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Vacation rentals in Caribbean

Book unique homes, vacation rentals, and more on Airbnb

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Private vacation rentals in Caribbean

Superhost
Home in Naples
4.86 out of 5 average rating, 271 reviews

Charming Keys Style house

Jay Rating, 5 stars3 weeks ago
Our stay was perfect with everything we needed for our stay. The patio out back was perfect for relaxing after a day at the beach. We enjoyed the front porch area as a more private area to relax. Great location.
Superhost
Apartment in Sosua
4.82 out of 5 average rating, 223 reviews

Luxury Apartment 5 min from sosua beach w/jacuzzi

StephenRating, 5 stars1 week ago
Easy to check in, very nice place just how it was described definitely coming back
Top guest favorite
Home in San Juan
4.98 out of 5 average rating, 176 reviews

Urban Beach Hideaway...a luxury family compound!

StevenRating, 5 stars2 weeks ago
This was hands down the nicest Airbnb I have ever stayed at. The photos do not do it justice at all!! Fernando was an amazing host and made the group and I feel right at home for my bachelor party. He was extremely responsive on questions, requests, and issues. 11/10 recommend!!!!
Superhost
Home in San Juan
4.93 out of 5 average rating, 122 reviews

Luxury Casa CA-LI-AD

JordanaRating, 5 stars1 week ago
Great place for our stay in PR! Spotless amenities. Only down side was the location is a bit far from the main attractions in the city and not all ubers accepted our rides, so a rental car is definitely recommended. Host was extremely responsive when we had questions or requests and sent a maintenance person to take care of an unlocked window super quickly! Will be returning!
Guest favorite
Home in Royal Palm Beach
4.9 out of 5 average rating, 209 reviews

POOL, 4 BEDROOMS -SPACIOUS HOUSE IN ROYAL PALM BCH

MaggieRating, 5 stars1 month ago
The pictures don’t do this house justice. It was lovely and felt, looked, and smelled clean. Lots of room for multiple guests and Luz is very responsive. We stayed for 5 nights and would do it again! Best experience I’ve had with Airbnb so far. Thanks Luz!
Guest favorite
Guesthouse in Vieques
4.97 out of 5 average rating, 151 reviews

Vieques casita with pool walk to ferry

MikelRating, 5 stars1 week 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
Superhost
Home in PALM BEACH ARUBA
4.83 out of 5 average rating, 166 reviews

NEW ! Contemporary Villa / Jacuzzi , Palm Beach

StephanieRating, 5 stars5 days ago
Great house in a great location. Never close to all major attractions. The host was amazing. Very nice people. Will come back here again
Guest favorite
Home in Puerto Viejo de Talamanca
4.94 out of 5 average rating, 126 reviews

Villa Milá - Private Pool - 100 Mbps

KatiaRating, 5 stars2 weeks ago
Something I liked about the place was the comfort of the beds and the perfect pillows to rest - being in a jungle environment there were a lot of mosquitoes, so I suggest bringing insecticide and repellent

Caribbean beach vacation rentals

Guest favorite
Condo in Luquillo
4.88 out of 5 average rating, 113 reviews

Amazing Beach View 2 bedrooms Condo

Richard & LouiseRating, 5 stars2 days ago
For anyone considering Melissa’s place, book it now before it gets rented. You will not go wrong with booking this condo. Melissa prides herself on making everything perfect so her place is super clean and has everything you will need for a short or extended stay. This is our second year booking with Melissa and she is indeed a super host. We were here for 5 weeks this time and we wished we could have stayed longer. Melissa’s condo patios have great panoramic views of the ocean. Inside the unit, we had a very comfortable bed, a great complete kitchen with everything that you’ll need and lots of hot water in the shower. This condo is mere steps from the beach which was super handy. Melissa is a great communicator and went above and beyond to make our stay a special one. Thank you for sharing your wonderful place with us Melissa and we hope to be back.
Top guest favorite
Home in San Nicolas
5 out of 5 average rating, 138 reviews

Ocean Front Family Vacation Home, at Baby Beach

ColinRating, 5 stars2 days ago
House was excellent. Very well equipped including, kitchen supplies, pool toys and beach supplies (umbrellas, coolers etc.). House was very clean on arrival and Joost was great. We would not hesitate to return.
Superhost
Home in Isla Verde
4.74 out of 5 average rating, 201 reviews

Luxury Beach House Isla Verde - Full Generator

CarolineRating, 5 stars1 week ago
My friends and I had a wonderful stay at Ricardo’s place — the house was spacious and clean and matched the pictures, but the best thing about this place is that it’s only a 2 minute walk from a beautiful, fairly quiet beach. We also really enjoyed the patio space of this airbnb, and used the space and the outdoor grill to have a cookout one of the nights we stayed here. Ricardo is very friendly, responsive, and quick to help out whenever we had any questions or needed something at the house. We all had a great time here and would definitely stay here again!
Top guest favorite
Home in Naples
4.96 out of 5 average rating, 112 reviews

* * Endless Summer * * Beach, Unique & Comfort

JacobRating, 5 stars2 weeks ago
we were only in town for a night so we didn't have much time to enjoy the home or the area but it served its purpose and was wonderful. Thank you
Guest favorite
Villa in Dorado
4.92 out of 5 average rating, 142 reviews

Beach Front (2) Villas in Dorado Beach.

