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.

Luxurious, private island with a full staff, six beaches, and every activity you could ask for. Calivigny Island - Just South of Woburn Bay, Greneda

Grenada

Beachfront | Pool | AC

from $120000/Nt
25 25
Details
Private island resort with rustic, eco-friendly design and every activity under the sun. Thatch Caye photo

Belize

Near Beach

from $9785/Nt
15 15
Details
This totally private island will make you feel like royalty. Has specials. Necker Island, BVI 2018 Helicopter view

Necker Island, BVI, British Virgin Islands

Beachfront | Pool | AC

from $62500/Nt
12 11
Details
Sophisticated, three-story home perfect for family vacation or getaway with friends. 5 BR rate available. The Beach House at Calivigny Island

Grenada

Beachfront | Pool | AC

from $40000/Nt
10 10
Details
An impressive pool and terrace winds throughout this luxury villa. 5, 6 & 9 BR rates available. Aerial View of Silent Waters

Montego Bay, Jamaica

Pool

from $2320/Nt
10 6
Details
Fully staffed, avant-garde villa with open-concept design and complimentary access to Eden Roc Beach. 5, 6, 7 & 8 BR rates available.
Has specials. Yarari Royale is a beautiful home located in Cap Cana

Cap Cana, Dominican Republic

Pool

from $2430/Nt
9 9+
Details
Chic and modern home with nine suites and tons of outdoor space. 5 BR rate available. The Overhang House at Calivigny Island

Grenada

Beachfront | Pool | AC

from $35000/Nt
9 9
Details
Over 20,000 square feet of enjoyment space. 2, 3, 4, 5, 6 & 7 BR rates available. Ultimacy Villa is located in Rose Hill in Island Harbor

Anguilla

Pool

from $1000/Nt
8 9+
Details
Privacy and luxury for large groups on a two acre, beachfront tropical haven. Sunrise Villa photo

Cabrera, Dominican Republic

Beachfront | Pool | AC

from $2000/Nt
8 8
Details
Sprawling estate with a panoramic view that's perfect for weddings, corporate retreats, and more. 1 & 5 BR rates available.
Has specials. The pool and ocean views from Eco Serendib!

Rendezvous Bay, St. John

Pool

from $2200/Nt
8 8+
Details
Enjoy a mini golf-course and five separate units at this oceanfront beauty. 3, 4 & 5 BR rates available. Lounge on a balcony patio over looking the ocean from Anguillitta Villa

Anguilla

Near Beach | Pool

from $1150/Nt
7 6+
Details
Beachfront villa great for families and groups, with entertainment for kids and adults alike. Coral Reef Villa is situated directly on Seven Mile Beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2860/Nt
7 7+
Details
This attractive getaway is perfect for couples or families who want privacy and tranquility. 1, 2, 3, 4, 5 & 6 BR rates available. Monte Bay Villa sits atop a hillside just above Monte Bay

Klein Bay, St. John

Near Beach | Pool

from $726/Nt
7 6+
Details
Enjoy unparalleled luxury on your own piece of island paradise, surrounded by views, activities, and amenities Cayo Espanto - Entire Island photo

Belize

Pool

from $13500/Nt
7 9
Details
Breathtaking ocean view from the pool, with private secluded beach just steps away 5 & 6 BR rates available.
Has specials. The beautiful Crystal Blue Villa is perched on a cliffside just off Queens Highway

Grand Cayman, Cayman

Pool

from $950/Nt
7 6+
Details
Large luxurious pool at Fratelli Cresta

St. Thomas, USVI

Pool

from $1185/Nt
7 7+
Details
Luxury blends with nature at this villa with Piton views. 4, 5 & 6 BR rates available. Cosmos photo

Soufriere, St. Lucia

Pool

from $935/Nt
7 7
Details
Three intimate villas perfect for a family vacation or romantic getaway. The beach front at the Beach Bungalows on Calivigny Island

Grenada

Beachfront | AC

from $27000/Nt
6 6
Details
Six-bedroom villa floor-to-ceiling windows and beach access. 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
6 6
Details
Five-star amenities and arrangements for any group of travelers. 3, 4 & 5 BR rates available. The elegant Shore Club Villas feature private swimming pools

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $4500/Nt
6 8
Details
Beachfront villa in the Tango Mar Resort with wildlife and activities at your fingertips. 2 BR rate available.
Has specials. The Beach at Tango Mar and Casa Oceano

Costa Rica

Beachfront | Pool | AC

from $1600/Nt
6 4
Details
An ideal getaway for couples traveling together. 3, 4 & 5 BR rates available. Summer Heights is located on a hillside above Nanny Cay

Tortola, BVI, British Virgin Islands

Pool

from $550/Nt
6 5+
Details
Luxury abounds at this sprawling, private retreat on the island of Providenciales. 3 BR rate available. Lounge on the deck and enjoy endless Caribbean views from Bajacu Villa

Turtle Tail, Turks and Caicos

Pool

from $3000/Nt
6 7+
Details
Near two popular beaches, Amancaya Villa is also near restaurants and groceries for ideal access during your St. Barts stay 1, 2, 3, 4 & 5 BR rates available. Amancaya Villa photo

Anse des Cayes, St. Barts

Pool

from $2429/Nt
6 6
Details
Two-building home near St. Lucia's Petit Piton, rainforest, botanical gardens, and dive sites. 2, 3 & 4 BR rates available.
Has specials. View from pool

Soufriere, St. Lucia

Near Beach | Pool

from $415/Nt
6 6
Details
Picture-perfect home with panoramic views, lush flower gardens, and a private beach cabana. 3, 4 & 5 BR rates available.
Has specials. Aurora Villa photo

Barbados

Pool

from $900/Nt
6 6+
Details
Three-story villa with gorgeous pool and serene views of the coastline of Terres Basses. 3, 4 & 5 BR rates available. Amazing views of the Caribbean form the deck at Grand View

Terres Basses (French side), St. Martin

Pool

from $600/Nt
6 6
Details
Costa Norte Villa: Bring your big family to this hilltop spot (or bring your friends and leave the kids with Grandma) Has specials. Costa Norte Villa photo

Cabrera, Dominican Republic

Pool

from $800/Nt
6 6+
Details
Amazing outside space with dining area by the pool, fantastic full service staff, access to Sandy Lane beach 3 & 4 BR rates available.
Has specials. Twilight on the patio at Sandalwood Cottage

Barbados

Near Beach | Pool

from $850/Nt
6 7
Details
Large families or groups of travelers will love this three-level oceanfront luxury home. 2 & 3 BR rates available. Sterling House sits just on the very east end of Long Bay

Tortola, BVI, British Virgin Islands

Beachfront | Pool | AC

from $600/Nt
6 7+
Details
Tons of room, seating, entertainment, and nothing can beat this hilltop scenery! 1, 2, 3, 4 & 5 BR rates available. Clairmont Overlook photo

St. Croix, USVI

Pool

from $600/Nt
6 6+
Details
Cliffside villa with ocean access and a guest cottage. 2, 3 & 4 BR rates available.
Has specials. The infinity edge pool at Sea\'s Edge has amazing views of the ocean

Rendezvous Bay, St. John

Pool

from $929/Nt
5 5+
Details
Beach lovers and adventurers will love this villa's private beach access and nearness to Kaibo Yacht Club and Rum Point Club. 4 BR rate available. Crystal Waters Villa sits beach front near the popular Water Cay and Kaibo Yacht Club

Grand Cayman, Cayman

Beachfront | Pool | AC

from $975/Nt
5 4
Details
St. Lucia's gorgeous Wild Orchid Villa has entertainment features for kids and grown ups alike 1, 2 & 3 BR rates available. Wild Orchid Villa photo

Cap Estate, St. Lucia

Near Beach | Pool

from $400/Nt
5 4
Details
Solare -- perfect for weddings or honeymoons with old world charm and sunset views of Great Cruz Bay 2 & 3 BR rates available. Enjoy beautiful views of Great Cruz Bay form Solare Villa

Great Cruz Bay, St. John

Near Beach | Pool

from $425/Nt
5 5
Details
A child friendly villa with a uniquely open design near the beach. 3 & 4 BR rates available.
Has specials. Lounge by the pool and enjoy views of the ocean in the distance at San Flamingo Villa

