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Vacation rentals in Caribbean

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Top-rated vacation rentals in Caribbean

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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, 256 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 welcoming outdoor area features a light-colored floor with a bamboo screen and a wooden door. A hammock chair is suspended near two metal chairs placed around a small table. Lush green plants, including various succulents, surround the seating area, enhancing the tranquil ambiance.
Apartment in San Juan
4.99 out of 5 average rating, 110 reviews

Walk 2Beach+Gated Prkg|Tend a garden/patio+hammock

Escape to our renovated 1-bedroom home in Santurce, San Juan. Steps from Loíza Street’s vibrant restaurants and shops & a 5-minute walk to Ocean Park Beach. Free gated parking provided! Relax in the outdoor area with a hammock chair & garden. Enjoy modern amenities including a queen-sized bed, washer-dryer, fully equipped kitchen & high-speed internet. Explore nearby attractions easily & enjoy tending to our beautiful garden. Perfect for couples or solo travelers. Book now for a memorable stay.

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, 116 reviews

Ícaro: Rooftop Pool!_Private_Modern_Nature

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
An outdoor gazebo is framed by lush greenery and palm trees, overlooking the ocean. Comfortable seating is arranged on the patio, inviting relaxation. Brightly colored flowers and plants surround the area, enhancing the natural ambiance and providing a tranquil setting by the water.
Guest suite in Savaneta
5 out of 5 average rating, 192 reviews

Cabin By the Sea - Ocean Suite

Completely new suite with an oceanfront view. You will be able to experience some of the most beautiful sunsets on the island firsthand! Outside facilities include a gazebo, hammock and dock providing easy access to the ocean, ideal for swimming. Kayaks and snorkeling gear are also available free of charge! Located at a relatively quiet part of the island, known as a prominent fishing area. Some of the best seafood restaurants are located on the same street (Zeerovers and Flying Fishbone).

Top guest favorite
A spacious living area features high vaulted ceilings with wooden beams. A large dining table accommodates guests, surrounded by cozy seating options. Along one wall, an extensive book library is displayed, complemented by vibrant artworks. Soft rugs enhance the inviting atmosphere of the room.
Villa in Charlotte Amalie
4.99 out of 5 average rating, 116 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
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, 110 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, 205 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 serene view of the turquoise ocean stretches beyond a well-maintained pool area. Lush palm trees and vibrant greenery frame the space, with a sandy beach visible nearby. The outdoor seating area is partially shaded, creating a relaxing atmosphere for guests.
Vacation home in Bodden Town
5 out of 5 average rating, 103 reviews

Art Beach House, boutique style luxury.

Private getaway for couples or singles perfect for honeymooners situated at beautiful frank sound. 25 mins from George town so car essential, many attractions nearby include the crystal caves 5 mins botanical gardens and rum point, and the beautiful east end. we also boast some of the the best dining on island. So lots to do or just chill on your private beach away from the crowds. the apartment is situated on ground floor level with art studio/Gallery above. with exclusive use of pool,

Guest favorite
A private pool features a gentle waterfall and is surrounded by lush greenery and colorful tropical plants. The clear blue water reflects the sky, inviting relaxation under the bright sunlight. The pool area is paved with light-colored tiles, enhancing the tranquil ambiance.
Home in Aguadilla
4.99 out of 5 average rating, 273 reviews

Suite with Private Pool

Casa Santiago Apartment #1 is a spacious, cozy, and modern space with a private pool featuring a waterfall that you can enjoy 24 hours a day. The property is equipped with air conditioning throughout, a Smart TV in both the bedroom and living room. Additionally, it boasts a fully equipped kitchen, private parking, and the convenience of being located within a 5 to 10-minute drive from the most beautiful beaches, restaurants, supermarkets, the (BQN) airport, and popular attractions.

Top guest favorite
An infinity pool cascades gently into a lower plunge pool, surrounded by lush greenery. The sparkling water reflects the sunlight, while the shimmering sea is visible in the background, enhancing the serene outdoor setting.
Villa in Treasure Beach
5 out of 5 average rating, 91 reviews

Treasure Beach Oceanfront Sanguine Villa

Sanguine's spacious fully staffed beachfront Villa with an infinity pool is located in Treasure Beach on Jamaica's South Coast. Treasure Beach is where one comes to get away from the hustle and bustle of everyday life and happily ensconce themselves in our laid-back community. Latoya will be here to ensure that you have a holiday of memorable meals, you sit back and relax while we do the grocery shopping and look after you. Message me re airport and transport options

Top guest favorite
Guest suite in Rincón
4.99 out of 5 average rating, 136 reviews

Mar Azul Villa - Tropical Views, Near Beach

Relaxing retreat ideal for couples, located in the heart of the Rincon surfing community. This immaculate studio offers a comfortable king-size bed, coastal décor, and a bright, tranquil interior. Enjoy a private balcony, a spacious terrace, and relaxing hammock with tropical views, plus access to a shared outdoor deck surrounded by lush gardens. Just minutes from world-class surfing, swimming, snorkeling beaches, and beautiful distant ocean and mountain sunsets.

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.

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