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

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Caribbean Islands 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, (192 reviews)
"Amazing stay"
United States
Stanley
The price is ￥16,201
￥17,659 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 ￥22,264
￥28,637 total
includes taxes & fees
Oct 25 - Oct 26
150 Sol by Stay with Bear
A beach with a wooden pier, lounge chairs, and jet skis.

3. 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 ￥21,317
￥96,398 total
includes taxes & fees
Oct 31 - Nov 1
Amazing Beachfront home the calm side of the island. Swimming & kayaking
An aerial view of a beach resort with a clear blue sea, a sandy beach, and a building with a blue roof.

4. 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 ￥27,650
￥118,579 total
includes taxes & fees
Oct 22 - Oct 23
Great Location, beautiful home on the water,beach, pool and top amenities
A wooden deck with a hammock and a chair, overlooking a body of water and hills.

5. 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 ￥38,212
￥66,577 total
includes taxes & fees
Nov 9 - Nov 10
SPECTACULAR Ensenada View @ Villa Ilusion Villa 3 - Punta Aloe #1
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 ￥41,523
￥53,150 total
includes taxes & fees
Oct 16 - Oct 17
Watermark Luxury Oceanfront All Suite Hotel
A dining area with a table, chairs, and a mirror.

7. 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.
La Casita del Este
A beach with clear turquoise water, palm trees, and a few people.

8. Colinas del Atlantico Vacational House 1st Floor

Colinas del Atlantico Vacational House 1st Floor
3.5 star property
Isabela
9.0 out of 10, Wonderful, (36 reviews)
"We enjoyed how spaciuos and clean the property is. Highly recommend!!!!"
United States
Chris and Devon
The price is ￥12,002
￥31,891 total
includes taxes & fees
Oct 25 - Oct 26
Colinas del Atlantico Vacational House 1st Floor
An outdoor seating area with a pool view, covered by white canopies, and surrounded by potted plants.

9. 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 ￥18,474
￥45,101 total
includes taxes & fees
Oct 10 - Oct 11
Sophisticated Beach Condo-Ocean View-Sapphire
Property grounds

10. 3BR 3BA Home w/ Pool & Tropical Garden

3BR 3BA Home w/ Pool & Tropical Garden
4.0 star property
Papaya
The price is ￥43,423
￥84,063 total
includes taxes & fees
Oct 14 - Oct 15
3BR 3BA Home w/ Pool & Tropical Garden
A beach with clear water, a sandy shore, and a rocky outcrop in the distance.

11. Casa vacacional en Arenales Isabela

Casa vacacional en Arenales Isabela
3.5 star property
Isabela
9.0 out of 10, Wonderful, (50 reviews)
"The property was nice and clean quiet area had everything included inside the house sent you air and the bedrooms were nice"
United States
Jaime
The price is ￥14,416
￥34,880 total
includes taxes & fees
Oct 13 - Oct 14
Casa vacacional en Arenales Isabela
A wooden deck with two Adirondack chairs facing a body of water, a flag, and a view of green hills.

12. SPECTACULAR Ensenada View @ Villa Ilusion Villa 2 - Punta Aloe #1

SPECTACULAR Ensenada View @ Villa Ilusion Villa 2 - Punta Aloe #1
Playa Sardinas II
9.0 out of 10, Wonderful, (29 reviews)
"Excellent view quiet peaceful very relaxing cold air inside had a blast "
United States
Randall
The price is ￥30,001
￥47,291 total
includes taxes & fees
Nov 9 - Nov 10
SPECTACULAR Ensenada View @ Villa Ilusion Villa 2 - Punta Aloe #1
A beach scene with two people running.

13. Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach

Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach
4.0 star property
Falmouth Historic Town Centre
10.0 out of 10, Exceptional, (21 reviews)
"This is my first time staying here, and it is a must-do! It has a great location, 24/7 security, and amazing amenities! The peace of the surrounding areas was also a great benefit to staying here! "
United States
Marcia
The price is ￥4,750
￥32,676 total
includes taxes & fees
Oct 18 - Oct 19
Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach
An outdoor bar area with a pool, covered seating, and a view of the pool.

14. BTS8

BTS8
3.0 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
The price is ￥14,361
￥24,568 total
includes taxes & fees
Oct 23 - Oct 24
BTS8
An outdoor kitchen with a gas stove, sink, and stone counter.

15. Garden Suite near the Beach and restaurants!

Garden Suite near the Beach and restaurants!
Ucares
9.8 out of 10, Exceptional, (96 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 ￥18,948
￥32,196 total
includes taxes & fees
Oct 12 - Oct 13
Garden Suite near the Beach and restaurants!
A clear view of Canuck Palms beach with turquoise waters and a rocky outcrop.

16. 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 ￥43,423
￥75,793 total
includes taxes & fees
Oct 11 - Oct 12
Modern vacation home with private yard, steps to the beach and centrally located
A coastal landscape with a rocky cliff and a beach.

17. 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 ￥27,056
￥49,501 total
includes taxes & fees
Oct 14 - Oct 15
Spacious Home with Beach Gear and Outdoor Space
A covered outdoor area with a wooden table and chairs, surrounded by lush greenery and a view of the landscape.

18. 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 ￥31,580
￥64,032 total
includes taxes & fees
Oct 10 - Oct 11
Casa Paradise Palms! Beautiful views from the rooftop. Walk to ferry/beach.
A balcony with a view of a marina and the sea.

19. Top of the Hill Blue Sunshine

Top of the Hill Blue Sunshine
Parham Town
10.0 out of 10, Exceptional, (14 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 ￥31,580
￥54,160 total
includes taxes & fees
Oct 10 - Oct 11
Top of the Hill Blue Sunshine
A balcony with a view of the beach, a table with chairs, and a hammock.

20. Ocean Front-Great Location

Ocean Front-Great Location
Playa Fortuna
9.8 out of 10, Exceptional, (70 reviews)
"Wonderful apartment and great beach. Close to everything. Highly recommend;"
United States
Heidi
The price is ￥17,685
￥40,082 total
includes taxes & fees
Oct 23 - Oct 24
Ocean Front-Great Location
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

Embassy Suites by Hilton San Juan Hotel & Casino

Embassy Suites by Hilton San Juan Hotel & Casino

10/10 Excellent
"Everything"
Immanuel S 3-night trip
Posted 1 hour ago
Embassy Suites by Hilton San Juan Hotel & Casino

Find out more about Caribbean Islands

Caribbean Islands Vacation Homes information

Number of reviews
1,021
Accommodation
172 Vacation Homes
Lowest Price
￥17,659
Highest Price
￥118,579