Barbados

Pool

from $635/Nt
5 5
Details
Beautiful beachfront property with its own tennis court has the best that Barbados offers under one ample roof 4 BR rate available.
Has specials. Heronetta Villa- Sandy Lane photo

Barbados

Beachfront | Pool | AC

from $1500/Nt
5 5+
Details
Named for its views, this villa is a paradise for weddings 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 $1400/Nt
5 5
Details
Beachfront villa with a full staff, a pool, and a game room. 3 & 4 BR rates available.
Has specials. La Paloma Villa photo

Barbados

Beachfront | Pool | AC

from $675/Nt
5 5
Details
One of the larger villas on the island, Stanford House is perfect for a large group that doesn't want to feel crowded 4 BR rate available.
Has specials. Stanford House photo

Barbados

Pool

from $1500/Nt
5 5
Details
Great for a small wedding or honeymoon, this hidden hillside villa has thought of everything 2, 3 & 4 BR rates available. Lounge poolside at Mystic villa and enjoy views of famous St. Jean Bay

Saint Jean, St. Barts

Pool

from $2136/Nt
5 5+
Details
A beautiful home with gorgeous furnishings, ideally suited to a large family. 1, 2, 3 & 4 BR rates available. Solitude House photo

St. Croix, USVI

Near Beach | Pool

from $429/Nt
5 4+
Details
Grand entrance, amazing views, and on a ridge on the West Coast of Barbados 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
5 5+
Details
Bali Dreams Villa offers 7200 feet of beauty on Orchid Bay Bali Dreams Villa photo

Cabrera, Dominican Republic

Near Beach | Pool

from $1200/Nt
5 6
Details
Classically Caribbean villa with an impressive pool and gorgeous mountain views. 3 BR rate available. Arc En Ciel Villa photo

Soufriere, St. Lucia

Near Beach | Pool

from $1900/Nt
5 5
Details
Super modern, upscale villa with glass walls and a spacious design. Lounge by the pool and enjoy amazing ocean views at Beaches Edge East Villa

Anguilla

Near Beach | Pool

from $1400/Nt
5 5+
Details
Privacy, luxury, and simplicity with a view await at beautiful Villa Aja 2, 3 & 4 BR rates available. Aja Villa photo

Tortola, BVI, British Virgin Islands

Near Beach

from $885/Nt
5 5
Details
Enjoy the private beachfront villa experience with the comforts of a five-star resort. 4 BR rate available.
Has specials. The Residences on Grace Bay

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $3400/Nt
5 5+
Details
This eco-friendly villa enjoys a beachfront location and resort amenities. 3 & 4 BR rates available.
Has specials. The interior pool and dining palapa at the Dunes Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $3200/Nt
5 5+
Details
Modern romantic retreat with expansive sea views. 1, 2 & 4 BR rates available.
Has specials. Truffle Villa photo

Terres Basses (French side), St. Martin

Near Beach | Pool

from $857/Nt
5 5
Details
Hillside villa with handicap access, an ideal location, and an open floor plan. 3 BR rate available. Alpaka Villa has beautiful views from its hillside location over Flamands Beach

Flamands, St. Barts

Pool

from $1143/Nt
4 4
Details
Three pools, the ocean, and the beach will keep guests entertained. Has specials. The Estate pools

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4800/Nt
4 4+
Details
Luxurious resort property with full service and amenities. Has specials. Grace Bay Club Resort pool

Grace Bay, Turks and Caicos

Beachfront | AC

from $5330/Nt
4 4
Details
Four equal king suites, two Jacuzzis, and resort amenities perfect for a couples' getaway. The Estate swimming pool

Grace Bay, Turks and Caicos

Beachfront | AC

from $8600/Nt
4 4
Details
Sleek, open-concept villa with modern architecture and Grace Bay access. Villa Islander is located just off the famous Grace Bay Beach

Grace Bay, Turks and Caicos

Near Beach | Pool

from $1880/Nt
4 4
Details
Blackgarden Bay villa with four bedrooms in two separate buildings. 3 BR rate available. Tasha Villa is a beautiful Villa in Black Garden Anguilla

Anguilla

Pool

from $550/Nt
4 4+
Details
If you love St. Jean Beach, the views from Nomade Villa in Lurin are a feast for the eyes 2 & 3 BR rates available. Nomade Villa photo

Lurin, St. Barts

Pool

from $1429/Nt
4 4
Details
A children's suite connected to the master bedroom combines with direct beach access for the ideal family vacation rental. Five Turtles Villa is just steps away from Taylor Bay Beach

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $1143/Nt
4 3+
Details
Filled with beauty and light, Mille Fleurs Villa in Terres Basses shines. 1, 2 & 3 BR rates available. Mille Fleurs Villa photo

Terres Basses (French side), St. Martin

Near Beach | Pool

from $571/Nt
4 4+
Details
What could make a vacation more perfect than to have the option for private massage and spa treatments delivered right to your door? 1, 2 & 3 BR rates available. Lounge in the sun and enjoy Caribbean views from the pool deck at Toa Toa House

Tortola, BVI, British Virgin Islands

Pool

from $400/Nt
4 4+
Details
Cadasse Villa is a unique property, recently renovated and sitting on a hilltop in Cap Estate, the views from the fantastic outside space are wonderful. The best part of this villa is the amazing staff, they cook meals you will talk about for years. 1, 2 & 3 BR rates available.
Has specials. Cadasse Villa has beautiful views and fun area for swimming and relaxing

Cap Estate, St. Lucia

Pool

from $315/Nt
4 4
Details
A deluxe villa on Gibbs Beach, this brand new property has thought of everything for your Caribbean adventure 3 BR rate available.
Has specials. Tropical surroundings greet you at the pool at Bonavista Villa

Barbados

Beachfront | Pool | AC

from $1280/Nt
4 4+
Details
With or without children, amenities at Fosters House can be enjoyed to the utmost Has specials. Ocean views and just steps away from the beach - Fosters House

Barbados

Beachfront | Pool | AC

from $1300/Nt
4 5
Details
Just across from Mullins Beach, this fully-equipped villa has an enviable location and a full staff. Has specials. Beautiful pool and tropical landscaping at Sundown Villa

Barbados

Near Beach | Pool

from $525/Nt
4 5
Details
Private, cliffside getaway on gorgeous Pointe Milou with four accommodating bedrooms and several lounging areas. 1, 2 & 3 BR rates available. Fregate Villa photo

Pointe Milou, St. Barts

Pool

from $714/Nt
4 4
Details
Rest and relax in this Mediterranean-style paradise just off Taylor Bay Beach. 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
4 4
Details
Ideal location near the beach and outdoor activities, with an open design. 1, 2 & 3 BR rates available.
Has specials. Casa del Sol is located close to Orient Beach

Orient Bay (French side), St. Martin

Near Beach | Pool

from $500/Nt
4 4
Details
Very private, waterfront vacation home with a huge infinity pool and beach access. Lounge by the infinity edge pool with amazing Caribbean views at Alandra

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1129/Nt
4 4+
Details
A private four-bedroom villa, Great Turtle Villa offers great views at an affordable rate! 2 & 3 BR rates available. Pool views of the ocean and island at Great Turtle villa

Coral Bay, St. John

Pool

from $430/Nt
4 4+
Details
Opulence and tranquility off the 16th fairway and a private pool to boot 3 BR rate available.
Has specials. Ixora Villa - Royal Westmoreland photo

Barbados

Pool

from $1070/Nt
4 4+
Details
Beachfront villa with kayaks, an entertainment system, and everything you need to relax. Picturesque beach front Villa - Five Little Cays

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $1071/Nt
4 4
Details
Morningside Villa is convenient to both Cruz Bay and Klein Bay's famous snorkeling. 1, 2 & 3 BR rates available.
Has specials. Morningside Villa photo

Klein Bay, St. John

Near Beach | Pool

from $543/Nt
4 4
Details
Located in the heart of Terres Basses, Sea Vous Play has a sense of classic Caribbean style and beautiful sunsets! 2 & 3 BR rates available.
Has specials. Sea Vous Play photo

Terres Basses (French side), St. Martin

Pool

from $446/Nt
4 4+
Details
This warm, tropical villa on West End Bay Beach relaxes guests with simple pleasures. Mangrove - is located in the Villas at Indigo Reef on West End Bay

