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

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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

Our top choices for Caribbean Islands vacation 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

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 ￥21,341
￥27,449 total
includes taxes & fees
Oct 19 - Oct 20
150 Sol by Stay with Bear
A dining area with a wooden table, white chairs, and a ceiling fan.

2. 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 ￥18,566
￥19,865 total
includes taxes & fees
Oct 18 - Oct 19
Blue House Joyuda
A hotel room with two beds, a nightstand, and a wall-mounted string of decorative leaves.

3. Villa Mar

Villa Mar
2.5 star property
Punta Cana
The price is ￥11,937
￥14,086 total
includes taxes & fees
Oct 17 - Oct 18
Villa Mar
A modern bedroom with a large bed, bedside tables with lamps, a wardrobe, and an air conditioning unit.

4. 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 ￥25,239
￥32,461 total
includes taxes & fees
Nov 11 - Nov 12
1120 Vieques by Stay with Bear
An outdoor seating area with a pool view, covered by white canopies, and surrounded by potted plants.

5. Sophisticated Beach Condo-Ocean View-Sapphire

Sophisticated Beach Condo-Ocean View-Sapphire
Smith Bay
9.0 out of 10, Wonderful, (45 reviews)
"Clean room, AC worked great, pool is very close. Overall, a really cool place to stay."
United States
Michael
The price is ￥18,495
￥45,152 total
includes taxes & fees
Oct 18 - Oct 19
Sophisticated Beach Condo-Ocean View-Sapphire
A poolside area with lounge chairs, a wooden deck, and a view of the ocean.

6. Watermark Luxury Oceanfront All Suite Hotel

Watermark Luxury Oceanfront All Suite Hotel
4.0 star property
Cabarete
8.8 out of 10, Excellent, (104 reviews)
"We had a great time staying at the watermark!"
United States
KIRSA
The price is ￥42,043
￥56,977 total
includes taxes & fees
Oct 23 - Oct 24
Watermark Luxury Oceanfront All Suite Hotel
A beach with a wooden pier, lounge chairs, and jet skis.

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

Amazing Beachfront home the calm side of the island. Swimming & kayaking
Exuma
10.0 out of 10, Exceptional, (69 reviews)
"Wonderful property, view is stunning, beach and water area is great. Outdoor kitchen area was a hit for us. We loved it, we would most definitely stay again."
United States
Kimberly H.
The price is ￥21,341
￥96,666 total
includes taxes & fees
Oct 31 - Nov 1
Amazing Beachfront home the calm side of the island. Swimming & kayaking
An outdoor kitchen with a gas stove, sink, and stone counter.

8. "Garden" Suite near the beach and restaurants!

"Garden" Suite near the beach and restaurants!
Ucares
9.8 out of 10, Exceptional, (97 reviews)
"Host was very accesible and communicative and worked proactively to fix inconvenience. The power was out in the vicinity upon arrival but property had solar panels so that was a plus."
United States
Gladys
The price is ￥18,970
￥32,391 total
includes taxes & fees
Oct 20 - Oct 21
"Garden" Suite near the beach and restaurants!
A balcony with a view of a swimming pool and the ocean.

9. BTS5

BTS5
3.0 star property
Montego Bay
The price is ￥18,812
￥29,696 total
includes taxes & fees
Oct 19 - Oct 20
BTS5
A balcony with a view of a marina and the sea.

10. Top of the Hill Blue Sunshine

Top of the Hill Blue Sunshine
Parham Town
10.0 out of 10, Exceptional, (15 reviews)
"Great location with an amazing view, our host was really nice and helpful with places to go and visit. Super clean, we recommend this place 100% !"
United States
aurelie A.
The price is ￥31,616
￥54,221 total
includes taxes & fees
Oct 18 - Oct 19
Top of the Hill Blue Sunshine
An aerial view of a beach resort with a clear blue sea, a sandy beach, and a building with a blue roof.

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

Great Location, beautiful home on the water,beach, pool and top amenities
Georgetown
10.0 out of 10, Exceptional, (104 reviews)
"Great location. Awesome place for kids to have plenty to do. Very responsive communication and gave us tons of advice on all the things to do down there. Jack and his team were easy to work with. "
United States
Adam B.
The price is ￥27,664
￥118,639 total
includes taxes & fees
Oct 22 - Oct 23
Great Location, beautiful home on the water,beach, pool and top amenities
A covered outdoor area with a wooden table and chairs, surrounded by lush greenery and a view of the landscape.

12. Casa Paradise Palms! Beautiful views from the rooftop. Walk to ferry/beach.

Casa Paradise Palms! Beautiful views from the rooftop. Walk to ferry/beach.
Bravos de Boston
9.8 out of 10, Exceptional, (31 reviews)
"Was very clean and host was very responsive and respectful!!! Will definitely stay here again!!"
United States
Adilene Y.
The price is ￥31,616
￥63,630 total
includes taxes & fees
Oct 17 - Oct 18
Casa Paradise Palms! Beautiful views from the rooftop. Walk to ferry/beach.
A stone-walled outdoor shower area with a metal rain showerhead.

