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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
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, 187 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 serene private pool area is seen, featuring clear turquoise water surrounded by a natural stone terrace. Shaded seating areas, including a thatched-roof gazebo, are positioned nearby, set against a backdrop of soft clouds and bright blue skies.
Apartment in Oranjestad
4.99 out of 5 average rating, 127 reviews

Dream Modern King Apt W/ Private Pool & King Bed

Everything you desire and beyond for your perfect tropical vacation. ✔ Private pool / Apartment (private entrance) in a safe villa neighbourhood ✔ Spacious patio with shaded outdoor seating/Palapa ✔ Free WiFi & Parking ✔ King bed & pillows /new mattress for ultimate comfort for your vacation ✔ Caribbean with clean Modern Decor ✔ Beach chairs & Cooler ✔ Fully equipped kitchen (with dishwasher) ✔ A/C & Hot water ✔ Beautiful night lighting in Patio/pool area for the ultimate relaxation.

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, 109 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 private porch overlooks the tranquil harbor, featuring blue chairs beside a white railing. A boat is secured at the dock, with sailboats moored in the distance. Bright sunlight reflects off the water's surface, creating a serene atmosphere.
Vacation home in Key Largo
4.99 out of 5 average rating, 234 reviews

Waterfront, GROUND LEVEL, Awesome Sunsets!!!

This ground level unique location is close to everything. Walk to some of the most iconic restaurants and bars Key Largo has to offer for fresh seafood and awesome drinks! We Do Not allow fishing on our Property! Dockage Available for additional fee! Enjoy the amazing sunsets over the water from your private porch and dock. John Pennekamp Coral Reef State Park close by. Walk to dolphin research center!! 28 day rental I am a licensed charter boat captain and offer discounts for all guests

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, 203 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, 102 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,

Top guest favorite
The image showcases an aerial view of the Eco-friendly Airstream RV surrounded by a lush cactus landscape, with a deck and a private saltwater pool. The Caribbean Sea is visible in the background, emphasizing the tranquil natural setting.
Home in Paradera
5 out of 5 average rating, 208 reviews

Airstream With Pool, Amazing Ocean & Nature Views

This beautifully appointed Eco friendly 30' Feet Flying Cloud RV is the only luxury Airstream glamping experience in the Caribbean. Located in peaceful nature on the North Coast of Aruba, featuring a private, deep saltwater pool and amazing cacti and ocean views. Exceptional service with attention to detail prioritizing sustainability. Connecting guests to unique local experiences and products, creating a truly one of a kind vacation. Looking for the coolest stay in Aruba? This is it!

Top guest favorite
A panoramic view captures Coral Bay, framed by lush green hills and dotted with moored boats. The serene blue waters reflect the sky, showcasing a backdrop of soft white clouds. The picturesque landscape highlights the natural beauty of St. John.
Cottage in Saint John
4.98 out of 5 average rating, 103 reviews

Bon Bini -Solar Power w/ Battery Back-Up & Hot Tub

Tucked high on Sea Grape Hill, Bon Bini Cottage is a peaceful retreat overlooking beautiful Coral Bay, St. John. The cottage boasts picturesque views, convenience to the town of Coral Bay and nearby beaches, and all of the amenities of home. KEY FEAUTRES --- One bedroom, one and a half bathroom home with air conditioning Washer/Dryer Full-sized kitchen StarLink Internet Hot Tub Stand-up paddleboards, floats, beach chairs, beach coolers with ice packs, & beach towels all provided

Top guest favorite
A spacious sleeping area features a handcrafted wooden bed topped with floral bedding, complemented by sheer mosquito nets. Natural light filters through wooden slats, illuminating a soft rug on the floor. A small reading chair is positioned nearby, enhancing the cozy ambiance of the cottage.
Cabin in Portsmouth
4.99 out of 5 average rating, 254 reviews

HIDEAWAYS-FouFou Cottage Open-air Paradise Seaview

"FouFou Cottage" Seen as "10 Most Affordable Caribbean Destinations" & Safe in Nature CERTIFIED. Sustainably handcrafted, private, self-contained treehouse-style cottage with spacious verandah perfect for birdwatching & relaxing. A natural sanctuary with breathtaking seaviews & cool mountain breezes. A unique, 2 level Open Air, Eco-cottage with Modern Ensuite Bath & Kitchenette. Quiet & Conveniently located less than a mile to sites, restaurants, shops & beaches of Portsmouth.

Top guest favorite
A serene outdoor area is illuminated at night with colorful lights reflecting in a resort-sized pool. Chic palapas are situated nearby, surrounded by palm trees. The vibrant atmosphere is enhanced by strategically placed plants and flowers along the edges.
Home in Palm Beach
5 out of 5 average rating, 242 reviews

Aruba Private Resort. Its All Yours and Only Yours

Welcome to Casa Carmela. Relax in the resort sized pool and outdoor oasis. Melt the day away under the exotic palapas or toast your buns in the sun. Whatever your pleasure, Casa Carmella aims to please. She’s a short walk to Palm Beach one of the top rated beaches in the world. Restaurants, casinos and nightlife are walkable as well. She comes with a comfy king size bed, gas grill, fully equipped kitchen, beach chairs & beach towels and cooler. This is all yours and only yours.

Top guest favorite
A spacious wooden deck features two light blue lounge chairs and a white umbrella, offering a relaxing spot to enjoy ocean views. The gentle waves of the Atlantic can be seen in the background, while the shore is lined with natural sand and small rocks.
Condo in Key West
4.97 out of 5 average rating, 111 reviews

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

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