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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.

Guest favorite

Home in San Cayetano de Venecia, Costa Rica

4.95 out of 5 average rating, 131 reviews

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.

Aug 24 – 31

R3,672 ZAR per night
Guest favorite

Farm stay in chambacú, Costa Rica

5.0 out of 5 average rating, 130 reviews

Glass 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

R4,073 ZAR per night
Guest favorite

Condo in Miami, Florida, US

4.9 out of 5 average rating, 141 reviews

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 5 – 12

R14,574 ZAR per night

Popular amenities for Caribbean vacation rentals

Private vacation rentals in Caribbean

Superhost

Home in CR, Costa Rica

4.86 out of 5 average rating, 138 reviews

Casa Pura Vida

Dec 8 – 15

R3,477 ZAR per night
Guest favorite

Loft in Poás, Costa Rica

4.98 out of 5 average rating, 508 reviews

Loft & Jacuzzi - Póas - con vista VillaGuadalupe

May 19 – 26

R1,607 ZAR per night
Guest favorite

Home in Sarasota, Florida, US

4.94 out of 5 average rating, 143 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

Sep 2 – 9

R8,720 ZAR per night
Superhost

Shipping container in Aguada, Puerto Rico

4.88 out of 5 average rating, 211 reviews

Visum Luxury Container House

Mar 10 – 17

R5,830 ZAR per night
Guest favorite

Apartment in San Jose, Costa Rica

4.9 out of 5 average rating, 242 reviews

Mountain & City View Experience

May 11 – 18

R3,028 ZAR per night
Guest favorite

Home in Havana, Cuba

4.97 out of 5 average rating, 310 reviews

Casa Colonial 1922-Entire apartment-DATA internet

Mar 19 – 26

R3,899 ZAR per night
Guest favorite

Villa in Guayacanes, Dominican Republic

4.9 out of 5 average rating, 121 reviews

Guayacanes Village- Front beach house

May 16 – 23

R11,696 ZAR per night
Superhost

Townhouse in Cartagena, Colombia

4.86 out of 5 average rating, 184 reviews

Beautiful Designer Loft in the Old City

Jan 9 – 16

R8,454 ZAR per night
Guest favorite

Townhouse in Ocho Rios, Jamaica

4.92 out of 5 average rating, 119 reviews

Beautiful vacation home in the heart of Ocho Rios

Feb 25 – Mar 4

R2,639 ZAR per night
Superhost

Villa in Monteverde, Costa Rica

4.95 out of 5 average rating, 176 reviews

Monteverde Million Dollar View Eco-Villa

Mar 11 – 18

R10,584 ZAR per night
Guest favorite

Dome in La Fortuna, Costa Rica

5.0 out of 5 average rating, 130 reviews

Moonlight Glamping Arenal

Sep 10 – 17

R2,933 ZAR per night
Superhost

Dome in Ponce, Puerto Rico

4.93 out of 5 average rating, 536 reviews

Bubble Puerto Rico

Jan 28 – Feb 4

R5,408 ZAR per night

House rentals in Caribbean

Guest favorite

Home in Borinquen, Puerto Rico

4.96 out of 5 average rating, 228 reviews

The Nest at Crash Boat. Only waterfront on Beach

Mar 22 – 29

R6,035 ZAR per night
Guest favorite

Home in Nosara, Costa Rica

4.94 out of 5 average rating, 137 reviews

Casa Lili - Peacefulness & Nature

May 23 – 30

R5,035 ZAR per night
Guest favorite

Home in Playa Tivives, Costa Rica

4.97 out of 5 average rating, 184 reviews

Lovely beachfront family house with private pool

Oct 26 – Nov 2

R4,396 ZAR per night
Guest favorite

Home in Nassau, Bahamas

4.94 out of 5 average rating, 143 reviews

Sunrise by the Sea - the ocean on your doorstep!

