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

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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 ￥19,731
￥25,379 total
includes taxes & fees
Oct 19 - Oct 20
150 Sol by Stay with Bear
A hotel room with two beds, a nightstand, and a wall-mounted string of decorative leaves.

2. Villa Mar

Villa Mar
2.5 star property
Punta Cana
The price is ￥11,919
￥14,064 total
includes taxes & fees
Oct 6 - Oct 7
Villa Mar
An aerial view of a beach resort with a clear blue sea, a sandy beach, and a building with a blue roof.

3. 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 ￥27,624
￥118,467 total
includes taxes & fees
Oct 22 - Oct 23
Great Location, beautiful home on the water,beach, pool and top amenities
A beach scene with two people running.

4. 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 ￥4,748
￥32,666 total
includes taxes & fees
Oct 17 - Oct 18
Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach
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 ￥18,468
￥44,928 total
includes taxes & fees
Oct 6 - Oct 7
Sophisticated Beach Condo-Ocean View-Sapphire
A beach with a wooden pier, lounge chairs, and jet skis.

6. 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, (68 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 ￥21,310
￥96,999 total
includes taxes & fees
Oct 31 - Nov 1
Amazing Beachfront home the calm side of the island. Swimming & kayaking
A poolside area with lounge chairs, a wooden deck, and a view of the ocean.

7. 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 ￥42,925
￥54,944 total
includes taxes & fees
Oct 13 - Oct 14
Watermark Luxury Oceanfront All Suite Hotel
A modern bedroom with a large bed, bedside tables with lamps, a wardrobe, and an air conditioning unit.

8. 1120 Vieques by Stay with Bear

1120 Vieques by Stay with Bear
3.5 star property
Santurce
9.2 out of 10, Wonderful, (190 reviews)
"Amazing stay"
United States
Stanley
The price is ￥14,633
￥15,950 total
includes taxes & fees
Nov 2 - Nov 3
1120 Vieques by Stay with Bear
A clear view of Canuck Palms beach with turquoise waters and a rocky outcrop.

9. 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 ￥43,409
￥75,768 total
includes taxes & fees
Oct 5 - Oct 6
Modern vacation home with private yard, steps to the beach and centrally located
A wooden deck with two Adirondack chairs facing a body of water, a flag, and a view of green hills.

10. 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 ￥29,992
￥47,277 total
includes taxes & fees
Oct 5 - Oct 6
SPECTACULAR Ensenada View @ Villa Ilusion Villa 2 - Punta Aloe #1
A wooden deck with a hammock and a chair, overlooking a body of water and hills.

11. 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 ￥38,200
￥64,504 total
includes taxes & fees
Oct 18 - Oct 19
SPECTACULAR Ensenada View @ Villa Ilusion Villa 3 - Punta Aloe #1
Terrace/patio

12. 3BR 3BA Home w/ Pool & Tropical Garden

3BR 3BA Home w/ Pool & Tropical Garden
4.0 star property
Papaya
The price is ￥43,409
￥84,036 total
includes taxes & fees
Oct 5 - Oct 6
3BR 3BA Home w/ Pool & Tropical Garden
An outdoor bar area with a pool, covered seating, and a view of the pool.

13. BTS8

BTS8
3.0 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
The price is ￥14,357
￥24,561 total
includes taxes & fees
Oct 14 - Oct 15
BTS8
A beach with clear turquoise water, palm trees, and a few people.

14. 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 ￥8,341
￥27,357 total
includes taxes & fees
Oct 6 - Oct 7
Colinas del Atlantico Vacational House 1st Floor
A covered outdoor area with a wooden table and chairs, surrounded by lush greenery and a view of the landscape.

15. 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 ￥31,570
￥62,367 total
includes taxes & fees
Oct 5 - Oct 6
Casa Paradise Palms! Beautiful views from the rooftop. Walk to ferry/beach.
A stone-walled outdoor shower area with a metal rain showerhead.

16. 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 ￥22,099
￥30,623 total
includes taxes & fees
Oct 5 - Oct 6
Cozy one bedroom studio
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 ￥27,048
￥49,013 total
includes taxes & fees
Oct 6 - Oct 7
Spacious Home with Beach Gear and Outdoor Space
An outdoor kitchen with a gas stove, sink, and stone counter.

18. 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 ￥18,942
￥32,186 total
includes taxes & fees
Oct 7 - Oct 8
Garden Suite near the Beach and restaurants!
A beach with clear turquoise water, rocky shoreline, and palm trees.

19. 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 ￥23,466
￥30,932 total
includes taxes & fees
Oct 5 - Oct 6
Kas di Amor: Ocean Views, Walk Downtown, Amazing House Reef, 2 Bedroom House
A dining area with a table, chairs, and a mirror.

20. 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 ￥14,049
￥32,175 total
includes taxes & fees
Oct 5 - Oct 6
La Casita del Este
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

San Juan Airport Hotel

San Juan Airport Hotel

10/10 Excellent
"Love the breakfast."
Vilmarie 1-night trip
Posted less than an hour ago
San Juan Airport Hotel

Find out more about Caribbean Islands

Caribbean Islands Vacation Homes information

Number of reviews
925
Accommodation
172 Vacation Homes
Lowest Price
￥14,064
Highest Price
￥118,467