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Caribbean 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.

Guest favorite
Home in San Cayetano de Venecia, Costa Rica
Quinta La Ceiba Modern Home with Pool in DairyFarm
A contemporary roomy vacation home situated in a dairy farm. Embrace serenity, unwind in a tranquil haven surrounded by cows grazing in lush green fields. It's a birdwatcher's paradise too. This is an ideal escape to disconnect and reconnect with nature. Dine and lounge outdoors make the most of the property's features. Our in-house travel concierge will be glad to arrange tours and activities for you at no additional cost. Consider our private chef service for an even more memorable experience.
Jan 10 – 17Individual Host,
€ 187 per night
4.96 out of 5 average rating, 126 reviews
Guest favorite
Condo in Miami, Florida, US
ICON 2B/2B Skyline Free Pool, Spa, HotTub
INSTA READY, This unit provides over 1,350SqFt of breathtaking ocean and city views with Two Bedrooms and Two Bathrooms. Located within the luxurious Icon building. The Icon is a 5 star condominium. It is located inside the heart of Downtown Miami/ Brickell. It includes the same amenities as the W Hotel, such as free access to spa, pool, hot tub, and 4 restaurants, including Cipriani. The apartment comes with three flat screen TVs, HighSpeed WiFi, and toiletries. As well as four separate beds.
Dec 6 – 13
€ 809 per night
4.9 out of 5 average rating, 136 reviews
Guest favorite
Tiny home in Sarasota, Florida, US
@Shellmateisland |tiny home| island| bikes| kayaks
⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)
Jun 5 – 12Individual Host,
€ 228 per night
4.96 out of 5 average rating, 276 reviews

Popular amenities for Caribbean vacation rentals

Private vacation rentals in Caribbean

Guest favorite
Farm stay in chambacú, Costa Rica
Glass Cabin Fortuna/Farm Experience/Private
Jul 13 – 20Individual Host,
€ 198 per night
5.0 out of 5 average rating, 119 reviews
Guest favorite
Condo in Montego Bay, Jamaica
Jus' Beachy! Luxury Apt in a B/front Gated Cmnty.
Sep 30 – Oct 7Individual Host,
€ 215 per night
4.92 out of 5 average rating, 359 reviews
Superhost
Cabin in Poás, Costa Rica
Villa Cola Blanca
Jul 20 – 27Individual Host,
€ 74 per night
4.8 out of 5 average rating, 255 reviews
Guest favorite
Villa in Montego Bay, Jamaica
VIBES COVE enjoy your stay while getting pampered
Sep 9 – 16Individual Host,
€ 698 per night
4.94 out of 5 average rating, 140 reviews
Guest favorite
Apartment in Monteverde, Costa Rica
Suite Camaleón , Monteverde panoramic view.
Jun 5 – 12Individual Host,
€ 481 per night
4.95 out of 5 average rating, 104 reviews
Guest favorite
Home in DO, Dominican Republic
Beautifull Guest House with panoramic views
Feb 23 – Mar 2Professional Host,
€ 300 per night
4.92 out of 5 average rating, 295 reviews
Guest favorite
Villa in Philipsburg, Sint Maarten
Villa Dream View Belair Sint Maarten SXM
Jan 15 – 22Individual Host,
€ 613 per night
4.99 out of 5 average rating, 216 reviews
Guest favorite
Loft in Poás, Costa Rica
Loft & Jacuzzi - Póas - con vista VillaGuadalupe
Apr 1 – 8Individual Host,
€ 81 per night
4.98 out of 5 average rating, 494 reviews
Superhost
Shipping container in Aguada, Puerto Rico
Visum Luxury Container House
Feb 2 – 9
€ 312 per night
4.88 out of 5 average rating, 209 reviews
Guest favorite
Dome in Ponce, Puerto Rico
Bubble Puerto Rico Eternal
Nov 6 – 13Professional Host,
€ 340 per night
4.92 out of 5 average rating, 398 reviews
Guest favorite
Home in Havana, Cuba
Casa Colonial 1922-Entire apartment-DATA internet
Nov 13 – 20Individual Host,
€ 221 per night
4.97 out of 5 average rating, 302 reviews
Guest favorite
Villa in Guayacanes, Dominican Republic
Guayacanes Village- Front beach house
Jul 19 – 26Individual Host,
€ 580 per night
4.9 out of 5 average rating, 120 reviews

