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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.

SUPERHOST
  1. Entire loft
  2. Heredia
Alianz Loft

Insta @ alianzloft. 20 minutes from San Jose airport. First loft built by Alianz.cr. It contains a decked terrace, jacuzzi, firepit, rabbits garden, two rooms, two balconies, entrance gate, private garden, private parking, BBQ area, AC in each bedroom, basketball court, luxury beds, and mountain views. Ideal for architecture lovers, romantic dates, or having a good time. It is a unique space of his kind. Only pets that do not harm rabbits are allowed.

$315 per night
SUPERHOST
  1. Entire home
  2. Sosua
Casa Cascada - Check out my other listing!

Ultimate 3 bed, 4 bath Vacation Luxury Villa. This house has all the amenities and built for entertaining with TV in every room. Pool Table, Privacy, 24hr security with a beautiful infinity pool & plunge pool with views. If you want an amazing experience this house has it! NO hidden fees, NO cleaning fees, Only 3 minutes to beautiful Sosua Beach, international restaurants and bars, 5 minutes to POP airport and 15 mins to Playa Dorado golf course. This is the best location on the north coast!

$279 per night
SUPERHOST
  1. Entire guest suite
  2. San Juan
Treehouse w floating deck at La Botanica

Treehouse at La Botanica Hotel + Wellness Center: labotanicahotel.com. You can also find us on IG @ casabotanica_ayurveda, this magical urban oasis has been built in the style of a treehouse, with cream aged wood, polished cement floors, high ceiling, skylights that eye level the magnificent trees in the luscious garden and floating deck with outdoor shower. I also serve a lovely breakfast and yoga in the garden and We have a local store and pop up farm to table dinners Check out our spa!

$188 per night

Vacation rentals for every style

Get the amount of space that is right for you

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Caribbean beach vacation rentals

SUPERHOST
  1. Entire villa
  2. Treasure Beach
Villa Elia~Private Seafront Tropical Paradise
$729 per night
SUPERHOST
  1. Entire cottage
  2. Grand Cayman
Kai Tana: Cozy Cottage on Private Beach w/Pristine Snorkeling Near Rum Point
$442 per night
SUPERHOST
  1. Entire condo
  2. Montego Bay
Jus' Beachy! Luxury Apt in a B/front Gated Cmnty.
$169 per night
SUPERHOST
  1. Entire rental unit
  2. Montego Bay
Oceanfront Apt w/ Beach Access, Pool, & Gym (2F)
$195 per night
  1. Entire rental unit
  2. Cartagena
26th Floor Spectacular 1 Bedroom Apt in Bocagrande
$73 per night
  1. Entire home
  2. Aguadilla Pueblo
Ta-Vera Oasis
$163 per night
SUPERHOST
  1. Entire villa
  2. Vieques
Stunning Eco-Luxury Villa on Caribbean Sea
$1,325 per night
LUXE
Professionally inspected
  1. Entire villa
  2. Montego Bay
Calypso Shores
$950 per night
SUPERHOST
  1. Entire villa
  2. Lowlands
NEW STUNNING VILLA, VILLA SONRISA, BEACHFRONT_OCEAN VIEW
$436 per night
SUPERHOST
  1. Entire condo
  2. Siesta Key
Siesta Key SunBum Studio; ON THE BEACH
$249 per night
SUPERHOST
  1. Private room
  2. La Habana
Casa Blanca B&B with beautiful terrace &sea views
$29 per night
  1. Entire villa
  2. Providenciales
Closest villa to the ocean on island!
$485 per night

Caribbean house rentals

SUPERHOST
  1. Entire home
  2. Key West
Blu on White - Work or Home School from Paradise!
$432 per night
  1. Entire home
  2. North Side
Ocean's Edge: Beachfront Home with Rooftop Views
$560 per night
SUPERHOST
  1. Entire home
  2. Fort Lauderdale
★Near Downtown & Beach- Luxury House /Heated spa★
$485 per night
  1. Entire home
  2. Marathon
Gulf-Front Retreat with Private Heated Pool, Hot Tub, Boat Ramp & New Dock
$857 per night
SUPERHOST
  1. Entire home
  2. Grand Cayman
Lone Palm: Oceanfront Pool, 2 Free Kayaks, & Wide Beachfront
$784 per night
  1. Entire home
  2. Placida
Camp GoodNow: Beachfront on a tropical island!
$470 per night
LUXE
  1. Entire home
  2. Harbour Island
Sea Siren
$5,500 per night
  1. Entire home
  2. Captiva
Manatee Haven - Upscale Beach View Home with Screened-in Pool, Spa and Elevator!
$600 per night
SUPERHOST
  1. Entire home
  2. Miami
ULTRA LUXURIOUS VILLA 4/3 LARGE POOL PFCT GETAWAY
$600 per night
SUPERHOST
  1. Entire home
  2. Tower Isle
Tranquil Times Villa Jamaica
$451 per night
SUPERHOST
  1. Entire home
  2. Guayama
Completely private, for couples.
$107 per night
SUPERHOST
  1. Entire home
  2. Cartagena
Super Luxury 7 Bedroom House in the Old City
$763 per night

Caribbean luxury vacation rentals

LUXE
  1. Entire villa
  2. The Bight
Villa Islander · Tropical Brutalist architecture near the beach
$3,150 per night
LUXE
Professionally inspected
  1. Entire villa
  2. Cabrera
Casa Kimball
$3,429 per night
LUXE
  1. Entire villa
  2. Montego Freeport
Afimi · Fully-staffed beach house on quiet lagoon
$2,358 per night
LUXE
Professionally inspected
  1. Entire villa
  2. Chalk Sounds
Alinna Villa · Tropical modern villa near Taylor Bay Beach
$1,749 per night
LUXE
  1. Entire villa
  2. Punta Cana
Villa Rosana · Minimalist resort villa near golf and the beach
$1,786 per night
LUXE
Professionally inspected
  1. Entire villa
  2. Grace Bay
Beach Kandi · Neomodernist villa on Grace Bay Beach
$1,749 per night
LUXE
  1. Entire villa
  2. Leeward Settlement
Sugar Apple
$1,300 per night
LUXE
Professionally inspected
  1. Entire villa
  2. Providenciales
Pearl West · Contemporary architecture on Long Bay
$7,700 per night
LUXE
  1. Entire villa
  2. Ocean Drive
Balinese · Modern Ocean Drive villa above the sea
$1,157 per night
LUXE
Professionally inspected
  1. Entire villa
  2. Les Terres Basses
Bamboo
$714 per night
LUXE
  1. Entire villa
  2. Lockrum
Champagne Shores · Contemporary oceanfront villa
$1,700 per night
LUXE
  1. Entire villa
  2. Montego Bay
Seaside Cottage
$3,572 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.


How do I get around Caribbean?

Most of the capital cities in the Caribbean have airports that receive direct flights from the United States, while islands further afield and smaller cities are serviced through connecting flights from Florida. For those wanting to island hop, regional Caribbean airlines will easily take you where you want to go – but if the thought of traveling by prop plane makes you uncomfortable, consider creating your itinerary via ferry. Public boats aren’t always frequent and plentiful, so it may take some planning.

If you’re set on exploring many islands, a combination of flights and ferries is your best bet. Hiring a private boat or yacht to take you between ports is also an option. Taxis are relatively easy to find on the islands. Local buses can be a good alternative and a great way to experience local life, but depending on the island, schedules and information can be ample or limited, so do some research before deciding on your travel routes.


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.