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Vacation rentals in Caribbean

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Top-rated vacation rentals in Caribbean

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Top guest favorite
A spacious deck is furnished with two comfortable chairs and a small table. Lush greenery surrounds the area, providing a serene view. Large glass doors connect the deck to the interior of the cabin, allowing natural light to illuminate the space.
Farm stay in Chambacu
5 out of 5 average rating, 249 reviews

Glass Cabin Fortuna/Free Farm Tour/Cows/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.

Top guest favorite
A stylish studio layout is visible, featuring a cozy bed with layered bedding. A dining area is positioned nearby, encompassing a small circular table and upholstered chairs. A kitchenette with modern appliances completes the space, complemented by art on the walls that adds character.
Villa in Providenciales
5 out of 5 average rating, 32 reviews

Nest at Oceanside PrivatePool OceanView SunSet

Nest is a sweet, cozy, stylish studio villa designed just for two. It has a gorgeous, expansive private OceanView of the Caicos Banks It is walking distance to a stunning peaceful beach Bring your floaties and drift away The sun sets in front of the villa Imagine a sunset dip in the Private Infinity Pool We are close driving distance to all the island’s beautiful beaches and great restaurants on the island Our Oceanside neighbourhood is safe and quiet Nest is private, well located and affordable

Top guest favorite
An aerial view shows a modern structure surrounded by lush greenery. A rectangular salt-water pool is visible, illuminated with varying shades of green. The outdoor space features lounge chairs and ambient lighting, enhancing the secluded, tranquil atmosphere of the surrounding nature.
Villa in La Fortuna
4.99 out of 5 average rating, 107 reviews

Ícaro: Rooftop Pool!_Private_Modern_Natura

Escape to a secluded 1750 sq. ft. industrial-style retreat, nestled in a lush farm just 2 km from La Fortuna's heart. This unique, windowless open-concept haven features a king-sized bed, a queen-sized sofa bed, and a fully equipped kitchen. An air system creates a refreshing breeze throughout the house, complemented by A/C for perfect comfort. Enjoy the rooftop pool with sunbathing, grilling and bar utensils. Explore the nearby creek and savor the tranquility of 32,000 sq. ft. of private land.

Top guest favorite
The spacious living area features high vaulted ceilings, with ample natural light from large windows. A long dining table accommodates multiple guests, while a cozy seating area is arranged for relaxation. A decorative bookshelf filled with various books extends along one wall, enhancing the inviting atmosphere.
Villa in Charlotte Amalie
4.99 out of 5 average rating, 106 reviews

Tropical Modern Loft | SoHo Style | Concierge

Single night bookings welcome! A luxe art loft experience in the heart of St. Thomas, this exclusive space in a convenient central location provides a chic home base, with sleek design, concierge options, + creative vibes. Perfect for both adventure and serenity. Ample space to lounge, with a balanced historic/contemporary aesthetic, and near beaches, restaurants, historic landmarks, boutiques, + ferry/airport/transportation. Private gated parking and a cafe and art gallery right downstairs.

Top guest favorite
A spacious outdoor platform features a curved wooden walkway leading to a dome tent amid lush greenery. Soft beige pillows are placed on a textured mat, inviting relaxation. The large windows of the dome reveal a stylish interior, seamlessly blending with the surrounding jungle.
Dome in Platanillo
5 out of 5 average rating, 225 reviews

Suave Vida Getaway - Jungle Dome

The Suave Vida Dome offers you its openness with a large bay window and skylight surrounded in Costa Rican Nature at its purest. You will feel emerged to the views of the Jungle and valley. Enriched with stylish furniture and decor themed to bring raw elements of nature inside the living area. You will find yourself in tranquility with the sounds of nature and the running stream. The Dome offers an adventurous and a little of a daring experience making it a unique luxurious glamping getaway.

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, 103 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.

