Caribbean Villas & Luxury Vacation Rentals

Luxury Villa Rentals for 2+ people






× 2 Guests × 1 Rooms


8 16 8 + 2 half
$35,714 - $50,000 /night
5 10 5
$21,429 - $64,286 /night
7 14 7 + 3 half
$19,500 - $21,600 /night
9 18 8 + 2 half
$17,800 - $35,700 /night
7 14 7 + 1 half
$16,900 - $18,000 /night
8 16 8 + 3 half
$16,800 - $25,000 /night
6 12 6
$15,643 - $64,286 /night
8 16 8 + 2 half
$15,560 - $40,295 /night
6 12 6 + 1 half
$15,300 - $19,500 /night

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Your Guide to Luxury Villa Rentals in the Caribbean

Few destinations evoke the kind of strong associations travelers usually have when they think of the Caribbean. But what else do you expect from a destination that’s centered around vibrant cultures, picture-perfect weather, and some of the most gorgeous ocean scenery in the world? And while there may be no shortage of hotels, connoisseurs know that there’s no better way to experience this tropical paradise than with with a luxury villa rental in the Caribbean.

Why Book a Villa in the Caribbean?

If the Caribbean is paradise, what’s better than having your own slice? Caribbean villas give you the chance to experience your destination of choice in a totally exclusive and personalized way thanks to their privacy, design, and service. St. Barts, Antigua, the British Virgin Islands - no matter which location you choose, true luxury and privacy can be yours when you book a villa in the Caribbean.

Luxury Vacation Rentals in the Caribbean

Whether you're planning a vacation for the whole family or want a romantic getaway with that special someone, there’s a luxury villa in the Caribbean that will be perfect for your group. We have Caribbean villas that can accommodate any size group, and your concierge can work with you to ensure that the rest of your villa vacation experience is completely personalized and tailored to your needs.

Caribbean Villas for Family Vacations

Every family may be a little different, but there’s a Caribbean villa out there that’s perfectly suited to yours. Whether you just want to lounge by the pool, prefer something beachfront, or even want to plan a destination wedding, Caribbean villa rentals give you the chance to enjoy an unparalleled level of service and privacy and truly connect with the people that matter most. Here are some of our top picks:

Seaclusion: With its floor to ceiling windows, modern design, and prized beachfront location on the shores of Turks and Caicos’ famous Grace Bay Beach, Seaclusion really is the epitome of the luxury Caribbean lifestyle. Throw in the private staff, the villa pre-stocking, and all the water sports equipment, and you have the making of an ideal family vacation.

Whispering Waters: Located in beautiful Discovery Bay - home to some of Jamaica’s very best beaches – the beachfront Whispering Waters is perfect for active families. It features private coral coves, two private beaches, two gyms, and even two tennis courts. It’s an especially great choice for two families who are traveling together, though everyone will surely come together and enjoy the lovely meals cooked by the private chef and served by the staff in the large outdoor dining table, which accommodates 14.

Chateau des Palmiers: If you’re traveling with an even bigger group or are planning a big family event like a destination wedding, then Chateau des Palmiers in the lovely Terres Basses of Saint Martin is an ideal choice. From staff that pamper you from head to toe to its unparalleled beachfront location, this villa really is a testament to luxury in a way that the whole family will appreciate.

Romantic Villa Getaways in the Caribbean

The Caribbean is easily one of the romantic destinations on earth, and each year couples flock to its white sand beaches to reconnect. If you're planning a honeymoon, anniversary or just looking for a romantic getaway, these luxury vacation rentals will give you an escape you'll never forget:

Rainbow: Located in the ultra-exclusive Oil Nut Bay, a private island in BVI, Rainbow is one of the finest and most romantic 1-bedroom villas you’ll ever find. It includes a private infinity pool, marble everything, and exquisite views of the beautiful turquoise waters of the Caribbean Sea for a romantic getaway you'll never forget.

Manonjul 2: If you want a private, secluded getaway for two that’s also a great value, this 1-bedroom villa in St. Barts offers panoramic views over the bay of Marigot and Grand Cul de Sac with beautiful indoor and alfresco dining areas, plus a jacuzzi where you can enjoy the gorgeous, romantic setting.

Beachfront Honeymoon Swim Up Suite: If you’re looking for a more traditional resort experience while still enjoying the privacy and service of a villa experience, then this honeymoon suite in Negril, Jamaica is perfect. It includes a private staff, ocean views, and allows guests to swim straight from their private terrace to a swim-up bar.

Beachfront Villas in the Caribbean

For many, the beach is the prime reason to visit the Caribbean, making a beachfront villa in the Caribbean a nearly unmatched luxury experience. It’s no surprise, then, that the beachfront villas in the Caribbean also tend to be some of the best in the world. Great options inlcude:

Emerald Cay: Easily one of the most spectacular estates in the Caribbean, Emerald Cay is located on a private island in Turks and Caicos, right by the beautiful Chalk Sounds National Park and Caicos Banks. Architecturally stunning, the entire property is surrounded by private beaches and lagoons and features a plethora of the finest amenities – from tennis courts to movie theatre to a 6,000-bottle wine cellar.

