Book Holiday Homes in Caribbean

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Featured Holiday Homes in Caribbean

1120 Vieques by Stay with Bear

1120 Vieques by Stay with Bear

3.5 out of 5
1120 C. Vieques San Juan San Juan
The price is NZ$166 per night from 17 May to 18 May
NZ$166
17 May - 18 May
includes taxes & fees
Stay at this business-friendly holiday home in San Juan. Enjoy free Wi-Fi, free parking and in-room washers/dryers. Popular attractions Casino del Mar at La ...
Opens in a new window1120 Vieques by Stay with Bear
150 Sol by Stay with Bear

150 Sol by Stay with Bear

3 out of 5
150 Sol St San Juan San Juan
The price is NZ$285 per night from 4 June to 5 June
NZ$285
4 June - 5 June
includes taxes & fees
Stay at this holiday home in San Juan. Enjoy free Wi-Fi, Netflix and an in-room coffee maker. Popular attractions Port of San Juan and Condado Beach are located ...
Opens in a new window150 Sol by Stay with Bear
Playa Nueva Romana

Playa Nueva Romana

3.5 out of 5
Autovía del Este Km 12 Ramón Santana San Pedro de Macoris
Stay at this beach holiday home in Ramón Santana. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions Farmarax and Bahia Mall are located ...
Opens in a new windowPlaya Nueva Romana
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The Suite Life

The Suite Life

4 out of 5
Steventon Rokers Point Exuma
The price is NZ$620 per night from 6 June to 7 June
NZ$620
6 June - 7 June
includes taxes & fees
Stay at this beach holiday home in Rokers Point. Enjoy free Wi-Fi, free parking and a private beach. Popular attractions Emerald Bay Beach and Three Sisters ...
Opens in a new windowThe Suite Life
Paradise! Private Beachfront Home w/ Pool & Beach WiFi!

Paradise! Private Beachfront Home w/ Pool & Beach WiFi!

George Town Exuma
Stay at this beach holiday home in George Town. Enjoy free Wi-Fi, private pools and a beach locale. Our guests praise the pool and the helpful staff in their ...
Opens in a new windowParadise! Private Beachfront Home w/ Pool & Beach WiFi!
Salt Box: an Enchanting Historical Property with a Pool

Salt Box: an Enchanting Historical Property with a Pool

Dunmore Harbour Island
Stay at this family-friendly holiday home in Dunmore Town. Enjoy free Wi-Fi, private pools and a fitness centre. Our guests praise the helpful staff in their ...
Opens in a new windowSalt Box: an Enchanting Historical Property with a Pool
Villa Vivace - New Luxurious Seaside Home

Villa Vivace - New Luxurious Seaside Home

Providenciales Caicos Islands
Stay at this holiday home in Providenciales. Enjoy private pools, laundry facilities and patios. Popular attractions Grace Bay Beach and Long Bay Beach are located ...
Opens in a new windowVilla Vivace - New Luxurious Seaside Home
Sugar Apple Bed & Breakfast

Sugar Apple Bed & Breakfast

3.5 out of 5
27 Prince St Christiansted St Croix
Stay at this holiday home in Christiansted. Enjoy free Wi-Fi, free parking and a garden. Popular attractions Judith's Fancy and Apothecary Museum are located ...
Opens in a new windowSugar Apple Bed & Breakfast
The Beach Pad

The Beach Pad

3 out of 5
Carretera 413 Km. 4.4 Rincon
Stay at this family-friendly holiday home in Rincon. Enjoy free Wi-Fi, free parking and a rooftop terrace. Our guests praise the property condition in their ...
Opens in a new windowThe Beach Pad
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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
13094 Holiday Homes
Lowest Price
NZ$166
Highest Price
NZ$620
Popular accommodation
1120 Vieques by Stay with Bear, 150 Sol by Stay with Bear, Playa Nueva Romana, The Suite Life, Paradise! Private Beachfront Home w/ Pool & Beach WiFi! , Salt Box: an Enchanting Historical Property with a Pool, Villa Vivace - New Luxurious Seaside Home, Sugar Apple Bed & Breakfast, The Beach Pad

Top trending hotels in Caribbean

Hotel El Convento

Hotel El Convento

4.5 out of 5
100 Cristo St San Juan
The price is NZ$564 per night from 1 June to 2 June
NZ$564
1 June - 2 June
includes taxes & fees
Stay at this luxury hotel in San Juan. Enjoy free Wi-Fi, breakfast (surcharge) and room service. Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowHotel 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 June to 2 June
NZ$501
1 June - 2 June
includes taxes & fees
Stay at this beach hotel in Nassau. Enjoy free Wi-Fi, 2 outdoor pools and 6 restaurants. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowBritish 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 NZ$423 per night from 24 May to 25 May
NZ$423
24 May - 25 May
includes taxes & fees
Stay at this business-friendly hotel in San Juan. Enjoy free Wi-Fi, breakfast (surcharge) and room service. Our guests praise the helpful staff and the clean ...
Opens in a new windowHotel 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 luxury resort in Paradise Island. Enjoy free Wi-Fi, a full-service spa and a private beach. Our guests praise the pool and the helpful staff in ...
Opens in a new windowThe 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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.