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.
Home in San Cayetano de Venecia, Costa Rica
4.95 out of 5 average rating, 131 reviewsQuinta 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.
Aug 24 – 31
Farm stay in chambacú, Costa Rica
5.0 out of 5 average rating, 130 reviewsGlass Cabin Fortuna/Farm Experience/Private
Welcome to Tres Volcanes, a luxury wood & glass Cabin located within a 56 acres ranch. Strategically built at the highest point of the property, from where you can see the Arenal, Tenorio and Rincón de la Vieja volcanoes on the horizon. You will be able to rest with the sound of the river that passes at the foot of the mountain and wake up to have a cup of coffee while the mist disappears through the treetops. Just in time to walk to the dairy and experience milking by your hands & collect eggs.
Sep 7 – 14
Condo in Miami, Florida, US
4.9 out of 5 average rating, 141 reviewsICON 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 5 – 12
Vacation rentals for every style
Get the amount of space that is right for you
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, US
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, 211 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
Townhouse in Ocho Rios, Jamaica
4.92 out of 5 average rating, 119 reviewsBeautiful vacation home in the heart of Ocho Rios
Feb 25 – Mar 4
Villa in Monteverde, Costa Rica
4.95 out of 5 average rating, 176 reviewsMonteverde Million Dollar View Eco-Villa
Mar 11 – 18
Dome in La Fortuna, Costa Rica
5.0 out of 5 average rating, 130 reviewsMoonlight Glamping Arenal
Sep 10 – 17
Dome in Ponce, Puerto Rico
4.93 out of 5 average rating, 536 reviewsBubble Puerto Rico
Jan 28 – Feb 4
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, US
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, US
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
Home in Fort Lauderdale, Florida, US
4.99 out of 5 average rating, 153 reviewsBeach area chic cabana home/pool/BBQ
Aug 3 – 10
Home in Rincon, Puerto Rico
4.91 out of 5 average rating, 202 reviewsCasa Ensenada- Rincon Puerto Rico
Mar 17 – 24
Home in Fort Lauderdale, Florida, US
4.96 out of 5 average rating, 129 reviewsBamboo House/step 2 beach/Heated Pool/Spa
Aug 14 – 21
Home in North Side, Cayman Islands
5.0 out of 5 average rating, 54 reviewsOcean's Edge: Beachfront Home with Rooftop Views
Oct 27 – Nov 3
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
Cottage in Saint Martin , St. Martin
4.89 out of 5 average rating, 165 reviewsBungalow avec jacuzzi vue lagon
Jul 4 – 11
Cottage in Rainbow Bay, Bahamas
4.95 out of 5 average rating, 119 reviews**NEW LUXE Villa Soreli - 1 B/R Oceanfront w/Pool
Jan 9 – 16
Cottage in El Burrito, Costa Rica
4.91 out of 5 average rating, 156 reviewsSecluded in nature 2 bedroom home near La Fortuna
Jan 31 – Feb 7
Cottage in Cartagena, Colombia
4.87 out of 5 average rating, 156 reviews6-BR House w/Pool & Direct Access to the Beach
Oct 11 – 18
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
- Rentals with a home theater Caribbean
- Rentals with a washer and dryer Caribbean
- Apartment rentals Caribbean
- Vacation home rentals Caribbean
- Houseboat rentals Caribbean
- Monthly Rentals Caribbean
- Guesthouse rentals Caribbean
- Rentals with a patio Caribbean
- Rentals with a fireplace Caribbean
- Rentals with a sauna Caribbean
- Rentals with a balcony Caribbean
- Hotel rentals Caribbean
- Boutique hotel rentals Caribbean
- Rentals with outdoor seating Caribbean
- Island rentals Caribbean
- Bed and breakfasts Caribbean
- Condo rentals Caribbean
- Beachfront rentals Caribbean
- Aparthotel rentals Caribbean
- Bungalow rentals Caribbean
- Townhouse rentals Caribbean
- Kid-friendly rentals Caribbean
- Tiny house rentals Caribbean
- Rentals with breakfast Caribbean
- Cabin rentals Caribbean
- Campsite rentals Caribbean
- Nature eco lodge rentals Caribbean
- Rentals with a hot tub Caribbean
- Rentals with a kayak Caribbean
- Shipping container rentals Caribbean
- Farmstay rentals Caribbean
- Hostel rentals Caribbean
- Rentals with a fire pit Caribbean
- Smoking-friendly rentals Caribbean
- Rentals with an EV charger Caribbean
- Fitness-friendly rentals Caribbean
- Private suite rentals Caribbean
- Boat rentals Caribbean
- Luxury rentals Caribbean
- Rentals with lake access Caribbean
- Rentals with an accessible height toilet Caribbean
- Beach house rentals Caribbean
- Earth house rentals Caribbean
- Rentals with pools Caribbean
- RV rentals Caribbean
- Chalet rentals Caribbean
- Cottage rentals Caribbean
- Resort rentals Caribbean
- Serviced apartment rentals Caribbean
- Rentals with an accessible height bed Caribbean
- Rentals with beach access Caribbean
- Loft rentals Caribbean
- Family-friendly rentals Caribbean
- Wheelchair accessible rentals Caribbean
- House rentals Caribbean
- Villa rentals Caribbean
- Pet-friendly rentals Caribbean
- Tent rentals Caribbean
- Waterfront rentals Caribbean
- Treehouse rentals Caribbean
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom