Resort vacation rentals in Caribbean

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Top-rated resort rentals in Caribbean

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

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Guest favorite

A private terrace features a round table with mosaic detailing, accompanied by two chairs. Clear ocean views extend across the water, framed by lush greenery and distant hills under a bright blue sky with scattered clouds.

Resort in East End

4.88 out of 5 average rating, 296 reviews

Point Pleasant USVI - Villa Sea Song - Waterfront

Built elevated above the tropical landscape in a glorious oceanfront setting, VILLA SEA SONG combines the finest in Caribbean style with an exquisite Balinese interior theme. This is a newly renovated private resort villa with Amazing Views overlooking Pineapple Beach, St. John, and the British Virgin Islands. Steps from the beach, its surrounded by spectacular ocean vistas and cooled by constant trade winds. If this villa is booked, don't worry! I also have other villas that may be available.

Top guest favorite

A spacious balcony features a round wicker table surrounded by two cushioned chairs. The ocean view stretches into the horizon, framed by a clear blue sky and gentle waves lapping against the shore, creating a serene outdoor space for relaxation.

Resort in Hollywood

4.96 out of 5 average rating, 134 reviews

Ocean view luxury condo on 5th FLoor @ LYFE Resort

This ocean front unit offers a breathtaking ocean view with 5-star amenities, fully furnished modern design. Wake up on the bed and see the sunrise through the balcony! 1 bedroom with 1 king size bed, 1 sofa bed in the living room with a 65” Smart TV. For your comfort the king size bed is upgraded with Tempur Ergo power base to help stop snoring, its wave form massage can also help you sleep better. Upgraded Full bathroom with luxury bidet toilet. RESORT FEE: $44/day/Room VALET: $38/day/Car

Guest favorite

A private terrace features a glass table set for two, complete with drinks and plants in the center. The ocean view reveals calm turquoise waters, dotted with boats and surrounded by lush greenery and distant islands under a clear sky.

Resort in East End

4.85 out of 5 average rating, 504 reviews

Point Pleasant - USVI - Villa East - Waterfront

Built elevated above the tropical landscape in a glorious oceanfront setting, VILLA EAST combines the finest in Caribbean style with an exquisite Balinese interior theme. This is a newly renovated private resort villa with amazing views overlooking Pineapple Beach, St. John, and the British Virgin Islands. Steps from the beach, Its surrounded by spectacular ocean vistas and cooled by constant trade winds. If Villa East is booked, don't worry! I also have other villas that may be available.

Guest favorite

A private terrace overlooks sparkling blue waters and distant islands. Comfortable lounge chairs are positioned along the railing, providing a perfect spot to enjoy scenic views of the Caribbean Sea and surrounding tropics.

Resort in East End

4.9 out of 5 average rating, 396 reviews

Point Pleasant - USVI - Villa Bali - Waterfront

VILLA BALI is a private resort villa, built elevated above the tropical landscape in a glorious oceanfront setting, Villa Bali combines the finest in Caribbean style with a Bali Style theme. This is a newly renovated private villa with amazing views overlooking Pineapple Beach, St. John, and the British Virgin Islands. Steps from the beach, Its surrounded by spectacular ocean vistas and cooled by constant trade winds. If Villa Bali is booked I also have other villas available.

Guest favorite

A private terrace features two lounge chairs, overlooking the vibrant turquoise waters. The surrounding landscape includes a view of nearby islands and coastal structures, while the gentle waves create a serene backdrop. The sun creates soft reflections on the water, enhancing the tranquil atmosphere.

Resort in East End

4.91 out of 5 average rating, 302 reviews

Point Pleasant USVI - Villa Salt Life - Waterfront

Built elevated above the tropical landscape in a glorious oceanfront setting VILLA SALT LIFE is a private resort villa, perched perfectly above the water to reveal a breathtaking Panoramic View of the Islands, while still only being a about 2 minutes walk to the Pool, Waterfront Bar, and Beach. The balcony is also extremely private! You will love this place and its Amazing Views! If Villa Salt Life is booked, don't worry! I also have other villas that may be available.

Guest favorite

A serene pool area is featured, with crystal-clear water reflecting the sky. Surrounding the pool, lush greenery and lounge chairs are positioned under large white umbrellas, offering shaded spots for relaxation. The vibrant turquoise ocean is visible in the background, enhancing the tranquil setting.

