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.

Tent in Miramar
Are you ready to be astounded? Perfect for those looking to get off the beaten path and enjoy a once-in-a-lifetime experience, come stay in this magical dome! Nestled in the jungle, you’ll find a tranquil peace you can’t find anywhere else. The incredible panoramic views of the Puntarena and the starry night sky will leave you breathless! ✔ 1 bed (sleeps 2)
 ✔ 1 bathroom w/ shower
 ✔ Fully equipped kitchen
 ✔ Amazing panoramic views 
✔ Pool & hammocks
 ✔ Convenient location near hikes & rivers
G$27,869 GYD per night
Condo in Montego Bay
Jus' Beachy! Luxury Apt in a B/front Gated Cmnty.
This new beach theme apartment is located in 22 Freeport – A gated community in Freeport Montego Bay. 22 Freeport is a beach front complex on a Marina that features 24 hour security, a gym, infinity edge pool and playground; whilst the unit on the ground floor opens onto a cozy back yard space that flows into an open green space. Be sure to check out my 2nd listing in this community "Jus' Beachy Deux" on my profile if your dates are not available here or if you would like to book both units.
G$40,343 GYD per night
Loft in San Roque de Barva
Alianz Loft @ Nebulae
20 minutes from San Jose airport. First loft built by Alianz. It contains a decked terrace, jacuzzi, firepit, rabbits garden, two rooms, two balconies, entrance gate, private garden, private parking, BBQ area, AC in each bedroom, basketball court, luxury beds, and mountain views. Ideal for architecture lovers, romantic dates, or having a good time. It is a unique space of his kind. Only pets that do not harm rabbits are allowed.
G$65,790 GYD per night

Caribbean winter vacation rentals

Hut in Bavaro
Hut #1 Romantic Luxury Beachfront
G$29,284 GYD per night
Tiny home in Rincón
Tree of Life🌿 Private Pool Tiny House in Rincon!!
G$43,064 GYD per night
Dome in Ponce
Bubble Puerto Rico
G$49,863 GYD per night
Guesthouse in Key Largo
Private Cottage, enjoy beach, sunsets & fishing.
G$42,036 GYD per night
Tiny home in Aguada
Container with Private Pool-Couple Retreat
G$35,962 GYD per night
Home in Siesta Key
Beachfront Getaway in Siesta Key
G$61,498 GYD per night
Cottage in Rincón
Cozy, private oceanfront beach house in Rincón
G$46,631 GYD per night
Serviced apartment in Playa Juan Dolio
Costa del Sol, spectacular, seafront and beachfront
G$31,732 GYD per night
Loft in Rio Grande
Modern Loft Style Apt w/ Beautiful View w/ Pool
G$23,995 GYD per night
Villa in Río Grande
Villa Morivivi / Beach Front
G$95,679 GYD per night
Cottage in Cockleshell Bay
Coconut Farm Cottage - Cockleshell Beach St Kitts
G$41,913 GYD per night
Condo in Venice
Vintage Villa, Thirty-Five
G$42,247 GYD per night

Caribbean luxury vacation rentals

Villa in Cul-de-Sac
G$211,543 GYD per night
Villa in Treasure Beach
Villa Elia~Private Seafront Tropical Paradise
G$169,235 GYD per night
Villa in Les Terres Basses
G$151,042 GYD per night
Villa in Isabela
🌴Isabela Retreat Over looking Golf Course & Ocean
G$166,153 GYD per night
Villa in Leeward Settlement
2BR Waterfront Villa- Piccolo Ponte+Sups+Pool+ BBQ
G$117,286 GYD per night
Home in Punta Rucia
Villa Mare - Ocean Front
G$161,590 GYD per night
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
G$144,545 GYD per night
Villa in Galina
*Luxury Rental* The Palms at Galina
G$163,946 GYD per night
Villa in Soufriere, Saint Lucia
Beautiful villa. CHEF, Housekeeper services.
G$151,103 GYD per night
Home in Hallandale Beach
Luxury Home on The Water 5BD
G$174,373 GYD per night
Villa in Playa Sardinas I
Melones Reserve Villa w/ Stunning Ocean View
G$208,461 GYD per night
Villa in Miami
Brand new Villa for 14 ! Pool / PING PONG
G$205,500 GYD per night

Caribbean beach vacation rentals

Place to stay in Quebradillas
Shalom on the Cliff (Black) Luxury Suite
G$95,195 GYD per night
Home in Grand Cayman
Lone Palm by Grand Cayman Villas
G$177,696 GYD per night
Home in Cul-de-Sac
Lodge over the water sea view and private pool
G$43,650 GYD per night
Tiny home in Sarasota
Tiny House Green Lifeguard Stand located 3/4 of a mile from the beach in our Tin
G$32,396 GYD per night
Condo in Hollywood
Awesome 1BR Apartment-Sea View and beach access.
G$37,775 GYD per night
Home in Naples
FAMILY FRIENDLY with CRIB**Heated Pool** Naples!!!
G$42,943 GYD per night
Condo in Naples
Couples Hideaway Short Walk to Beach
G$39,982 GYD per night
Home in Marathon
Off the Hook ~ Modern, Exclusive, Luxury Pool Home
G$207,171 GYD per night
Private room in VI
Beachfront Luxury Resort Studio Condo
G$40,889 GYD per night
Villa in Leeward Settlement
Langley - Caribbean Style Waterfront Villa
G$94,075 GYD per night
Loft in Santa Marta
Apartment Facing the Sea, Santa Marta
G$11,587 GYD per night
Vacation home in Cartagena de Indias
Cartagena Luxurious Resort Condo Radisson
G$14,544 GYD 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.