Caribbean house rentals

Guest favorite
Home in Borinquen, Puerto Rico
The Nest at Crash Boat. Only waterfront on Beach
Sep 29 – Oct 6Professional Host,
€ 319 per night
4.95 out of 5 average rating, 221 reviews
Guest favorite
Home in Nassau, Bahamas
Sunrise by the Sea - the ocean on your doorstep!
Jul 18 – 25Individual Host,
€ 495 per night
4.94 out of 5 average rating, 140 reviews
Guest favorite
Home in Hollywood, Florida, US
Pool House 3B/2B King Bed EV-Charger Hollywood, FL
Sep 21 – 28Individual Host,
€ 482 per night
4.86 out of 5 average rating, 153 reviews
Guest favorite
Home in Cartagena, Colombia
Cartagena walled casa Mónaco
Nov 16 – 23Individual Host,
€ 883 per night
4.95 out of 5 average rating, 167 reviews
Guest favorite
Home in Naples, Florida, US
Island lifestyle family vacation home (Salt Pool)
Dec 6 – 13Individual Host,
€ 264 per night
4.98 out of 5 average rating, 200 reviews
Guest favorite
Home in Fort Lauderdale, Florida, US
Beach area chic cabana home/pool/BBQ
Aug 5 – 12Individual Host,
€ 357 per night
4.99 out of 5 average rating, 152 reviews
Guest favorite
Home in Punta Rucia, Dominican Republic
Villa Arena - Beach Front
Jan 18 – 25Professional Host,
€ 694 per night
4.99 out of 5 average rating, 139 reviews
Guest favorite
Home in Rincon, Puerto Rico
Casa Ensenada- Rincon Puerto Rico
Sep 27 – Oct 4Individual Host,
€ 498 per night
4.9 out of 5 average rating, 199 reviews
Superhost
Home in Fort Lauderdale, Florida, US
Bamboo House/step 2 beach/Heated Pool/Spa
Oct 2 – 9Individual Host,
€ 600 per night
4.96 out of 5 average rating, 123 reviews
Superhost
Home in Fort Lauderdale, Florida, US
700 Home Private Pool: 2 Bed/1 Bath- Victoria Park
Mar 14 – 21Professional Host,
€ 447 per night
4.78 out of 5 average rating, 184 reviews
Guest favorite
Home in Adjuntas, Puerto Rico
Secluded Coffee Farm House w/Chimney & Heated Pool
Oct 6 – 13Professional Host,
€ 693 per night
4.97 out of 5 average rating, 179 reviews
Guest favorite
Home in Lake Worth, Florida, US
Tropical Beach Villa with Heated Salt Water Pool
May 25 – Jun 1
€ 554 per night
4.97 out of 5 average rating, 147 reviews

Condo rentals in Caribbean

Guest favorite
Condo in Miami, Florida, US
2B/2B w Water View • FREE Parking • Pool • Lux Spa
Aug 16 – 23Individual Host,
€ 522 per night
4.95 out of 5 average rating, 186 reviews
Guest favorite
Condo in Carolina, Puerto Rico
Beach Front Condo with Endless Ocean Views
Jul 31 – Aug 7Individual Host,
€ 412 per night
4.99 out of 5 average rating, 133 reviews
Guest favorite
Condo in Carolina, Puerto Rico
Front & BackyardBeach Studio For 2
Sep 6 – 13Individual Host,
€ 156 per night
4.89 out of 5 average rating, 186 reviews
Superhost
Condo in Miami, Florida, US
Waterfront Spacious Luxury 1 Bedroom IconBrickell
Jul 8 – 15Individual Host,
€ 244 per night
4.79 out of 5 average rating, 151 reviews
Superhost
Condo in Miami, Florida, US
Large Designer Condo, Unique Ocean Views, SmartTVs
Mar 17 – 24Professional Host,
€ 657 per night
4.88 out of 5 average rating, 123 reviews
Superhost
Condo in Carolina, Puerto Rico
Breathtaking Views, Beachfront, Remodeled!
May 29 – Jun 5Professional Host,
€ 600 per night
4.92 out of 5 average rating, 177 reviews
Guest favorite
Condo in Santo Domingo, Dominican Republic
Condominium with private terrace-jacuzzi-parrilla
Jan 21 – 28Individual Host,
€ 54 per night
4.92 out of 5 average rating, 233 reviews
Guest favorite
Condo in Santa Marta, Colombia
An apartment with spectacular ocean views.
Jul 19 – 26Individual Host,
€ 36 per night
4.9 out of 5 average rating, 187 reviews
Superhost
Condo in Santo Domingo, Dominican Republic
Welcoming Studio Surrounded by Beautiful Garden
Jul 24 – 31Individual Host,
€ 72 per night
4.89 out of 5 average rating, 532 reviews
Guest favorite
Condo in Cartagena, Colombia
New apartment overlooking the private sea-Jacuzzi
Jul 21 – 28Individual Host,
€ 75 per night
4.91 out of 5 average rating, 248 reviews
Guest favorite
Condo in Kingston, Jamaica
★Light &Bright 1-bedroom apartment w pool & grill
Oct 18 – 25Individual Host,
€ 120 per night
4.96 out of 5 average rating, 114 reviews
Superhost
Condo in Punta Cana, Dominican Republic
SwimUp Luxury Apt Steps Away From The Beach
Oct 18 – 25Individual Host,
€ 134 per night
4.82 out of 5 average rating, 105 reviews

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.

Destinations to explore