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Vacation rentals in Caribbean

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Top-rated vacation rentals in Caribbean

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Treehouse in Laborie
4.96 out of 5 average rating, 186 reviews

Driftwood Treehouse • Private Pool • Near Beach

An elevated hideaway in an authentic St Lucian village, Driftwood Treehouse sits just back from Laborie beach with its own private plunge pool, made for easy island living. Driftwood is run by Nick and Ben, your main point of contact throughout. Built largely from local wood, it’s designed for sea breezes and the easy rhythm of island life, with a fully air-conditioned bedroom for cool nights. Guests love its privacy, character and connection to village life — many stay for their entire trip.

Top guest favorite
Home in Whale Point
5 out of 5 average rating, 114 reviews

Lazy Turtle: "Best place we've EVER stayed!"

40 STEPS FROM THE BEACH AT ELEUTHERA'S BEST HIDDEN TREASURE: WHALE POINT 5% DISCOUNT for stays of 7 days or more! The Lazy Turtle is a newly built 2 bedroom, 1.5 bathroom villa with spectacular water views from every aspect. Located on the secluded peninsular of Whale Point, North Eleuthera, Lazy Turtle House is nestled between a pretty lagoon and a turquoise harbor where you will find some of the calmest and clearest water on the planet - sea turtles and reef fish just waiting to say hello.

Top guest favorite
Loft in La Fortuna
4.98 out of 5 average rating, 213 reviews

Natural & Cozy Arenal Getaway

Un hospedaje para escapar de la rutina y conectar con la naturaleza, tiene un diseño moderno con una cálida decoración, rodeado de naturaleza donde podrás observar muchas aves, una linda vista al volcán, balcón, terraza, una refrescante piscina y jacuzzi privado. Un lugar ideal para parejas, amigos o para que puedas teletrabajar tranquilamente. Ubicados estratégicamente cerca de todas las actividades principales y a tan solo 2.5 km del centro de La Fortuna y a 1 km de La catarata La Fortuna.

Top guest favorite
A private hot tub is positioned on a wooden deck, inviting relaxation with views of the lush forest beyond. Situated next to a glamping dome, the spacious interior is visible through large transparent panels, featuring a cozy bed adorned with white bedding.
Dome in Monteverde
5 out of 5 average rating, 418 reviews

Hot Tub | Sunset + Gulf View | Loft Net

*** COMPLIMENTARY WINE BOTTLE WHEN BOOKING 2 NIGHTS OR MORE *** Welcome to Ananta Forest—our beautiful glamping dome in the cloud forest. Relax in the hot tub, loft net or hammock garden where you can enjoy stunning sunset, mountain, and gulf views. Equipped with 2 king size beds, panoramic views, kitchen, bathroom, and high speed internet, you'll have everything you need to create a memorable vacation. 5 min downtown 10 min adventure parks, Santa Elena Reserve 15 min Monteverde Reserve

Top guest favorite
The entrance to the cob round house is adorned with vibrant murals, featuring an eye motif and colorful designs. Natural earth tones are complemented by carved details on the walls. Lush green leaves frame the entrance, adding a touch of nature to the inviting facade.
Earthen home in Utuado
4.96 out of 5 average rating, 103 reviews

Earth Home on Eco Farm w/River

Come experience life in a real cob round house! This is an incredibly special opportunity to stay in a one of a kind home, hand sculpted with clay from our land. The casita has a private adjoining outdoor bathroom with compost toilet and hot shower. We are off grid, all our water comes from our spring and we have solar power. The casita is next to a large, well equipped outdoor kitchen and surrounded by lush nature. Take a hike down to our creek or amazing river with big waterfalls and pools.

Top guest favorite
A private infinity pool is situated on a terrace, overlooking lush greenery and a panoramic ocean view. A vibrant rainbow arcs across the horizon, while gentle waves suggest a tranquil atmosphere. The pool's edge blends seamlessly with the surrounding landscape.
Guesthouse in Saint Thomas
5 out of 5 average rating, 113 reviews

Sunrise Cottage - Secluded, Romantic, Private

Sunrise cottage is located on the cool & breezy north side of St. Thomas. A relaxing 1 bedroom cottage with a full kitchen & living area. You can soak up the sun on the sundeck or hang out in your private soaking pool, while appreciating the breath taking view during the day & the abundance of stars at night. When venturing out you are 20 mins to Magen’s Bay Beach, 15 mins to Town, 30 mins to Red Hook. Note: The hosts live on property with 2 dogs and this cottage is adult only 18 or older.