Anguilla

Beachfront | Pool | AC

from $900/Nt
4 4
Details
Beyond Fabulous Kitchen, amazing villa just minutes to the renowned Shoal Bay. Sandcastle Pointe Villa is located on the waterfront on Shoal Bay

Anguilla

Pool

from $1000/Nt
4 4
Details
Open-air villa in Pointe Milou features modern style and amazing views of the sunset 1 & 3 BR rates available. Bali Villa has uninterrupted view of Lorient and the sunset past St. Jean Bay

Pointe Milou, St. Barts

Pool

from $786/Nt
4 4
Details
Privacy and gigantic ocean views, this four-bedroom truly lives up to its name. 3 BR rate available. The View photo

Colombier, St. Barts

Pool

from $2429/Nt
4 4
Details
Enjoy beachfront and sunset views just a few feet from Shoal Bay East. 1, 2 & 3 BR rates available. BP Villa is located near Shoal Bay Beach

Anguilla

Near Beach | Pool

from $1000/Nt
4 4+
Details
Your own small, private beach and great views to boot. 1, 2 & 3 BR rates available. Vista Villa has a beautiful private pool and great ocean views

Anguilla

Pool

from $500/Nt
4 4
Details
Jolly Harbor's most comfortable locale with lots of island activities to choose from. The vibrant colors at Turtle Villa provide for a fun atmosphere right on the beach

Jolly Harbour, Antigua

Beachfront | Pool | AC

from $1843/Nt
4 4+
Details
A deck for every bedroom at this gorgeous villa, just a quick jaunt to the beach 2 & 3 BR rates available. Songbird Villa has an amazing infinity edge pool

Anguilla

Near Beach | Pool

from $650/Nt
4 4+
Details
Every bedroom leads to the deck and pool at this chic villa. 2 & 3 BR rates available. Seabird Villa has beautiful sunset views

Anguilla

Near Beach | Pool

from $650/Nt
4 4+
Details
Great for large families or four couples who want privacy and plenty of space. 2 & 3 BR rates available. Amarillo Villa is located in True Blue Grenada

Grenada

Near Beach | Pool

from $390/Nt
4 4
Details
Art lovers take note: Sunspot villa offers modern architecture while maintaining island charm 2 & 3 BR rates available. Sunspot Villa photo

Peter Bay, St. John

Near Beach | Pool

from $1453/Nt
4 4+
Details
Gorgeous 4 bedroom villa in Vitet Close to Everything You Need 2 & 3 BR rates available. Pool and deck

Vitet, St. Barts

from $786/Nt
4 4
Details
Four couples can enjoy great views and shopping opportunities from this ocean view villa. 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
4 4+
Details
Great Cruz Bay's La Bella Vita Villa: Perfect for counting islands (we count fourteen on a clear day) or counting stars at night 1, 2 & 3 BR rates available.
Has specials. Pool at La Bella Vita

Virgin Grand Estates, St. John

Pool

from $643/Nt
4 4+
Details
Secluded villa with plenty of room for the whole family 1, 2 & 3 BR rates available. Mystic Ridge Villa photo

Bordeaux, St. John

Pool

from $571/Nt
4 4+
Details
Tropical luxury on Sandy Hill Beach. 1, 2 & 3 BR rates available. The beautiful Bird of Paradise Villa

Anguilla

Near Beach | Pool

from $1850/Nt
4 4+
Details
Whether honeymooning or traveling with small children, Prana Villa at Dawn Beach has something for everyone. 1, 2 & 3 BR rates available.
Has specials. Lounge by the pool at Prana Villa

Dawn Beach (Dutch side), St. Martin

Near Beach | Pool

from $286/Nt
4 4+
Details
This Grace Bay beauty has modern luxury, a fantastic pool bar, and an upstairs dining room. Beautiful resort-like pool and landscaping at Avalon Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1857/Nt
4 4
Details
Open and airy 4-bedroom villa on St. Barts looks out over the sparkling sea and is great for families or couples 2 & 3 BR rates available. Ocean\'s 5 Villa photo

Flamands, St. Barts

Pool

from $1000/Nt
4 4
Details
Cool, calming villa overlooks the ocean and has plenty of space for 4 couples who want to explore St. Barts 1, 2 & 3 BR rates available. Views over Lorient Bay from the pool deck at Mirande Villa

Pointe Milou, St. Barts

Pool

from $414/Nt
4 3
Details
Modern design and sleek finishes make this villa totally luxurious. Has specials. Atelier Villa has modern architectural lines and a beautiful pool

Barbados

Near Beach | Pool

from $1500/Nt
4 3+
Details
Located in the exclusive Leeward development, only a short walk from the best part of Grace Bay Beach. 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
4 3+
Details
Beachfront villa, close to water sports and local restaurants 2 BR rate available.
Has specials. Bora Bora Lower apartment offers a beautiful beachfront

Barbados

Beachfront | AC

from $325/Nt
4 4
Details
Perfect blend of seclusion and excitement close to Holetown 2 BR rate available.
Has specials. Bora Bora Upper Villa photo

Barbados

Beachfront | AC

from $310/Nt
4 4
Details
Spacious, contemporary hillside home with plunge pool. 2 & 3 BR rates available. Rose Dog Villa has a beautiful infinity edge pool

Vitet, St. Barts

Pool

from $945/Nt
4 4
Details
Chic villa with panoramic, tropical views. 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
4 4
Details
Two-story villa with large bedrooms and luxury finishes. Latitude Adjustment photo

St. Thomas, USVI

Pool

from Call for rates
4 3+
Details
This penthouse villa has completely amazing views: miles of sand and blue sea. Has specials. Penthouse at The Venetian photo

Grace Bay, Turks and Caicos

Beachfront | AC

from $1425/Nt
3 3
Details
Minimalist three bedroom overlooking Lorient Bay. 1 & 2 BR rates available. Bikini Villa photo

Lorient, St. Barts

Near Beach | Pool

from $414/Nt
3 3
Details
Minimalist, convenient villa located in the heart of St. Jean. 2 BR rate available.
Has specials. Alaia photo

Saint Jean, St. Barts

Near Beach | Pool

from $864/Nt
3 3
Details
Oceanfront property with spacious Great Room and proximity to all the island's hot spots. Has specials. Lone Palm Villa is located on a beautiful white sand beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $550/Nt
3 3
Details
Extremely private, oceanfront villa with access to the island's best shallow snorkeling site. Has specials. The private pool at Babylon Reef has a man made -beach- surrounding it

Grand Cayman, Cayman

Beachfront | Pool | AC

from $550/Nt
3 2+
Details
A chic and spacious villa right on the Royal Westmoreland golf course. Has specials. Sienna Villa

Barbados

Pool

from $1000/Nt
3 3
Details
Enjoy easy access to Grace Bay and luxurious service from the resort. Has specials. The Estate at Grace Bay Club

Grace Bay, Turks and Caicos

Beachfront | AC

from $3700/Nt
3 3+
Details
Sunset views in Silly Creek, with a private and serene location that has drop down access to the water. 1 BR rate available.
Has specials. Sublime Villa is just a short distance to Taylor Bay

Chalk Sound, Turks and Caicos

Pool

from $695/Nt
3 3+
Details
Dramatic sunset views and a great family house. Has specials. Osprey is located on the ocean side of Chalk Sound

Taylor Bay/Sapodilla Bay, Turks and Caicos

Pool

from $1050/Nt
3 3
Details
Private villa located right on Baie Longue Beach is the ideal getaway on St. Martin 1 & 2 BR rates available.
Has specials. Baie Longue Beach House photo

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $771/Nt
3 3
Details
Sand Dollar villa stands out among St. Lucia's northern point villas, great for a romantic getaway of a small family. 1 & 2 BR rates available.
Has specials. Sand Dollar Villa photo

Cap Estate, St. Lucia

Pool

from $290/Nt
3 3
Details
Saline Reef: Two pools and a waterfall will tempt you to stay home and skip all of the nearby activities 2 BR rate available. Saline Reef has a beautiful pool and patio

Cap Estate, St. Lucia

Near Beach | Pool

from $580/Nt
3 3
Details
The drinks never stop flowing at this stunning, modern home with breathtaking ocean views. 1 & 2 BR rates available.
Has specials. Lounge poolside with amazing views of the ocean

