of Silent Waters

Montego Bay, Jamaica

Pool

from $2482/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
If you want to hear the ocean from every room, then Sunrise Villa is the perfect setting for your next ... Sunrise Villa photo

Cabrera, Dominican Republic

Beachfront | Pool | AC

from $1600/Nt
Located on a hillside in St. John, Eco Serendib is a spacious 8-suite villa that serves as an ideal setting ... 1 & 5 BR rates available.
Has specials.
The pool and ocean views from Eco Serendib!

Rendezvous Bay, St. John

Pool

from $1843/Nt
Monte Bay Villa is an attractive getaway with a master suite that will make you want to spend your entire ... 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
Cayo Espanto strips away the world-weary savviness of travelers who have been everywhere and seen everything, leaving every guest feeling ... Cayo Espanto - Entire Island photo

Belize

Pool

from $13995/Nt
Cosmos is perfect if you love being outside and want to be one with nature. You could rent The Lodge ... 4, 5 & 6 BR rates available. Cosmos photo

Soufriere, St. Lucia

Pool

from $950/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. The Estate at Daniel Bay #024, is situated in Willoughby Bay

English Harbour, Antigua

Beachfront | Pool | AC

from $1161/Nt
These resort villas are perfect for any group that wants to vacation in style. The villas range from three to ... 4 & 5 BR rates available. The elegant Shore Club Villas feature private swimming pools

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $6000/Nt
White Coral is a bright, modern villa right on the Leeward Canal. The six bedrooms are great for a family ... White Coral Villa is located right on the Leeward Canal

Leeward, Turks and Caicos

Pool

from $1700/Nt
At Summer Heights, you can jumpstart your day with coffee in bed while you watch the sailboats and yachts head ... Summer Heights is located on a hillside above Nanny Cay

Tortola, BVI, British Virgin Islands

Pool

from $750/Nt
Bajacu Villa has a totally unique design that gives you the best of both worlds: hilltop views and easy ocean ... Bajacu photo

Turtle Tail, Turks and Caicos

Pool

from $6000/Nt
With fantastic sweeping water and hillside views, Amancaya is a private and beautifully landscaped villa near Anse des Cayes and ... 1, 2, 3, 4 & 5 BR rates available. Amancaya Villa photo

Anse des Cayes, St. Barts

Pool

from $2429/Nt
Colibri Cottage is ideal for a nature-centric getaway in St. Lucia. The villa has gorgeous views of Petit Piton and ... 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
Aurora Villa is a five-bedroom luxury villa perfect for couples or families with children over the age of ten. The ... 3, 4 & 5 BR rates available.
Has specials.
Aurora Villa is located in between Sandy Lane and Paynes Bay’s beaches

Barbados

Pool

from $1000/Nt
There’s something for everyone at Sandalwood House. You can enjoy a round of golf and a romantic dinner for ... 3 & 4 BR rates available.
Has specials.
Twilight on the patio at Sandalwood Cottage

Barbados

Near Beach | Pool

from $925/Nt
This six-bedroom Clairmont Overlook Villa is absolutely perfect for large family getaways, employee retreats, or for a group of friends ... 1, 2, 3, 4 & 5 BR rates available. Clairmont Overlook photo

St. Croix, USVI

Pool

from $629/Nt
If you're looking for an oceanfront honeymoon or group vacay villa, Sea's Edge is perfect. It has easy ocean access, ... 2, 3 & 4 BR rates available. Sea’s Edge sits above Rendezvous Bay with amazing ocean views

Rendezvous Bay, St. John

Pool

from $1000/Nt
Crystal Waters, formerly known as Mudslide, is the perfect villa for your next family vacation. Every room is oversized, and ... 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
The Five Bedroom Beach Level residences are perfect for families or three couples to share. They're right on Grace Bay ... 4 BR rate available. The Grace Bay Club Estate

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4800/Nt
Dunes 2 by Grace Bay Resorts is an easy, breezy way to relax in luxury in Turks and Caicos. This villa ... 3 BR rate available. Dunes 2 on Grace Bay

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4800/Nt
Residence 2 lets you enjoy the convenience of a resort community and the comforts of home, in one villa. The villa ... 4 BR rate available. 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
The Residences is a beachfront, resort community within the exclusive Grace Bay Club. Residence 3 enjoys luxurious design inside and out, ... 4 BR rate available. Residence 3 photo

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $5100/Nt
Tre Vista is a super tranquil, comfortable villa perfect for you and your closest friends. There's a separate suite for ... 1, 2, 3 & 4 BR rates available.
Has specials.
Tre Vista Estate sits on a hill top above Great Cruz Bay and Chocolate Hole

Chocolate Hole, St. John

Pool

from $786/Nt
Blue Lagoon has all the amenities needed for an amazing couples’ retreat. You can enjoy sunset cocktails on the pool ... Blue Lagoon Villa is located in the exclusive Garden Area

Barbados

Beachfront | Pool | AC

from $4350/Nt
Your Caribbean vacation will be something special when you stay at the beautiful Wild Orchid villa. The house itself is ... 1, 2 & 3 BR rates available.
Has specials.
Wild Orchid Villa photo

Cap Estate, St. Lucia

Near Beach | Pool

from $400/Nt
With sunsets and fresh breezes, Inn Love is the perfect villa for a honeymoon couple. Spend time playing one of ... 2, 3 & 4 BR rates available. Enjoy beautiful views of Great Cruz Bay form Solare Villa

Great Cruz Bay, St. John

Near Beach | Pool

from $443/Nt
This villa would be lovely for a family vacation. You and the kids can play all day on the tennis ... 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
Heronetta has an enviable location between Sandy Lane Beach and Paynes Bay. On Sandy Lane, guests can enjoy exclusive access ... 4 BR rate available.
Has specials.
Heronetta Villa- Sandy Lane photo

Barbados

Beachfront | Pool | AC

from $1500/Nt
Point of View Villa is a five-bedroom villa in the heart of the Sandy Lane Estate. Thanks to its central ... 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
Because La Paloma Villa sits directly on the beach, you have access to unlimited snorkeling and kayaking. For evenings in, ... 3 & 4 BR rates available.
Has specials.
La Paloma Villa photo

Barbados

Beachfront | Pool | AC

from $675/Nt
One acre of tropical beauty and privacy are the hallmark of the gorgeous Stanford House. You can get married in ... 4 BR rate available.
Has specials.
Stanford House photo

Barbados

Pool

from $1500/Nt
Mystic Villa is located on a St. Jean hillside and is ideal for a family with older children, four couples, ... 2, 3 & 4 BR rates available. Mystic Villa overlooks the beautiful St. Jean Bay and the famous Eden Rock hotel

Saint Jean, St. Barts

Pool

from $2136/Nt
Take a path down to the beach from Solitude House and enjoy the ease of access to snorkeling and the ... 1, 2, 3 & 4 BR rates available. Solitude House photo

St. Croix, USVI

Near Beach | Pool

from $429/Nt
Pandanus Villa rests on a ridge on the West Coast of Barbados and offers everything you could want in a ... 2 & 4 BR rates available.
Has specials.
Pandanus Villa has beautiful gardens and is on a private ridge overlooking the Caribbean

Barbados

Pool

from $700/Nt
Refined perfection and luxurious privacy reign supreme at Isla Vista. The panoramic island views create a memorable backdrop for lazy ... 3 & 4 BR rates available. Isla Viasta is located in the hills of St. john with amazing views

Caneel Hill, St. John

Pool

from $1050/Nt
If you are looking for a vacation villa that is just steps away from the beach with a full staff ... Bali Dreams Villa photo

Cabrera, Dominican Republic

Near Beach | Pool

from $1200/Nt
Arc En Ciel is set in an exotic wonderland with volcanos, waterfalls, and the Piton mountain range. Its near diving, ... 3 BR rate available.
Has specials.
Arc En Ciel Villa photo

Soufriere, St. Lucia

Near Beach | Pool

from $1900/Nt
Beaches Edge villa has a smart design that maximizes the ocean views. Of course there's a pool, daily maid service, ... Has specials. Lounge by the pool and enjoy amazing ocean views at Beaches Edge East Villa

Anguilla

Near Beach | Pool

from $1400/Nt
Book a magical vacation unlike any other when you stay at Aja Villa. Located in the ideal spot to see ... 2, 3 & 4 BR rates available. Aja Villa photo

