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
The price is NZ$217 per night from 13 Apr to 14 Apr
NZ$217
13 Apr - 14 Apr
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
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 business-friendly holiday home in San Juan. Enjoy free Wi-Fi, free parking and in-room washers/dryers. Popular attractions Condado Beach and Port ...
Opens in a new window1120 Vieques 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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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
Isla Verde-Beach -Bar -Restaurante  
Also  a cool quick Stop-N-Go Near Airport

Isla Verde-Beach -Bar -Restaurante Also a cool quick Stop-N-Go Near Airport

Carolina Carolina
The price is NZ$265 per night from 23 Mar to 24 Mar
NZ$265
23 Mar - 24 Mar
includes taxes & fees
Stay at this holiday home in Carolina. Enjoy free Wi-Fi, a garden and an in-room coffee maker. Popular attractions Condado Beach and Port of San Juan are located ...
Opens in a new windowIsla Verde-Beach -Bar -Restaurante Also a cool quick Stop-N-Go Near Airport
Casa Parcha

Casa Parcha

3.5 out of 5
Carr 191 km 27.9 Naguabo Naguabo
The price is NZ$335 per night from 15 Apr to 16 Apr
NZ$335
15 Apr - 16 Apr
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
OCEAN VIEW VILLA WITH PRIVATE POOL ,STEPS FROM SECLUDED BEACH, GATED COMMUNITY!

OCEAN VIEW VILLA WITH PRIVATE POOL ,STEPS FROM SECLUDED BEACH, GATED COMMUNITY!

Yabucoa
Stay at this beach holiday home in Yabucoa. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Palmas del Mar Beach and Playa El Cocal are ...
Opens in a new windowOCEAN VIEW VILLA WITH PRIVATE POOL ,STEPS FROM SECLUDED BEACH, GATED COMMUNITY!
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
Stay at this golf holiday home in Río Grande. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowYes! This is your retreat, view of El Yunque, inside Coco Beach Resort.
Charming 3-bedroom house in San Juan with WiFi and AC

Charming 3-bedroom house in San Juan with WiFi and AC

San Juan San Juan
Stay at this holiday home in San Juan. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Isla Verde Beach and Jose Miguel Agrelot Coliseum ...
Opens in a new windowCharming 3-bedroom house in San Juan with WiFi and AC
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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
13683 Holiday Homes
Lowest Price
NZ$217
Highest Price
NZ$1,157
Popular accommodation
150 Sol by Stay with Bear, 1120 Vieques by Stay with Bear, Playa Nueva Romana, Sugar Apple Bed & Breakfast, Isla Verde-Beach -Bar -Restaurante Also a cool quick Stop-N-Go Near Airport , Casa Parcha, OCEAN VIEW VILLA WITH PRIVATE POOL ,STEPS FROM SECLUDED BEACH, GATED COMMUNITY!, Yes! This is your retreat, view of El Yunque, inside Coco Beach Resort. , Charming 3-bedroom house in San Juan with WiFi and AC

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$1,157 per night from 15 Apr to 16 Apr
NZ$1,157
15 Apr - 16 Apr
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$569 per night from 13 Apr to 14 Apr
NZ$569
13 Apr - 14 Apr
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$512 per night from 6 Apr to 7 Apr
NZ$512
6 Apr - 7 Apr
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.