Anguilla

Near Beach | Pool

from $990/Nt
3 3
Details
Let reflection be your goal in the Asian-inspired surroundings of Serenity Villa 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
3 3
Details
A rooftop terrace offers private sunbathing with uninterrupted views of the Caribbean Sea. 2 BR rate available.
Has specials. Mongoose Run photo

Terres Basses (French side), St. Martin

Pool

from $443/Nt
3 3
Details
Secluded villa on 4.4 acres in Terres Basses has a huge pool, a private path to the beach, and more amenities than you could ask for. Joie de Vivre photo

Terres Basses (French side), St. Martin

Near Beach | Pool

from $1643/Nt
3 3+
Details
Peaceful oceanfront oasis with breathtaking ocean views. Pool side at Balinese Villa - endless Caribbean views

Turtle Tail, Turks and Caicos

Pool

from $1043/Nt
3 3
Details
Walk to famous St. Jean beach, nearby restaurants and shops! 1 & 2 BR rates available. Maison Villa photo

Saint Jean, St. Barts

Near Beach | Pool

from $707/Nt
3 3
Details
This luxurious, chic villa is divided between a pavilion with common areas and a pavilion with three suites. 1 & 2 BR rates available.
Has specials. Le Mas des Sables sits just east of Bai Rouge Beach at Davids Hole

Terres Basses (French side), St. Martin

Pool

from $786/Nt
3 3+
Details
Canefield House is a distinctive island estate with 10 acres of tropical plants and trees to color your stay-a photographer's dream. 1 & 2 BR rates available. Canefield House photo

Tortola, BVI, British Virgin Islands

Pool

from $541/Nt
3 3+
Details
Open and airy villa in Vitet with stunning water views and extreme privacy. 2 BR rate available. Abby Villa photo

Vitet, St. Barts

Pool

from $857/Nt
3 3
Details
Perfect for a group vacation, with a minimalist design that doesn't distract from the gorgeous ocean views. 1 & 2 BR rates available. Royal Palm Villa photo

Vitet, St. Barts

Pool

from $393/Nt
3 3
Details
Bright and open, La Magnolia is a splendid getaway for all types of travelers seeking peace, privacy, and relaxation. 1 & 2 BR rates available. View out to the ocean beyond at La Magnolia Villa

Terres Basses (French side), St. Martin

Pool

from $457/Nt
3 3
Details
St. Barth's romantic Dasha Villa is quickly building a following of ardent admirers 1 & 2 BR rates available. Dasha Villa photo

Lurin, St. Barts

Pool

from $943/Nt
3 3
Details
Great for families and children, Cactus Villa on the northwest side of St. Barts will keep you entertained 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
3 3
Details
All the amenities you expect plus a few surprises (bocce ball, anyone?) at the popular Tamarindo Villa. 1 & 2 BR rates available. Tamarindo Villa photo

Cruz Bay, St. John

Pool

from $386/Nt
3 3
Details
Mahogany Villa is close to Flamands Beach and many water sport activities 1 & 2 BR rates available.
Has specials. Lounge by the pool with great ocean views at Mahogany Villa

Flamands, St. Barts

Near Beach | Pool

from $400/Nt
3 2
Details
Multi-level residence on a Flamands hillside that is great for couples or a family with older children. 2 BR rate available. Datcha Villa photo

Flamands, St. Barts

Pool

from $829/Nt
3 3
Details
Just one minute from Plum Bay Beach, Monchal Villa comes with tons of room and a private pool/jacuzzi. 1 & 2 BR rates available.
Has specials. Monchal Villa photo

Terres Basses (French side), St. Martin

Near Beach | Pool

from $279/Nt
3 3
Details
Three-bedroom beachfront villa on Turks and Caicos, with beachside luxury and relaxation. Has specials. COMO Villa at COMO Parrot Cay photo

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $4500/Nt
3 3
Details
Amazing views within walking distance of three beaches. 1 & 2 BR rates available. Island Views photo

St. Croix, USVI

Near Beach | Pool

from $550/Nt
3 3+
Details
Beachfront luxury on the best part of Grace Bay Beach, with fantastic outdoor space and privacy. Poolside views of the Caribbean from Villa del Sol

Leeward, Turks and Caicos

Near Beach | Pool

from $1215/Nt
3 3
Details
Refuge Villa is a new property that is true to its name: find solace and comfort here 1 & 2 BR rates available. Stunning caribbean views from the private plunge pool at Refuge

Tortola, BVI, British Virgin Islands

Near Beach | Pool

from $612/Nt
3 3+
Details
Views abound and amenities are numerous: Isla Vista has thought of everything for your Caribbean stay. 1 & 2 BR rates available. Isla Viasta is located in the hills of St. john with amazing views

Caneel Hill, St. John

Pool

from $1185/Nt
3 2+
Details
Modern villa with island touches bring the tropics inside 2 BR rate available.
Has specials. A view to the ocean from the patio at Church Point Two

Barbados

Near Beach | Pool

from $500/Nt
3 3+
Details
Peaceful and private hillside villa for those wanting to get away from it all 1 & 2 BR rates available. Andara Villa has amazing views over Haulover Bay

East End, St. John

Pool

from $643/Nt
3 3+
Details
Charming three-bedroom cottage on St. John with exotic brush palms surrounding the pool 1 & 2 BR rates available.
Has specials. Esprit Villa photo

Bordeaux, St. John

Pool

from $429/Nt
3 3+
Details
Classic yet chic beachfront villa on Gibbes Bay. Has specials. Plunge pool and gardens leading to the beach at Waverly Villa

Barbados

Beachfront | Pool | AC

from $700/Nt
3 2
Details
Perfect as a staging point, Ocean's Edge is situatd at the heart of the action in St. James Has specials. Ocean\'s Edge Villa - Merlin Bay photo

Barbados

Beachfront | Pool | AC

from $500/Nt
3 3
Details
Spacious villa with views galore and a private infinity pool 1 & 2 BR rates available. Carolina Villa photo

Coral Bay, St. John

from $514/Nt
3 3
Details
Kayaks, a private beach, and a rooftop deck complete this villa and guest cottage. 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
3 3+
Details
Cozy and affordable Beacon Hill villa has 3 bedrooms, great views, and easy walking access to town. 1 & 2 BR rates available. La Casita Villa photo

Beacon Hill (Dutch side), St. Martin

Near Beach | Pool

from $343/Nt
3 6
Details
Get in touch with nature by taking advantage of the outdoor shower and private, au natural swimming pool. 1 & 2 BR rates available.
Has specials. Resort style pool and surroundings at Sol e Luna Villa

Terres Basses (French side), St. Martin

Pool

from $521/Nt
3 3
Details
Spacious villa on St. John with superb views of Rendezvous Bay and steps aways from great snorkeling 1 & 2 BR rates available.
Has specials. Latitude Villa photo

Klein Bay, St. John

Near Beach | Pool

from $643/Nt
3 3+
Details
Secluded and laid-back retreat in West End Village. 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
3 3
Details
Newly Refurbished Reeds House Penthouse #14 offers luxury and gorgeous views 2 BR rate available.
Has specials. Amazing Caribbean views from Reeds House Penthouse #14

Barbados

Beachfront | AC

from $795/Nt
3 3
Details
Waterfall Villa: A waterfall infinty pool is the centerpiece of this gorgeous estate property 1 & 2 BR rates available.
Has specials. Waterfall Villa is located on a tropical hillside over looking the Caribbean

Rendezvous Bay, St. John

Pool

from $479/Nt
3 3+
Details
Small wedding or renewing your vows? this pantation-style villa is the ideal island spot. 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
3 3
Details
Small, quiet, luxurious resort with ocean views from every room and five-star amenities. 1 & 2 BR rates available.
Has specials. Tuscany photo

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $775/Nt
3 3
Details
Fountains and lush gardens invite guests to relax and rest at this luxuriously spacious villa. Villa Gardenia is surrounded by beautiful tropical foliage

St. Thomas, USVI

Pool

from Call for rates
3 3+
Details
Great 3-bedroom villa on Flamands Beach in St. Barts boasts stunning views and a convenient location 2 BR rate available. Private waterfront pool at Ecoute les Vagues

