Skip to content
Some info has been automatically translated. Show original language

Caribbean vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Caribbean

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Entire home · North Side
Ocean's Edge: Beachfront Home with Rooftop Views
Oceanfront property with beauty all around. Walk right out your backdoor and into crystal clear water. Snorkeling, paddle boarding, kayaking, and more can be experienced steps away from your home. Nearby are grocery stores, restaurants, bars, as well as the famous attraction the Cayman Crystal Caves. The house is bright and full of space. 4 bedrooms all have attached bathrooms. YOU WILL NOT FORGET THE ROOFTOP. Plenty of outdoor furniture to sit back, relax, and enjoy the views from Ocean's Edge
ﺩ.ﺇ1,433 per night
Entire guest suite · San Juan
Treehouse w floating deck at La Botanica
Treehouse at La Botanica Hotel + Wellness Center: You can also find us on IG @ casabotanica_ayurveda, this magical urban oasis has been built in the style of a treehouse, with cream aged wood, polished cement floors, high ceiling, skylights that eye level the magnificent trees in the luscious garden and floating deck with outdoor shower. I also serve a lovely breakfast and yoga in the garden and We have a local store and pop up farm to table dinners Check out our spa!
ﺩ.ﺇ699 per night
Entire home · Stake Bay
Modern Oceanfront, 2Primary Suites, sleeps 6, pool
We offer a Hurricane Worry-free Guarantee. Only a short 25-minute flight from Grand Cayman, this newer home provides stunning oceanfront vistas with all modern amenities to enjoy barefoot luxury. Large windows and the open concept floor plan allow for breathtaking views of the pool and sea and include a fully-equipped kitchen, dining, and living areas. Also overlooking the ocean are two master king-size bed suites with tiled baths. A third bedroom has a queen bed and views of tropical foliage.
ﺩ.ﺇ1,433 per night

Vacation rentals for every style

Get the amount of space that is right for you

  • Houses
  • Apartments
  • Cottages

Caribbean beach vacation rentals

Entire villa · Treasure Beach
Villa Elia~Private Seafront Tropical Paradise
ﺩ.ﺇ2,755 per night
Entire home · Grand Cayman
Lone Palm by Grand Cayman Villas
ﺩ.ﺇ2,446 per night
Entire home · Placida
Camp GoodNow: Stunning new beachfront home, privat
ﺩ.ﺇ1,616 per night
Entire home · Grand Cayman
Kai Tana by Grand Cayman Villas
ﺩ.ﺇ1,624 per night
Entire villa · Les Terres Basses
Terrasse De Mer
ﺩ.ﺇ3,515 per night
Entire cottage · Tortola
BVI Village - available for Christmas 2022!
ﺩ.ﺇ1,734 per night
Entire cottage · Central Eleuthera
Bird of Paradise, Golden Chalice
ﺩ.ﺇ1,414 per night
Entire bungalow · Freeport
Stunning House right on the beach!
ﺩ.ﺇ992 per night
Entire villa · Friis Bay
Siempre Azul | Walkable Beach Access
ﺩ.ﺇ1,616 per night
Entire villa · Les Terres-Basses
ﺩ.ﺇ3,673 per night
Hotel room · Rincon
Tres Sirenas Boutique Hotel Oceanfront Suite
ﺩ.ﺇ1,153 per night
Entire villa · Kralendijk
Villa Shores 32, private stunning oceanfront villa
ﺩ.ﺇ2,149 per night

Caribbean house rentals

Entire home · Key West
Grand Home/Heated, Salt Water Pool/Dog Friendly
ﺩ.ﺇ1,541 per night
Entire home · Las Terrenas
Amazing sea view luxury modern, fully staffed
ﺩ.ﺇ1,902 per night
Entire home · Fort Lauderdale
★Near Downtown & Beach- Luxury House /Heated spa★
ﺩ.ﺇ1,270 per night
Entire home · Miami
ﺩ.ﺇ1,837 per night
Entire home · San Cayetano de Venecia
Quinta La Ceiba Modern Home with Pool in DairyFarm
ﺩ.ﺇ677 per night
Entire home · Cape Coral
Completely Remodeled 3 Bedroom Home With A Pool
ﺩ.ﺇ643 per night
Entire home · Cartagena
Super Luxury 7 Bedroom House in the Old City
ﺩ.ﺇ3,052 per night
Entire home · Aguadilla Pueblo
Ta-Vera Oasis
ﺩ.ﺇ626 per night
Entire home · Guayama
Vikings style completely private, for couples.
ﺩ.ﺇ388 per night
Entire home · Port Charlotte
Book Today to Escape + Relax! 3 Bdrm, Pool + Lanai
ﺩ.ﺇ556 per night
Entire home · La Caña
Modern house with pool and jacuzzi in Playa Nueva Romana with fast internet
ﺩ.ﺇ1,032 per night
Entire home · Siesta Key
Beachfront Getaway in Siesta Key
ﺩ.ﺇ945 per night

