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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.

Home in La Fortuna
Mayoli House Private Pool with Volcano View
Enjoy our little slice of paradise during your vacation to La Fortuna! Whether you’re exploring the surrounding rainforest and Arenal volcano long-term or just passing through, this house provides a comfortable, luxurious experience for couples, large families and groups of friends. The house is located a short 15 minute drive from downtown La Fortuna and sits in the countryside in a quaint, friendly neighborhood. It is surrounded by pasture and hosts incredible views of the Arenal Volcano.
$200 per night
Bus in Tierras Morenas
Sunset view BUS, unique stay, 5min to lake Arenal
Ideal for travelers that are looking for something unique! We converted an old bus to a great experience bringing mini apartment with a view. Bus is located next to our wood shop but we installed a good insulation to make sure you would't hear us working. You will have a complete privacy since all the windows are facing a nice valley of fields and sometimes cows. We made sure you could work remotely too, WIFI is fast. We offer self served breakfast! Follow us on IG: santos_skoolie
$116 per night
Private room in La Habana
Casa Colonial Fauria(Room 3)
Our house adjoins the Café-Bar Madrigal. Just 100 meters away is the axis of Avenida Paseo, which connects the Plaza de la Revolución with the Malecón Habanero. You will love my place due to the cozy space, location ,ventilation, features of the neo-colony, the early decades of the 20th century,with high struts. My accommodation is good for couples,friends and business travelers. The house is located in a quiet neighborhood called Vedado,with several manifestations of architecture.
$26 per night

Private Caribbean vacation rentals

Villa in Cul-de-Sac
$1,000 per night
Loft in San Roque de Barva
Alianz Loft @ Nebulae
$318 per night
Villa in Collectivité de Saint-Martin
Villa Karukera - Hope Hill - Baie Orientale
$885 per night
Home in North Side
Ocean's Edge: Beachfront Home with Rooftop Views
$334 per night

Caribbean home rentals

Home in Key West
Family Perfect - Home with Pool and Chef's Kitchen
$180 per night
Home in Marathon
100' Dockage, Pool, Kayaks, Paddle Board, Bikes!
$475 per night
Home in Hartswell
Sunset Cove
$325 per night
Home in Frederiksted
Turtle Cove
$330 per night

Caribbean condo rentals

Condo in Montego Bay
Jus' Beachy! Luxury Apt in a B/front Gated Cmnty.
$189 per night
Condo in Collectivity of Saint Martin
Holidays in the Paradise on the Beach
$153 per night
Condo in Rum Point
Starfish Paradise Beachfront Condo
$280 per night
Condo in Tower Isle
SerenitybytheSea Sea Palms O/view sleeps up to 6
$218 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.

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.

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.