Top Vacation Homes in Caribbean in 2026

A tropical beach with clear turquoise waters, lush green hills, and a small red building on a hill.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Top Cities in Caribbean

A beach with clear turquoise water, a sandy shore, and a city skyline with tall buildings including a Marriott hotel.

Our top choices for Caribbean vacation homes

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

1. 1120 Vieques by Stay with Bear

Santurce

Stanley

AED 371 total

includes taxes & fees

2 Nov - 3 Nov

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.

2. 150 Sol by Stay with Bear

Old San Juan

Jose

AED 591 total

includes taxes & fees

19 Oct - 20 Oct

A living room with a sofa, a TV, a lamp, and a painting on the wall.

3. 152 Sol by Stay with Bear

Old San Juan

Nicole

AED 697 total

includes taxes & fees

11 Oct - 12 Oct

A beach with clear turquoise water, a sandy shore, and wooden deck chairs under blue umbrellas.

4. Private Pool House By the Beach. 3 Min Walk to Grace Bay Beach • Sleeps 4

Grace Bay

Kellie C.

A modern building with a staircase leading to a door, surrounded by greenery and white railings.

5. Alto Vista Hills

Noord

Jacob

A covered outdoor seating area with a view of the ocean, a pool, and lounge chairs.

6. Ocean Front Property With Pool. - George Town

Exuma

Jennifer P.

A compact kitchen with a microwave, sink, and washing machine. There is a small dining area with stools and a table.

7. Residence Nokoshima

Fort-de-France

Karen

A modern living room with a grey sofa set, a white coffee table, and a kitchen area in the background.

8. Coral Cove: Nearby Baha Mar, Pool & Patio, Gated, Beach Walkable

Cable Beach

Locke D.

AED 1,407 total

includes taxes & fees

6 Oct - 7 Oct

View all properties

Find vacation rentals that suit your style

Villas

Houseboats

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

Top Caribbean Hotel Reviews

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

8/10 Good

"Staff were excellent, resort itself is in need of some refurbishment, food was good, rooms were basic more like a hotel than a resort, beach is great other than the guy trying to sell drugs to new people checking in everyday between 2-5, I would think the security staff should be doing more about that issue."

Comfort Suites Paradise Island

10/10 Excellent

"We had a great stay!! comfort Suites is that a location accessible to all the Paradise Island and over to downtown Nassau. The staff was exceptionally pleasant and welcomed us right away. The daily breakfast was delicious, was about the same every morning, but you knew what you were getting and it was good. We will stay here again!"

Renaissance Wind Creek Curacao Resort

10/10 Excellent

"I would highly suggest the daily breakfast buffet but not the all-inclusive. This place is not a Cancun type all-inclusive. There are not people everywhere to get you a drink, ask you for a drink, and there are limited restaurants in the hotel. The walking distance to so many restaurants are close by and are excellent. I would highly suggest asking to stay on the second floor. The pool/infinity pool is off the second floor. The hotel has a weird design of long, similar looking hallways. The hallways are not very well marked on where things are located. Depending on what floor and place in the hallway you are, it might take several days to get used to where to go. There were several days where our room was never cleaned and it was 4:30-5:00. They were in the hallway but we just asked for new towels and we didn't want them to be cleaning at 6:00 at night. All the staff was very friendly. The tipping thing is weird since it is a Dutch country. Service charges are added to every bill automatically, whether in the hotel or out. We were told you don't need to tip unless you wanted to add extra. You will probably notice throughout town at restaurants or bars that the service fee is fine for what you get. They are definitely not jumping through hoops to earn a high tip. I would also recommend renting a car to hit the snorkeling areas and the other parts of the island. There is a car rental place right in front of the hotel. Very convenient."

Explore a world of travel with Expedia

Punta Cana Vacations

St. John Vacation Rentals

Vacation Homes in Caribbean

Check prices for these dates

Top Cities in Caribbean

San Juan

Our top choices for Caribbean vacation homes

1. 1120 Vieques by Stay with Bear

2. 150 Sol by Stay with Bear

3. 152 Sol by Stay with Bear

4. Private Pool House By the Beach. 3 Min Walk to Grace Bay Beach • Sleeps 4

5. Alto Vista Hills

6. Ocean Front Property With Pool. - George Town

7. Residence Nokoshima

8. Coral Cove: Nearby Baha Mar, Pool & Patio, Gated, Beach Walkable

9. NÔA curacao

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

11. Luxurious and Beautiful Isla Verde Beach house with private pool

12. Oceanfront Paradise in Exuma: Pool, Kayaks & Stunning Views Await You!

13. Ocean Front-Great Location

14. Blue House Joyuda

15. Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!

16. 7BR Oasis in Paradise on One Happy Island

17. The Sandbar Luxury Oceanfront Home, 5 Bedroom 5 Bath, Infinity Pool/Hot Tub

18. Blue Hues! Secluded Exuma Beachfront + Private Pool / Whole-House Generator

19. BeauSoleil Beach House, Luxury Private Ocean Front with Infinity Pool/Hot Tub

20. Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.

Find vacation rentals that suit your style

Top Caribbean Hotel Reviews

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

Explore a world of travel with Expedia