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

Caribbean Private Home Rentals

Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Top Cities in Caribbean

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

San Juan

San Juan
A cruise ship docked at a port with a clear blue sea and a small island in the background.
Private Holiday HomesPrivate Holiday Homes

Nassau

Nassau

Our top choices for Caribbean holiday homes

Hypo-allergenic bedding, desk, laptop workspace, blackout curtains

1. 1120 Vieques by Stay with Bear

1120 Vieques by Stay with Bear
3.5 star property
Santurce
9.2 out of 10, Wonderful, (182 reviews)
"It was a really nice place to stay, I really recommend booking with them, everything’s is super close by, and you have access to everything super close, really nice stay I would stay there again!"
United States
Joselyn
The price is S$167
includes taxes & fees
27 Sept - 28 Sept
1120 Vieques by Stay with Bear
Outdoor dining

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, (64 reviews)
"Great location !Parking sucks , if you drive park on one of the parking garage"
United States
Amy
The price is S$195
includes taxes & fees
7 Oct - 8 Oct
150 Sol by Stay with Bear
Living area

3. Blue House Joyuda

Blue House Joyuda
3.5 star property
Cabo Rojo
9.4 out of 10, Exceptional, (51 reviews)
"Excelent place in front of the ocean, beautiful property"
United States
Samary
The price is S$164
includes taxes & fees
14 Sept - 15 Sept
Blue House Joyuda
Living area

4. 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 S$213
includes taxes & fees
13 Sept - 14 Sept
152 Sol by Stay with Bear
Shared kitchen

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
Outdoor pool, free pool cabanas, pool umbrellas

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
Property grounds

7. Alto Vista Hills

Alto Vista Hills
3.5 star property
Noord
8.8 out of 10, Excellent, (13 reviews)
"Good room, perfect for 2 people(the suite we got) Pretty clean, AC was nice No laundry at facility- I think maybe adding a drying rack would be nice :). Other than that everything went very smooth and it was very fun"
United States
Jacob
Alto Vista Hills
Terrace/patio

8. Playa Nueva Romana

Playa Nueva Romana
3.5 star property
Ramón Santana
9.0 out of 10, Wonderful, (59 reviews)
"Amazing stay! Clean, staff was so nice and helpful"
United States
Antonio
Playa Nueva Romana
Balcony view

9. The Beach Pad

The Beach Pad
3.0 star property
Rincon
9.8 out of 10, Exceptional, (81 reviews)
"Fantastic place to stay. Clean, easy check in, and the most beautiful drive to and from Rincon. Highly recommend staying here."
United States
Maria Elizabeth
The Beach Pad
Front of property

10. The Suite Life

The Suite Life
4.0 star property
Rokers Point
8.0 out of 10, Very good, (19 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 S$544
includes taxes & fees
12 Sept - 13 Sept
The Suite Life
Beach

11. Las Mariposas

Las Mariposas
3.0 star property
Las Galeras
8.8 out of 10, Excellent, (15 reviews)
"Great pleace to stay with the family! It was peaceful! "
United States
Stephanie
The price is S$54
includes taxes & fees
13 Sept - 14 Sept
Las Mariposas
Outdoor pool

12. 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
Front of property

13. DeJee Lodging

DeJee Lodging
3.5 star property
Ocho Rios
9.0 out of 10, Wonderful, (4 reviews)
"The facility is safe clean attractive and the rooms have everything you needed for ur comfort experience was wonderful 100/100👍"
United States
Winston
The price is S$163
includes taxes & fees
1 Oct - 2 Oct
DeJee Lodging
Aerial view

14. Suite Pepper

Suite Pepper
2.5 star property
Mahaut
The price is S$488
includes taxes & fees
8 Oct - 9 Oct
Suite Pepper
Terrace/patio

15. 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
Interior

16. 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
Exterior

17. Eagle Vacation Home

Eagle Vacation Home
4.0 star property
Oranjestad
9.4 out of 10, Exceptional, (16 reviews)
"Nice quiet area easy walk to beach"
United States
teresa
Eagle Vacation Home
Property grounds

18. Cayman Luxury Rentals at Ocean Paradise

Cayman Luxury Rentals at Ocean Paradise
4.0 star property
North Side
9.8 out of 10, Exceptional, (43 reviews)
"Family friendly, very equipped accommodation. Caring and quick responsive staff. Would definitely recommend the place."
Canada
Mustapha
Cayman Luxury Rentals at Ocean Paradise
Exterior

19. Hacienda Elena Paraiso Tropical

Hacienda Elena Paraiso Tropical
3.5 star property
Canóvanas
8.0 out of 10, Very good, (20 reviews)
"Great place to stay, the place is beautiful! Thanks"
United States
Ana
Hacienda Elena Paraiso Tropical
Outdoor pool

20. Puerto Rico Villa Guesthouse

Puerto Rico Villa Guesthouse
3.0 star property
Barceloneta
7.6 out of 10, Good, (15 reviews)
"No hot water dog Doodoo on the front lawn right by the walkway smells in front from old garbage that was in the cans since before we got there found a cockroach in one of the rooms water fall never worked and the pool could’ve used as serious Cleaning you can see the mold and mildew in it I was never told that there was going to be cameras in a private sitting area outside by pool"
United States
Kenneth
Puerto Rico Villa Guesthouse
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Caribbean Hotel Reviews

Renaissance Santo Domingo Jaragua Hotel & Casino

Renaissance Santo Domingo Jaragua Hotel & Casino

8/10 Good
"My second stay. Attentive staff. Everyone pleasant and helpful. Will stay again."
Mark A 3-night trip
Posted 2 hours ago
Renaissance Santo Domingo Jaragua Hotel & Casino

Find out more about Caribbean

Caribbean Private Holiday Homes information

Number of reviews
533
Accommodation
1162 Private Holiday Homes
Lowest Price
S$54
Highest Price
S$544

Explore a world of travel with Expedia