LoriRating, 5 stars4 weeks ago
We took a group trip of 6 (3 couples) and Brenda's place was perfect. Each couple had their own rooms/space and bathroom. The back patio area connecting the two villas is amazing - perfect for having morning breakfasts and grilling out at night. The beach is clean and directly across the street - you can see and hear the ocean from the back patio area. Plenty of great food/bars within walking distance. The villas are gated properties which made you feel safe, and felt very safe walking around the neighborhood. The properties were clean and just as described/pictured. Brenda was very communicative when we had questions and gave excellent recommendations. If we travel to Puerto Rico again would DEFINITELY stay here again.
Superhost
Apartment in Río Grande
4.9 out of 5 average rating, 122 reviews

Beachfront Luxury @ Wyndham Rio Mar Resort

CatherineRating, 5 stars1 month ago
The condo is located in an ideal spot. Thanks to the trade winds, there is always a breeze. The view is beautiful and the beach is fairly private. We enjoyed the restaurants in the neighboring hotel. As avid hikers, we were thrilled to be so close to El Yunque. We also enjoyed the proximity to Fajardo and the amazing bio luminescent lagoon. The condos in this complex are starting to show their age, but overall, I highly recommend it!
Guest favorite
Condo in Hollywood
4.94 out of 5 average rating, 158 reviews

Charming apartment right on the Beach.

IsmelRating, 5 stars2 weeks ago
Host is very kind and goes above and beyond to satisfy a client.
Guest favorite
Condo in Cabo Rojo
4.91 out of 5 average rating, 301 reviews

Beach front Sandy Villa

MaryRating, 5 stars5 days ago
We had a wonderful stay at Viviana’s. It is exactly as the pictures. The view and sunsets are spectacular. Lots of restaurants and beaches nearby. Great place to stay to explore the southwest part of the island.

Dog friendly vacation rentals in Caribbean

Superhost
Home in Venice
4.78 out of 5 average rating, 130 reviews

South Venice, FL. Ideal vacation home.

KayRating, 5 stars3 days ago
We enjoyed Jan’s house. It was a quiet neighborhood, perfect for walking the dog. Short drive to restaurants, beaches, grocery stores, Shamrock Park, Brohard dog beach, pretty much anything we wanted to do. The lanai was a nice area to sit in the shade. Wish I had a way to post a recording of all the various birds chirping away! Home was clean and Jan was a responsive host with any questions we had. Yard was private and fenced in nicely for our dog. Appreciated having laundry soap, body wash, dish detergent, & paper goods to get through our stay. So often all you get is enough for a few days, if that. Comfortable beds too! We would stay again. Thanks Jan!
Guest favorite
Home in Fort Myers
4.95 out of 5 average rating, 102 reviews

Waterfront Home w/ Pool. Minutes to Sanibel

ParthuRating, 5 stars1 week ago
Great place to spend time with friends and family. Accessible to the places we wanted to visit. Definitely made a ton of memories! Thank you for the amazing stay.
Guest favorite
Guesthouse in Sarasota
4.82 out of 5 average rating, 291 reviews

Sarasota Getaway Guest House

MaryRating, 5 starstoday
Arthur’s place was everything we needed for a weekend stay in Sarasota! The bed was comfortable and the bathroom was clean. It was an easy walk into town with lots to do! Arthur and Julie were very welcoming and helpful our whole stay. Would definitely book again!
Guest favorite
Bungalow in Lake Worth
4.96 out of 5 average rating, 185 reviews

Tropical, 2BR, Dog-Friendly Cottage w/ Plunge Pool

ScottRating, 5 stars1 month ago
Great place. Nice backyard and great to have a reserved parking spot behind the house!
Superhost
Home in Key Colony Beach
4.73 out of 5 average rating, 133 reviews

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach

CherylRating, 5 stars2 months ago
Mary's place was in a very safe and beautiful location. Everyone was friendly and there were endless dining options. There were even local conveniences that I didn't expect nearby such as Dollar Tree, Winn Dixie, Home Depot, etc. Showers had great water pressure, hot water, and had zero sulphur smell. Decor was lovely and ample storage space for your things. A/C and heat works great and no musty smells anywhere. Beds, outdoor furniture and couches very comfortable. Convenient off-street parking. Was too busy to enjoy the cabana amenities but visited it briefly and it looked wonderful. Thank you Mary hope to return in the future!
Guest favorite
Home in Naples
4.94 out of 5 average rating, 110 reviews

Family Coastal Home - 1 Mile from Beach

KJRating, 5 stars1 week ago
The house was exactly as described-great central location in Naples! Very quiet safe neighborhood-walked around it multiple times a day (to 7-11 for coffee too!) It was clean, well decorated and we enjoyed the sunsets and the lanai outdoors. Well stocked for the 2 weeks we were there. My husband and I would definitely go back! Thank you Viktoria
Guest favorite
Home in Fort Myers
4.94 out of 5 average rating, 123 reviews

So Beachy! Pet friendly and free early check-in!

KathleenRating, 5 stars2 months ago
Shawn’s house is very comfortable and pleasant. The furniture is comfortable, the appliances and amenities are excellent.
Guest favorite
Townhouse in Marathon
4.91 out of 5 average rating, 127 reviews

~Coral Lagoon* last minute wknd available! Save$

MichelleRating, 5 stars1 month ago
We stayed at the villa for a long weekend in January for my husband's birthday. It was great. The location was a perfect distance from Key West (~1 hour) and Islamorada (~30-40 minutes). The place was clean, wlecoming and looked just like the photos. Stephanie was a fantastic host. She was super responsive even when I sent her a message a month before asking for a fishing charter recommendation. I would highly recommend staying there.

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