Tortola, BVI, British Virgin Islands

Near Beach

from $800/Nt
Looking for a remote home experience with all of the services and perks of a first-class resort? The Residences on ... 4 BR rate available. 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
The Dunes 1 is perfect for any traveler who wants five-star resort amenities on picturesque Grace Bay. Stroll along the beach ... 3 BR rate available. The interior pool and dining palapa at the Dunes 1 Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4800/Nt
Truffle Villa is perfect for romantic getaways. The master bedroom is really well-designed, you can open your door to the ... 1, 2 & 4 BR rates available.
Has specials.
Truffle Villa photo

Terres Basses (French side), St. Martin

Near Beach | Pool

from $857/Nt
This villa is a great choice for any group of travelers. The villa is only a few minutes from Flamands ... 3 BR rate available. Alpaka Villa has beautiful views from its hillside location over Flamands Beach

Flamands, St. Barts

Pool

from $914/Nt
The Penthouse Suite in the Villas at Grace Bay Club is perfect for travelers who want to be as close ... Grace Bay Club Resort pool

Grace Bay, Turks and Caicos

Beachfront | AC

from $5330/Nt
Villa Islander is an architect's dream. Its surrounded by greenery, has floor-to-ceiling windows in every room, and uses only the ... Villa Islander is located just off the famous Grace Bay Beach

Grace Bay, Turks and Caicos

Near Beach | Pool

from $1880/Nt
Four bedrooms with adjoining baths make this property a good fit for up to four couples, but it also welcomes ... 2 & 3 BR rates available. Nomade Villa photo

Lurin, St. Barts

Pool

from $953/Nt
Oceanside Tower is a magnificent oceanfront villa with unforgettable views of the Caribbean Sea and the Caicos Bank. This four-bedroom ... Oceanside Tower Villa is located in the Silly Creek area

Providenciales, Turks and Caicos

Pool

from $1286/Nt
Turks and Caicos is well known for its beautiful beaches, and Five Turtles Villa gives you direct access to one ... Five Turtles Villa is just steps away from Taylor Bay Beach

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $1214/Nt
If you are looking for a place to have a couple's get-away or to honeymoon, consider Cadasse Villa. The maid ... 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
Bonavista Villa is located in a gated community, and is just steps away from Gibbs Beach. It has a cook, ... 3 BR rate available.
Has specials.
Tropical surroundings greet you at the pool at Bonavista Villa

Barbados

Beachfront | Pool | AC

from $1375/Nt
Fosters House is a gorgeous beachfront property directly on Mullins Beach. It offers 4 bedrooms, all with air-conditioning and their own ... Has specials. Fosters House Villa is located right on Mullins Bay Beach

Barbados

Beachfront | Pool | AC

from $1300/Nt
Sundown Villa provides views of the ocean with the security of a gated entrance. Whether you're honeymooners or a vacationing ... Has specials. Sundown Villa is located near Mullins Beach

Barbados

Near Beach | Pool

from $650/Nt
Just one minute from local cuisine and ten minutes from the airport, Fregate Villa houses four bedrooms that sleep up ... 1, 2 & 3 BR rates available. Fregate Villa photo

Pointe Milou, St. Barts

Pool

from $786/Nt
With a rooftop sundeck, swimming pool, and easy access to the beach, you'll be amazed by this waterfront villa. Whether ... The shaded pool at Jasmine Villa is a great place to relax

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $790/Nt
Alamandra Villa is a spacious luxury villa with the best waterfront views in Silly Creek. There's a 20 x 35 infinity edge ... Alamandra is located in Silly Creek with great waterfront views

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1129/Nt
St John's Las Brisas Caribe Villa is tropical Caribbean architecture at its best! What could be better than waking up ... 2 & 3 BR rates available. Las Brisas Caribe is located on Maria Bluff in St. John

Great Cruz Bay, St. John

Pool

from $750/Nt
Great Turtle sits nestled within the hills and enjoys wonderful views of Coral Bay, the Caribbean Sea, and the Bordeaux ... 2 & 3 BR rates available. Great Turtle Villa is nestled on a tropical hillside above Coral Bay

Coral Bay, St. John

Pool

from $430/Nt
Ixora Villa is located off of the Royal Westmoreland Golf Course’s 16th fairway. This luxurious villa is ensconced in ... 3 BR rate available.
Has specials.
Ixora Villa is located in the gated Royal Westmoreland neighborhood on the Golf Course 16th fairway

Barbados

Pool

from $1070/Nt
Located in the peaceful Turtle Tail area, Sandy Shore has direct beach access, a private onsite swimming pool, a kayak, ... Sandy Shore Villa is located on the beach of the beautiful Taylor Bay

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $1071/Nt
The area of Terres Basses, on the French side of St. Martin, is highly sought-after due to its location and ... 2 & 3 BR rates available.
Has specials.
Sea Vous Play photo

Terres Basses (French side), St. Martin

Pool

from $446/Nt
If you love to cook, a great kitchen can make a huge difference. At Mangrove Villa at Indigo Reef, there's ... Mangrove - is located in the Villas at Indigo Reef on West End Bay

Anguilla

Beachfront | Pool | AC

from $900/Nt
If you know what Poggenpohl and Miele are, you know you want them in your kitchen. Not only do guests ... Sandcastle Pointe Villa is located on the waterfront on Shoal Bay

Anguilla

Pool

from $1200/Nt
The View Villa is a four-bedroom, four-bath property in Columbier that hangs over the ocean (therefore the name, "The View"). ... 3 BR rate available. The View photo

Colombier, St. Barts

Pool

from $2429/Nt
If you love a beautiful sunset view, come to BP Villa. This villa offers a heated pool, covered porches, and ... 1, 2 & 3 BR rates available.
Has specials.
BP Villa is located near Shoal Bay Beach

Anguilla

Near Beach | Pool

from $1000/Nt
Vista Villa offers panoramic views and a small, private beach next to a reef perfect for snorkeling. The home is ... 1, 2 & 3 BR rates available. Vista Villa has a beautiful private pool and great ocean views

Anguilla

Pool

from $500/Nt
More luxurious than other St. John villas, Heaven's Gate is ideal for a family reunion, an off-site corporate retreat, or ... 1, 2 & 3 BR rates available. Heaven's Gate Villa photo

Coral Bay, St. John

from $447/Nt
With a private pool, onsite restaurants and activities, and a beachfront location, you and your family will never want to ... The vibrant colors at Turtle Villa provide for a fun atmosphere right on the beach

Jolly Harbour, Antigua

Beachfront | Pool | AC

from $1843/Nt
If you like both contemporary and Caribbean styles, you'll love the beautiful browns, blues and whites at Seabird Villa. This ... 2 & 3 BR rates available. Seabird Villa has beautiful sunset views

Anguilla

Near Beach | Pool

from $650/Nt
What a wonderful place for a large family or several friends and families to take a beach vacation. This large, ... 2 & 3 BR rates available. Amarillo Villa is located in True Blue Grenada

Grenada

Pool

from $500/Nt
Sunspot Villa manages to combine modern architecture with island charm. It can be used for a family gathering or for ... 2 & 3 BR rates available. Sunspot Villa photo

Peter Bay, St. John

Near Beach | Pool

from $1453/Nt
Kaya has everything guests need, including four air-conditioned bedrooms, U.S. satellite TV, and WiFi. This villa is a short ... 2 & 3 BR rates available. Kaya Villa located in Vitet and overlooks Lorient Bay

Vitet, St. Barts

from $1000/Nt
Island Rider overlooks some of the clearest Caribbean water you've ever seen. You can spend hours just relaxing on the ... 1, 2 & 3 BR rates available.
Has specials.
Impressive views of the Caribbean from the pool and deck area at Island Rider Villa

Rendezvous Bay, St. John

Pool

from $886/Nt
Westshore Beach House is ideal for two couples or families who are traveling together. Both levels have two bedrooms, seating ... Westshore Beach House is located right on the beach between Alleyne's Bay and Reeds Bay

Barbados

Beachfront | Pool | AC

from $950/Nt
Every room in this villa has breathtaking water views! Whether you're relaxing on the covered deck or creating a light ... 1, 2 & 3 BR rates available.
Has specials.
Pool at La Bella Vita