Nov 11 – 18

R9,683 ZAR per night
Guest favorite

Home in Hollywood, Florida, US

4.86 out of 5 average rating, 153 reviews

Pool House 3B/2B King Bed EV-Charger Hollywood, FL

Oct 6 – 13

R8,223 ZAR per night
Guest favorite

Home in Cartagena, Colombia

4.95 out of 5 average rating, 168 reviews

Cartagena walled casa Mónaco

Aug 3 – 10

R18,014 ZAR per night
Guest favorite

Home in Naples, Florida, US

4.98 out of 5 average rating, 203 reviews

Island lifestyle family vacation home (Salt Pool)

Oct 7 – 14

R3,882 ZAR per night
Guest favorite

Home in Punta Rucia, Dominican Republic

4.99 out of 5 average rating, 140 reviews

Villa Arena - Beach Front

Jun 22 – 29

R14,093 ZAR per night
Guest favorite

Home in Fort Lauderdale, Florida, US

4.99 out of 5 average rating, 153 reviews

Beach area chic cabana home/pool/BBQ

Aug 3 – 10

R5,301 ZAR per night
Guest favorite

Home in Rincon, Puerto Rico

4.91 out of 5 average rating, 202 reviews

Casa Ensenada- Rincon Puerto Rico

Mar 17 – 24

R9,016 ZAR per night
Superhost

Home in Fort Lauderdale, Florida, US

4.96 out of 5 average rating, 129 reviews

Bamboo House/step 2 beach/Heated Pool/Spa

Aug 14 – 21

R9,764 ZAR per night
Guest favorite

Home in North Side, Cayman Islands

5.0 out of 5 average rating, 54 reviews

Ocean's Edge: Beachfront Home with Rooftop Views

Oct 27 – Nov 3

R12,792 ZAR per night

Cottage rentals in Caribbean

Guest favorite

Cottage in Rincón, Puerto Rico

4.93 out of 5 average rating, 336 reviews

Cozy, private oceanfront beach house in Rincón

Aug 30 – Sep 6

R5,182 ZAR per night
Guest favorite

Cottage in Monteverde, Costa Rica

4.94 out of 5 average rating, 115 reviews

Miramar Cottage - Nestled in the Cloud Forest!

Oct 14 – 21

R7,623 ZAR per night
Guest favorite

Cottage in La Romana, Dominican Republic

5.0 out of 5 average rating, 139 reviews

Chic Cottage Nature Casa de Campo

Nov 14 – 21

R6,492 ZAR per night
Guest favorite

Cottage in Monteverde, Costa Rica

4.97 out of 5 average rating, 146 reviews

Villa 3 - Heated private pool and amazing sunsets

Mar 18 – 25

R8,351 ZAR per night
Guest favorite

Cottage in San Isidro, Costa Rica

4.92 out of 5 average rating, 129 reviews

Country house with panoramic view

Jul 16 – 23

R1,258 ZAR per night
Guest favorite

Cottage in Ocho Rios, Jamaica

5.0 out of 5 average rating, 406 reviews

"Tumbleweed Cottage"

Jun 10 – 17

R3,800 ZAR per night
Guest favorite

Cottage in Montego Bay, Jamaica

4.93 out of 5 average rating, 167 reviews

Glory @ Montego Bay

Dec 25 – Jan 1

R5,393 ZAR per night
Superhost

Cottage in Atenas, Costa Rica

4.92 out of 5 average rating, 261 reviews

Casa Arazari

Jan 3 – 10

R2,096 ZAR per night
Guest favorite

Cottage in Saint Martin , St. Martin

4.89 out of 5 average rating, 165 reviews

Bungalow avec jacuzzi vue lagon

Jul 4 – 11

R2,953 ZAR per night
Guest favorite

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

R5,439 ZAR per night
Superhost

Cottage in El Burrito, Costa Rica

4.91 out of 5 average rating, 156 reviews

Secluded in nature 2 bedroom home near La Fortuna

Jan 31 – Feb 7

R2,055 ZAR per night
Superhost

Cottage in Cartagena, Colombia

4.87 out of 5 average rating, 156 reviews

6-BR House w/Pool & Direct Access to the Beach

Oct 11 – 18

R15,593 ZAR 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.


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