Search 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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Browse Select Caribbean Islands Holiday Homes

1120 Vieques by Stay with Bear
Relax in this inviting living room with a beige sofa, armchair, and coffee table.

1120 Vieques by Stay with Bear

4.0 star property
9.6 out of 10, Exceptional, (30)
"It is extremely clean, nice and cozy, looks like everything is new. Very clear instructions on how to get in and everything."
1120 Vieques by Stay with Bear
The Beach Pad
Relax in this stylish room with a large bed, sofa, and dining area, plus a balcony with a view of lush greenery.

The Beach Pad

3.0 star property
9.8 out of 10, Exceptional, (56)
"Great place , perfect location ."
The Beach Pad
Casa Parcha
Stroll through the serene garden to a charming single-story retreat.

Casa Parcha

3.5 star property
9.8 out of 10, Exceptional, (29)
"Very nice place to stay."
The price is Rp2.768.790
Rp3.206.911 total
includes taxes & fees
11 Aug - 12 Aug
Casa Parcha
2058 Espana by Stay with Bear
Apartment, 3 Bedrooms, Beachside | Private kitchen | Full-sized fridge, microwave, oven, stovetop

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
Residencia Katya
Compact kitchen with gas stove, sink, and range hood built into a single island, featuring dark cabinets and a tiled backsplash.

Residencia Katya

3.0 star property
9.8 out of 10, Exceptional, (6)
"Perfect location and beautiful house "
The price is Rp745.375
Rp879.542 total
includes taxes & fees
11 Aug - 12 Aug
Residencia Katya
Gorgeous Hideout
Relax by the resort's pool surrounded by palm trees and a sandy 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
Enjoy a tranquil beach experience surrounded by palm trees.

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
Villa Serenity by the water
Enjoy cooking in this well-equipped kitchen with a dishwasher and ample countertop space.

Villa Serenity by the water

3.5 star property
8.4 out of 10, Very good, (30)
"Nice place to stay"
The price is Rp3.298.117
Rp5.340.832 total
includes taxes & fees
10 Aug - 11 Aug
Villa Serenity by the water
Columbus Heights Sea View
Relax in this stylish living space with a sofa, dining table, and kitchen area.

Columbus Heights Sea View

3.0 star property
9.6 out of 10, Exceptional, (16)
"Great Place, Will Be Back Soon!"
Columbus Heights Sea View
The Cottage at Villa Indigo
Cozy living space with a sofa, ottoman, and dining area, featuring a kitchenette and natural light.

The Cottage at Villa Indigo

3.0 star property
8.8 out of 10, Excellent, (15)
"We love St. Thomas This property was in a safe location as long as you are willing to drive on the left side of the road."
The price is Rp4.382.832
Rp7.404.844 total
includes taxes & fees
18 Aug - 19 Aug
The Cottage at Villa Indigo
4BR 14 pax Twin Villa-Bbq & private pool
Relax by the rectangular pool surrounded by a concrete border and white walls.

4BR 14 pax Twin Villa-Bbq & private pool

3.0 star property
10.0 out of 10, Exceptional, (1)
"A+ is my assesment of this accomidation. The owner/renter went through great lengths to make my stay comfortable. Communication was excellent, the property condition was excellent. It has a full kitchen with every appliance needed! The bedrooms were excellent with a tv in every room, AC in every room and comfortable linens. It is in a gated community not far from shopping or restaurants. Plaza San Juan 5 minutes, Los Corales beach was 20 minutes. I am running out of room so I will add that I...
4BR 14 pax Twin Villa-Bbq & private pool
Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach
Guests can enjoy a lively atmosphere and swim in the pool surrounded by lush greenery.

Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach

4.0 star property
9.8 out of 10, Exceptional, (17)
"This is my first time staying here, and it is a must-do! It has a great location, 24/7 security, and amazing amenities! The peace of the surrounding areas was also a great benefit to staying here! "
The price is Rp844.123
Rp3.309.555 total
includes taxes & fees
26 Aug - 27 Aug
Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach
Diamante 15
Relax by the serene pool surrounded by lush greenery and palm trees.

Diamante 15

3.0 star property
10.0 out of 10, Exceptional, (1)
Diamante 15
Primaveral 2
Relax by the serene pool surrounded by lush greenery and a modern architectural setting.

Primaveral 2

3.5 star property
5.2 out of 10, (5)
Primaveral 2
Taste of Paradise
Guests can enjoy a deck with two chairs, offering a view of the surrounding area.

Taste of Paradise

4.0 star property
8.4 out of 10, Very good, (37)
"Great stay"
The price is Rp2.374.647
Rp5.081.544 total
includes taxes & fees
20 Aug - 21 Aug
Taste of Paradise
Sunshine Lodge- Your Home Away From Home
Enjoy breathtaking ocean views from this coastal retreat.

Sunshine Lodge- Your Home Away From Home

4.0 star property
7.4 out of 10, Good, (3)
"It was beautiful on the inside and had an amazing view of Montego Bay."
The price is Rp1.187.322
Rp1.381.707 total
includes taxes & fees
20 Aug - 21 Aug
Sunshine Lodge- Your Home Away From Home
Eagle Vacation Home
Relax by the serene pool surrounded by lush tropical vegetation and modern architecture.

Eagle Vacation Home

4.0 star property
9.6 out of 10, Exceptional, (8)
"Nice quiet area easy walk to beach"
Eagle Vacation Home
Puerto Rico Villa Guesthouse
Relax by the pool surrounded by a stone wall and a building with a red-tiled roof.

Puerto Rico Villa Guesthouse

3.0 star property
8.0 out of 10, Very good, (3)
"Very beautiful "
The price is Rp3.827.445
Rp9.058.015 total
includes taxes & fees
12 Aug - 13 Aug
Puerto Rico Villa Guesthouse
Sunny-shore Hideaway
House, 3 Bedrooms, Smoking, Patio | Pool | Outdoor pool

Sunny-shore Hideaway

2.0 star property
The price is Rp2.102.347
Rp3.699.213 total
includes taxes & fees
1 Sept - 2 Sept
Sunny-shore Hideaway
Casa Cielo
Porch

Casa Cielo

3.5 star property
9.6 out of 10, Exceptional, (20)
"Very welcome I love it "
Casa Cielo
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
Sign in
Sign up, it's free