Virgin Grand Estates, St. John

Pool

from $643/Nt
Perched on a mountainside, Mystic Ridge Villa allows guests to get away from the hustle and bustle of Cruz Bay ... 1, 2 & 3 BR rates available. Mystic Ridge is located on a lush hillside with in the National Park

Bordeaux, St. John

Pool

from $614/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
Avalon Villa, located right on the world-famous Grace Bay Beach, is where fun meets relaxation. This lush, tropical island getaway ... Beautiful resort-like pool and landscaping at Avalon Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2000/Nt
2B at Peter Bay Villa is known for its spacious design, high end furnishings, and waterfront location. This spectacular home ... 2B at peter Bay is perched on a tropical hillside above the west end of Peter Bay

North Shore, St. John

Near Beach | Pool

from $1857/Nt
St. Barts is known for its vibrant Caribbean charm, and the Ocean's 5 villa puts you right in the middle of ... 2 & 3 BR rates available. Ocean's 5 Villa photo

Flamands, St. Barts

Pool

from $1000/Nt
Mirande Villa, in the hills of Pointe Milou, offers a relaxing getaway for up to 3 couples. The villa is done ... 2 & 3 BR rates available. Views over Lorient Bay from the pool deck at Mirande Villa

Pointe Milou, St. Barts

Pool

from $500/Nt
Atelier's architect, Alistair Downie, infused tranquility and serenity into every modern detail at this two-story villa. From the master bedroom ... Has specials. Atelier Villa has modern architectural lines and a beautiful pool

Barbados

Near Beach | Pool

from $1500/Nt
With beautifully clear ocean views from every room, Cocoa at Pelican’s Nest is ideal for any family or group ... 3 BR rate available. Pelican's Nest Villas - Cocoa is located near Grace Bay Beach

Grace Bay, Turks and Caicos

Near Beach | Pool

from $857/Nt
Right on the coastline, the Bora Bora Lower Villa provides easy access to the water sports and beaches that make ... 2 BR rate available.
Has specials.
Dining

Barbados

Beachfront | AC

from $350/Nt
Looking out over the waters of Paynes Bay Beach, the Bora Bora Upper Villa is the complete mix of privacy ... 2 BR rate available.
Has specials.
Bora Bora Upper Villa photo

Barbados

Beachfront | AC

from $335/Nt
Rose Dog is truly an eclectic gem on the island of St. Barts. It has a comfortable layout, unique design, ... 2 & 3 BR rates available.
Has specials.
Rose Dog Villa has a beautiful infinity edge pool

Vitet, St. Barts

Pool

from $1043/Nt
Island Girl has not only gorgeous views, but also spreads four bedrooms out across four levels. I love the layout ... 1, 2 & 3 BR rates available.
Has specials.
View of Coral Bay from the villa pool area

Coral Bay, St. John

Pool

from $714/Nt
Turks and Caicos is well-known as one of the best areas in the Caribbean for beach lovers, and the Venetian ... Has specials. Penthouse at The Venetian photo

Grace Bay, Turks and Caicos

Beachfront | AC

from $1425/Nt
Bikini Villa is simply cozy. An open floor plan allows you to see all your guests relaxing, and the rooms ... 1 & 2 BR rates available. Bikini Villa photo

Lorient, St. Barts

Near Beach | Pool

from $457/Nt
Alaia is chic and convenient! The decor is very minimalist and modern, and the villa is just a short walk ... 2 BR rate available.
Has specials.
Alaia photo

Saint Jean, St. Barts

Near Beach | Pool

from $1071/Nt
Lone Palm gives guests an up close and personal view of the ocean. In fact, the sea is a few ... Has specials. Lone Palm Villa is located on a beautiful white sand beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $475/Nt
Babylon Reef feels like a classic beach house, with every amenity you could ask for. It's oceanfront, with a great ... Has specials. The private pool at Babylon Reef has a man made -beach- surrounding it

Grand Cayman, Cayman

Beachfront | Pool | AC

from $425/Nt
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 $1000/Nt
This vacation rental is perfect if you want to be in the middle of the action on Grace Bay. It ... The Estate at Grace Bay Club

Grace Bay, Turks and Caicos

Beachfront | AC

from $3700/Nt
This resort villa is the perfect choice if you want a convenient, blissful family vacation on Seven Mile Beach. You ... The Residences at Seafire are located on Seven Mile Beach

Grand Cayman, Cayman

Beachfront | AC

from $1500/Nt
This three-bedroom resort villa has everything you need for an easy family vacation. Everything has been thought of for you, ... Seafire Resort

Grand Cayman, Cayman

Beachfront | AC

from $1500/Nt
With sunset views, a large and private swimming pool, and direct ocean access, you'll begin to relax the moment you ... 1 BR rate available. Sublime Villa is situated near Silly Creek, and just a short distance to Taylor Bay

Chalk Sound, Turks and Caicos

Pool

from $750/Nt
Osprey villa has gorgeous sunset views and outdoor amenities perfect for a family vacation. The waterfront location is enhanced by ... Has specials. Osprey is located on the ocean side of Chalk Sound

Taylor Bay/Sapodilla Bay, Turks and Caicos

Pool

from $1100/Nt
The north-facing Anais Villa has lots of great features, but one of the best is the incredible ocean views that ... 1 & 2 BR rates available. Anais villa has amazing ocean views

Vitet, St. Barts

Pool

from $371/Nt
With its contemporary West Indian design, Baie Longue Beach House provides a much-needed relaxing getaway for couples, friends, or families ... 1 & 2 BR rates available.
Has specials.
Baie Longue Beach House Villa overlooks the beautiful Beach and Bay

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $771/Nt
This is an ideal vacation spot for two couples or a small family. Within walking distance of Flamands Beach, you ... 1 & 2 BR rates available. Lounge on the deck at Flamands Blue and enjoy views of the ocean

Flamands, St. Barts

Near Beach

from $379/Nt
Surrounded by palms and offering views of the Caribbean Sea and Pigeon Island, the Sand Dollar is everything you would ... 1 & 2 BR rates available.
Has specials.
Sand Dollar Villa photo

Cap Estate, St. Lucia

Pool

from $290/Nt
The beautifully landscaped and stylish Saline Reef is a great vacation spot for families with children over 12, or adults who ... 2 BR rate available. 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
Tequila Sunrise is a beachfront villa perfect for anyone who wants to have a truly relaxing vacation. It's extremely private, ... 1 & 2 BR rates available.
Has specials.
Lounge poolside with amazing views of the ocean

Anguilla

Near Beach | Pool

from $990/Nt
It's rare that the name of a vacation rental could truly summarize the benefits you will find inside, but this ... 1 & 2 BR rates available. Villa Serenity has a beautiful deck and unparalleled views of Gustavia Harbour

Gustavia, St. Barts

Near Beach | Pool

from $1071/Nt
Mongoose Run offers seclusion and privacy that will give you time to relax and get in touch with your family ... 2 BR rate available.
Has specials.
Mongoose Run Villa is located just at the north western end of Baie Rouge

Terres Basses (French side), St. Martin

Pool

from $443/Nt
Located in Terres Basses, Joie de Vivre is one of St. Martin's finest homes. It sits on over 4 acres and ... Has specials. Joie de Vivre sits above a beautiful stretch of Baie Rouge Beach

Terres Basses (French side), St. Martin

Near Beach | Pool

from $1357/Nt
Balinese truly is a Caribbean oasis. You can jump directly into the pool from two of the bedrooms, which also ... Balinese Villa sits in the Turtle Tail area of Providenciales

Turtle Tail, Turks and Caicos

Pool

from $1043/Nt
Maison Villa is ideal for those who want to be within walking distance to all that St. Jean has to ... 1 & 2 BR rates available. Maison Villa photo

Saint Jean, St. Barts

Near Beach | Pool

from $707/Nt
Le Mas de Sables is one of the most gorgeous villas on St. Martin, both inside and out. It has ... 1 & 2 BR rates available.
Has specials.
Le Mas des Sables Villa sits on the waterfront in beautiful Terres Basses

Terres Basses (French side), St. Martin

Pool

from $714/Nt
You're bound to enjoy the gardens, but there are many other features in this estate to make you feel at ... 1 & 2 BR rates available. Canefield house sits on a lovely hillside in the heart of Tortola