Flamands, St. Barts

Beachfront | Pool | AC

from $600/Nt
3 2
Details
Great for three couples, enjoy ocean views from every room! 1 & 2 BR rates available. Beautiful views of the Caribbean from the pool deck at Grand Large Villa

Gouverneur, St. Barts

Pool

from $829/Nt
3 3
Details
Excellent location overlooking St. Jean Bay, Lataniers Villa on St. Barts is cute, comfortable, and affordable 1 & 2 BR rates available. Beautiful views from Lataniers Villa

Saint Jean, St. Barts

Pool

from $514/Nt
3 2
Details
Quiet and private villa with beautiful local beaches nearby. 1 & 2 BR rates available. Perched on the hillside of Colombier - Hurakan provides beautiful views of Gustavia Harbour

Colombier, St. Barts

from $469/Nt
3 3
Details
Each villa has a balcony overlooking Grace Bay at this luxury resort complex. 1 & 2 BR rates available.
Has specials. The Venetian photo

Grace Bay, Turks and Caicos

Beachfront | AC

from $875/Nt
3 3+
Details
Spacious contemporary villa has great ocean views and plenty of privacy for your group 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
3 3
Details
For luxurious views, accommodations, and privacy, this beachfront three-bedroom villa is a dream come true (literally!) 1 & 2 BR rates available.
Has specials. A Dream Come True Villa has amazing ocean views and a fun pool area

Devers Bay, St. John

Beachfront | AC

from $400/Nt
3 3+
Details
Stunning contemporary villa offers extreme privacy and lots of space, and you will love the incredible sunset views over the ocean 2 BR rate available. Ti Moun Villa sits just above Gustavia Harbor

Lurin, St. Barts

from $1143/Nt
3 3
Details
Peaceful and private this villa is the perfect choice for couples, and the ocean views and excellent location make it even better. 1 & 2 BR rates available. Kessai Villa photo

Colombier, St. Barts

Pool

from $300/Nt
3 3
Details
Invite relaxation into your life when you stay at Les Amis du Vent Villa 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
3 6
Details
Striking modern home with infinity lap pool and spectacular ocean views 1 & 2 BR rates available. Luxurious pool with spectacular views at Villa Sunrise

Orient Bay (French side), St. Martin

from $400/Nt
3 3
Details
Explore Your Wild Side When You Reserve La Roche Dans L'Eau Villa 1 & 2 BR rates available. A beautiful beach entry pool at La Roche dans l’Eau

Grand Fond, St. Barts

Pool

from $557/Nt
3 3
Details
Private hillside villa with secluded beach and panoramic ocean views 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
3 2
Details
Serene, private Caribbean vacation retreat in the gated community of Villas on the Green Fairwind Villa is located very near to the St. Lucia golf club

Cap Estate, St. Lucia

Near Beach | Pool

from $250/Nt
3 3
Details
Indulgent beach living offers ocean view from penthouse porch in a gated community 1 & 2 BR rates available.
Has specials. The Lookout - Schooner Bay 307 at the Schooner Bay Resort

Barbados

Beachfront | Pool | AC

from $800/Nt
3 3
Details
Exquisitely posh 3 bedroom villa close to Orient Bay and Grand Case 1 BR rate available.
Has specials. Emvie Villa photo

Orient Bay (French side), St. Martin

Pool

from $557/Nt
3 3
Details
A 3-bedroom Terres Basses property with Plum Bay Beach access, plenty of deck space, and modern amenities for any group’s ultimate enjoyment 1 & 2 BR rates available.
Has specials. Spectacular swimming pool and second story sun deck highlights Grand Palms Villa

Terres Basses (French side), St. Martin

Near Beach | Pool

from $671/Nt
3 3
Details
Family-friendly villa with views over wild Toiny Bay. 1 & 2 BR rates available. Enzuma Villa photo

Toiny, St. Barts

Pool

from $571/Nt
3 2+
Details
Modern and convenient with an island view. 1 & 2 BR rates available. Bruka Villa photo

Saint Jean, St. Barts

Pool

from $429/Nt
3 2
Details
Family villa in the hills looking over the forests of St. Barth. Patio deck and pool at Villa Indyana

Lurin, St. Barts

Pool

from $829/Nt
2 2+
Details
1 BR rate available. Blue Canopy photo

St. Thomas, USVI

Pool

from $473/Nt
2 2+
Details
Well-appointed two bedroom villa a short walk from Meads Bay Beach. Has specials. Beachside 2 Villa at Meads Bay has direct access to Meads Bay Beach

Anguilla

Near Beach

from $750/Nt
2 2+
Details
Short walk to one of the top-rated beaches in the world. 1 BR rate available.
Has specials. Beachside Villa 3 at Meads Bay has a personal pool, and beach access

Anguilla

Near Beach | Pool

from $550/Nt
2 2+
Details
Charming 2 bedroom villa on the Vitet hillside, private and surrounded by tropical gardens. 1 BR rate available. Salamandres has a private pool nestled in the Vitet hillside

Vitet, St. Barts

Pool

from $429/Nt
2 2
Details
Trunk Nest villa has amazing views of Trunk Bay

Tortola, BVI, British Virgin Islands

Pool

from Call for rates
2 2
Details
Beachfront villa on Gibbes Beach with ample outdoor dining and an outdoor shower. Has specials. La Lune is located on Gibbs Bay Beach

Barbados

Beachfront | AC

from $750/Nt
2 2+
Details
Understated luxury and ultimate privacy right on the beach. Has specials. The Two Bedroom Beach House at Como Parrot Cay

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $3250/Nt
2 2
Details
Secluded island getaway at Rockworks Villa, St. Thomas? 1 BR rate available. Rockworks photo

St. Thomas, USVI

Pool

from $343/Nt
2 2
Details
The Captain’s House provides peace and privacy within the villa while reveling in the beauty of Long Bay right from your balcony! 1 BR rate available. Captain\'s House villa commands a breathtaking view of the ocan

Tortola, BVI, British Virgin Islands

Pool

from $310/Nt
2 2
Details
Cute, modern cottage overlooking the beach, yet within walking distance Has specials. High atop the bluff above Sandy Lane

Barbados

Beachfront | AC

from $500/Nt
2 2
Details
Secluded apartment with private beach is spacious and ideally located near restaurants Has specials. Secret Cove #1 photo

Barbados

Beachfront | AC

from $445/Nt
2 2
Details
Fully staffed Sea Pearl Villa by Smuggler's Cove Beach is for water lovers and their families. The private pool and gardens are perfect for small groups, yet its just minutes from Rodney Bay. 1 BR rate available.
Has specials. Sea Pearl Villa photo

Cap Estate, St. Lucia

Near Beach | Pool

from $415/Nt
2 2
Details
St Lucia's famous Smuggler's Nest Villa: The writers of Architectural Digest found this hidden gem, but nosy tourists won't 1 BR rate available.
Has specials. Ocean front gazebo at Smugglers Nest Villa

Cap Estate, St. Lucia

Near Beach | Pool

from $500/Nt
2 2
Details
Secluded home on 5 tropical acres has great ocean views and is close to Plum Beach 1 BR rate available. Falaise Des Oiseaux photo

Terres Basses (French side), St. Martin

Near Beach | Pool

from $300/Nt
2 2
Details
Private hillside retreat with amazing Caribbean views 1 BR rate available. Pool area has great views at VEL Villa

Camaruche, St. Barts

Pool

from $357/Nt
2 2
Details
Wonderfully comfortable villa in Terres Basses has sea views, a private pool, and tons of space. 1 BR rate available. Little Provence Villa photo

Terres Basses (French side), St. Martin

Pool

from $371/Nt
2 2
Details
Expansive and private villa in Colombier is a remote island hideaway for adults only 1 BR rate available.
Has specials. Byzance Villa photo

Colombier, St. Barts

Pool

from $857/Nt
2 2
Details
A terrific two bedroom cottage at Cap Estate for the couple who loves to golf 1 BR rate available.
Has specials. D\'arcy Villa photo

Cap Estate, St. Lucia

Pool

from $215/Nt
2 2
Details
Near Gustavia and Shell Beach, Sky Vista is an ideal accommodation for island romance A beautiful view from the pool and deck at Sky Vista Villa

Gustavia, St. Barts

Near Beach | Pool

from $857/Nt
2 2
Details
Harbor view villa with two lovely bedrooms on either side. 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 $829/Nt
2 2
Details
With a huge private pool, tennis courts, and gym, this villa is perfect for active couples or families. 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
2 2
Details
Perfect for honeymooners, you'll enjoy all the amenities offered at Reef Madness 1 BR rate available. Coral Harbor boasts a beautiful hillside infinity edge pool

Coral Bay, St. John

Pool

from $421/Nt
2 2+
Details
Two pavilions separate the common areas and suites, making this an ideal spot for honeymooners or two couples. 1 BR rate available. St. Somewhere is located on the Peterborg peninsula above Meagans Bay

St. Thomas, USVI

Pool

from Call for rates
2 2
Details
Near Lorient Beach, Amalie Villa's views from the hillside keep vacationing simple and simply amazing 1 BR rate available. Amalie Villa photo

Camaruche, St. Barts

from $1071/Nt
2 2
Details
Magic View Villa on St. John's Island offers just that -- a magical view for one couple or two 1 BR rate available. Magic View Villa has its own private swimming pool!

