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Vacation rentals in Caribbean

Book unique homes, vacation rentals, and more on Airbnb

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Popular amenities for Caribbean vacation rentals

Private vacation rentals in Caribbean

Superhost
Home in Naples
4.86 out of 5 average rating, 277 reviews

Charming Keys Style house

LeonardoRating, 5 stars2 weeks ago
Really recommend this place , I live here in naples and have my own place but 6 members from my family were visiting from italy so i needed more space, everything was perfect, location, space,communication with carlos. 10/10 experience!!!
Superhost
Apartment in Sosúa
4.82 out of 5 average rating, 228 reviews

Luxury Apartment 5 min from sosua beach w/jacuzzi

BrianRating, 5 stars2 weeks ago
Francisco was the absolute best host. He was incredibly accommodating with any questions or requests we had but just went above and beyond with recommendations and coordinating things in Sosua. We had the best time. The space was perfect for our family of 3, it was spacious and comfortable. The pool and private jacuzzi were a huge plus. Highly recommend!
Superhost
Home in San Juan
4.92 out of 5 average rating, 131 reviews

Luxury Casa Caliad • Countryside in the City

DevanRating, 5 stars2 weeks ago
Calix, and the beautiful house was everything you need on a vacation in Puerto Rico. Not only was communication very quick and helpful, the location was very private and secure. Cameras, gated and very safe. This house had everything you need to relax, have a good time or just binge movies. Having a pool and pool table was also nice. Outside restroom was a bonus. Owners have taken very good care of this house. I will be back to utilize the property again!
Guest favorite
Guesthouse in Vieques
4.97 out of 5 average rating, 151 reviews

Vieques casita with pool walk to ferry

MikelRating, 5 stars2 months ago
David is a wonderful host very helpful lives on site but you wouldn’t he know they were there. Checked in a couple of times to see if we needed anything. Also directed us to his favorite beach . Close to all the good restaurants. Bakery across the street and Nice market around the corner . Perfect place to stay kinda hip outdoor living space with pool in your area. And AC in bedroom bath area
Guest favorite
Home in PALM BEACH ARUBA
4.81 out of 5 average rating, 172 reviews

NEW ! Contemporary Villa / Jacuzzi , Palm Beach

MarjorieRating, 5 stars1 week ago
We loved the house, we felt like home. Backyard is fantastic, we had breakfast and really enjoyed the privacy. We will recommend and will stay here again, eventually. Host and owner friendly. in one word TOP!
Guest favorite
Villa in Dorado
4.92 out of 5 average rating, 148 reviews

Beach Front (2) Villas in Dorado Beach.

YolandaRating, 5 stars3 weeks ago
We had a wonderful stay at Brenda and Rafael’s beautiful beachfront property. It was the perfect spot for quality time with our adult children and grandchildren. The shared terrace and the incredibly close beach access made our vacation truly special. We also had the pleasure of meeting Brenda and Rafael—such lovely, hospitable hosts. The location is great, with plenty of bars and eateries nearby that stayed open late, which was a nice bonus. Highly recommend this place for a relaxing and memorable family getaway!
Guest favorite
Tiny home in San Sebastián
4.86 out of 5 average rating, 415 reviews

Spectacular view minutes away from the Gozalandia River.

StephanieRating, 5 stars2 weeks ago
If you are looking for a nice romantic getaway, this is your place to This nice cozy home was homie and warm And let’s not talk about the VIEW !!! 😍
Guest favorite
Home in Puerto Viejo de Talamanca
4.93 out of 5 average rating, 135 reviews

Villa Milá - Private Pool - 100 Mbps

IsabelRating, 5 stars1 week ago
This was a great place to stay in Puerto Viejo. The walk into town was less than 2 miles. We didn’t have a car and were fine walking and using taxi services. The house was super nice and clean. The hosts were very responsive, friendly, and helpful. I would recommend this place to anyone looking to travel in this area!!

House rentals in Caribbean

Top guest favorite
Home in Guayama
4.85 out of 5 average rating, 116 reviews

Avi's House (Solar Energy/AC in all house)

ThomasRating, 5 stars2 weeks ago
Great location close to everything fast food, restaurants, mall etc. very quiet neighborhood 👌
Superhost
Home in Sarasota
4.76 out of 5 average rating, 117 reviews

Downtown New Construction House

BenRating, 5 stars2 weeks ago
Stay was great. Really appreciated the location and we had all that we needed, especially in a relatively small space. Maria was responsive to a couple minor concerns that came up beyond her control. The space was in great shape and while on the smaller side, it worked out well for our itinerary.
Guest favorite
Home in Miami
4.89 out of 5 average rating, 114 reviews

Beautiful Quiet Neighborhood

BobbiRating, 5 stars2 weeks ago
My family thoroughly enjoyed our stay at Javier's home. The house was a bit old and very well-kept, so quite charming. The garden was very pretty, and the kitchen had all that we needed to cook in it. Javier & his brother Pablo were very responsive and friendly if we had any questions. The only downside was a couple stray ants in the kitchen & bathroom. We would definitely stay here again!
Guest favorite
Home in CARTAGENA
4.87 out of 5 average rating, 134 reviews

