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

Vacation Homes in Caribbean

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Top Cities in Caribbean

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

San Juan

San Juan

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

1120 Vieques by Stay with Bear
3.5 star property
Santurce
9.2 out of 10, Wonderful, (194 reviews)
"Amazing stay"
United States
Stanley
The price is P6,292
P6,858 total
includes taxes & fees
Nov 2 - Nov 3
1120 Vieques by Stay with Bear
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

150 Sol by Stay with Bear
3.0 star property
Old San Juan
8.6 out of 10, Excellent, (66 reviews)
"Great location, easy access to property."
United States
Jose
The price is P8,691
P11,179 total
includes taxes & fees
Oct 19 - Oct 20
150 Sol by Stay with Bear
A living room with a sofa, a TV, a lamp, and a painting on the wall.

3. 152 Sol by Stay with Bear

152 Sol by Stay with Bear
2.5 star property
Old San Juan
9.6 out of 10, Exceptional, (4 reviews)
"We had a great stay! The place was very clean, tidy, and exactly as expected. The location was perfect, and the host was very helpful and responsive. We really enjoyed our time here and would definitely stay again!"
Canada
Nicole
The price is P10,407
P11,343 total
includes taxes & fees
Oct 20 - Oct 21
152 Sol by Stay with Bear
A modern building with a staircase leading to a door, surrounded by greenery and white railings.

4. Alto Vista Hills

Alto Vista Hills
3.5 star property
Noord
8.8 out of 10, Excellent, (13 reviews)
"Very clean place The host and his Mom were very very helpful and very kind people Very fast response time with any help needed Would definitely stay there again"
United States
Douglas
Alto Vista Hills
A compact kitchen with a microwave, sink, and washing machine. There is a small dining area with stools and a table.

5. Residence Nokoshima

Residence Nokoshima
Fort-de-France
9.6 out of 10, Exceptional, (4 reviews)
"The apartment was very clean, a good price, but much smaller than the pictures make it look."
Canada
Karen
Residence Nokoshima
A swimming pool with lounge chairs and palm trees, surrounded by buildings and a clear sky.

6. NÔA curacao

NÔA curacao
4.0 star property
Saliña
9.8 out of 10, Exceptional, (7 reviews)
"Beds were comfortable, a lot of kitchen utensils so cooking was easy there. Great location. Nice outdoor sitting area. You don't have a lot of privacy though."
United States
Stephanie
NÔA curacao
A dining area with a wooden table, white chairs, and a ceiling fan.

7. Blue House Joyuda

Blue House Joyuda
3.5 star property
Cabo Rojo
9.6 out of 10, Exceptional, (54 reviews)
"Excelent place in front of the ocean, beautiful property"
United States
Samary
The price is P7,397
P7,915 total
includes taxes & fees
Oct 22 - Oct 23
Blue House Joyuda
A residential area with houses, a view of the ocean, and hills in the background.

8. Suite Pepper

Suite Pepper
2.5 star property
Mahaut
The price is P3,779
P24,310 total
includes taxes & fees
Oct 18 - Oct 19
Suite Pepper
A clear blue pool surrounded by palm trees and lounge chairs, with a view of the ocean.

9. Playa Nueva Romana

Playa Nueva Romana
3.5 star property
Ramón Santana
9.0 out of 10, Wonderful, (60 reviews)
"Excellent service. Quick responses !!"
United States
Beislyn
Playa Nueva Romana
A covered outdoor area with a wooden deck, a green railing with pineapple decorations, and palm trees in the background.

10. Sunshine Lodge- Your Home Away From Home

Sunshine Lodge- Your Home Away From Home
4.0 star property
Montego Bay
7.6 out of 10, Good, (5 reviews)
"Very cool place to stay. Very few minor issues, communication was great. Any real issue we had was not reflective on the property, if you ever drove in Jamaica roads are a little bit rough and the one going up to the property is a little rough but not impossible by any means. The view is amazing the place is clean and the AC in the bedroom works amazing. We had an issue with the gas for the stove, but that might have been more of a user issue than anything else. Everything else worked out fine."
United States
DUSTIN
The price is P4,308
P5,379 total
includes taxes & fees
Nov 13 - Nov 14
Sunshine Lodge- Your Home Away From Home
A modern interior with a large window, a potted plant, and a door leading outside.

