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

Holiday Homes in Caribbean

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Caribbean holiday 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, (188 reviews)
"Amazing stay"
United States
Stanley
The price is 2.339.280 ₫
2.549.815 ₫ total
includes taxes & fees
20 Oct - 21 Oct
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, (65 reviews)
"Great location !Parking sucks , if you drive park on one of the parking garage"
United States
Amy
The price is 3.300.984 ₫
4.245.726 ₫ total
includes taxes & fees
20 Oct - 21 Oct
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 4.514.810 ₫
4.921.143 ₫ total
includes taxes & fees
29 Sept - 30 Sept
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)
"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
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
9.4 out of 10, Exceptional, (53 reviews)
"Excelent place in front of the ocean, beautiful property"
United States
Samary
The price is 3.366.230 ₫
3.601.814 ₫ total
includes taxes & fees
25 Oct - 26 Oct
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 1.558.440 ₫
10.025.964 ₫ total
includes taxes & fees
10 Oct - 11 Oct
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, (59 reviews)
"Amazing stay! Clean, staff was so nice and helpful"
United States
Antonio
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
7.0 out of 10, Good, (4 reviews)
"It was beautiful on the inside and had an amazing view of Montego Bay."
United States
AGNES
The price is 3.060.558 ₫
3.695.088 ₫ total
includes taxes & fees
17 Oct - 18 Oct
Sunshine Lodge- Your Home Away From Home
A covered outdoor patio with a round table and chairs, a chandelier, and a view of greenery.

11. 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 3.381.191 ₫
6.413.425 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Villa Serenity by the water
A modern interior with a large window, a potted plant, and a door leading outside.

12. Miramar by PMI Puerto Rico

Miramar by PMI Puerto Rico
3.0 star property
Santurce
10.0 out of 10, Exceptional, (1 review)
The price is 2.209.320 ₫
6.047.038 ₫ total
includes taxes & fees
28 Sept - 29 Sept
Miramar by PMI Puerto Rico
A pool area with a clear blue pool, surrounded by lush greenery and a building with a white balcony.

13. 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
Tobago Hibiscus Villas and Apartments
A resort with a large swimming pool, multiple overwater bungalows, and a clear blue sky.

14. 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 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

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 view of the ocean.

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 5.142.852 ₫
11.177.392 ₫ total
includes taxes & fees
1 Oct - 2 Oct
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

British Colonial - Nassau

British Colonial - Nassau

10/10 Excellent
"I can't say enough how blessed I was to stay here! I had a random herniated disk in my back while staying there. The pain was so intense I had to go to the hospital twice. The staff there went above and beyond assisting me and my family with everything we needed. Wheelchairs, pushing me back and forth to and from my room multiple times. Offered prefered parking at no cost. One employee even walked to the nearby pharmacy just to confirm what time they opened. They even allowed us to check out at 3pm since we had a 6pm flight. Not to mentioned the hotel itself is a marvel and the room was perfect. I never leave these long reviews unless something really bad happened but this was the total opposite and I am extremely thankful for the staff at British Colonial. Thanks guys, TOP TIER SERVICE!"
Larry 1-night trip
Posted 13 hours ago
British Colonial - Nassau

Find out more about Caribbean

Caribbean Holiday Homes information

Number of reviews
326
Accommodation
1159 Holiday Homes
Lowest Price
2.549.815 ₫
Highest Price
11.177.392 ₫