Caribbean luxury vacation rentals

Entire villa · Terres Basses
Just in Paradise
ﺩ.ﺇ3,464 per night
Entire villa · Silly Creek
Villa Sublime
ﺩ.ﺇ2,975 per night
Entire villa · Pointe Milou
ﺩ.ﺇ3,673 per night
Entire villa · Punta Cana
La Cana H3
ﺩ.ﺇ3,673 per night
Entire villa · Terres-Basses
ﺩ.ﺇ3,012 per night
Entire villa · Punta Cana
Hacienda A21
ﺩ.ﺇ3,673 per night
Entire villa · Les Terres-Basses
La Hacienda
ﺩ.ﺇ2,729 per night
Entire villa · Pointe Milou
ﺩ.ﺇ3,412 per night
Entire villa · Weston
Marsh Mellow
ﺩ.ﺇ3,393 per night
Entire villa · Les Terres Basses
Mer Soleil
ﺩ.ﺇ3,673 per night
Entire villa · Deve
La Magnifica
ﺩ.ﺇ2,097 per night
Entire villa · Les Terres-Basses
Sol e Luna
ﺩ.ﺇ2,362 per night

Your guide to Caribbean

All About the Caribbean

The Caribbean is made up of 26 island countries surrounded by bejeweled blue and green waters and is known around the world as a holiday paradise. People flock here, especially in the winter, for warm sands, golden sunshine, and that sense of island time abandon — plus, the fruity drinks under towering palm trees. The Dominican Republic is the most visited of all the islands due to its vibrant city and cultural life and postcard-perfect beaches. West of that is Cuba, famous for its Old World architecture, rich jazz and music scenes, and several UNESCO World Heritage Sites. Closer to South America is little St. Lucia, known for its rainforests, colorful coral reefs (perfect for diving and snorkeling), and, of course, pristine beaches surrounded by the island’s volcanic peaks.

The countries in the Caribbean are extremely diverse, not only in their histories, cultures, and languages, but their landscapes and topographies. For example, vibrant Jamaica could not be more different from super-chill Aruba and swanky St. Barts. So whether you’re seeking an island that’s large or small, glitzy or low-key, in the Caribbean there is a sanctuary for everyone.

When is the best time to stay in a vacation rental in Caribbean?

Thanks to trade winds, the weather in the Caribbean is sunny and pleasant all year round. The only caveat is that tropical storms and hurricanes occur to varying degrees of intensity here, and their likelihood increases from about July to November. But it’s the dry season from December through March that makes the region so popular. Villas to rent in the Caribbean are in demand during the winter, as many feel the urge to escape the colder weather up north and take in the sun, fun, and the many festivals — like Trinidad’s Carnival, the biggest of the Caribbean’s carnivals, and the Bahamas’ Junkanoo, a cultural street festival and celebration dating back centuries that takes place between Boxing and New Year’s Day. There are also plenty of Caribbean rentals in May and June, if you don’t mind the chance of a little rain.

What are the top things to do in Caribbean?

Santo Domingo

Santo Domingo, the capital of the Dominican Republic, is the oldest continuously inhabited colonial settlement in the Western Hemisphere and was founded in 1496. The historic city center, Zona Colonial, is a UNESCO World Heritage Site, with cobblestone streets, colorful houses, and colonial-style architecture and structures like the 16th-century Basilica Cathedral of Santa María la Menor, the oldest surviving cathedral in the Americas.


Sitting off the coast of Venezuela is the Dutch island of Curaçao, lesser known than its neighbors, but with just as much to offer — including its lack of hurricane seasons. Willemstad, the capital, is one of the few UNESCO World Heritage cities in the Caribbean, and it’s pulsing with nightlife and festivals like Carnival and King’s Day. The diving here is top-notch, there are dozens of stunning beaches to choose from, and the lodging ranges from hostels to five-star resorts — so there’s something here for everyone.

Reggae in Jamaica

Jamaica is the birthplace of reggae. The music took off in the late 1960s, and by the 1970s, with the superstardom of Bob Marley and the Wailers, it became known throughout the world. If you’re in Kingston, check out the clubs, still playing the dub style that made the genre so popular. The best of the best musicians have been known to play at the annual reggae festival held in June.