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Featured Holiday Homes in Caribbean

Playa Nueva Romana

Playa Nueva Romana

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
Casa Carlos Rico

Casa Carlos Rico

2.5 out of 5
Calle San Lázaro 462, Entre Campanario y Perseverancia, Havana, Havana
The price is AU$35 per night from 31 May to 1 Jun
AU$35
per night
31 May - 1 Jun
With a stay at Casa Carlos Rico, you'll be centrally located in Havana, steps from Malecón and 13 minutes by foot from Central Park.
Casa Carlos Rico
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
The price is AU$185 per night from 26 May to 27 May
AU$185
per night
26 May - 27 May
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 Puerto Rico Convention Center.
Isla Verde Beach/Bars/Restaurants also perfect for a Near Airport Stop-N-Go
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Luxurious and Beautiful Isla Verde Beach house with private pool

Luxurious and Beautiful Isla Verde Beach house with private pool

Carolina
Located in Carolina (Isla Verde), this vacation home is within a 15-minute walk of Isla Verde Beach and Carolina Beach.
Luxurious and Beautiful Isla Verde Beach house with private pool
Villa Serenity by the water

Villa Serenity by the water

3.5 out of 5
Turtle Creek Dr, Providenciales, Caicos Islands
The price is AU$256 per night from 22 May to 23 May
AU$256
per night
22 May - 23 May
Located in Providenciales (Discovery Bay), Villa Serenity by the water is within a 5-minute drive of Turtle Cove and Providenciales Beaches.
Villa Serenity by the water
Beautiful Spacious Safe close to Airport - Beaches

Beautiful Spacious Safe close to Airport - Beaches

Carolina
The price is AU$265 per night from 22 May to 23 May
AU$265
per night
22 May - 23 May
With a stay at this vacation home, you'll be centrally located in Carolina, within a 15-minute drive of Condado Beach and Puerto Rico Convention Center.
Beautiful Spacious Safe close to Airport - Beaches
Sugar Apple Bed & Breakfast

Sugar Apple Bed & Breakfast

3.5 out of 5
27 Prince St, Christiansted, St Croix
When you a stay at Sugar Apple Bed & Breakfast in Christiansted, you'll be near the airport, within a 5-minute walk of Holy Cross Catholic Church and Judith's ...
Sugar Apple Bed & Breakfast
El Yunque, Private Home with Spectacular views and pool!!

El Yunque, Private Home with Spectacular views and pool!!

Rio Grande
With a stay at this vacation home in Río Grande, you'll be near the beach, within a 15-minute drive of El Yunque National Forest and Mandara Spa at the Westin ...
El Yunque, Private Home with Spectacular views and pool!!
3 Bedroom Oceanfront Beach House

3 Bedroom Oceanfront Beach House

3.5 out of 5
348 PR-4466, Isabela, Isabela
Located in Isabela, this vacation home is on the beach, a 4-minute walk from Jobos Beach and within a 5-minute drive of Pozo de Jacinto.
3 Bedroom Oceanfront Beach House
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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
9755 Holiday Homes
Lowest Price
AU$35
Highest Price
AU$454
Popular accommodation
Playa Nueva Romana, Casa Carlos Rico, Isla Verde Beach/Bars/Restaurants also perfect for a Near Airport Stop-N-Go , Luxurious and Beautiful Isla Verde Beach house with private pool, Villa Serenity by the water, Beautiful Spacious Safe close to Airport - Beaches , Sugar Apple Bed & Breakfast, El Yunque, Private Home with Spectacular views and pool!!, 3 Bedroom Oceanfront Beach House

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
The price is AU$454 per night from 22 May to 23 May
AU$454
per night
22 May - 23 May
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
The price is AU$357 per night from 19 May to 20 May
AU$357
per night
19 May - 20 May
With a stay at British Colonial - Nassau , you'll be centrally located in Nassau, within a 15-minute drive of Cabbage Beach and Cable Beach.
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
Fully refundableReserve now, pay when you stay
The price is AU$275 per night from 9 Jun to 10 Jun
AU$275
per night
9 Jun - 10 Jun
With a stay at Hotel Rumbao, a Tribute Portfolio Hotel by Marriott, you'll be centrally located in San Juan, steps from Pier 3 and within a 5-minute walk of ...
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
With a stay at The Reef at Atlantis in Paradise Island, you'll be next to a golf course, within a 10-minute drive of Cabbage Beach and Lucayan Archipelago.
The Reef at Atlantis
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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.

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^Subject to availability and chosen travel dates.