Tortola, BVI, British Virgin Islands

Pool

from $541/Nt
Abby Villa is the perfect St. Barts getaway for three couples who want a cozy, peaceful location near multiple beaches. ... 2 BR rate available. Abby Villa photo

Vitet, St. Barts

Pool

from $857/Nt
Cogui Villa is a cliffside property offering not only magnificent panoramic ocean views, but peace, privacy, and complete island relaxation. ... 1 & 2 BR rates available.
Has specials.
Amazing views of the Caribbean from the balconies at Coqui Villa

Great Cruz Bay, St. John

Pool

from $600/Nt
If you want to spend a lot of time outside, Royal Palm Villa is for you. The decor and design ... 1 & 2 BR rates available. Royal Palm Villa photo

Vitet, St. Barts

Pool

from $500/Nt
Terres Basses in St. Martin is known for fine beaches and great scenery, and La Magnolia Villa is situated to ... 1 & 2 BR rates available.
Has specials.
La Magnolia sits on a hilltop over Baie Longue with a great view of the ocean

Terres Basses (French side), St. Martin

Pool

from $457/Nt
Dasha Villa is quickly building a roster of loyal fans. A recent visitor summed up her stay at the villa ... 1 & 2 BR rates available. Dasha Villa photo

Lurin, St. Barts

Pool

from $943/Nt
The large pool is a focal point for this light-filled, 3-bedroom villa. Kids can play without getting in each others ... 2 BR rate available. Cactus Villa has amazing views of Gustavia Harbor wether it be by day or by night

Colombier, St. Barts

Pool

from $714/Nt
Tamarindo Villa is the perfect Caribbean escape for a family or one to two couples traveling together. With its private ... 1 & 2 BR rates available. Tamarindo Villa photo

Cruz Bay, St. John

Pool

from $386/Nt
Once you settle into this villa, you may never want to leave! The views are as entertaining as any movie ... 2 BR rate available. Datcha Villa photo

Flamands, St. Barts

Pool

from $629/Nt
Surrounded by mature tropical plants, Monchal Villa on St. Martin has a very private and secluded feel about it. Step ... 1 & 2 BR rates available.
Has specials.
Monchal Villa is located just a short distance from Plum Bay Beach

Terres Basses (French side), St. Martin

Near Beach | Pool

from $279/Nt
COMO Villa is perfect if you want ocean views and lots of privacy. With a staff that’s delighted to ... Has specials. COMO Villa at COMO Parrot Cay photo

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $5490/Nt
The heated pool at Island Views has a waterfall, and it's a nice place for those who enjoy swimming. Island ... 1 & 2 BR rates available. Island Views is located is on the corner of Chenay Bay lookin out to Buck Island

St. Croix, USVI

Near Beach | Pool

from $550/Nt
Villa del Sol's infinity pool and beachfront location make the perfect backdrop for week in the sun. With nearby golf, ... Poolside views of the Caribbean from Villa del Sol

Leeward, Turks and Caicos

Beachfront | Pool | AC

from $1750/Nt
Refuge Villa is located on a hillside and offers a bird's eye view of Brewer's Bay Beach. You can spend ... 1 & 2 BR rates available. Refuge Villa sits on a hill overlooking Brewers Bay

Tortola, BVI, British Virgin Islands

Near Beach | Pool

from $612/Nt
Church Point #2 is a cozy mix of urban living and island casual. The vaulted ceilings keep the house cool by ... 2 BR rate available.
Has specials.
A view to the ocean from the patio at Church Point Two

Barbados

Beachfront | Pool | AC

from $500/Nt
Andara Villa is a peaceful, private hillside villa perfect for travelers who want to get away from it all. Located ... 1 & 2 BR rates available. Andara Villa has amazing views over Haulover Bay

East End, St. John

Pool

from $643/Nt
Esprit Villa is a charming three-bedroom cottage on St. John. This unique island home has everything one could need for ... 1 & 2 BR rates available.
Has specials.
Esprit Villa is located in the Virgin Islands National Park on Bordeaux Mountain

Bordeaux, St. John

Pool

from $429/Nt
Gibbes Beach is one of Barbados' nicest white sand beaches on the West Coast. Shops, groceries, and restaurants are only ... Has specials. Plunge pool and gardens leading to the beach at Waverly Villa

Barbados

Beachfront | Pool | AC

from $600/Nt
Ocean's Edge puts you close to golfing, tennis, water sports, and duty-free retail therapy. You can relax by the plunge ... Has specials. Ocean's Edge Villa  - Merlin Bay photo

Barbados

Beachfront | Pool | AC

from $500/Nt
Carolina Villa is perfect for any traveler who loves ocean views and lots of privacy. The home is comfortably furnished ... 1 & 2 BR rates available. Carolina Villa photo

Coral Bay, St. John

from $514/Nt
At L'Embellie, there's no shortage of activities. Along with kayaks and fishing gear, you get a snorkeling beach right on ... 1 & 2 BR rates available. L'Embellie Villa is located near Forest Bay and has a beautiful pool

Anguilla

Beachfront | Pool | AC

from $575/Nt
The Dutch side of St. Martin is known for its great beaches and exciting night life, and La Casita Villa ... 1 & 2 BR rates available.
Has specials.
La Casita Villa photo

Beacon Hill (Dutch side), St. Martin

Near Beach | Pool

from $343/Nt
Sol e Luna is very private with gardens that surround the house giving guests the option of dressing or not. ... 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
Located just 10 minutes from Cruz Bay, Latitude Villa on Klein Bay has some of the best views on the island! ... 1 & 2 BR rates available.
Has specials.
Latitude Villa photo

Klein Bay, St. John

Near Beach | Pool

from $643/Nt
Panarea Villa is truly beautiful, with a great housekeeper and lush gardens all around. I think this villa is ideal ... 1 & 2 BR rates available. Panarea is located in Anguilla's West End, just minutes away from the island's most beautiful beache

Anguilla

Near Beach | Pool

from $492/Nt
Reeds House is a private beach-front development between the Royal Pavilion and Cobblers Cove Hotel in St. James. Reeds House ... 2 BR rate available.
Has specials.
Amazing Caribbean views from Reeds House Penthouse #14

Barbados

Beachfront | AC

from $795/Nt
Waterfall Villa can accommodate up to 6 guests within its 3 luxurious bedrooms. Light and open, Waterfall is situated to enjoy island ... 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
Blue Horizon Villa may look like a plantation from the outside, but inside it is everything modern and comfortable. The ... 1 & 2 BR rates available. njoy the views of the Caribbean from the deck at Blue Horizon Villa

Camaruche, St. Barts

Pool

from $486/Nt
Tuscany Resort is one of my favorite properties on Turks and Caicos. At WhereToStay.com, we only list resorts that ... 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
A stay at Villa Gardenia will make you feel like you're a world away from the stress of everyday life. ... 1 & 2 BR rates available. Villa Gardenia is surrounded by beautiful tropical foliage

St. Thomas, USVI

Pool

from $499/Nt
Located within walking distance to a grocery store and restaurants, Ecoute les Vagues sits right on Flamands Beach, giving guests ... 2 BR rate available. Private waterfront pool at Ecoute les Vagues

Flamands, St. Barts

Beachfront | Pool | AC

from $600/Nt
One thing every traveler wants from their villa is a view from every room...at Grand Large Villa, you get ... 1 & 2 BR rates available. Beautiful views of the Caribbean from the pool deck at Grand Large Villa

Gouverneur, St. Barts

Pool

from $857/Nt
Situated on a hillside, Lataniers Villa has a great view of St. Jean Bay and the surrounding island greenery. Guests ... 1 & 2 BR rates available. Beautiful views from Lataniers Villa

Saint Jean, St. Barts

Pool

from $514/Nt
There is no mistaking that you are on island time when you step foot in Hurakan Villa. Each room has ... 1 & 2 BR rates available. Perched on the hillside of Colombier - Hurakan provides beautiful views of Gustavia Harbour

Colombier, St. Barts

from $469/Nt
Turks and Caicos is well-known as one of the best areas in the Caribbean for beach lovers, and the Venetian ... 1 & 2 BR rates available.
Has specials.
The Venetian photo