13. Cozy one bedroom studio

Cozy one bedroom studio
Sea Rocks
9.8 out of 10, Exceptional, (10 reviews)
"Great place with washer and dryer. Really close to Shoal Bay. Best French bakery near apartment."
United States
LEHANG
The price is ￥22,131
￥30,667 total
includes taxes & fees
Oct 21 - Oct 22
Cozy one bedroom studio
A wooden deck with a hammock and a chair, overlooking a body of water and hills.

14. SPECTACULAR Ensenada View @ Villa Ilusion Villa 3 - Punta Aloe #1

SPECTACULAR Ensenada View @ Villa Ilusion Villa 3 - Punta Aloe #1
Culebra
9.0 out of 10, Wonderful, (66 reviews)
"Perfect place for my family. Had what we needed. Location and everything we need to enjoy our vacation. "
United States
Adriana G.
The price is ￥33,039
￥60,439 total
includes taxes & fees
Oct 18 - Oct 19
SPECTACULAR Ensenada View @ Villa Ilusion Villa 3 - Punta Aloe #1
A clear view of Canuck Palms beach with turquoise waters and a rocky outcrop.

15. Modern vacation home with private yard, steps to the beach and centrally located

Modern vacation home with private yard, steps to the beach and centrally located
Mt Thompson
10.0 out of 10, Exceptional, (48 reviews)
"Our family of four adults had a great stay at this home! It was so comfortable, clean and well stocked. We had everything we needed. It’s in a quiet neighborhood near a beautiful beach. We would recommend it to anyone and will be back!"
United States
Penny W.
The price is ￥43,472
￥75,720 total
includes taxes & fees
Oct 17 - Oct 18
Modern vacation home with private yard, steps to the beach and centrally located
A coastal landscape with a rocky cliff and a beach.

16. Spacious Home with Beach Gear and Outdoor Space

Spacious Home with Beach Gear and Outdoor Space
Esperanza
10.0 out of 10, Exceptional, (37 reviews)
"Such a wonderful home! Location was perfect, home was clean and had all the amenities, would stay here again easily."
United States
Jill K.
The price is ￥27,087
￥49,400 total
includes taxes & fees
Oct 25 - Oct 26
Spacious Home with Beach Gear and Outdoor Space
A dining area with a table, chairs, and a mirror.

17. La Casita del Este

La Casita del Este
Fajardo
10.0 out of 10, Exceptional, (11 reviews)
"Excellent place but location is a bit out of the way."
United States
Kristina M.
The price is ￥14,069
￥32,063 total
includes taxes & fees
Oct 20 - Oct 21
La Casita del Este
A patio area with a table and chairs, surrounded by large banana plants and a white wall.

18. Isla Verde Walk To Beach -Bars-Restaurants Near Airport Good for a Stop-N-Go

Isla Verde Walk To Beach -Bars-Restaurants Near Airport Good for a Stop-N-Go
Isla Verde
9.2 out of 10, Wonderful, (53 reviews)
"It was so nice staying at this place! Easy check in and out! Truly recommended! Close to beach and restaurants!"
United States
Vadym
The price is ￥10,670
￥21,345 total
includes taxes & fees
Oct 20 - Oct 21
Isla Verde Walk To Beach -Bars-Restaurants Near Airport Good for a Stop-N-Go
A table with two glasses of champagne and a flower, overlooking a body of water and a grassy area.

19. Romantic Beachfront Paradise Villa with Incredible Ocean Views & Outdoor Event Space

Romantic Beachfront Paradise Villa with Incredible Ocean Views & Outdoor Event Space
Islote Arecibo
9.2 out of 10, Wonderful, (95 reviews)
"What a fantastic place. Very unique and very beautiful. We thoroughly enjoyed our stay and highly recommend!"
United States
Anonymous traveler
The price is ￥21,287
￥39,540 total
includes taxes & fees
Oct 17 - Oct 18
Romantic Beachfront Paradise Villa with Incredible Ocean Views & Outdoor Event Space
A beach with clear turquoise water, rocky shoreline, and palm trees.

20. Kas di Amor: Ocean Views, Walk Downtown, Amazing House Reef, 2 Bedroom House

Kas di Amor: Ocean Views, Walk Downtown, Amazing House Reef, 2 Bedroom House
Playa
10.0 out of 10, Exceptional, (31 reviews)
"Great place for the two of us. Quiet, super convenient, pleasant in every aspect ! Would highly recommend & absolutely stay again."
United States
Andrea L.
The price is ￥23,500
￥30,977 total
includes taxes & fees
Oct 18 - Oct 19
Kas di Amor: Ocean Views, Walk Downtown, Amazing House Reef, 2 Bedroom House
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 Islands Hotel Reviews

Hotel Riu Montego Bay - Adults Only - All Inclusive

Hotel Riu Montego Bay - Adults Only - All Inclusive

10/10 Excellent
"It was good"
Christina 4-night trip
Posted 1 hour ago
Hotel Riu Montego Bay - Adults Only - All Inclusive

Find out more about Caribbean Islands

Caribbean Islands Vacation Homes information

Number of reviews
1,050
Accommodation
172 Vacation Homes
Lowest Price
￥14,086
Highest Price
￥118,639