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Vacation rentals in Caribbean

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Top-rated vacation rentals in Caribbean

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

Dome in Orocovis
The LM1 Domescape
Acompáñanos a un lugar mágico e inolvidable en los interiores de nuestra isla, Orocovis PR. Disfruta del encantador entorno de este Domo y todo de lo que ha de ofrecer. A solo minutos de lugares turísticos como lo es Toro Verde, Toro Negro y ciertos rios en donde puedes dar un chapuzon! Además estamos a solo minutos de ciertos restaurantes donde puedes tener un brunch, almuerzo, cena o simplemente pasar a darse un trago o picadera. Estaremos dando uña champaña por visita y agua por la casa!
Individual Host
Cottage in Eleuthera Island Shores
SHOREBREAK ECO COTTAGE
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!
Individual Host
SUPERHOST
Dome in Guayabos
Unique Dome with hot tub, bbq, jacuzzi, near beach
Secret Experience is a sophisticated and cozy Geo Dome treasure, surrounded by nature and with an unmistakable style. Located between a private 4 acres of land away from the hustle and bustle of the city, while being close to the most exquisite restaurants and beaches of the west side (5-10minutes), we are ready to welcome you and your plus one.
SUPERHOST

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Other great vacation rentals in Caribbean

Home in Las Terrenas
Amazing sea view luxury modern, fully staffed
Individual Host
Villa in Punta Cana
Villa Jazmines & SPA Jacuzzi- Punta Cana Village
Individual Host
SUPERHOST
Condo in Montego Bay
Jus' Beachy! Luxury Apt in a B/front Gated Cmnty.
Individual Host
SUPERHOST
Treehouse in Heredia
Cabaña Treehouse Mountain View
Individual Host
SUPERHOST
Rental unit in Rincon
Bohemian Suites Private pool & outdoor tub #7
Professional Host
Tiny home in Rincón
Tree of Life🌿 Private Pool Tiny House in Rincon!!
Individual Host
SUPERHOST
Condo in Collectivity of Saint Martin
Paradise vacation on La Plage
Individual Host
SUPERHOST
Serviced apartment in Punta Cana
Punta Cana Ocean View - Luxury Bavaro Beachfront!
Individual Host
SUPERHOST
Rental unit in Rincon
Private Pool Villa floating bed Bohemian Suites
Professional Host
Private room in La Habana
Casa Blanca B&B with beautiful terrace &sea views
Individual Host
SUPERHOST
Townhouse in Cartagena
Beautiful Designer Loft in the Old City
Individual Host
SUPERHOST
Cabin in San Isidro
Mountain View Cabin
Individual Host
SUPERHOST

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.

Curaçao

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.