Grace Bay, Turks and Caicos

Beachfront | AC

from $875/Nt
Bayugita is perched on the hillside of Pointe Milou, an ideal home away from home for vacationers. A large, open ... 1 & 2 BR rates available.
Has specials.
Villa Bayugita enjoys great views of Lorient Bay

Pointe Milou, St. Barts

Pool

from $571/Nt
Situated on a Vitet hillside, Carmen Villa is a contemporary home that enjoys a great location with nice ocean views. ... 1 & 2 BR rates available. Enjoy views of Marigot Bay in the distance from the pool deck at Carmen Villa

Vitet, St. Barts

Pool

from $543/Nt
Dream Come True Villa delivers not only privacy, but magnificent ocean views. Just steps above Devers Bay, this three-bedroom villa ... 1 & 2 BR rates available. A Dream Come True Villa has amazing ocean views and a fun pool area

Devers Bay, St. John

Beachfront | AC

from $400/Nt
Ti Moun Villa has one of the best locations in St. Barts! Situated on a hillside in Lurin, this villa ... 2 BR rate available. Ti Moun Villa sits just above Gustavia Harbor

Lurin, St. Barts

from $1271/Nt
This is just what every couple needs! A perfect, cozy hideaway that has everything you and your special someone need ... 1 & 2 BR rates available. Always Villa is located in Colombier with amazing views of the Caribbean

Colombier, St. Barts

Pool

from $300/Nt
Your next holiday should help you unwind like never before, and at Les Amis du Vent Villa, you will find ... 1 & 2 BR rates available. Stunning outdoor areas with views to the caribbean at Les Amis Du Vent

Mont Jean, St. Barts

Pool

from $1429/Nt
The perfect location for your dream vacation is right here at Villa Sunrise. This modern home is designed for relaxation ... 1 & 2 BR rates available.
Has specials.
Luxurious pool with spectacular views at Villa Sunrise

Orient Bay (French side), St. Martin

from $400/Nt
Luxury, beauty, and a walk on the wild side of Grand Fond await when you reserve La Roche Dans L'eau ... 1 & 2 BR rates available. A beautiful beach entry pool at La Roche dans l’Eau

Grand Fond, St. Barts

Pool

from $557/Nt
This 3 bedroom villa is a modern paradise for those who want to get away, relax and soak in the beauty ... 1 & 2 BR rates available. Infinity edge pool with amazing views of Trunk Bay Beach at Soleil villa

Tortola, BVI, British Virgin Islands

Near Beach | Pool

from $560/Nt
Recently renovated, the Fairwind Villa at Cap Estate is ideally situated for a private getaway to St. Lucia. Located in ... Fairwind Villa is located very near to the St. Lucia golf club

Cap Estate, St. Lucia

Near Beach | Pool

from $250/Nt
Dining outdoors has never been more picturesque as you watch the beautiful sunset from your porch overlooking the ocean. With ... 1 & 2 BR rates available.
Has specials.
The Lookout - Schooner Bay 307 at the Schooner Bay Resort

Barbados

Beachfront | Pool | AC

from $800/Nt
Emvie is super modern and crisp, which I love because it only makes the view better. The master bedroom is ... 1 BR rate available.
Has specials.
Emvie Villa photo

Orient Bay (French side), St. Martin

Pool

from $557/Nt
When you look out from the second-level deck at Grand Palms, you’ll see luscious St. Martin flora and a ... 1 & 2 BR rates available.
Has specials.
Grand Palms is located in the exclusive Terres Basses with views of tropical flora and distant views

Terres Basses (French side), St. Martin

Near Beach | Pool

from $671/Nt
Perched high above Toiny, Enzuma is a true haven for families who want tons of privacy, comfort, and a sweeping ... 1 & 2 BR rates available. Enzuma sits on the hillside above Toiny with amazing views of Toiny Bay

Toiny, St. Barts

Pool

from $571/Nt
This villa is super conveniently located, just a few minutes from town and the beach. I love the villa's simple ... Patio deck and pool at Villa Indyana

Lurin, St. Barts

Pool

from $829/Nt
This villa is only a 30 second walk up to the beach, which has plenty of beach chairs and umbrellas for ... Has specials. Beads Bay Beachside Villa 2 is in the Meads Bay Villas

Anguilla

Near Beach

from $750/Nt
This villa has everything you could want on a romantic vacation, and balances privacy and comfort. You'll have your own ... 1 BR rate available.
Has specials.
Beads Bay Beachside Villa 3 is in the Meads Bay Villas

Anguilla

Near Beach | Pool

from $550/Nt
This villa is charming, with a spacious outdoor area and plenty of seating to enjoy the hillside view. I recommend ... 1 BR rate available. Salamandres has a private pool nestled in the Vitet hillside

Vitet, St. Barts

Pool

from $429/Nt
Trunk Nest villa has amazing views of Trunk Bay

Tortola, BVI, British Virgin Islands

Pool

from $986/Nt
La Lune is great for entertaining and sits right on the beach. Gibbes Beach is an island favorite because it's ... Has specials. La Lune is located on Gibbs Bay Beach

Barbados

Beachfront | AC

from $750/Nt
If you love the sea, then this beachfront home will be the perfect fit for your next vacation. This cozy ... Has specials. The Two Bedroom Beach House at Como Parrot Cay

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $4195/Nt
Rockworks Villa is situated in a cocoon of lush, tropical gardens. The two-bedroom villa is designed to be the perfect ... 1 BR rate available. Rockworks photo

St. Thomas, USVI

Pool

from $343/Nt
The Captain's House is a perfect getaway for celebrating anniversaries or to just be together on beautiful Tortola. With 2 pavilions-a ... 1 BR rate available. Captain's House villa commands a breathtaking view of the ocan

Tortola, BVI, British Virgin Islands

Pool

from $310/Nt
Bluff Cottage on Barbados is named for its location overlooking Sandy Lane Beach. With two bedrooms and two bathrooms, the ... Has specials. High atop the bluff above Sandy Lane

Barbados

Near Beach

from $500/Nt
Secret Cove #1 is part of a 4-apartment cluster that comes complete with its own private beach where you can swim ... Has specials. Secret Cove #1 photo

Barbados

Beachfront | AC

from $445/Nt
Want privacy? Like to snorkel? Love to relax? If you answered yes, the Sea Pearl in St. Lucia has what ... 1 BR rate available.
Has specials.
Sea Pearl Villa photo

Cap Estate, St. Lucia

Near Beach | Pool

from $415/Nt
If you're after true privacy, Smuggler's Nest has got you covered. Surrounded by lush vegetation and not visible from the ... 1 BR rate available. Ocean front gazebo at Smugglers Nest Villa

Cap Estate, St. Lucia

Near Beach | Pool

from $500/Nt
Nestled up on a hill in Camaruche, this property has lots of charm with its lush vegetation and beautiful, tropical ... 1 BR rate available. Pool area has great views at VEL Villa

Camaruche, St. Barts

Pool

from $357/Nt
Overlooking the Caribbean Sea, Byzance Villa in Colombier is the ideal getaway for one or two couples. Outside, there is ... 1 BR rate available. Byzance Villa is located in Colombier overlooking the Flamands Bay

Colombier, St. Barts

Pool

from $857/Nt
If you're looking for a fun getaway with another couple, D'arcy Villa is exactly what you need. This two-bedroom, two-bath ... 1 BR rate available.
Has specials.
D'arcy Villa photo

Cap Estate, St. Lucia

Pool

from $215/Nt
There are plenty of modern amenities that make Sky Vista a simple vacation destination that can easily accommodate a relaxation ... A beautiful view from the pool and deck at Sky Vista Villa

Gustavia, St. Barts

Near Beach | Pool

from $857/Nt
Shell Beach is perfect for a romantic getaway or family vacation. It has two equally charming bedrooms, and one bedroom ... 1 BR rate available. Shell Beach Villa sits just around the corner from its namesake - with views of Gustavia Harbor

Gustavia, St. Barts

Near Beach | Pool

from $857/Nt
La Niña is very inviting, with a convenient location perfect for exploring the island. We were able to easily ... 1 BR rate available.
Has specials.
La Nina is located in Terres Basses overlooking the Caribbean

Terres Basses (French side), St. Martin

Pool

from $371/Nt
If great views and lots of privacy are on your priority list for your Caribbean vacation, then you'll be pleased ... 1 BR rate available. Coral Harbor boasts a beautiful hillside infinity edge pool

