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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.

Villa in Lake Worth
Bliss Villa 4 w/Heated Pool +BEST Rate & Location!
Welcome to Lake Worth Beach's coolest vacation rental. This million+ dollar property boasts an amazing courtyard with a HEATED pool, dining nooks, lounge chairs, grill, outdoor shower & cabana BA - surrounded by 4 private villas. Renovated 440 sq/ft *Villa 4* is perfect for those who want to walk to downtown cafes/nightlife/parks AND also be near a beautiful beach. Villa 4 is an accessible space w/king bed, work desk w/1Gig Internet, washer/dryer, kitchen, central AC, & on-site parking.
ﺩ.ﺇ599 per night
Cottage in Eleuthera Island Shores
This beachfront eco Cottage is located on the Atlantic coastline of Eleuthera. The cottage is a 10 minute walk to the world famous Surfer's Beach. The quaint and authentically Bahamian Gregory Town is 2 miles to the North. All of the photos on this listing have been taken at ShoreBreak cottage. Recently built and authentic cottage, vaulted exposed beam ceilings, 2 bedrooms, 2 baths, sleeps 4. Ideal for 2 couples or make it a romantic and private getaway for two!
ﺩ.ﺇ1,451 per night
Treehouse in San Carlos
Rainforest Tree House with Hot Springs
No children under 5 years of age for safety reasons. The Tree House is hand-crafted, one of 3 casitas and 3 treehouses at the Bio Thermales natural resort organically integrated into our 35 acre rainforest. Guests enjoy free access, from 9 am to 10 pm to the 15 natural hot and cool springs pools of various temperatures and rainforest trails.
ﺩ.ﺇ422 per night

Caribbean winter vacation rentals

Tiny home in Rincón
Tree of Life🌿 Private Pool Tiny House in Rincon!!
ﺩ.ﺇ767 per night
Cottage in Runaway Bay
Bahia - Charming seaside cabin, loft/wood shutters
ﺩ.ﺇ992 per night
Guesthouse in Key Largo
Private Cottage, enjoy beach, sunsets & fishing.
ﺩ.ﺇ707 per night
Rental unit in Rincon
Private Pool Villa floating bed Bohemian Suites
ﺩ.ﺇ977 per night
Tiny home in Rincon
Casa Valentina
ﺩ.ﺇ667 per night
Tiny home in Aguada
Container with Private Pool-Couple Retreat
ﺩ.ﺇ624 per night
Home in Siesta Key
Beachfront Getaway in Siesta Key
ﺩ.ﺇ1,047 per night
Home in Delray Beach
Dream Tropical Pool House Delray Beach near Ocean
ﺩ.ﺇ1,161 per night
Cabin in San José de la montaña
Antares - City view - indoor jacuzzi
ﺩ.ﺇ496 per night
Home in Cape Coral
Skyline Paradise-5 Bed Retreat Pool&hotub-LakeView
ﺩ.ﺇ2,179 per night
Villa in San Nicolas
BeachFront Villa w/ Pool, Sleeps 16, Dining, & Tub
ﺩ.ﺇ3,385 per night
Dome in Cayey
Escape Puerto Rico
ﺩ.ﺇ1,095 per night

Caribbean luxury vacation rentals

Villa in Treasure Beach
Villa Elia~Private Seafront Tropical Paradise
ﺩ.ﺇ2,938 per night
Villa in Les Terres Basses
ﺩ.ﺇ2,622 per night
Home in Marathon
100' Dockage, Pool, Kayaks, Paddle Board, Bikes!
ﺩ.ﺇ2,020 per night
Villa in Isabela
🌴Isabela Retreat Over looking Golf Course & Ocean
ﺩ.ﺇ2,974 per night
Home in Las Terrenas
Amazing sea view luxury modern, fully staffed
ﺩ.ﺇ2,188 per night
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
ﺩ.ﺇ2,510 per night
Villa in Galina
*Luxury Rental* The Palms at Galina
ﺩ.ﺇ2,847 per night
Villa in Soufriere, Saint Lucia
Beautiful villa. CHEF, Housekeeper services.
ﺩ.ﺇ2,624 per night
Villa in Les Terres Basses
Terrasse De Mer
ﺩ.ﺇ3,515 per night
Home in Hallandale Beach
Luxury Home on The Water 5BD
ﺩ.ﺇ2,992 per night
Villa in Playa Sardinas I
Melones Reserve Villa w/ Stunning Ocean View
ﺩ.ﺇ3,619 per night
Villa in Miami
Brand new Villa for 14 ! Pool / PING PONG
ﺩ.ﺇ3,594 per night

Caribbean beach vacation rentals

Cabin in Culebra
Flamenco Toe - Glamping
ﺩ.ﺇ1,561 per night
Cabin in Bluefields
Cozy Oceanview Cabin
ﺩ.ﺇ336 per night
Condo in Montego Bay
Jus' Beachy! Luxury Apt in a B/front Gated Cmnty.
ﺩ.ﺇ697 per night
Villa in Philipsburg
Villa Dream View Belair Sint Maarten SXM
ﺩ.ﺇ1,451 per night
Place to stay in Quebradillas
Shalom on the Cliff (Black) Luxury Suite
ﺩ.ﺇ1,653 per night
Dome in Guayabos
Unique Dome with hot tub, bbq, jacuzzi, near beach
ﺩ.ﺇ1,061 per night
Rental unit in Miami
ﺩ.ﺇ774 per night
Home in Borinquen
The Nest at Crash Boat. Only waterfront on Beach
ﺩ.ﺇ1,075 per night
Home in Isabela
Oceanfront Hideaway Main Floor
ﺩ.ﺇ604 per night
Serviced apartment in Puerto Plata
Beachfront Condo, Steps from the Sand
ﺩ.ﺇ694 per night
Serviced apartment in Playa Juan Dolio
Costa del Sol, spectacular, seafront and beachfront
ﺩ.ﺇ551 per night
Condo in Venice
Vintage Villa, Thirty-Five
ﺩ.ﺇ739 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.