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, 200 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 coastal view captures the vibrant turquoise waters of the Caribbean Sea meeting rugged rocky shores. Lush green hills rise in the background, bordered by scattered homes and palm trees under a clear blue sky with wispy clouds.
Villa in Cruz Bay
5 out of 5 average rating, 142 reviews

BLUE VIEW VILLA - Bluest View - Brand New...

Blue View is brand new construction! A classic soft modern Caribbean architecture set on a full acre with sweeping views from sunrise over Ram Head peninsula to sunset over St. Thomas. It is a very special property sited with the utmost care to capture Leeward breezes with an unobstructed view to St. Croix 40mi away. Find the perfect amount of sun or shade you desire at any time during the day. Blue View is a separate villa located adjacent to our main Villa and 6 minutes to Cruz Bay

Top guest favorite
The octagonal structure features a vibrant exterior with a wrap-around porch, surrounded by lush greenery and palm trees. Pathways of stone lead through the well-maintained lawn, providing a warm invitation to explore the outdoor living spaces.
Home in Davie
4.99 out of 5 average rating, 144 reviews

Tropical Octagon Oasis Hideaway Close to Hard Rock

The Octagon Oasis is a perfect getaway in the heart of South Florida. This amazing hand built home is nestled within a bamboo forest, and provides the tranquil escape you have been looking for all while only minutes away from the Hard Rock Hotel, Ft. Lauderdale Beach, and other South Florida offerings. Please DO NOT inquire for hosting gatherings or parties at this location. We do not allow filming. FLL airport- 10 min drive Hard Rock casino- 5 min drive Fort Lauderdale Beach-15 mins

Top guest favorite
A sweeping view captures the vibrant turquoise waters of the coastline, framed by lush green hills. Islands dot the horizon under a clear blue sky, while the wooden railing in the foreground provides a picturesque viewing point of the landscape.
Guesthouse in BL
4.98 out of 5 average rating, 182 reviews

les Ramiers

Spend your holidays at Villa les Ramiers, where the sun is with you from sunrise and throughout the day. The accommodation is independent, not overlooked, with its small kitchen and terrace overlooking the pool, a top-deck to enjoy the sunrise, a large bedroom overlooking the covered patio with lounge area with sea view. Located on the well-ventilated heights with stunning views of Petite Anse. Private parking is located next to the Villa. Welcome!

Top guest favorite
A welcoming entrance is framed by vibrant pink bougainvillea, creating a natural arch over the doorway. The light-colored door stands open, inviting guests into the interior, while petals cover the ground, enhancing the entrance's charm.
Cottage in Spanish Wells
4.97 out of 5 average rating, 146 reviews

Cozy Cay Casita 3 min walk to beach

Live life like a local! Centrally located on Spanish Wells close to the beach, restaurants and grocery store. Cay Casita is an island style tiny house (studio apartment layout) perfect for a mellow and stress free getaway. Multiple amenities included with your stay is use of bicycles, stand up paddle board, gas grill, a well stocked kitchen ,beach stuff, large covered patio space, free Wifi high speed internet and a spacious outdoor shower.

Top guest favorite
An outdoor dining area features a wooden table surrounded by four chairs. Large windows provide a view of lush greenery and the pool area. Soft sunlight filters through trees, creating a warm atmosphere. Decorative items are arranged on the table.
Condo in Playa Santa Teresa
4.99 out of 5 average rating, 231 reviews

Purapura _Jungle House w/ pool, walk to beach

Apartamento JUNGLE HOUSE Precioso alojamiento a nivel de jardín y piscina, con una amplia terraza, en una ubicación inmejorable en Santa Teresa. A distancia a pie de la playa, los mejores restaurantes y tiendas. Nuestro Jungle House dispone de piscina que comparte con otros huéspedes, con vistas al atardecer. Un alojamiento cómodo y céntrico, que te brinda todo lo que necesitas. Solo 300m de la playa Santa Teresa (4 minutos caminando)

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