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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.

Cottage · Central Eleuthera
Bird of Paradise, Golden Chalice
Located on the tinted pink sand of Bird Point Beach, only a few steps away from the famous Tippy's Restaurant, "Bird of Paradise Beachfront Cottages" are the perfect getaway. The "Golden Chalice" is modern and unique with all the comforts of home. Beachfront deck, private pool, direct beach access, free WiFi, and time standing still are what you'll find here.
Aug 28 – Sep 4
$453 per night
Villa · 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!
Dec 7 – 14
$350 per night
Home · Grand Cayman
Pools of the Kai #3 by Grand Cayman Villas
May 15 – 22
$420 per night

Vacation rentals for every style

Get the amount of space that is right for you

  • Houses
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Caribbean beach vacation rentals

Home · North Side
Ocean's Edge: Beachfront Home with Rooftop Views
Jul 25 – Aug 1
$550 per night
Home · Stake Bay
Modern Oceanfront, 2Primary Suites, sleeps 6, pool
Sep 29 – Oct 6
$375 per night
Villa · Treasure Beach
Villa Elia~Private Seafront Tropical Paradise
Aug 11 – 18
$800 per night
Home · Placida
Camp GoodNow: Stunning new beachfront home, privat
Dec 2 – 9
$448 per night
Home · Grand Cayman
Kai Tana by Grand Cayman Villas
Sep 21 – 28
$442 per night
Cottage · Tortola
BVI Village - available for Christmas 2022!
May 12 – 19
$486 per night
Bungalow · Freeport
Stunning House right on the beach!
Sep 16 – 23
$270 per night
Villa · Friis Bay
Siempre Azul | Walkable Beach Access
Oct 16 – 23
$440 per night
Hotel room · Rincon
Tres Sirenas Boutique Hotel Oceanfront Suite
Jan 8 – 15
$517 per night
Apartment · Isabela
Villa Shacks 2 bedroom-Unit 1
Oct 18 – 25
$285 per night
Apartment · Montego Bay
Oceanfront Apt w/ Beach Access, Pool, & Gym (2F)
Feb 17 – 24
$209 per night
Hut · Bavaro
Rekindle a Romance in a Retro Thatched Hut on the Beach
May 22 – 29
$225 per night

Caribbean house rentals

Home · Las Terrenas
Amazing sea view luxury modern, fully staffed
Sep 12 – 19
$660 per night
Home · Fort Lauderdale
★Near Downtown & Beach- Luxury House /Heated spa★
Dec 17 – 24
$697 per night
Home · San Cayetano de Venecia
Quinta La Ceiba Modern Home with Pool in DairyFarm
Apr 21 – 28
$177 per night
Home · Cape Coral
Completely Remodeled 3 Bedroom Home With A Pool
Nov 22 – 29
$175 per night
Home · Cartagena
Super Luxury 7 Bedroom House in the Old City
Aug 27 – Sep 3
$854 per night
Home · Aguadilla Pueblo
Ta-Vera Oasis
Jun 5 – 12
$205 per night
Home · Guayama
Vikings style completely private, for couples.
Sep 13 – 20
$130 per night
Home · Tower Isle
𝐄𝐧𝐭𝐢𝐫𝐞 𝐯𝐢𝐥𝐥𝐚 𝐰/𝐜𝐡𝐞𝐟 &𝐝𝐫𝐢𝐯𝐞𝐫
May 22 – 29
$500 per night
Home · Port Charlotte
Book Today to Escape + Relax! 3 Bdrm, Pool + Lanai
Jan 18 – 25
$234 per night
Home · La Caña
Modern house with pool and jacuzzi in Playa Nueva Romana with fast internet
Feb 24 – Mar 3
$273 per night
Home · Siesta Key
Beachfront Getaway in Siesta Key
Jun 16 – 23
$285 per night
Home · Hollywood
Private jungle hideaway w/pool-close to beach!
Mar 28 – Apr 4
$455 per night

Caribbean luxury vacation rentals

Villa · Les Terres Basses
Jul 19 – 26
$714 per night
Villa · Terres Basses
Just in Paradise
Sep 27 – Oct 4
$943 per night
Villa · Silly Creek
Villa Sublime
May 22 – 29
$900 per night
Villa · Terres-Basses
Jul 25 – Aug 1
$820 per night
Villa · Les Terres-Basses
La Hacienda
Aug 26 – Sep 2
$743 per night
Villa · Weston
Marsh Mellow
Sep 16 – 23
$965 per night
Villa · Deve
La Magnifica
May 12 – 19
$629 per night
Villa · Les Terres-Basses
Sol e Luna
Sep 22 – 29
$643 per night
Villa · Les Terres-Basses
Nid d'Amour
Aug 22 – 29
$686 per night
Villa · Windward Road
Villa Equinox
Jul 8 – 15
$950 per night
Villa · Nassau
Turtle Reef Villa
Sep 11 – 18
$695 per night
Villa · Rum Point
Sep 28 – Oct 5
$950 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.