Top guest favorite
An infinity pool is featured with views of surrounding mountains and lush greenery. Sunlight reflects off the water's surface, creating a serene atmosphere. Chaise lounges are positioned nearby, offering a comfortable space to relax and enjoy the picturesque landscape.
Tiny home in Caonillas Arriba
5 out of 5 average rating, 124 reviews

Sol y Luna Mountain Retreat Hacienda

Enjoy the lovely setting of this romantic spot in nature and discover the serenity in our cozy farmhouse. This private villa wraps you in a lovely and peaceful environment with majestic mountains all around. The house is fully equipped for your convenience. It is ideal for couples in need of a nice getaway or just reconnect with yourself and nature. It is on a gorgeous tropical private 3 acre estate with private pool. Located in Villalba, Puerto Rico, just 50 minutes from Ponce's Airport.

Guest favorite
A wooden deck is surrounded by lush greenery, featuring two comfortable lounge chairs and a small round table. An umbrella provides shade, and natural light filters through the trees, creating a serene outdoor space for relaxation.
Cabin in Minca
4.98 out of 5 average rating, 232 reviews

La Casa Del Mono

Welcome to La Casa Del Mono! We are a unique place :) Enjoy your own incredible wooden house in the middle of the jungle while having access to our incredible private viewpoint (2 min walk) where you can enjoy the most amazing sunsets. You will find binoculars in your house and hopefully you will be able to see the Monkeys, Toucans and many other birds! We are located only 10-15 minutes walk from Minca town, 15 minutes from Pozo Azul waterfalls and 10 minutes from the hidden waterfall.

Top guest favorite
A spacious living area features a plush blue sofa with yellow accent pillows. Large sliding glass doors provide a panoramic view of the valley below, leading to a furnished terrace. Natural light enhances the modern design, complemented by indoor plants and wooden accents.
Home in Escazu
4.99 out of 5 average rating, 302 reviews

KING BED, deluxe stay, @HillView, green areas, A/C

Enjoy this king-bed deluxe apartment, you will find everything needed for an enjoyable stay. It is situated in a prime location yet you will feel away from the city. Close to malls, restaurants, tours, etc. You will be impressed by every beautiful detail handcrafted by Giulio, a passionate architect who loves to create harmonious and inviting spaces. The apartment is bright and cozy, with large windows that let in natural light and offer a breathtaking view of the city and the countryside.

Top guest favorite
A serene outdoor area features a sparkling pool surrounded by lush greenery and tropical plants. A shaded seating area is provided by a large umbrella, along with a cozy hanging chair in the background. The peaceful ambiance is enhanced by bright blue skies.
Guest suite in Luquillo
5 out of 5 average rating, 214 reviews

Casa Encanto Rainforest Retreat

This Guest Suite, on the lower level of our exclusive luxury villa, Casa Encanto, is the perfect tropical getaway. Nestled in the peaceful and lush foothills of the El Yunque Rain Forest, Located in Luquillo with many nearby attractions. You’ll have easy access to downtown Luquillo, El Yunque National Rainforest, Luquillo Beach, Caribali Adventure Park, Las Paylas, charter boat trips, snorkeling, zip lines and much more. The Guest Suite is fully solar with Tesla Batteries and backup water

Top guest favorite
A modern cabin with a large glass facade is nestled among lush green hydrangea gardens. The structure features a sloped roof and is surrounded by trees, providing a serene natural setting. The inviting outdoor area includes a small terrace with seating.
Cabin in Alajuela
5 out of 5 average rating, 131 reviews

Armadillo Cabin at "Encuentro" (Meeting)

Located on the slopes of the Poás Volcano this property is surrounded by trees that create a natural barrier and make you feel immersed in the bird songs and howling wind. Perfect to rest, meditate or charge your body with natural energy. The house sleeps up to four people, great for families and couples. Located at 4km from Poás Volcano National Park. It is close to a variety of restaurants, grocery stores, gas station and souvenir shops. From the SJO Airport, it's a 40-minute drive.

Top guest favorite
Apartment in Simpson Bay
5 out of 5 average rating, 236 reviews

The Beach House Apartment

A stylishly modern one bedroom apartment directly located on the beautiful white sand beach of Simpson Bay. Enjoy the crystal clear waters by day and explore the Caribbean charm of our bustling nightlife. Our island getaway provides you with the full relaxation experience complete with beach chairs, umbrellas, outdoor shower, snorkel gear and paddle boards to complete beach side experience Amenities include free WIFI, kitchen, king size bed, beach chairs, umbrella's and much more

Popular amenities for Caribbean vacation rentals

All about 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.

What are the 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