Book Holiday Homes in Caribbean

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Featured Holiday Homes in Caribbean

150 Sol by Stay with Bear

150 Sol by Stay with Bear

3 out of 5
150 Sol St San Juan San Juan
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 Pan American Pier are ...
Opens in a new window150 Sol by Stay with Bear
1120 Vieques by Stay with Bear

1120 Vieques by Stay with Bear

3.5 out of 5
1120 C. Vieques San Juan San Juan
Stay at this holiday home in San Juan. Enjoy free Wi-Fi, free parking and patios. Popular attractions Condado Beach and Pan American Pier are located ...
Opens in a new window1120 Vieques by Stay with Bear
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
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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
Casa Parcha

Casa Parcha

3.5 out of 5
Carr 191 km 27.9 Naguabo Naguabo
The price is NZ$340 per night from 19 Dec to 20 Dec
NZ$340
19 Dec - 20 Dec
includes taxes & fees
Stay at this holiday home in Naguabo. Enjoy free parking, on-site spa services and a garden. Popular attractions El Yunque National Forest and Charco El Hippie ...
Opens in a new windowCasa Parcha
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
Villa Serenity by the water

Villa Serenity by the water

3.5 out of 5
Turtle Creek Dr Providenciales Caicos Islands
The price is NZ$427 per night from 4 Jan to 5 Jan
NZ$427
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this holiday home in Providenciales. Enjoy free Wi-Fi, free parking and free bicycles on-site. Popular attractions Grace Bay Beach and Turtle Lake are ...
Opens in a new windowVilla Serenity by the water
Sea Shanty -  Ocean view, Private pool, Walk to Beach, Prime Central Location.

Sea Shanty - Ocean view, Private pool, Walk to Beach, Prime Central Location.

governors harbour eleuthera
The price is NZ$531 per night from 19 Dec to 20 Dec
NZ$531
19 Dec - 20 Dec
includes taxes & fees
Stay at this holiday home in Governor's Harbour. Enjoy a garden, patios and an in-room coffee maker. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowSea Shanty - Ocean view, Private pool, Walk to Beach, Prime Central Location.
Gordon's Island Art Loft

Gordon's Island Art Loft

Charlotte Amalie
Stay at this holiday home in St. Thomas. Enjoy a garden, patios and an in-room coffee maker. Popular attractions Magens Bay Beach and Bolongo Bay are located ...
Opens in a new windowGordon's Island Art Loft
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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
13681 Holiday Homes
Lowest Price
NZ$340
Highest Price
NZ$747
Popular accommodation
150 Sol by Stay with Bear, 1120 Vieques by Stay with Bear, Sugar Apple Bed & Breakfast, Playa Nueva Romana, Casa Parcha, The Beach Pad, Villa Serenity by the water, Sea Shanty - Ocean view, Private pool, Walk to Beach, Prime Central Location. , Gordon's Island Art Loft

Top trending hotels in Caribbean

Hotel El Convento

Hotel El Convento

4.5 out of 5
100 Cristo St San Juan
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
The price is NZ$747 per night from 19 Dec to 20 Dec
NZ$747
19 Dec - 20 Dec
includes taxes & fees
Stay at this beach hotel in Nassau. Enjoy free Wi-Fi, 2 outdoor pools and 8 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
The price is NZ$410 per night from 22 Dec to 23 Dec
NZ$410
22 Dec - 23 Dec
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.

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^Subject to availability and chosen travel dates.