House Encanto, Cartagena 4B/2.5 BTH

AntonioRating, 5 stars1 week ago
One of the best Airbnbs I’ve stayed at so far! The communication with the host was Superb! Will be returning in the future!
Superhost
Home in Fort Lauderdale
4.83 out of 5 average rating, 160 reviews

Large Waterfront House with Pool 4bd/2ba

JaclynRating, 5 stars3 weeks ago
Everything was amazing Hosts were amazing. They truly accommodated us with our early arrival. This house was absolutely immaculate. When you walk in, you can actually smell how clean the entire house is. I saw reviews that others had issues with the construction going on. We had no issues with noise. If you are outside on the pool having a good time, you don’t even know they are there and the house is pretty much sound proof, so you do not hear them while you are inside. I would definitely want to go back. Thank you both for your amazing house
Guest favorite
Home in Arroyo
4.88 out of 5 average rating, 154 reviews

Arroyo Guest House near the Beach

AnitraRating, 5 stars1 month ago
Our family enjoyed our time at Damaris’s place. She was quick to respond and everything was easily accessible. We had to call maintenance for the front door and she immediately responded and got the door knob replaced with friendly maintenance staff. We will definitely stay here again.
Guest favorite
Home in DO
4.89 out of 5 average rating, 184 reviews

Bali a Las Terrenas next to the fishermen's village

CharlotteRating, 5 stars1 week ago
It was a great stay at François's place, very responsive to the questions we asked him. The accommodation is top!! Everything is within walking distance;)
Superhost
Home in Santiago de los Caballeros
4.72 out of 5 average rating, 106 reviews

TIMESHARE ZURZA . WiFi EXCLUSIVE MODERN DESIGN

OnoriaRating, 5 stars2 months ago
The best in the area For a family ❤️

Dog friendly vacation rentals in Caribbean

Guest favorite
Home in Holmes Beach
4.95 out of 5 average rating, 176 reviews

Be an AMI

AlexandraRating, 5 stars2 weeks ago
The best Airbnb we have ever stayed in! Spotlessly clean, close to everything, and just the coziest and most wonderful place! Will definitely stay again
Superhost
Home in Lake Worth Beach
4.81 out of 5 average rating, 16 reviews

Cozy Place next to Beach

JaviaRating, 5 stars2 weeks ago
The house was amazing . The house is Pretty and Miss Rose was very helpful. I definitely will get this house again. The backyard was big and very a vibe.
Superhost
Villa in Sarasota
4.75 out of 5 average rating, 126 reviews

Aloha Villa Pet Friendly 3 miles to Siesta Key #2

AwildaRating, 5 stars1 month ago
I visited Sarasota with my family from the state of Rhode Island from April 4 to April 7 and we stayed at Jason’s & Laura house and it was an amazing experience. The house was very clean and organized. The house is located on a great neighborhood, super safe and great amenities. The house was stocked with beach supplies like beach chairs, beach towels, a boogie board and a beach cooler that was so nice. The house was exactly what we were expecting, I would recommended to everyone. Thank you Josh and laura.
Top guest favorite
Apartment in Naples
5 out of 5 average rating, 11 reviews

Chic-kee bungalow 3

Dylan & KaylinRating, 5 stars1 month ago
I will for sure return to this property. The property is perfect & the owners were great to work with.
Guest favorite
Guesthouse in Sarasota
4.83 out of 5 average rating, 309 reviews

Sarasota Getaway Guest House

CarlosRating, 5 stars1 week ago
Great stay. Close to city center.
Guest favorite
Home in Englewood
4.9 out of 5 average rating, 105 reviews

Tranquil, pet-friendly-yard and 6 mins from beach

KellyRating, 5 stars3 days ago
This was such a relaxing trip for for my husband & I and our dogs! It was close to the beaches & good restaurants! The house was clean & cozy and had a big backyard for the dogs to roam. Jorge was very nice and accommodating.
Guest favorite
Home in Sarasota
4.97 out of 5 average rating, 32 reviews

Retreat in the midst of Sarasota

DebRating, 5 stars3 weeks ago
Barbara's place was great! She left water and blueberry muffins for us! Such a nice touch. Barbara said they live only 2 minutes away, so if we needed anything, to let them know. Well, everything was in such great shape and easy to find, there was no need to contact her at all! We were there for 5 days. The kitchen was stocked with some spices and plenty of cooking pans and utensils. There was also coffee available. It was nice to sit outside in the private yard to enjoy meals and morning coffee with a book. There is also a piano if you want to tickle the ivories! I would definitely stay there again!
Guest favorite
Guest suite in Boca Raton
4.9 out of 5 average rating, 105 reviews

Tropical oasis studio in the heart of Boca Raton

SamRating, 5 stars3 weeks ago
Great stay and exactly what we needed. Close to the beach and brewery. Very clean and the host was available if needed. Would highly recommend if you need a place with two beds. Much more pleasant than the surrounding hotel options.

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