Resort in Long Bay Hills

4.94 out of 5 average rating, 33 reviews

Serene Studio w/ Beautiful Garden Views

Welcome to H2O life. style. resort, a luxury beachfront boutique resort on Long Bay Beach in Turks & Caicos, known for its crystal-clear waters, soft white sand, and world-class kiteboarding conditions. Enjoy complimentary kayaks, paddleboards, bikes, and a Hobie Cat, along with two pools, hot tubs, and personalized services including grocery provisioning, private chefs, and transportation. A perfect blend of laid-back island living and modern luxury.

Guest favorite

Resort in Road Town

4.96 out of 5 average rating, 48 reviews

Fort Recovery Oceanfront 1BR Premium Villa

Fort Recovery’s premium 1BR oceanfront villa is a spacious corner retreat set just steps from the shoreline. These larger one-bedroom villas feature a private patio or balcony, comfortable living area, full kitchen, separate bedroom, and private bathroom. French doors open to sweeping Caribbean views, with St. John visible in the distance. Available in select ground-level and upstairs layouts, offering space, privacy, and an elevated oceanfront stay.

Top guest favorite

A private terrace with a round table set for two overlooks turquoise waters. Two glasses filled with orange juice and a vase of flowers adorn the table. Stylish black chairs complement the scenic view of sailboats and lush hills in the background.

Resort in East End

4.89 out of 5 average rating, 283 reviews

Point Pleasant USVI - Villa Latitudes - Waterfront

VILLA LATITUDES is a private resort villa, right on the water. This private oceanfront villa hovers right above the waterline, with unobstructed water views of Pineapple Beach, St. John, and the British Virgin Islands. Located within a gated Resort community with all the amenities PLUS Amazing Views, tropical landscape, and ultimate privacy. This is the one! If Villa Latitudes is booked, don't worry! I also have other villas that may be available.

Guest favorite

A clear swimming pool is surrounded by lounge chairs and umbrellas in vibrant colors. Palm trees sway gently in the breeze, with the resort buildings visible in the background. The sun reflects off the water, creating a serene atmosphere.

Resort in East End

4.95 out of 5 average rating, 22 reviews

Island Paradise Studio @ Margaritaville St Thomas

This resort, nestled in a cove fringed by waving palm trees, is a perfect tropical dream-come-true. So grab a beach chair, kick off your flip-flops, sip a tasty boat drink — and let your gaze rest upon an expanse of fine white sand, crystal-clear waters, and St. John island in the distance. Wyndham Margaritaville St Thomas | Studio Balcony Suite • Size: 324 - 324 • Kitchen: Partial • Baths: 1 • Accommodates: 2 Guests • Beds: King Bed

Superhost

A serene beach scene features several beach chairs arranged under thatched umbrellas. Soft sand extends toward calm waters, where gentle waves reflect the warm glow of a setting sun. The backdrop includes palm trees and distant hills, enhancing the tranquil coastal atmosphere.

Resort in VI

4.84 out of 5 average rating, 110 reviews

Beachfront Resort Studio, Pool & Swim Up Bar

This beachside location is nestled in a cove fringed by waving palm trees. It’s the perfect escape for anyone with a sense of adventure looking for music and fun on your next vacation. Or if you’re dreaming of a more laid-back experience — grabbing that beach chair, kicking off your flip-flops, sipping a margarita while looking out onto an expanse of fine white sand, crystal-clear waters and St. John island in the distance.

A private screened-in balcony features a glass table set with breakfast items and a beverage. Two wicker chairs surround the table, while a guest enjoys the ocean view in the background, framed by palm trees and an evening sky.

Resort in Key West

4.9 out of 5 average rating, 10 reviews

Hyatt Windward Pointe Resort: Beachfront Condo

Experience this tropical paradise as you relax in a family friendly timeshare within the Hyatt Residence Club. Have breakfast on the oceanfront balcony followed by a dip in the pool/hot tub or visit the nearby spa. There are 2 bedrooms and 1 sofa bed which can fit 6 people. 2 bathrooms with a spa tub in master bedroom. Fully functioning kitchen and dining area in addition to an in-home washer/dryer unit.

Guest favorite

A two-story townhouse is surrounded by lush palm trees and tropical plants. The facade features a welcoming porch with white railings and bright accents. A parked car is visible in the gravel driveway, set against a clear blue sky.

Resort in Key Largo

4.82 out of 5 average rating, 101 reviews

Coral Townhome

Built as a townhouse-style apartment with two levels, the Coral Townhome includes one bedroom with a king-size bed and a full bathroom, while the downstairs level offers a private bedroom in the back with a full-size mattress bunk bed, a full kitchen, another bathroom, and a living room equipped with a sofa bed. Featuring two bedrooms, these townhouses accommodate up to five guests.