Holiday Homes in Caribbean Islands

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Caribbean Islands

1120 Vieques by Stay with Bear

4.0 star property
9.6 out of 10, Exceptional, (34)
"Overall great experience!"
1120 Vieques by Stay with Bear

The Beach Pad

3.0 star property
9.8 out of 10, Exceptional, (56)
"Great place , perfect location ."
The Beach Pad

Isla Verde Beach/Bars/Restaurants also perfect for a Near Airport Stop-N-Go

8.6 out of 10, Excellent, (41)
"Exactly as described. Clean and comfortable and a good value in the bustling Isla Verde district. No frills, but just what I was looking for and good communication. "
The price is NZ$206
includes taxes & fees
25 Aug - 26 Aug
Isla Verde Beach/Bars/Restaurants also perfect for a Near Airport Stop-N-Go

Charming Home Airport-Beach-Water Solar Panels

9.6 out of 10, Exceptional, (100)
"I lo e every thing about this place"
The price is NZ$287
includes taxes & fees
27 Aug - 28 Aug
Charming Home Airport-Beach-Water Solar Panels

Casa Parcha

3.5 star property
9.8 out of 10, Exceptional, (29)
"Very nice place to stay."
The price is NZ$333
includes taxes & fees
16 Aug - 17 Aug
Casa Parcha

View of El Yunque, 3 bed/3 bath located inside Coco Beach Golf Resort

10.0 out of 10, Exceptional, (159)
"We had an absolutely amazing time. The house was extremely cozy and fully stocked with everything you need for the beach, as well as a fully stocked kitchen to cook a good meal. We loved the golf cart to get around the premises. It was a secure community. Princess was very responsive and communicative. Would definitely come and stay at this property again."
View of El Yunque, 3 bed/3 bath located inside Coco Beach Golf Resort

4-bedroom House with private Pool - walking distance to Baha Mar and Beach

9.4 out of 10, Exceptional, (6)
"The house was wonderful. And the owners were super nice. It was a wonderful week away. "
The price is NZ$1,075
includes taxes & fees
27 Aug - 28 Aug
4-bedroom House with private Pool - walking distance to Baha Mar and Beach

2058 Espana by Stay with Bear

4.0 star property
10.0 out of 10, Exceptional, (3)
"Very clean , location is 167 steps to the beach. I didn’t realize how close we were to the beach so that was such a nice surprise. The place is in a gated community, that closes at 6 pm. You’re able to access via the gate guard on camera. The home was perfect for the 6 of us. 3 rooms, 2 bathrooms and the living room was perfect size to hangout with everyone without feeling squished. We watched the sunrise , watched the sunset and ate at a restaurant that was 2 mins walking from the home. Walmart...
2058 Espana by Stay with Bear

Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!

9.6 out of 10, Exceptional, (21)
"Very much enjoyed the stay. Spectacular view!!!"
Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!

Residencia Katya

3.0 star property
9.8 out of 10, Exceptional, (6)
"Perfect location and beautiful house "
The price is NZ$91
includes taxes & fees
16 Aug - 17 Aug
Residencia Katya

Sapphire Breeze, Majestic Views & Island Vibes w/ Infinity Pool, Waterfall & Covered Porches

9.6 out of 10, Exceptional, (15)
"This property exceeded our expectations in every way! We had a fantastic stay on St. John with three families - the house was perfect for kids and adults alike. The view from the infinity pool will blow your mind. We can’t wait to come back! "
Sapphire Breeze, Majestic Views & Island Vibes w/ Infinity Pool, Waterfall & Covered Porches

Cozy home 5 minutes to beach Fajardo is a hidden gen of Puerto Rico

9.8 out of 10, Exceptional, (9)
"Everything was as advertised. Would stay here again."
The price is NZ$338
includes taxes & fees
31 Aug - 1 Sept
Cozy home 5 minutes to beach Fajardo is a hidden gen of Puerto Rico

R Villa - Walk to Steps Beach with POOL, Ocean View & BOCCE Court

10.0 out of 10, Exceptional, (179)
"Our 3rd time staying in R Villa. Come to surf and enjoy the beach. Great property with everything you need. Can’t beat the location, easy walk to the marina and restaurants, plus 5-10 minutes to plenty of surf."
The price is NZ$1,414
includes taxes & fees
21 Aug - 22 Aug
R Villa - Walk to Steps Beach with POOL, Ocean View & BOCCE Court

Pink Palms at Cable Beach - 4 Bedroom - 1 Minute to Beach

9.6 out of 10, Exceptional, (17)
"We had a fantastic stay! The house was so adorable, clean and safe. Great location and Sam the host was awesome with her communication. We are going to recommend this place to our friends and family! "
Pink Palms at Cable Beach - 4 Bedroom - 1 Minute to Beach

Gorgeous Hideout

3.0 star property
10.0 out of 10, Exceptional, (1)
"Host was very on top on things great safe area "
Gorgeous Hideout

Playa Nueva Romana

3.5 star property
9.6 out of 10, Exceptional, (25)
"I enjoyed the privacy, kindness of people around and overall the calm culture. "
Playa Nueva Romana

Oceanfront 8-bedroom Villa with Pool, Fully Fenced for Privacy, Incredible Views

2.5 star property
8.8 out of 10, Excellent, (8)
Oceanfront 8-bedroom Villa with Pool, Fully Fenced for Privacy, Incredible Views

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

10.0 out of 10, Exceptional, (148)
"Beautiful property, great communication from host, felt very safe!!"
OCEAN VIEW VILLA WITH PRIVATE POOL, STEPS FROM SECLUDED BEACH, GATED COMMUNITY!

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

9.6 out of 10, Exceptional, (5)
"I came with my kids wife and mother and everything was amazing would definitely stay again"
Charming 3-bedroom house in San Juan with WiFi and AC

Cozy house next to the beach in Boca Catalina Aruba. Modern and Spacious.

10.0 out of 10, Exceptional, (66)
"Loved the beautiful home ,location ,and easiness of renting.Perfect!"
Cozy house next to the beach in Boca Catalina Aruba. Modern and Spacious.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Caribbean Islands Hotel Reviews