11. Miramar by PMI Puerto Rico

Miramar by PMI Puerto Rico
3.0 star property
Santurce
9.0 out of 10, Wonderful, (2 reviews)
"J"
United States
Elisaul
The price is P5,353
P14,652 total
includes taxes & fees
Nov 1 - Nov 2
Miramar by PMI Puerto Rico
A covered outdoor patio with a round table and chairs, a chandelier, and a view of greenery.

12. Villa Serenity by the water

Villa Serenity by the water
3.5 star property
Cooper Jack Bay Settlement
8.4 out of 10, Very good, (34 reviews)
"Nice place to stay"
United States
Roodmy
The price is P8,198
P15,551 total
includes taxes & fees
Oct 26 - Oct 27
Villa Serenity by the water
A resort with a large swimming pool, multiple overwater bungalows, and a clear blue sky.

13. Richmond Villa Rental Management

Richmond Villa Rental Management
3.5 star property
Ocho Rios
6.0 out of 10, (2 reviews)
"Property met out expectations. Close to the pool. Kid friendly. Great place to have a relaxintion vacation. "
United States
Lucien
Richmond Villa Rental Management
A pool area with a clear blue pool, surrounded by lush greenery and a building with a white balcony.

14. Tobago Hibiscus Villas and Apartments

Tobago Hibiscus Villas and Apartments
3.5 star property
Bethel
8.8 out of 10, Excellent, (6 reviews)
"Clinton (host) was excellent. Great communication throughout. Waited up for us to arrive and even brought us fresh fruits! Kids loved the pool as well. "
United Kingdom
Michael
The price is P6,235
P6,859 total
includes taxes & fees
Nov 3 - Nov 4
Tobago Hibiscus Villas and Apartments
A beach with palm trees, ocean waves, and a sunset.

15. KAY TI SABLE

KAY TI SABLE
Le Diamant
KAY TI SABLE
A kitchen with wooden cabinets, a gas stove, a sink, and a window with curtains.

16. Vince's house

Vince's house
2.5 star property
Tabarre
Vince's house
Interior

17. Treasure Manor

Treasure Manor
3.0 star property
Ocho Rios
2.0 out of 10, (1 review)
"This property was a scam and expedia was of no assistance in helping me get my money back. From before I reached Jamaica I contacted expedia to let them know I was unable to get in contact with the property. I did not have access to the property and yet expedia sees no issue with taking my money to give to these scammers."
United States
Raquelle
Treasure Manor
A white door with a window, leading to a balcony with a view of dense foliage.

18. Binks appartments

Binks appartments
3.0 star property
Roseau
8.2 out of 10, Very good, (12 reviews)
"Great stay"
United Kingdom
shakiyl
Binks appartments
A covered outdoor seating area with wicker furniture and a bottle of champagne, overlooking a beach with clear turquoise water.

19. The Suite Life

The Suite Life
4.0 star property
Rokers Point
8.2 out of 10, Very good, (20 reviews)
"The property is exactly how you see it listed. Our favorite part was that we had the beach foot steps away from out back door."
United States
ALIDA
The price is P11,336
P25,730 total
includes taxes & fees
Oct 31 - Nov 1
The Suite Life
A clear swimming pool surrounded by palm trees and a stone wall, with a building in the background.

20. Eagle Vacation Home

Eagle Vacation Home
4.0 star property
Oranjestad
9.6 out of 10, Exceptional, (17 reviews)
"Nice quiet area easy walk to beach"
United States
teresa
Eagle Vacation Home
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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Top Caribbean Hotel Reviews

The Reef at Atlantis

The Reef at Atlantis

8/10 Good
"Water and ocean are just perfect"
francois 5-night trip
Posted 2 hours ago
The Reef at Atlantis

Find out more about Caribbean

Caribbean Vacation Homes information

Number of reviews
396
Accommodation
1163 Vacation Homes
Lowest Price
P5,379
Highest Price
P25,730

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