Coral Bay, St. John

Pool

from $395/Nt
The floor plan of St. Somewhere Villa offers seclusion and privacy, open areas for conversation and meals, and gorgeous views ... St. Somewhere is located on the Peterborg peninsula above Meagans Bay

St. Thomas, USVI

Pool

from $549/Nt
If you're on your first, second or twelfth honeymoon, Fletch's Cove is perfect. It's small enough that you won't feel ... 1 BR rate available.
Has specials.
Fletch's Cove is located between LockRum Bay and Little Harbour on the coast of Anguilla

Anguilla

Near Beach | Pool

from $529/Nt
Amalie Villa is a roomy villa perfect for a honeymooning couple or for those looking for some time away together. ... 1 BR rate available. Amalie Villa photo

Camaruche, St. Barts

from $1393/Nt
Les Jardins d'Emmanuel is a great two-bedroom villa for couples. Both bedrooms are equally outfitted and sized, and the common ... 1 BR rate available. Les Jardins d'Emmanuel is located in Lorient between St. Jean Bay and Lorient Bay

Lorient, St. Barts

Near Beach | Pool

from $600/Nt
Magic View Villa is the perfect Caribbean vacation home for honeymooners or two couples traveling together. The unique floor plan ... 1 BR rate available. Magic View Villa has its own private swimming pool!

Great Cruz Bay, St. John

Pool

from $357/Nt
If you want your own beach villa but still want the convenience of a front desk and concierge, beautiful Meads ... Has specials. Beads Bay Beachside Villa 1 is in the Meads Bay Villas

Anguilla

Near Beach | Pool

from $750/Nt
L'Enclos Villa is only a 10-minute drive from Flamands or Corossol beaches, and only a five-minute drive from both groceries ... L'Enclos Villa photo

Colombier, St. Barts

Pool

from $857/Nt
This very modern villa comes with contemporary furnishings and is great for a family with young children or two couples. ... 1 BR rate available. Les Embruns Villa photo

Flamands, St. Barts

Near Beach | Pool

from $467/Nt
La Vie En Bleu is situated right on the beach in one of St. Martin's nicest areas, the Baie Rouge ... Has specials. La Vie En Bleu Villa photo

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $1500/Nt
Villa Zatarra is a wonderful find, designed and decorated by a local couple, Rob and Veron. Rob is known on ... Perfect pool - Walk out the door and take a dip!!

Cap Estate, St. Lucia

Pool

from $300/Nt
Victoria Villa allows for all the comforts of the Caribbean. There's partial air-conditioning, but screened doors and windows let the ... 1 BR rate available. Victoria Villa photo

Vitet, St. Barts

Pool

from $867/Nt
The view is truly the focal point of this home, and it can be enjoyed all over the villa! The ... 1 BR rate available.
Has specials.
Nid d'Amour Villa features the grecian like columns that are the landmark for this villa

Terres Basses (French side), St. Martin

Pool

from $643/Nt
Manon Villa requires a four-by-four to reach the villa, but the visit is well worth the drive. Manon Villa has ... 1 BR rate available. Manon Villa photo

Colombier, St. Barts

Pool

from $476/Nt
Kids and athletes alike will love Chambord's lap pool, and everyone will love the ocean views! If you're just here ... 1 BR rate available. Relax by the pool and enjoy beautiful views of the Caribbean from the pool deck at Chambord

Petit Cul de Sac, St. Barts

Pool

from $629/Nt
This quaint villa has a pool nearby and internet access. There's partial air-conditioning in the bedrooms, which are non-smoking for ... 1 BR rate available. Amazing views over Anse Toiny from Oceana Villa

Vitet, St. Barts

from $414/Nt
Bamboo Villa on St. Martin's French side is a private home featuring 2 bedrooms, 2.5 bathrooms, and much more. The kitchen is ... 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
La Magnifica is a very open villa with modern amenities. This includes partial air-conditioning in the bedrooms, and it is ... 1 BR rate available.
Has specials.
La Magnifica Villa photo

Deve, St. Barts

Pool

from $621/Nt
Isia Villa is comfortably furnished and can accommodate up to 4 people. The home is best suited for one or two ... Perched on the hillside - Isia Villa overlooks beautiful St. Jean Bay

Saint Jean, St. Barts

Pool

from $829/Nt
Wastra Villa is within a short walking distance to Shell Beach, and it sports very nice sunset views. Good for ... Wastra Villa photo

Gustavia, St. Barts

Near Beach | Pool

from $600/Nt
You are close to everything. The airport, shopping, restaurants, and a bakery that will make you feel right at home. ... Grain de Folie Villa photo

Colombier, St. Barts

Pool

from $714/Nt
Petit Lagon is a great place for a honeymoon, a family with older children, or two couples who want to ... 1 BR rate available. Petit Lagon is perched on a tropical hillside in Petit Cul de Sac

Petit Cul de Sac, St. Barts

Near Beach | Pool

from $486/Nt
Marie is a sweet villa, sitting on the hillside of Camaruche. It has air-conditioning in the bedrooms, making it nice ... 1 BR rate available. Lounge by the pool at Marie Villa and enjoy views of the ocean

Pointe Milou, St. Barts

Pool

from $929/Nt
Romantic Retreat Villa is idyllic in its location and cozy in its privacy, quietly hiding above Cruz Bay. Close to ... 1 BR rate available. Amazing views from the private swimming pool

Cruz Bay, St. John

Pool

from $321/Nt
Lune de Miel means "honeymoon" in French, and this St. Martin hideaway on 2.5 private acres definitely fits the bill. While ... 1 BR rate available.
Has specials.
Lune de Miel Villa is located hillside in Terres Basses

Terres Basses (French side), St. Martin

Pool

from $500/Nt
Schooner Bay, on the West Coast of Barbados, is a stylish condominium complex that sits beachfront near Speightstown. #206, or The ... 1 BR rate available.
Has specials.
Schooner Bay #206 - The Palms photo

Barbados

Beachfront | AC

from $350/Nt
Reeds House is a private development located right on the beach in Barbados. Penthouse #13 is a comfortable 2-bedroom unit with ... 1 BR rate available.
Has specials.
The patio at Reeds Penthouse #13

Barbados

Beachfront | Pool | AC

from $450/Nt
If you want to relax in a private swimming pool next to the Virgin Islands National Park, then Caneel Trailside ... 1 BR rate available.
Has specials.
Caneel Trailside Villa is located right next to the Virgin Islands National Park

Cruz Bay, St. John

Pool

from $386/Nt
Natural beauty abounds at La Bagatelle Villa, located in Soufriere, St. Lucia. The views of the Pitons and the ocean ... La Bagatelle Villa photo

Soufriere, St. Lucia

Pool

from $440/Nt
At Royal Palms Villa, you can spend a day playing tennis, then return to a gated community knowing that you'll ... 1 BR rate available. Royal Palms Villa photo

St. Croix, USVI

Pool

from $525/Nt
La Falaise is a secluded getaway for the couple that wants to bask in the beauty and luxury of St. ... 1 BR rate available. La Falaise photo

Pointe Milou, St. Barts

Pool

from $450/Nt
This cozy villa may be in a quiet part of the island, but that just makes the views even more ... 1 BR rate available. Lemon Tree villa has panoramic views over Anse Du Cap Beach and to Pigeon Island National Park

Cap Estate, St. Lucia

Pool

from $395/Nt
Kyody Villa has tall rooms with natural wood and stone décor. Artistic windows open up to an ocean view. ... 1 BR rate available. The pool is situated in a beautiful tropical setting at Kyody Villa

Marigot, St. Barts

Pool

from $371/Nt
Lumiere Villa is a gorgeous hillside residence with an impressive view overlooking Flamands. It works well for a family with ... 1 BR rate available. Lumiere Villa photo

Flamands, St. Barts

Pool

from $500/Nt
Lorient Sunset is a bright and open villa that is located hillside in the Lorient area of St. Barts. With ... 1 BR rate available. Lorient Sunset Villa photo

Lorient, St. Barts

Pool

from $471/Nt
Perfect for a couples retreat or a honeymooners escape, Panorama is an exquisite property with much to offer! This two ... 1 BR rate available.
Has specials.
Lounge by the pool with the ocean as your background at Panorama

