Caribbean Islands Vacation Homes

A beach with clear turquoise water, white sand, and palm trees.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Caribbean Islands holiday homes

A spacious dining area with a long wooden table and four black chairs, a large green plant, and a view of a white building with arches.

1. 150 Sol by Stay with Bear

Old San Juan

Amy

HK$1,261 total

includes taxes & fees

19 Oct - 20 Oct

A hotel room with two beds, a nightstand, and a wall-mounted string of decorative leaves.

2. Villa Mar

Punta Cana

HK$699 total

includes taxes & fees

5 Oct - 6 Oct

An aerial view of a beach resort with a clear blue sea, a sandy beach, and a building with a blue roof.

3. Great Location, beautiful home on the water,beach, pool and top amenities

Georgetown

Adam B.

HK$5,888 total

includes taxes & fees

22 Oct - 23 Oct

4. Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach

Falmouth Historic Town Centre

Marcia

HK$1,624 total

includes taxes & fees

27 Oct - 28 Oct

An outdoor seating area with a pool view, covered by white canopies, and surrounded by potted plants.

5. Sophisticated Beach Condo-Ocean View-Sapphire

Smith Bay

Michael

HK$2,241 total

includes taxes & fees

3 Oct - 4 Oct

A beach with a wooden pier, lounge chairs, and jet skis.

6. Amazing Beachfront home the calm side of the island. Swimming & kayaking

Exuma

Kimberly H.

HK$4,821 total

includes taxes & fees

31 Oct - 1 Nov

A poolside area with lounge chairs, a wooden deck, and a view of the ocean.

7. Watermark Luxury Oceanfront All Suite Hotel

Cabarete

KIRSA

HK$3,001 total

includes taxes & fees

5 Oct - 6 Oct

A modern bedroom with a large bed, bedside tables with lamps, a wardrobe, and an air conditioning unit.

8. 1120 Vieques by Stay with Bear

Santurce

Stanley

HK$839 total

includes taxes & fees

2 Nov - 3 Nov

View all properties

Find holiday rentals that suit your style

Aparthotels

Villas

Save an average of 15% on thousands of hotels when you're signed in

Top Caribbean Islands Hotel Reviews

Barceló Bávaro Palace - All Inclusive

10/10 Excellent

"Good"

Sunscape Coco Punta Cana - All Inclusive

8/10 Good

"My private concierge franlin made my stay as I expected did everything I was hoping for really recommend to have something like this even lower our price for the fish restaurant that was great and and joining from the reception in the VIP was awesome. This guy also got me good accommodation took care of the room and make sure that I’ll stay is fabulous."

Ocean Blue & Sand Beach Resort - All Inclusive

8/10 Good

"Overall, Ocean Blue Resort is a very nice hotel, especially for young people. There is so much to do: a great atmosphere, good entertainment, delicious food, and a fun nightclub. You almost don’t even need to leave the resort to have a good time. The resort feels like a small city, with different areas and plenty of activities. I also really liked the transportation within the resort; it was very convenient and well organized. The food was absolutely delicious, and the entertainment was great. In terms of activities, atmosphere, and things to do, I really enjoyed my stay. Unfortunately, my first impression of the hotel was very bad because of the room I was given. There was a machine in the room for moisture control, and I immediately started having problems with it. I could barely breathe comfortably in the room. I had to go all the way back to the front desk to ask for another room. What bothered me the most was that it seemed like the hotel already knew there was a problem with this room. Thankfully, I was eventually given another room, but that kind of first impression stays with you. Another major downside was the staff and customer service. I did not find many of the staff members very friendly or attentive. You have to ask for almost everything. many local guests at the resort. This creates a different atmosphere compared with a resort that mainly has international tourists. This is not necessarily a negative thing, but it is something totally be aware."

Find out more about Caribbean Islands