The Caribbean
Find irresistibly luxurious Caribbean villas in breathtaking destinations across the region, including Barbados, Turks and Caicos, Jamaica, and more.
Caribbean villas
When you step off the plane in the Caribbean, you'll be forgiven for thinking you've arrived in paradise, and our beautiful Caribbean villas only enhance that feeling! This corner of the tropics is the stuff of daydreams, where tropical beaches, tasty rum punch, and lively reggae beats are never far away.
There are more than 7,000 islands and cays in the Caribbean; some are desert islands inhabited only by local wildlife, while others – like Barbados and Jamaica – are among the world’s most exclusive vacation destinations. Each region has its own charm and appeal, but they all share the same warm hospitality and distinct laid-back vibe.
Caribbean villas in breathtaking destinations
We offer a range of Caribbean villa rentals across all of the region’s best travel destinations, whether you’re looking for a romantic retreat for a honeymoon, a large villa for a family vacation, Caribbean golf villas, or a sprawling home for an all-out special occasion. With unbeatable amenities offering an all-inclusive Caribbea vacation experience, our increible, luxurious Caribbean villas are the ultimate places to stay in paraidse.
Explore Caribbean villa rentals
Kempa Kai
Avanti
Arc En Ciel
Seaclusion St James
Bambu
Villa Dunes
Shiloh Estate
Cap Cana 1
Lizard Lounge
Villa Wake Up
Casa De Campo 0
Sentosa
FAQs
Where is the Caribbean?
What countries are in the Caribbean?
When is hurricane season in the Caribbean?
Are passports needed for the Caribbean?
Is the Caribbean part of the United States?
What is the number one island in the Caribbean?
Which Caribbean island has the best beaches?
What vaccinations do I need for Caribbean vacations?
What languages are spoken in the Caribbean?
What is the Caribbean famous for?
The best time to visit the Caribbean
The best time to visit the Caribbean is during the Northern Hemisphere winter, particularly between December and April. During this time, the weather is beautifully warm, sunny, and dry, with little rainfall, making it perfect for lazy beach days and exploring the attractions of these amazing islands. Temperatures are also cool enough at night that you'll get a comfortable night's sleep (or enjoy all-night parties).
If you want to avoid the crowds, steer clear of the winter weeks around the Holiday Season. Around Christmas and New Year's, festive sun seekers flock to the Caribbean, making for a busy time on the islands.
Food in the Caribbean
The Caribbean is a real foodie’s destination. From fresh-from-water seafood to traditional Creole cuisine, international fare to established daily favorites, there is something to delight and surprise every palette. Each island has its own distinctive culinary personality, with must-try delicacies tempting visitors from beachfront bars and restaurants. Some classic Caribbean dishes include the famous jerk chicken of Jamaica, roast pork dishes, lobster and crab, pepperpot stew, and of course, rum punch. For those with a sweet tooth, the Caribbean is home to a plethora of desserts and treats to get your teeth into. Take a look at some of our favorites in our guide to Caribbean desserts.
The Caribbean is famously the birthplace of rum, and whichever island you visit, you'll have the opportunity to sample some delicious rum-based cocktails, or even visit a distillery and learn more about this iconic Caribbean export.
For fine dining aficionados, the Caribbean is home to several Michilin Star restaurants, showcasing the best local and international cuisine. From Chef Eric Ripert’s Blue on Gradn Cayman, which holds the AAA Five Diamond level of regnition, to Chef Jean-Georges Vongerichten's Dune in the Bahamas and Chef Jean Claude Dufour's L'Espirit on the exclusive island of St Barthelemey, there are world-class eateries on almost every island.
Getting to and around the Caribbean
Flights to the Caribbean
Transport on islands
Island hopping in the Caribbean
- From the famed Grace Bay on Turks and Caicos to the glamorous beaches of Barbados, countless beautiful beaches exist for unforgettable days of relaxation in the Caribbean sun.
Beaches
- From snorkeling colorful coral reefs to free diving with mighty humpback whales, there is a plethora of breathtaking opportunities to go diving in the Caribbean.
Diving
- Whether you want a full-on adventure scaling mountains or a more leisurely stroll through nature reserves, the Caribbean has plenty of places for hiking enthusiasts.
Hiking
- November through April is the prime time for surfing in the Caribbean's most popular spots to catch a wave or two, which include Barbados and Jamaica.
Surfing
- From ancient caves to old pirate ports, and garrisons to beautifully-preserved Colonial mansions, the Caribbean has so much for history buffs to get their teeth into.
Historic sites
Personal
Travel Planners to help you find the perfect vacation rental and enhance your stay with a range of Travel Extras.