Cap Estate, St. Lucia

Pool

from $430/Nt
There is no other place to stay in St. Barts and feel quite as relaxed as you will here at ... Val Andre Villa is just steps away from the ocean

Saint Jean, St. Barts

Near Beach

from $920/Nt
Open to the elements, enjoy the short walk to Flamands Beach at Villa Tichka! So close and with private access, ... The view from the pool at Tichka Villa of Flamands Beach

Flamands, St. Barts

Near Beach

from $1571/Nt
Wake up and see turtles in the morning at Villa Les Sables, or spend the afternoon snorkeling or lounging on ... Les Sables sits just at the end of Lorient Bay

Lorient, St. Barts

Beachfront | Pool | AC

from $671/Nt
Shalimar Villa is a versatile property on a Lurin hillside that can be rented as either a 1- or 2-bedroom, ... Shalimar Villa photo

Lurin, St. Barts

Pool

from $929/Nt
Samsara Villa, located in the hills of Pointe Milou, is perfectly positioned for those wanting a place with an incredible ... 1 BR rate available. Views from the pool patio

Pointe Milou, St. Barts

Pool

from $786/Nt
Serene villa’s separate, yet connected, pods offers privacy and tranquility. The home overlooks Chalk Sound, where the views are ... Ocean views from the pool at Serene Villa

Chalk Sound, Turks and Caicos

Near Beach | Pool

from $400/Nt
Overlooking Saint Jean Bay, Eden View Villa comes with unforgettable water views that can be enjoyed both indoors and out. ... 1 BR rate available. Amazing views from the pool deck at Eden View Villa!

Saint Jean, St. Barts

Near Beach | Pool

from $1157/Nt
It is difficult to tell where the infinity pool stops and the ocean view starts. La Vue Panoramique is literally ... 1 BR rate available. La Vue Panoramique Villa photo

Mont Jean, St. Barts

Pool

from $829/Nt
At FAY villa, you only need to step off the terrace to find yourself on the beach. Lounge there or ... Lounge on the beachfront deck at Fay Villa

Flamands, St. Barts

Beachfront | AC

from $857/Nt
If you ever wondered what it would be like to be the only person (or only four people!) in the ... 1 BR rate available. A beautiful private pool at MAK Villa

Saint Jean, St. Barts

Near Beach | Pool

from $571/Nt
If you are looking for a great getaway for two, a couples' retreat to enjoy with friends, or simply a ... Dine al fresco with amazing ocean views

Pointe Milou, St. Barts

Pool

from $1000/Nt
Four of you can get away from the pace of your day-to-day life at Polaris Villa. A two-bedroom villa, where ... 1 BR rate available. Polaris Villa photo

Flamands, St. Barts

Beachfront | AC

from $571/Nt
A new space, Diamond Villa has much to offer those on holiday including intense seclusion, beautiful views, and spacious accommodations. ... 1 BR rate available. Diamond Villa offers great views over Gustavia

Saint Jean, St. Barts

Pool

from $929/Nt
This Rio Mar Luxury 2 bedroom Ocean Villa is for anyone with a need for relaxation and a desire for that ... Rio Mar Beach Resort Luxury Ocean Villa photo

Northeast Coast, Puerto Rico

Beachfront | Pool | AC

from $450/Nt
This chic and contemporary two bedroom villa is a great find for those wanting to visit St. Barts and enjoy ... 1 BR rate available. Beautiful views and absolute quiet at Valley Villa!

Vitet, St. Barts

Pool

from $643/Nt
This villa is designed to make you feel like a movie star, with a luxurious yet clean and sophisticated feel ... 1 BR rate available. Teddy Villa has a beautiful infinity edge pool

Vitet, St. Barts

Pool

from $629/Nt
Your next vacation should be about the two of you. It should be a measure of intimacy designed to ensure ... 1 BR rate available. Beachfront pool at La Sirène Villa

Flamands, St. Barts

Beachfront | Pool | AC

from $553/Nt
Oceana Villa only has two-bedrooms, but with over 5,000 square feet there is plenty of room to spread out. The outdoor ... 1 BR rate available. Oceana Villa is located on a hill above Crocus Bay

Anguilla

Near Beach | Pool

from $420/Nt
Set on a ridge overlooking Taylor Bay beach, Blanca Villa offers 360º views of the Caribbean Sea, Chalk Sound, and Silly ... Blanca Villa sits on a small hill above the beach

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $464/Nt
Basically, the best and worst thing about Villa Micela is that you may never want to leave! At night you ... 1 BR rate available. Villa Micela sits just on the beach at Flamands Bay

Flamands, St. Barts

Beachfront | Pool | AC

from $929/Nt
This villa defies expectations, with stunning views and a quality grill. It's comfortable, well-renovated, and has a nicely equipped kitchen. ... 1 BR rate available. Villa Pastel overlooks Lorient Bay and further to St. Jean bay

Pointe Milou, St. Barts

Pool

from $714/Nt
Wild Cherry is unlike any other villa I've been to. Everywhere you look you'll see the ocean. The inside of ... Wild Cherry photo

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $686/Nt
This villa is just a few minutes from the beach, dining, and shopping on the other side of the road ... 1 BR rate available. Le Sab Villa photo

Saint Jean, St. Barts

Near Beach | Pool

from $714/Nt
Miami Vice 2's two-bedroom villa is a fantastic option for any small family or pair of traveling couples. Wake up ... Miami Vice 2 is located on Sapodilla Bay

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $629/Nt
This new villa is spotless, and has every conceivable amenity. Aya has gorgeous views from L'Estang all the way to ... 1 BR rate available. Aya Villa photo

Saint Jean, St. Barts

Near Beach | Pool

from $529/Nt
This villa offers privacy, fabulous views, an infinity pool, and is very spacious for a 2 bedroom. Well-suited for families, with ... 1 BR rate available. Lina Villa photo

Colombier, St. Barts

Pool

from $1214/Nt
This villa is near Flamands Beach, which is perfect for windsurfing, boogie boarding, and long walks. Flamands Bay is just ... 1 BR rate available. Flamands Bay Villa offers amazing views!

Flamands, St. Barts

Near Beach | Pool

from $929/Nt
Anse de Lezards is one of the best surf spots on the island, it is a special treat that the ... 1 BR rate available. Palm House Villa photo

Anse des Cayes, St. Barts

Pool

from $366/Nt
Amethyste brings to mind one word: chic. This villa isn't fussy or frou frou, but the design sets it apart ... Amethyste Villa photo

Petit Cul de Sac, St. Barts

Pool

from $1500/Nt
This villa has one of the coolest views on St. John - you can see the ocean, the western side ... 1 BR rate available. Exotic View Villa photo

Great Cruz Bay, St. John

Pool

from $393/Nt
I love this villa's clean, unique architecture. I was able to keep an eye on the kids wherever we were, ... The luxury pool with swim up cocktail bar at White Villa 1

Long Bay, Turks and Caicos

Near Beach | Pool

from $486/Nt
The beachfront villa at Meads Bay Beach Villas is the most popular property for an obvious reason... it sits steps ... Has specials. Meads Bay Beachfront Villa 1 is located on a beautiful stretch of Meads Bay Beach

Anguilla

Beachfront | Pool | AC

from $950/Nt
MBA Villa reminds me of Greece or Italy, with the lush foliage and in-your-face coastline view. Since it's on a ... 1 BR rate available. MBA Villa photo

Pointe Milou, St. Barts

Pool

from $643/Nt
1 BR rate available. View from the balcony at Breakers

St. Croix, USVI

Near Beach | Pool

from $357/Nt
Bari is a gorgeous villa, but what sets it apart from other luxury villas is the gorgeous beach it sits ... Sun set from the patio at Bari Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $547/Nt
Capri sits on Sapodilla Bay, which is an absolutely gorgeous beach on the secluded end of Turks. Sapodilla is very ... The beachfront pool at Capri Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $547/Nt
Sardinia is awesome because it's close to three different beaches that are all breathtaking. Each beach has crystal blue water, ... Sardinia Villa is located near Taylor Bay on the beach

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $547/Nt
Passage is the perfect romantic getaway for water lovers. It's a short walk downhill to Corossol Bay, and you can ... Villa Passage overlooks the Caribbean from the Corossol hillside

