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Caribbean beach vacation rentals

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Top-rated vacation rentals in Caribbean

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

Hut in Bavaro
Rekindle a Romance in a Retro Thatched Hut on the Beach
We also have another two house very similar next door. Get back to basics in a grass-roofed hut surrounded by palm trees and sand. Spend days sunbathing on a deck, mesmerized by the endless blue horizon. Interior furnishings are mostly locally crafted and perfectly compliment the bohemian off-grid vibe. We personally deliver the house giving extensive information about the area and the house. Varied breakfast is included and you will find it in fridge and wardrobes for you to do it to your liking. Wifi, bicycles, barbecue, beach games, amacas, etc...
$177 per night
Hotel room in Rincon
Tres Sirenas Boutique Hotel Oceanfront Suite
Located in the 5/5 Tripadvisor rated Tres Sirenas Beach B&B, this breakfast included Oceanfront Studio is a beautiful contemporary full apartment boasting direct oceanfront views from both the interior and private balcony area this unit offers. Located on the first level of the villa, this accommodation offers breathtaking ocean views, ideal to enjoy the magnificent Rincon sunsets. Tres Sirenas Beach Hotel is a world renowned B&B situated in front of the beautiful Rincon beach in Puerto Rico.
$365 per night
Villa in Punta Cana
Villa Jazmines & SPA Jacuzzi- Punta Cana Village
Villa Jasmines is a luxury home, decorated with a tropical theme, perfect place for accommodation and pleasant rest in Punta Cana Village. Located in a private community (24 h. security) & walking distance from supermarket, shopping, parks, playground, tennis courts, restaurants and just few min drive from the airport, 5 min drive to the golf course, luxury beach clubs with bars, and Ecological Reserve with natural lagoons. Within 10 min from the famous Coco Bongo Show and Disco!
$266 per night

Caribbean vacation rentals

Dome in La Fortuna
$145 per night
Private room in La Habana
Fauria Colonial House (Room 3)
$29 per night
Cabin in Bluefields
Cozy Oceanview Cabin
$91 per night
Rental unit in Rincon
Private pool Suite & exterior tub @ Casa Florencia
$214 per night
Villa in Philipsburg
Villa Dream View Belair Sint Maarten SXM
$550 per night
Townhouse in Montego Bay
Hospitality Expert NCB1: Pool, Beach, Shops & Chef
$140 per night
Home in Aguadilla Pueblo
Ta-Vera Oasis
$202 per night
Townhouse in Ocho Rios
Beautiful vacation home in the heart of Ocho Rios
$119 per night
Home in Borinquen
The Nest at Crash Boat. Only waterfront on Beach
$303 per night
Rental unit in Atalaya
Garden Apartment II at Ocaso Luxury Villa
$174 per night
Condo in Miami
JUST LISTED! Amazing Miami River&City Views
$365 per night
Rental unit in Rincón
Rincón Beachfront Retreat King Master Private Balcony &pools
$199 per night

Caribbean house rentals

Home in North Side
Ocean's Edge: Beachfront Home with Rooftop Views
$695 per night
Home in Las Terrenas
Amazing sea view luxury modern, fully staffed
$522 per night
Home in Fort Lauderdale
LUX House /Heated Spa- Downtown & Beach
$523 per night
Home in Key West
Grand Home/Heated, Salt Water Pool/Dog Friendly
$434 per night
Home in Grand Cayman
Kai Tana by Grand Cayman Villas
$700 per night
Home in Marathon
100' Dockage, Pool, Kayaks, Paddle Board, Bikes!
$550 per night
Home in San Cayetano de Venecia
Quinta La Ceiba Modern Home with Pool in DairyFarm
$200 per night
Home in Grand Cayman
Pools of the Kai #3 by Grand Cayman Villas
$588 per night
Home in Cape Coral
Completely Remodeled 3 Bedroom Home With A Pool
$178 per night
Home in Lauderdale-by-the-Sea
Heated Pool! Massive Yard+Walk To Beach & Shops!
$646 per night
Home in Cartagena
Super Luxury 7 Bedroom House in the Old City
$945 per night
Home in La Caña
Modern and cozy house in Playa Nueva Romana Golf
$207 per night

Beach house rentals in Caribbean

Home in Siesta Key
Beachfront Getaway in Siesta Key
$414 per night
Home in Bathsheba
Caribbean Chic Beach House on the East Coast
$274 per night
Home in Upper Sugarloaf Key
Pink Beach Paradise
$725 per night
Home in Sugarloaf Key
Palms Resort at Sugarloaf Beach - Green House
$643 per night
Home in St. Thomas
Stunning Water Views
$650 per night
Home in Luquillo
La orilla beach house
$797 per night
Home in Gros Islet
Villa Moringa (we are Covid certified)
$350 per night
Home in Marco Island
Luxury 4 Bedroom House ⭐️ Heated Pool ⭐️ Near Beach
$850 per night
Home in Isabela
Oceanfront Hideaway Main Floor
$161 per night
Home in Río Grande
$875 per night
Home in Cap-Haitien
$170 per night
Home in Isabela
Costa Bonita Beach House /With Solar System
$275 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.