Sand Club: The appropriately-named Sand Club has one of the most privileged locations in St Barts – right on the soft white sands of Flamands Beach, where it stands out among some of the world’s top luxury hotels and villas with its impeccable sense of style, as well as the unsurpassed privacy it offers guests.

Lazy Lizard: Located on Jumby Bay Island in Antigua, this private beachfront estate is ideal for large groups who want to enjoy seclusion, privacy, and the sea. It consists of eight pavilions that can accommodate up to twelve guests, a floating dining pavilion that’s perfect for entertaining, and interiors the have been meticulously designed and adorned with the finest materials.

Staffed Villas in the Caribbean

Nothing beats the experience of having a fully staffed villa in the Caribbean. Not only are the staff professional and skilled, but they’re also personalizing their service to your taste. Plus, the staff is fun and friendly and often end up being a highlight of the trip. Options here include:

Cove Spring House: Located in Barbados and just down the stairs from the secluded, intimate Cove Spring Beach, Cove Spring House features meticulous service from its five-star staff, as well as water sports, full spa service, a fitness center, and dinner service, all on site and personalized to your tastes.

Aerial: Situated on Buck Island in the British Virgin Islands, Aerial is like having your own private island resort. It’s ideal for large groups since it consists of five villas that can accommodate up to 30 guests, each with its own style, surroundings, and staff, creating an impeccable vacation experience.

Palmier Royal Estate: Located in Mont Jean, St Barts, Villa Palmier Royal Estate consists of two villas with 11 bedrooms and direct access to the protected bay of Marigot. Not only is this estate stunning inside and out, but the villas also include a full-time chef, waitresses/butlers and maids providing turn-down service, making it ideal for two families who are traveling together.

Caribbean FAQ

What Should I Know Before Traveling to the Caribbean?

If you're planning a holiday to the Caribbean, you should know a few things. First, prices fluctuate depending on the season, with high season typically lasting from December-April.

Second, some more secluded locations may have less cell phone service, so this may be something you want to inquire about.

Third, Caribbean destinations vary greatly from island to island, and even within the same island, so be sure to do some research or ask a Rental Escapes villa specialist about different destinations to find the one that is right for you.

How to Travel to the Caribbean?

It's easy to get a flight into the Caribbean, with Jamaica and Saint Martin being home to the most popular airports. From there, your concierge can assist with getting to your destination, whether that involves fairies, connecting flights, or just a simple airport transfer.

How do I get around in the Caribbean?

The Caribbean has a very sophisticated tourism infrastructure in place, so you should be able to get around relatively easily, including through private drivers, taxis, buses, and rental cars. You can also find domestic ferry routes between some islands if you want to explore. Again, speak to your concierge to arrange any sort of transportation.

Best Time of the Year to Visit the Caribbean?

This depends on what your goal is. If you want to go at a time when there will be lots of flights, tourists, and activities, you're better off visiting during the high season, which is late December to early April. However, prices will be better in the off-season (mid-April to mid-December), though we do suggest taking Hurricane season (mid-August to late-October) into account - even though your chances of running into a hurricane are still very low during this season (many Caribbean destinations are also off the hurricane belt, which further lowers your chance of being caught in a significant storm).

Best Things to do in the Caribbean?

The Caribbean has more than enough activities to keep anyone busy, with some favorites being water sports (jet skiing, wakeboarding, kite surfing, paddle boarding, kayaking, and much more), as well as fishing, hiking, golfing, zip lining, snorkeling, and, of course, chilling out by the beach. And if you want to cut loose, there's usually a bustling nightlife scene in many Caribbean destinations as well.

How’s the Food in the Caribbean?

Each island usually has its own specialty, from cracked conch in Turks & Caicos, fish & fungi in the British Virgin Islands, ackee and saltfish in Jamaica, and more. In general, though, you can expect tons of fresh seafood, French and West Indian cuisine, and well-crafted takes on Italian, Japanese, and American favorites.

What’s the Weather Like in the Caribbean?

During the high season, you can expect very little rain and comfortable, warm temperatures in the high 80s Fahrenheit (low 30s Celsius). During low season, the heat is more potent, as is the humidity, so expect the high 80s or low 90s (about 33°C), as well as a chance of showers in the afternoon.

Book a Villa in the Caribbean with Rental Escapes

When you book a Caribbean villa with Rental Escapes, you can rest assured that your holiday will be worry-free. Your concierge works with you up to and during your trip to make sure everything is perfectly suited to your tastes, and we have partners on the ground at all destinations who will help us coordinate your arrival and departure and provide you with plenty of help throughout your stay.

Contact us today to book your next dream holiday!

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