Corossol, St. Barts

Pool

from $857/Nt
Villa Suite Acajous is a great choice for you and your significant other's next getaway. There's a private pool, wooden ... Villa Suite Acajous overlooks the St. Jean Bay

Saint Jean, St. Barts

Pool

from $600/Nt
Plumeria's House is dreamy and cozy, totally perfect for an anniversary celebration or honeymoon. It's two-level deck maximizes the view ... Plumeria's House Villa looks over Marigot Bay

Marigot, St. Barts

Near Beach | Pool

from $550/Nt
This villa would be ideal for a honeymoon or romantic getaway. I love how the master suite is separated from ... Lounge on the deck at Ti Lama with ocean views in the distance

Flamands, St. Barts

Near Beach | Pool

from $400/Nt
At Leamington Cottage, you can take it easy. Let the trained staff take care of your needs. A cook can ... Has specials. Just step through the gate and you are on the beach

Barbados

Beachfront | Pool | AC

from $595/Nt
Guests who love the idea of outdoor living will feel right at home at Petit Saint Louis Villa. The main ... Petit Saint Louis Villa ha great views over Gustavia Harbor

Corossol, St. Barts

Near Beach | Pool

from $357/Nt
A beautiful one bedroom space, Villa BBE is the ideal romantic spot for those looking for a quiet holiday location ... BBE Villa photo

Pointe Milou, St. Barts

Pool

from $393/Nt
If you’re looking for a warm, beachfront, one-bedroom villa on Grace Bay, you’re in the right place. Beach ... Beach Shack Villa is located near Turtle Cove right on Grace Bay

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $636/Nt
If your idea of vacation is reading a book, relaxing on the beach, and swinging in a hammock, then Callaloo ... Callaloo Cottage is located on Grace Bay

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $400/Nt
This charming villa is located minutes from Grace Bay Beach, and offers a private swimming pool. Nutmeg sits close to ... Nutmeg Cottage is just a short walk to the beautiful white sands of Grace Bay Beach at Smith's Reef

Grace Bay, Turks and Caicos

Near Beach | Pool

from $293/Nt
Within walking distance of the Grand Cul de Sac lagoon, La Belle Epoque is a roomy one bedroom, one bathroom ... La Belle Epoque has a great pool and views of Grand Cul de Sac lagoo

Grand Cul de Sac, St. Barts

Near Beach | Pool

from $600/Nt
Ti Ylang Villa in Flamands, St. Barts is a great getaway for couples who want to experience privacy, relaxation, and ... Ti Ylang Villa photo

Flamands, St. Barts

Pool

from $498/Nt
Located on a hillside in Pointe Milou, Bonbonniere Villa has great views of the sea and surrounding Caribbean landscape. The ... Bonbonniere Villa photo

Pointe Milou, St. Barts

Pool

from $543/Nt
Located in the lively town of Gustavia, St. Barts, Gustavia Villa has the advantage of being "in town" while still ... Relax and enjoy views of the Ocean from the deck at Gustavia Hill Villa

Gustavia, St. Barts

Pool

from $500/Nt
Alphane Villa is not only ideal for adventurous honeymooners, but its perfect for couples looking to get away from the ... Alphane Villa is a one bedroom villa on the Arrowmarine Property

Mont Jean, St. Barts

Pool

from $500/Nt
Camille Villa is perfect for the couple or friends who want to get away but also want to enjoy the ... Camille is located close to the shops and restaurants in the heart of Gustavia

Gustavia, St. Barts

Near Beach

from $543/Nt
Cap Frehel Villa is a spacious two story villa with one bedroom. The main floor is white, modern, airy and ... Enjoy an ocean side walk at Cap Frehel

Saint Jean, St. Barts

Beachfront | AC

from $610/Nt
Nestled among the palm trees on luxuriously landscaped grounds is Dahouet Villa. Upstairs, the master suite has a deluxe king ... Dahouet Villa is cozy ocean front property on the far end of St. Jean Bay

Saint Jean, St. Barts

Near Beach

from $610/Nt
Water Edge lives up to its name with its location directly on Grace Bay Beach. With the sandy beach just ... Private pool at Water Edge Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $529/Nt
Ocean Edge Villa is one of three private homes that sits right on Grace Bay. At Ocean Edge, you'll find ... Sea Edge, Ocean Edge, and Water's Edge

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $471/Nt
Perfect for a couple on a honeymoon or just looking for a great vacation, the 1-bedroom condo at the West ... Has specials. The West Bay Club has a beautiful pool

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $630/Nt
Facing the coastline and ocean surrounding St. Bart's, Ti Agave Villa provides a perfect place to escape and enjoy a ... Ti Agave Villa photo

Camaruche, St. Barts

Pool

from $457/Nt
If you're looking for the perfect place to host that romantic getaway, Adage Villa is just that place. A wonderful ... Adage Villa photo

Pointe Milou, St. Barts

Pool

from $421/Nt
Aptly named, this charming home truly is a rare "jewel," ideal for a honeymoon or for some much needed alone ... Has specials. Gouverneur Jewel photo

Gouverneur, St. Barts

Pool

from $843/Nt
With a private pool, open and airy floor plan, and ocean views to last a lifetime, Colibri Villa is a ... Colibri Villa offers great views of the ocean from the patio balcony

Pointe Milou, St. Barts

Pool

from $357/Nt
Miami Vice 1 is ideal for couples that are ready for an intimate, oceanfront getaway on Turks and Caicos. There are ... Miami Vice 1 Villa is located on Sapodilla Bay

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $443/Nt
Island Dreams Villa is a single-bedroom hillside house that gives any couple plenty of living space and views for days. ... Island Dreams Villa photo

Bordeaux, St. John

Pool

from $390/Nt
Azure is a condominium villa in the seaside, resort-like village of Porto Cupecoy where shopping, restaurants, sports activities, and water ... Has specials. Aazure Villa photo

Cupecoy (Dutch side), St. Martin

Near Beach

from $229/Nt
Sheherazade is private and romantic, and has great views since it's above Gustavia Harbor. I love watching the boats go ... Villa Sheherazade photo

Corossol, St. Barts

Pool

from $857/Nt
A true lovers hideaway, the BelAmour Villa is an artsy rental that’s perfect for any vacationing couple. This one-bedroom ... BelAmour Villa photo

Pointe Milou, St. Barts

Pool

from $986/Nt
Positano Villa on Sapodilla Bay is a couple's dream stay for a honeymoon, anniversary vacation, or even a spontaneous getaway. ... Positano is located at the very end of Sapodilla Bay with a small stretch of sandy beach

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $547/Nt
Honeymoons, anniversaries, and romantic getaways go to the next level at Little Plum Cottage. This chic one-bedroom villa is right ... Little Plum Cottage is a single bed unit on Grace Bay Beach

Grace Bay, Turks and Caicos

Near Beach | Pool

from $371/Nt
It’s the amenities like a cozy rooftop deck and private infinity pool that make Sugar Kube a sweet stay ... Sugar Cube Villa sits directly on Grace Bay Beach

Grace Bay, Turks and Caicos

Near Beach | Pool

from $514/Nt
The Loft defies its one bedroom status with ample seating and dining options perfect for entertaining. I love how it ... The Loft Villa photo

Gustavia, St. Barts

Pool

from $986/Nt
Casa Solana is a great choice for a honeymoon, romantic getaway, or Instagram-worthy vacation. Its right on the water on ... Cayo Espanto - Casa Solana photo

Belize

Beachfront | Pool | AC

from $1595/Nt
If you want to soak up as much sunshine and saltwater as possible, Casa Olita is perfect for you. You ... Cayo Espanto - Casa Olita photo

Belize

Beachfront | Pool | AC

from $1995/Nt
This one-bedroom beauty is perfect for your honeymoon or anniversary celebration. It's open-air, so you can breathe in the salty ... Cayo Espanto - Casa Mañana photo

Belize

Beachfront | Pool | AC

from $1895/Nt
Casa Brisa is the perfect honeymoon destination for a couple who wants to explore all Belize has to offer without ... Cayo Espanto - Casa Brisa photo

Belize

Beachfront | Pool | AC

from $1795/Nt
Ventanas is perfect if you want a one-bedroom with as much privacy as possible without renting your own island. Most ... Cayo Espanto - Ventanas photo

Belize

Beachfront | AC

from $1695/Nt

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