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Featured Holiday Homes in Caribbean

Numero Uno Piñones

Numero Uno Piñones

3 out of 5
PR-187 KM 5.6, Torrecilla Baja, Loiza, PR
Stay at this 3-star vacation home in Loiza. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Isla Verde Beach and Carolina Beach are ...
Numero Uno Piñones
New rental, Newly Renovated/2 ensuites/open main room/beautiful view/large pool

New rental, Newly Renovated/2 ensuites/open main room/beautiful view/large pool

2 out of 5
Cruz Bay
Book a stay at this business-friendly vacation home in St. John. Enjoy free WiFi, private pools, and a garden. Popular attractions Trunk Bay and Cinnamon Bay ...
New rental, Newly Renovated/2 ensuites/open main room/beautiful view/large pool
Charming  Home Airport-Beach-Water
Solar Panels

Charming Home Airport-Beach-Water Solar Panels

Carolina
Stay at this vacation home in Carolina. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Isla Verde Beach and Carolina Beach ...
Charming Home Airport-Beach-Water Solar Panels
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Las Mariposas

Las Mariposas

3 out of 5
Las Galeras Samaná, Las Galeras, Samaná
The price is NZ$69 per night from 22 Nov to 23 Nov
NZ$69
includes taxes & fees
22 Nov - 23 Nov
Stay at this 3-star vacation home in Las Galeras. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Rincon Beach and Playa Grande ...
Las Mariposas
Spanish Duplex / Private Patio  / Walk to Ocean

Spanish Duplex / Private Patio / Walk to Ocean

2 out of 5
San Juan
Stay at this vacation home in San Juan. Enjoy a garden, an in-room coffeemaker, and air conditioning. Popular attractions Port of San Juan and Pan American Pier ...
Spanish Duplex / Private Patio / Walk to Ocean
Waterfront Villa Dockside Patio Kayaks SUV Boat Seadoo Beaches Pool Coming Aug25

Waterfront Villa Dockside Patio Kayaks SUV Boat Seadoo Beaches Pool Coming Aug25

Cooper Jack Bay Settlement
Book a stay at this family-friendly vacation home in Providenciales. Enjoy free WiFi, a water park, and a garden. Popular attractions Turtle Cove and Grace Bay ...
Waterfront Villa Dockside Patio Kayaks SUV Boat Seadoo Beaches Pool Coming Aug25
"New" 5 bedroom Exuma Beach Front Estate w/ Pool & No Neighbors on either side!

"New" 5 bedroom Exuma Beach Front Estate w/ Pool & No Neighbors on either side!

Harts
Book a stay at this beach vacation home in Rokers Point. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Sandals Emerald Reef Golf Club ...
"New" 5 bedroom Exuma Beach Front Estate w/ Pool & No Neighbors on either side!
Jay’s home by the beach and rainforest couples retreat

Jay’s home by the beach and rainforest couples retreat

luquillo
Stay at this vacation home in Luquillo. Enjoy free WiFi, private pools, and a garden. Popular attractions Luquillo Beach and Wyndham Rio Mar Casino are located ...
Jay’s home by the beach and rainforest couples retreat
ONE OF A KIND PROPERTY! Breathtaking Views, Ocean Breezes, Huge Dock, Peaceful

ONE OF A KIND PROPERTY! Breathtaking Views, Ocean Breezes, Huge Dock, Peaceful

Georgetown
Book a stay at this beach vacation home in George Town. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Palm Bay Beach and Rolletown Tombs ...
ONE OF A KIND PROPERTY! Breathtaking Views, Ocean Breezes, Huge Dock, Peaceful
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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
10708 Holiday Homes
Lowest Price
NZ$69
Highest Price
NZ$549
Popular accommodation
Numero Uno Piñones, New rental, Newly Renovated/2 ensuites/open main room/beautiful view/large pool , Charming Home Airport-Beach-Water Solar Panels, Las Mariposas , Spanish Duplex / Private Patio / Walk to Ocean, Waterfront Villa Dockside Patio Kayaks SUV Boat Seadoo Beaches Pool Coming Aug25, "New" 5 bedroom Exuma Beach Front Estate w/ Pool & No Neighbors on either side!, Jay’s home by the beach and rainforest couples retreat , ONE OF A KIND PROPERTY! Breathtaking Views, Ocean Breezes, Huge Dock, Peaceful

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 NZ$549 per night from 25 Nov to 26 Nov
NZ$549
includes taxes & fees
25 Nov - 26 Nov
Book a stay at this boutique hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
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 NZ$501 per night from 1 Dec to 2 Dec
NZ$501
includes taxes & fees
1 Dec - 2 Dec
Stay at this 4-star beach hotel in Nassau. Enjoy free WiFi, 2 outdoor pools, and 8 restaurants. Our guests praise the helpful staff and the clean rooms in our ...
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 refundable
The price is NZ$384 per night from 25 Nov to 26 Nov
NZ$384
includes taxes & fees
25 Nov - 26 Nov
Stay at this 4-star business-friendly hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
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
Stay at this 4.5-star luxury resort in Paradise Island. Enjoy free WiFi, a full-service spa, and a private beach. Our guests praise the pool and the helpful ...
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.