Great Cruz Bay, St. John

Pool

from $357/Nt
2 2
Details
The privacy of a villa and convenience of a full-service concierge all under one roof on Meads Bay. Has specials. Enjoy endless Caribbean views from the Meads Bay Beachside Villa

Anguilla

Near Beach | Pool

from $750/Nt
2 2+
Details
A private villa with 3 private bungalows in Colombier with a lovely view over Flamands L\'Enclos Villa photo

Colombier, St. Barts

Pool

from $814/Nt
2 2
Details
Contemporary and modern villa with all the amenities, perfect for exploring Flamands Beach 1 BR rate available. Les Embruns Villa photo

Flamands, St. Barts

Near Beach | Pool

from $467/Nt
2 2
Details
Impeccable and secluded villa in the exclusive Baie Rouge area has incredible sea views and tons of perks. La Vie En Bleu Villa photo

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $1500/Nt
2 2
Details
Your very own exotic, secluded paradise with an earthy, open feel Perfect pool - Walk out the door and take a dip!!

Cap Estate, St. Lucia

Pool

from $300/Nt
2 2
Details
Enjoy a shower for two at this honeymoon retreat, offering a host of other romantic amenities 1 BR rate available. Victoria Villa photo

Vitet, St. Barts

Pool

from $867/Nt
2 2
Details
Huge views, an infinity pool, and a gorgeous home make this property ideal for a tropical getaway. 1 BR rate available.
Has specials. Nid d\'Amour Villa photo

Terres Basses (French side), St. Martin

Pool

from $643/Nt
2 2
Details
A private villa with modern amenities and a lovely view of Flamands Beach 1 BR rate available. Manon Villa photo

Colombier, St. Barts

Pool

from $529/Nt
2 2
Details
Ideal for guests who want privacy and space with a gorgeous outdoor area. 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
2 2
Details
Ocean Villa is a quiet, tropical retreat for two couples in Vitet with a view of Toiny Bay 1 BR rate available. Amazing views over Anse Toiny from Oceana Villa

Vitet, St. Barts

from $414/Nt
2 2
Details
Bamboo Villa sounds like a place you'd like to stay on a tropical island, doesn't it? 1 BR rate available.
Has specials. Bamboo Villa is located less than a mile from Long Bay

Terres Basses (French side), St. Martin

Pool

from $545/Nt
2 2+
Details
La Magnifica is an open, modern villa for families located at the far end of Vitet with scenic views 1 BR rate available. La Magnifica Villa photo

Deve, St. Barts

Pool

from $563/Nt
2 2
Details
Gorgeous Saint Jean Villa overlooking the Caribbean Sea is ideal for active couples Perched on the hillside - Isia Villa overlooks beautiful St. Jean Bay

Saint Jean, St. Barts

Pool

from $829/Nt
2 2
Details
This villa has a unique media room and is only a short walk to Shell Beach Wastra Villa photo

Gustavia, St. Barts

Near Beach | Pool

from $600/Nt
2 2
Details
With no stairs here and easy access to St. Jean Beach, Lumiere de Soleil Villa is an ideal retreat all on one level Lounge by the pool and soak up the Caribbean sun at Lumiere de Soleil Villa

Saint Jean, St. Barts

Near Beach

from $971/Nt
2 2
Details
Beautifully furnished with a great water view, Cocoland Villa is the perfect choice for couples or families Look out to beautiful views of the Caribbean from Cocoland Villa

Pointe Milou, St. Barts

Pool

from $1286/Nt
2 3
Details
Stunning contemporary villa offers sun, fun, and endless views for a luxurious vacation experience Grain de Folie Villa photo

Colombier, St. Barts

Pool

from $700/Nt
2 2
Details
Adorable Petit Lagon is within easy walking distance of the beach and great for honeymooners 1 BR rate available. Petit Lagon photo

Petit Cul de Sac, St. Barts

Near Beach | Pool

from $571/Nt
2 2
Details
This Camaruche villa is off the beaten path and ideal for a family with older children 1 BR rate available. Lounge by the pool at Marie Villa and enjoy views of the ocean

Pointe Milou, St. Barts

Pool

from $786/Nt
2 2
Details
A castle towering above the Caribbean Sea. 1 BR rate available. Light Castle photo

Cap Estate, St. Lucia

Pool

from $250/Nt
2 2
Details
'Romantic Retreat' Villa is idyllic in its location and cozy in its privacy, hiding above Cruz Bay 1 BR rate available. Amazing views from the private swimming pool

Cruz Bay, St. John

Pool

from $321/Nt
2 2
Details
Open and breezy, Lune de Miel Villa in Terres Basses is the ideal escape for honeymooners. 1 BR rate available.
Has specials. Lune de Miel Villa photo

Terres Basses (French side), St. Martin

Pool

from $500/Nt
2 2
Details
Two-bedroom condo with luxury furnishings, huge communal pool, and quick access to the beach 1 BR rate available.
Has specials. Schooner Bay #206 - The Palms photo

Barbados

Beachfront | AC

from $350/Nt
2 2
Details
This cozy and comfy penthouse boasts spectacular ocean views and easy access to the beach, plus lots of amenities 1 BR rate available.
Has specials. The patio at Reeds Penthouse #13

Barbados

Beachfront | Pool | AC

from $450/Nt
2 2
Details
Caneel Trailside Cottage Caneel Trailside Cottage offers great access to nature in the heart of VI National Parkin the heart of VI National Park 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
2 2
Details
Water enthusiasts will never want to leave this gorgeous villa in Soufriere La Bagatelle Villa photo

Soufriere, St. Lucia

Pool

from $440/Nt
2 3
Details
Within exclusive Estate Shoys, Royal Palms Villa is close to golf and tennis activities, as well as the beach 1 BR rate available. Royal Palms Villa photo

St. Croix, USVI

Pool

from $525/Nt
2 2+
Details
A fantasy stay at Pointe Milou that is a perfect destination for honeymoons, anniversaries, or any sort of romantic vacation! 1 BR rate available. La Falaise photo

Pointe Milou, St. Barts

Pool

from $450/Nt
2 2
Details
Quiet, tranquil villa with gorgeous views and bright interiors. 1 BR rate available.
Has specials. 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
2 2
Details
A naturalistic villa on a hillside in Marigot will make your St. Barts vacation perfect 1 BR rate available. The pool is situated in a beautiful tropical setting at Kyody Villa

Marigot, St. Barts

Pool

from $371/Nt
2 2
Details
An architectural feast for the eyes, Lumiere Villa overlooks Flamands Beach 1 BR rate available. Lumiere Villa photo

Flamands, St. Barts

Pool

from $500/Nt
2 3
Details
Cozy villa tucked into St. Barts hillside boasts amazing sunset views, a private pool, and all the privacy you could want 1 BR rate available. Lorient Sunset Villa photo

Lorient, St. Barts

Pool

from $471/Nt
2 2
Details
Modern villa, amazing sea views looking out towards Martinique! 1 BR rate available. Lounge by the pool with the ocean as your background at Panorama

Cap Estate, St. Lucia

Pool

from $430/Nt
2 2
Details
Relaxing hideaway with amenities and beaches close by Val Andre Villa is just steps away from the ocean

Saint Jean, St. Barts

Near Beach

from $920/Nt
2 2
Details
Steps away from Flamands Beach...take a dip in the ocean or lay under the caribbean sun! The view from the pool at Tichka Villa of Flamands Beach