Choice
Giving you the world's best homes and destinations in trending hot spots
Confidence
Excellence as standard giving you what you deserve at every stay
Caribbean villa rentals with staff
If you want to enjoy the benefits of a hotel stay with the solitude and peace that a private vacation brings, then our Caribbean villa rentals with staff, whether it is a vacation rental with private chef and maid, as well as other staff, are just the thing that you’re looking for. These incredible villas offer an all-inclusive vacation expereince, where you can enjoy the benefits of a staffed vacation rental throughout your stay.
From housekeeping services to private chefs and even boat captains, our fabulous Caribbean villa rentals with staff are guaranteed to make every Caribbean adventure extra special. As well as fantastic staff, there's a whole host of amazing Travel Extras that you can add to your Caribbean villa rentals, from airport transfers to in-home spa services and grocery deliveries.
Popular resorts in the Caribbean
All inclusive beachfront villas Caribbean
If there is one thing that is synonymous with the Caribbean, it’s beautiful beaches. Our beachfront Caribbean villa rentals occupy some of the most desirable places in the region, from the unblemished sands of Grace Bay in Turks and Caicos to the glamorous shores of Barbados’ St James.
As well as offering some of the best sea views that you’ll find anywhere in the world, our beachfront villas in the Caribbean also have a host of fantastic amenities, including private pools, staff, and direct access to some seriously stunning beaches. Whether you're looking for a small and romantic home, all-inclusive family villas in the Caribbean, or Caribbean vacation rentals for large groups, our beautiful range of luxury beachfront villas are the perfect places to stay in the region.
Discover beachfront Caribbean villa rentals
Casa Cervo
Waverly One
Whispering Waters on the Beach
Sandcastle Villa
Rio Chico on the Beach
Foster's House
Turtle Nest
Villa Javacanou
Bamboo
Frankfort on the Beach
Villa Val Andre
Lockrum Point Villa
Caribbean villa rentals by number of bedrooms
- 1-bedroom Caribbean villa rentals
- 2 bedroom villa Caribbean
- 3-bedroom Caribbean vacation rentals
- 4-bedroom Caribbean villas for rent
- Luxury villas Caribbean with 5 bedrooms
- Luxury Caribbean villas with 6 bedrooms
- 7-bedroom Caribbean villas for rent
- 8-bedroom luxury villas Caribbean
- 9+ bedroom luxury vacation rentals Caribbean
Luxury Caribbean villas with private pools
A private pool is the height of luxury in a vacation rental, and many of our incredible Caribbean villas offer sublime infinity pools, plunge pools, and more, perfect for relaxing and cooling off the sunshine. These private pools often feature breathtaking views, and many of our villas with pools in places such as Barbados, Jamaica, Turks and Caicos, and St Barts look out over the Caribbean Sea.
Our Caribbean vacation rentals with private pools also feature amenities such as seating areas for dining and unwinding, submerged sun loungers, swim-up bars, and much more. These private pools are the places to be if you want to add a little extra glamor to your Caribbean vacation.
Explore luxury Caribbean vacation rentals with private pools
Mariposa
Belle Fontaine
Coral Pavilion
Sugar Hill - Illusion
Triton Estate
La Dolce Vita
Caye Blanche
Villa African Queen
Bambu
Greensleeves
Silent Waters
Longview Villa on Round Hill
Caribbean vacation rentals for large groups
Whether it’s a family reunion or group getaway with your friends, our Caribbean villas for large groups is the ideal place to stay. Our biggest home in the region sleeps 46 guests, and we have numerous properties with the capacity to accommodate 20 or 30 people. A large villa rental gives everyone their own private space, with bedrooms, en-suite bathrooms, dining, and entertaining areas that the whole group will love.
Our Caribbean vacation rentals for large groups are the pinnacle of excellence in accommodation. For villas with ocean-view infinity pools, large homes with private chefs, and places that are perfect for multi-generational vacations no matter the size of your part, you'll be able to find Caribbean vacation rentals for large groups amongst our award-winning collection of villas.
Find more Caribbean vacation rentals for large groups
Sentosa
La Bella Casa
Pearls of Long Bay Estate
Cabarete 1
Casa De Campo 222
Seaclusion Oasis - Grace Bay
Mount Hartman Bay Estate
The Great House
Villa Mora
Casa de Campo 1
La Bella Casa
Sun Salutations
Frequently searched
- Caribbean condos and apartments
- Caribbean villa rentals with game rooms
- Caribbean vacation rentals with gyms
- Pet-friendly luxury villa rentals Caribbean
- Luxury villa rentals Caribbean with home gyms
- Honeymoon villas Caribbean
- Staffed villas Caribbean
- Caribbean oceanfront villas
- Caribbean luxury villas with home theaters