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Featured Holiday Homes in Caribbean

1120 Vieques by Stay with Bear

1120 Vieques by Stay with Bear

4 out of 5
1120 C. Vieques, San Juan, San Juan
With a stay at 1120 Vieques by Stay with Bear in San Juan (Santurce), you'll be within a 5-minute drive of Condado Beach and Pan American Pier.
1120 Vieques by Stay with Bear
Casa Parcha

Casa Parcha

3.5 out of 5
Carr 191 km 27.9, Naguabo, Naguabo
Located in Naguabo, Casa Parcha is on the riverwalk, within a 15-minute drive of El Yunque National Forest and Malecón de Naguabo.
Casa Parcha
The Beach Pad

The Beach Pad

3 out of 5
Carretera 413 Km. 4.4, Barrio Puntas, Rincon
Located in Rincon, The Beach Pad is a 1-minute drive from Sandy Beach and 6 minutes from Punta Higuero Light.
The Beach Pad
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Isla Verde- Beach/Bar/Restaurants
Near Airport

Isla Verde- Beach/Bar/Restaurants Near Airport

Carolina
With a stay at this vacation home in Carolina (Isla Verde), you'll be a 1-minute drive from Carolina Beach and 8 minutes from Pan American Pier.
Isla Verde- Beach/Bar/Restaurants Near Airport
Playa Nueva Romana

Playa Nueva Romana

4.5 out of 5
Autovía del Este Km 12, Ramón Santana, San Pedro de Macorís, Ramón Santana, San Pedro de Macoris
With a stay at Playa Nueva Romana in Ramón Santana, you'll be 3.8 mi (6.1 km) from Cueva de las Maravillas National Park and 16.6 mi (26.8 km) from La Romana ...
Playa Nueva Romana
Laid back Island Vibe Beachy Bungalow on the beach steps to the ocean

Laid back Island Vibe Beachy Bungalow on the beach steps to the ocean

Christiansted
With a stay at this vacation home in Christiansted, you'll be on the beach, just a 4-minute walk from Buccaneer Beach and 5 minutes by foot from Mermaid ...
Laid back Island Vibe Beachy Bungalow on the beach steps to the ocean
Safe Cozy Studio near Airport, Beaches

Safe Cozy Studio near Airport, Beaches

Carolina
With a stay at this apartment, you'll be centrally located in Carolina, within a 15-minute drive of Condado Beach and Pan American Pier.
Safe Cozy Studio near Airport, Beaches
Safe Oversized studio close to Beaches and Airport

Safe Oversized studio close to Beaches and Airport

Carolina
With a stay at this apartment, you'll be centrally located in Carolina, within a 15-minute drive of Condado Beach and Pan American Pier.
Safe Oversized studio close to Beaches and Airport
Isla Verde Beach/Bars/Restaurants also  perfect for a
Near Airport  Stop-N-Go

Isla Verde Beach/Bars/Restaurants also perfect for a Near Airport Stop-N-Go

Carolina
With a stay at this vacation home in Carolina (Isla Verde), you'll be a 1-minute drive from Carolina Beach and 8 minutes from Pan American Pier.
Isla Verde Beach/Bars/Restaurants also perfect for a Near Airport Stop-N-Go
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Caribbean Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Caribbean vacation homes are the perfect way for you to wing it.

Holiday houses in Caribbean let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Caribbean in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Caribbean adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Caribbean with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Caribbean vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Caribbean Holiday Homes essential information

Accommodation
13405 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
1120 Vieques by Stay with Bear, Casa Parcha, The Beach Pad, Isla Verde- Beach/Bar/Restaurants Near Airport , Playa Nueva Romana, Laid back Island Vibe Beachy Bungalow on the beach steps to the ocean, Safe Cozy Studio near Airport, Beaches , Safe Oversized studio close to Beaches and Airport, Isla Verde Beach/Bars/Restaurants also perfect for a Near Airport Stop-N-Go

Top trending hotels in Caribbean

Hotel El Convento

Hotel El Convento

4.5 out of 5
100 Cristo St, San Juan
Fully refundableReserve now, pay when you stay
With a stay at Hotel El Convento in San Juan (Old San Juan), you'll be steps from Catedral Basilica Menor de San Juan Bautista and 3 minutes by foot from San ...
Hotel El Convento
British Colonial - Nassau

British Colonial - Nassau

4 out of 5
Number One Bay St, Nassau
Fully refundableReserve now, pay when you stay
With a stay at British Colonial - Nassau , you'll be centrally located in Nassau, within a 10-minute drive of Aquaventure and Ocean Club Golf Course.
British Colonial - Nassau
Hotel Rumbao, a Tribute Portfolio Hotel

Hotel Rumbao, a Tribute Portfolio Hotel

4 out of 5
100 Brumbaugh Street, San Juan, Puerto Rico
With a stay at Hotel Rumbao, a Tribute Portfolio Hotel, you'll be centrally located in San Juan, steps from Pier 3 and within a 5-minute walk of Pier 1.
Hotel Rumbao, a Tribute Portfolio Hotel
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The Reef at Atlantis

The Reef at Atlantis

4.5 out of 5
Paradise Beach Drive, Paradise Island, New Providence
When you stay at The Reef at Atlantis in Paradise Island, you'll be next to a golf course, a 2-minute drive from Aquaventure and 6 minutes from Ocean Club Golf ...
The Reef at Atlantis
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^Subject to availability and chosen travel dates.