Flamands, St. Barts

Near Beach

from $1500/Nt
2 2
Details
Just steps from Lorient Beach, this very private and cozy villa is the perfect getaway for honeymooners Les Sables sits just at the end of Lorient Bay

Lorient, St. Barts

Beachfront | Pool | AC

from $571/Nt
2 3
Details
Shalimar Villa: Great location, stunnng views, and tons of privacy! Shalimar Villa photo

Lurin, St. Barts

Pool

from $857/Nt
2 2+
Details
Great contemporary villa boasts stunning ocean views and every comfort imaginable, indoors and out. 1 BR rate available.
Has specials. Villa Bayugita enjoys great views of Lorient Bay

Pointe Milou, St. Barts

Pool

from $529/Nt
2 2
Details
Enjoy spectacular sunsets over the sea and easy access to several beaches at this cozy and modern 2-bedroom villa 1 BR rate available. Views from the pool patio

Pointe Milou, St. Barts

Pool

from $714/Nt
2 2
Details
Beautiful and comfortable home sits right on Chalk Sound, offering tons of privacy and unique views of the sound. Ocean views from the pool at Serene Villa

Chalk Sound, Turks and Caicos

Near Beach | Pool

from $375/Nt
2 2+
Details
Breathtaking ocean views and tons of space make this 2 bedroom villa the ideal getaway for couples 1 BR rate available. Amazing views from the pool deck at Eden View Villa!

Saint Jean, St. Barts

Near Beach | Pool

from $1014/Nt
2 2+
Details
Ultimate views, pool, terraces, and luxurious accommodations make this two-bedroom villa a vacationer's paradise 1 BR rate available. La Vue Panoramique Villa photo

Mont Jean, St. Barts

Pool

from $829/Nt
2 3
Details
Flamands Beach villa with a wraparound terrace and all-white interior. Lounge on the beachfront deck at Fay Villa

Flamands, St. Barts

Beachfront | AC

from $857/Nt
2 2
Details
Gorgeous two-bedroom villa with Indonesian-inspired decor, pool, views, and privacy just minutes from town 1 BR rate available. A beautiful private pool at MAK Villa

Saint Jean, St. Barts

Near Beach | Pool

from $571/Nt
2 2
Details
Zen Villa is a terrific getaway for one couple or two, offering stunning sunset views and relaxation Villa Zen is a great Caribbean getaway complete with a private pool

Pointe Milou, St. Barts

Pool

from $1000/Nt
2 2
Details
Privacy awaits your every move on vacation at Polaris Villa 1 BR rate available. Polaris Villa photo

Flamands, St. Barts

Beachfront | AC

from $500/Nt
2 2
Details
Contemporary amenities with a breathtaking view defines Diamond Villa 1 BR rate available. Diamond Villa offers great views over Gustavia

Saint Jean, St. Barts

Pool

from $929/Nt
2 2
Details
A Wyndham Resort stay with a beachfront location and tons of activity options! Rio Mar Beach Resort Luxury Ocean Villa photo

Northeast Coast, Puerto Rico

Beachfront | Pool | AC

from $450/Nt
2 2
Details
Secluded villa perfect for a relaxing Caribbean vacation 1 BR rate available. Beautiful views and absolute quiet at Valley Villa!

Vitet, St. Barts

Pool

from $643/Nt
2 2
Details
Modern home with beautiful ocean views 1 BR rate available. Teddy Villa has a beautiful infinity edge pool

Vitet, St. Barts

Pool

from $629/Nt
2 2
Details
When privacy and luxury are your biggest holiday concerns, La Sirène Villa is the only way to go 1 BR rate available. Beachfront pool at La Sirène Villa

Flamands, St. Barts

Beachfront | Pool | AC

from $553/Nt
2 1
Details
Bright and airy villa set on a hilltop with stunning panoramic ocean views. 1 BR rate available. Oceana Villa is located on a hill above Crocus Bay

Anguilla

Near Beach | Pool

from $420/Nt
2 2
Details
Bright and chic two-bedroom villa just steps away from Taylor Bay. Blanca Villa sits on a small hill above the beach

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $421/Nt
2 2
Details
Modern oceanfront home with gorgeous swimming pool 1 BR rate available. Villa Micela sits just on the beach at Flamands Bay

Flamands, St. Barts

Beachfront | Pool | AC

from $929/Nt
2 2
Details
Beautiful view over St Jean Bay, within walking distance to Christopher Hotel. 1 BR rate available. Villa Pastel overlooks Lorient Bay and further to St. Jean bay

Pointe Milou, St. Barts

Pool

from $714/Nt
2 2
Details
The best snorkeling spot on the island. Wild Cherry photo

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $700/Nt
2 2+
Details
Clean and open great room just a few minutes from town. 1 BR rate available. Le Sab Villa photo

Saint Jean, St. Barts

Near Beach | Pool

from $714/Nt
2 2
Details
This two-bedroom villa will show you luxury, comfort, and a new perspective of Providenciales' south shore. Miami Vice 2 is located on Sapodilla Bay

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $629/Nt
2 2
Details
Two-bedroom villa with beautiful St. Jean views. 1 BR rate available. Aya Villa photo

Saint Jean, St. Barts

Near Beach | Pool

from $529/Nt
2 2
Details
Well-suited for families and private. 1 BR rate available. Lina Villa photo

Colombier, St. Barts

Pool

from $1214/Nt
2 2
Details
Edenhouse Villa: A private stay just off remote Long Bay Beach yet only a short drive from all the activities of Grace Bay. Edenhouse Villa is located just a short distance from Long Bay Beach

Long Bay, Turks and Caicos

Near Beach | Pool

from $470/Nt
2 2
Details
Tropical villa that feels like a treehouse, with easy access to surfing. 1 BR rate available. Palm House Villa photo

Anse des Cayes, St. Barts

Pool

from $366/Nt
2 2
Details
A jewel for design-minded guests and nature lovers. Amethyste Villa photo

Petit Cul de Sac, St. Barts

Pool

from $1500/Nt
2 2
Details
Two-story villa with stunning views and two equal bedrooms. 1 BR rate available. Exotic View Villa photo

Great Cruz Bay, St. John

Pool

from $393/Nt
2 2+
Details
Clean lines, modern style lots of space. White Villa 1 will accomodate up to six guests and features lush tropical landscaping

Long Bay, Turks and Caicos

Near Beach | Pool

from $486/Nt
2 3
Details
Two villas sit on top of one another to create the perfect couples' retreat. 1 BR rate available. Alfresco Dining on the Honeymoon Suite Deck

Peter Bay, St. John

Near Beach

from $445/Nt
2 2
Details
Intimate resort community with two-bedroom villas and a beautiful beachfront location. Has specials. Meads Bay Beachfront photo

Anguilla

Beachfront | Pool | AC

from $950/Nt
2 2+
Details
Airy villa right on the coast of Pointe Milou with ample outdoor space. 1 BR rate available. MBA Villa photo

Pointe Milou, St. Barts

Pool

from $643/Nt
2 2
Details
1 BR rate available. View from the balcony at Breakers

St. Croix, USVI

Near Beach | Pool

from $357/Nt
2 2+
Details
Ideal spot for honeymooners and lovebirds. Beautiful hillside views from the pool and sundeck at Villa Angel Sunset

Colombier, St. Barts

Pool

from $479/Nt
1 1
Details
Romantic one bedroom within minutes of Flamands Beach. Enjoy views of the ocean and nearby islands from Villa MJS

Flamands, St. Barts

from $557/Nt
1 1
Details
Romantic getaway just a few steps from the beach and a short walk from pristine Chalk Sound. Sun set from the patio at Bari Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $521/Nt
1 2
Details
One of three honeymooner villas on the gentle and tranquil Sapodilla Bay. The beachfront pool at Capri Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $521/Nt
1 1+
Details
Walk from this romantic villa to the beach and dining on the beach. Sunset from the bedoom balcony at Sardinia Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $521/Nt
1 2
Details
Sleek, modern villa with impressive views of the Gustavia harbor. Villa Passage overlooks the Caribbean from the Corossol hillside

