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
Stay at this 3.5-star vacation home in San Juan. Enjoy free WiFi, free parking, and patios. Popular attractions Condado Beach and Pan American Pier are located ...
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$222 per night from 5 Nov to 6 Nov
NZ$222
5 Nov - 6 Nov
includes taxes & fees
Stay at this 3-star vacation home in San Juan. Enjoy free WiFi, Netflix, and an in-room coffeemaker. Popular attractions Port of San Juan and Pan American Pier ...
Opens in a new window150 Sol 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 3.5-star vacation home in Christiansted. Enjoy free WiFi, free parking, and a garden. Popular attractions Judith's Fancy and Apothecary Museum are ...
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 Macorís, Ramón Santana, San Pedro de Macoris
Stay at this 3.5-star beach vacation home in Ramón Santana. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Farmarax and Bahia Mall are ...
Opens in a new windowPlaya Nueva Romana
Sophisticated Beach Condo-Ocean View-Sapphire

Sophisticated Beach Condo-Ocean View-Sapphire

Smith Bay
The price is NZ$434 per night from 9 Nov to 10 Nov
NZ$434
9 Nov - 10 Nov
includes taxes & fees
Stay at this vacation home in St. Thomas. Enjoy free WiFi and an in-room coffeemaker. Popular attractions Sapphire Beach and Magens Bay Beach are located ...
Opens in a new windowSophisticated Beach Condo-Ocean View-Sapphire
Casa vacacional en Arenales Isabela

Casa vacacional en Arenales Isabela

3.5 out of 5
Calle Karimar Calle Elionai, Isabela, Puerto Rico
The price is NZ$309 per night from 9 Nov to 10 Nov
NZ$309
9 Nov - 10 Nov
includes taxes & fees
Stay at this 3.5-star vacation home in Isabela. Enjoy free WiFi, free parking, and a garden. Popular attractions Carribbean Cinemas Isabela and Paseo Lineal ...
Opens in a new windowCasa vacacional en Arenales Isabela
THIS IS IT! SEAFRONT RETREAT W/ BEACH ACCESS & POOL

THIS IS IT! SEAFRONT RETREAT W/ BEACH ACCESS & POOL

St. Croix
Book a stay at this beach vacation home in Kingshill. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Cane Bay and Cane Bay Beach are ...
Opens in a new windowTHIS IS IT! SEAFRONT RETREAT W/ BEACH ACCESS & 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 NZ$431 per night from 5 Nov to 6 Nov
NZ$431
5 Nov - 6 Nov
includes taxes & fees
Stay at this 3.5-star vacation home in Providenciales. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Grace Bay Beach and Turtle ...
Opens in a new windowVilla Serenity by the water
Yes! This is your retreat, view of El Yunque, inside Coco Beach Resort.

Yes! This is your retreat, view of El Yunque, inside Coco Beach Resort.

Río Grande
Book a stay at this golf vacation home in Río Grande. Enjoy free WiFi, a garden, and laundry facilities. Our guests praise the helpful staff in our reviews. ...
Opens in a new windowYes! This is your retreat, view of El Yunque, inside Coco Beach Resort.
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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
13433 Holiday Homes
Lowest Price
NZ$222
Highest Price
NZ$1,209
Popular accommodation
1120 Vieques by Stay with Bear, 150 Sol by Stay with Bear, Sugar Apple Bed & Breakfast, Playa Nueva Romana, Sophisticated Beach Condo-Ocean View-Sapphire, Casa vacacional en Arenales Isabela, THIS IS IT! SEAFRONT RETREAT W/ BEACH ACCESS & POOL, Villa Serenity by the water, Yes! This is your retreat, view of El Yunque, inside Coco Beach Resort.

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$1,209 per night from 13 Nov to 14 Nov
NZ$1,209
13 Nov - 14 Nov
includes taxes & fees
Stay at this 4.5-star luxury hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
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$575 per night from 17 Nov to 18 Nov
NZ$575
17 Nov - 18 Nov
includes taxes & fees
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 ...
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$316 per night from 17 Nov to 18 Nov
NZ$316
17 Nov - 18 Nov
includes taxes & fees
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 ...
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 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 ...
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.