Caribbean vacation rentals
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Top-rated vacation rentals in Caribbean
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Vacation rentals for every style
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Popular amenities for Caribbean vacation rentals
Private vacation rentals in Caribbean
Home in CR, Costa Rica
4.86 out of 5 average rating, 138 reviewsCasa Pura Vida
Dec 8 – 15
Loft in Poás, Costa Rica
4.98 out of 5 average rating, 508 reviewsLoft & Jacuzzi - Póas - con vista VillaGuadalupe
May 19 – 26
Home in Sarasota, Florida
4.94 out of 5 average rating, 143 reviewsModern, Bright Downtown SRQ A-Frame West of Trail
Sep 2 – 9
Shipping container in Aguada, Puerto Rico
4.88 out of 5 average rating, 212 reviewsVisum Luxury Container House
Mar 10 – 17
Apartment in San Jose, Costa Rica
4.9 out of 5 average rating, 242 reviewsMountain & City View Experience
May 11 – 18
Home in Havana, Cuba
4.97 out of 5 average rating, 310 reviewsCasa Colonial 1922-Entire apartment-DATA internet
Mar 19 – 26
Villa in Guayacanes, Dominican Republic
4.9 out of 5 average rating, 121 reviewsGuayacanes Village- Front beach house
May 16 – 23
Townhouse in Cartagena, Colombia
4.86 out of 5 average rating, 184 reviewsBeautiful Designer Loft in the Old City
Jan 9 – 16
House rentals in Caribbean
Home in Borinquen, Puerto Rico
4.96 out of 5 average rating, 228 reviewsThe Nest at Crash Boat. Only waterfront on Beach
Mar 22 – 29
Home in Nosara, Costa Rica
4.94 out of 5 average rating, 137 reviewsCasa Lili - Peacefulness & Nature
May 23 – 30
Home in Playa Tivives, Costa Rica
4.97 out of 5 average rating, 184 reviewsLovely beachfront family house with private pool
Oct 26 – Nov 2
Home in Nassau, Bahamas
4.94 out of 5 average rating, 143 reviewsSunrise by the Sea - the ocean on your doorstep!
Nov 11 – 18
Home in Hollywood, Florida
4.86 out of 5 average rating, 153 reviewsPool House 3B/2B King Bed EV-Charger Hollywood, FL
Oct 6 – 13
Home in Cartagena, Colombia
4.95 out of 5 average rating, 168 reviewsCartagena walled casa Mónaco
Aug 3 – 10
Home in Naples, Florida
4.98 out of 5 average rating, 203 reviewsIsland lifestyle family vacation home (Salt Pool)
Oct 7 – 14
Home in Punta Rucia, Dominican Republic
4.99 out of 5 average rating, 140 reviewsVilla Arena - Beach Front
Jun 22 – 29
Cottage rentals in Caribbean
Cottage in Rincón, Puerto Rico
4.93 out of 5 average rating, 336 reviewsCozy, private oceanfront beach house in Rincón
Aug 30 – Sep 6
Cottage in Monteverde, Costa Rica
4.94 out of 5 average rating, 115 reviewsMiramar Cottage - Nestled in the Cloud Forest!
Oct 14 – 21
Cottage in La Romana, Dominican Republic
5.0 out of 5 average rating, 139 reviewsChic Cottage Nature Casa de Campo
Nov 14 – 21
Cottage in Monteverde, Costa Rica
4.97 out of 5 average rating, 146 reviewsVilla 3 - Heated private pool and amazing sunsets
Mar 18 – 25
Cottage in San Isidro, Costa Rica
4.92 out of 5 average rating, 129 reviewsCountry house with panoramic view
Jul 16 – 23
Cottage in Ocho Rios, Jamaica
5.0 out of 5 average rating, 406 reviews"Tumbleweed Cottage"
Jun 10 – 17
Cottage in Montego Bay, Jamaica
4.93 out of 5 average rating, 167 reviewsGlory @ Montego Bay
Dec 25 – Jan 1
Cottage in Atenas, Costa Rica
4.92 out of 5 average rating, 261 reviewsCasa Arazari
Jan 3 – 10
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.
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.
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