Corossol, St. Barts

Pool

from $857/Nt
1 1
Details
Romantic getaway villa with Italian shower massage jets, private pool, and proximity to St. Jean Beach. Villa Suite Acajous overlooks the St. Jean Bay

Saint Jean, St. Barts

Pool

from $600/Nt
1 1
Details
Romantic honeymoon villa just outside of Gustavia. Aloes Villa is located on a hilltop above Gustavia Harbor

Lurin, St. Barts

Pool

from $414/Nt
1 1
Details
Secluded, roomy, relaxing home with direct beach access to Baie Rouge. Has specials. Les Palmiers Villa photo

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $1000/Nt
1 1
Details
Enjoy views, privacy, luxurious accommodations, and exceptional service at this intimate one-bedroom cottage Has specials. Just step through the gate and you are on the beach

Barbados

Beachfront | Pool | AC

from $545/Nt
1 1
Details
Spacious private home located directly on the beach has every amenity you need La Perla Classic Villa photo

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $1000/Nt
1 1
Details
AJA is a cozy one-bedroom with water views and romance built in -- perfect for honeymooners AJA Villa photo

Grand Cul de Sac, St. Barts

Pool

from $343/Nt
1 1
Details
A beautiful setting with endless views await at Piment Villa Relax in the hot tub or take a refreshing dip in the pool at Piment Villa

Anse des Cayes, St. Barts

Near Beach | Pool

from $521/Nt
1 1
Details
Honeymoon getaway with a small second suite for kids or staff. View from balcony

Anguilla

Near Beach | Pool

from $529/Nt
1 1+
Details
This spacious, open villa with private beach access is perfect for couples who love the water. Petit Saint Louis Villa ha great views over Gustavia Harbor

Corossol, St. Barts

Near Beach | Pool

from $357/Nt
1 1
Details
Charming intimacy combines with beautiful views to create the ideal vacation space at Villa BBE BBE Villa photo

Pointe Milou, St. Barts

Pool

from $393/Nt
1 1
Details
Airy North Shore romantic retreat on the far west end of Grace Bay beach. Ballyhoo Cottage sits on Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $471/Nt
1 1
Details
Restful and serene Caribbean beachfront retreat. Callaloo Cottage is located on Grace Bay

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $471/Nt
1 1
Details
Great villa in Grand Cul de Sac features stellar water view and private pool 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
1 1
Details
Tropical views in a serene Caribbean location make Ti Ylang Villa great for couples Ti Ylang Villa photo

Flamands, St. Barts

Pool

from $498/Nt
1 1
Details
Very private and secluded with a sandy beach just steps away, La Perla Bianca is all modern elegance. La Perla Bianca Villa photo

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $1000/Nt
1 1
Details
Newly refurbished Bonbonniere Villa offers great views and privacy for couples Bonbonniere Villa photo

Pointe Milou, St. Barts

Pool

from $500/Nt
1 1
Details
Beautiful views make Gustavia Villa the ideal place for honeymooners Relax and enjoy views of the Ocean from the deck at Gustavia Hill Villa

Gustavia, St. Barts

Pool

from $500/Nt
1 1
Details
Gorgeous water views make Banana Villa in Colombier a great choice for couples Leana Villa photo

Colombier, St. Barts

Pool

from $407/Nt
1 1+
Details
Peaceful, private, and spacious home overlooking Flamands Beach is an ideal island retreat Has specials. Pool area with ocean view

Colombier, St. Barts

Pool

from $414/Nt
1 1+
Details
The perfect bungalow for honeymooners who expect the very best. Alphane Villa is a one bedroom villa on the Arrowmarine Property

Mont Jean, St. Barts

Pool

from $500/Nt
1 1
Details
Romantic getaway villa within walking distance to Shell Beach, shopping, food and more! Camille is located close to the shops and restaurants in the heart of Gustavia

Gustavia, St. Barts

Near Beach

from $500/Nt
1 1
Details
Spacious and modern paradise for two with a beautiful sea view Enjoy an ocean side walk at Cap Frehel

Saint Jean, St. Barts

Beachfront | AC

from $610/Nt
1 1
Details
Ideal for honeymooners with ocean views from your terrace Dahouet Villa is cozy ocean front property on the far end of St. Jean Bay

Saint Jean, St. Barts

Near Beach

from $610/Nt
1 1
Details
Modern luxury for two directly on the western end of Grace Bay Beach. Private pool at Water Edge Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $550/Nt
1 1
Details
The perfect honeymoon getaway just steps from a white sand beach. Sea Edge, Ocean Edge, and Water\'s Edge

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $471/Nt
1 1
Details
This 1 bedroom resort villa is luxurious and comfortable, and right on the beach Has specials. The West Bay Club has a beautiful pool

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $630/Nt
1 1
Details
Private one-bedroom villa overlooking the coast Ti Agave Villa photo

Camaruche, St. Barts

Pool

from $400/Nt
1 1
Details
Secluded, romantic villa perfect for honeymooners Adage Villa photo

Pointe Milou, St. Barts

Pool

from $464/Nt
1 1
Details
Secluded and quiet honeymooners' haven next to exclusive beach. Gouverneur Jewel photo

Gouverneur, St. Barts

Pool

from $714/Nt
1 1
Details
A comfortable and cozy getaway for two with perfect views of the water and neighboring islands Colibri Villa offers great views of the ocean from the patio balcony

Pointe Milou, St. Barts

Pool

from $357/Nt
1 1
Details
Miami Vice 1 is a modern, peaceful, and private villa just steps away from the water. Miami Vice 1 Villa is located on Sapodilla Bay

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $443/Nt
1 1
Details
A couple's island dream with lots of room for two, especially on the deck that overlooks the waters of Bordeaux Island Dreams Villa photo

Bordeaux, St. John

Pool

from $390/Nt
1 2
Details
Easy resort lifestyle like on-site dining and shopping, and quick access to Cupecoy Beach Has specials. Aazure Villa photo

Cupecoy (Dutch side), St. Martin

Near Beach

from $229/Nt
1 1+
Details
Uniquely designed villa with Moroccan accents and fully retractable walls. Villa Sheherazade photo

Corossol, St. Barts

Pool

from $857/Nt
1 1
Details
Art and romance come together in this one-bedroom with cliff-side views of the Caribbean Sea and surrounding islands BelAmour Villa photo

Pointe Milou, St. Barts

Pool

from $986/Nt
1 1
Details
An intimate one-bedroom right on Sapodilla Beach with a private pool, second-story bedroom, and views that you will remember forever 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 $521/Nt
1 1+
Details
A romantic one-bedroom couple’s retreat with complete access to Grace Bay Beach, a wonderful spot for snorkeling, and nearby restaurants. Little Plum Cottage is a single bed unit on Grace Bay Beach

Grace Bay, Turks and Caicos

Near Beach | Pool

from $414/Nt
1 1
Details
A romantic and modern Grace Bay villa that is close to all that Turtle Cove can offer. Sugar Cube Villa sits directly on Grace Bay Beach

Grace Bay, Turks and Caicos

Near Beach | Pool

from $514/Nt
1 1+
Details
Luxury loft in the heart of Gustavia with ample seating and dining. The Loft Villa photo

Gustavia, St. Barts

Pool

from $986/Nt
1 1
Details
The ocean surrounds this one-bedroom beauty off the coast of Belize. Cayo Espanto - Casa Solana photo

Belize

Beachfront | Pool | AC

from $1495/Nt
1 1
Details
Rekindle romance just inches from the turquoise sea. Cayo Espanto - Casa Olita photo

Belize

Beachfront | Pool | AC

from $1895/Nt
1 1
Details
1500 square foot, one-bedroom bungalow on a private island. Cayo Espanto - Casa Mañana photo

Belize

Beachfront | Pool | AC

from $1795/Nt
1 1
Details
Gorgeous honeymoon suite with open-air design and easy ocean access. Cayo Espanto - Casa Brisa photo

Belize

Beachfront | Pool | AC

from $1695/Nt
1 1
Details
This over-the-water villa is surrounded by the sea and sits at the end of a 150-ft dock. Cayo Espanto - Ventanas photo

Belize

Beachfront | AC

from $1595/Nt
1 1
Details
Warm, quaint honeymoon villa with gorgeous views. Alfresco Dining on the Honeymoon Suite Deck

Peter Bay, St. John

Near Beach

from $445/Nt
1 1
Details