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 dining area with a wooden table, white chairs, and a ceiling fan.

1. 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 ￥18,559
￥19,858 total
includes taxes & fees
Oct 19 - Oct 20
Blue House Joyuda
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 ￥19,712
￥25,353 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.

3. Villa Mar

Villa Mar
2.5 star property
Punta Cana
The price is ￥11,932
￥14,079 total
includes taxes & fees
Oct 19 - Oct 20
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 ￥15,470
￥16,862 total
includes taxes & fees
Nov 2 - Nov 3
1120 Vieques by Stay with Bear
Interior

5. Slice of Paradise- 2 mins from Spotts Beach!

Slice of Paradise- 2 mins from Spotts Beach!
Patricks Island
8.4 out of 10, Very good, (31 reviews)
"Quiet and convenient, was exactly what we needed for a nights stay!!!!"
United States
Matt D.
The price is ￥22,123
￥27,180 total
includes taxes & fees
Oct 19 - Oct 20
Slice of Paradise- 2 mins from Spotts Beach!
An outdoor seating area with a pool view, covered by white canopies, and surrounded by potted plants.

6. 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 ￥18,488
￥45,135 total
includes taxes & fees
Oct 19 - Oct 20
Sophisticated Beach Condo-Ocean View-Sapphire
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 ￥42,027
￥56,957 total
includes taxes & fees
Oct 20 - Oct 21
Watermark Luxury Oceanfront All Suite Hotel
A wooden deck with a hammock and a chair, overlooking a body of water and hills.

8. 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 ￥33,026
￥60,890 total
includes taxes & fees
Oct 19 - Oct 20
SPECTACULAR Ensenada View @ Villa Ilusion Villa 3 - Punta Aloe #1
An outdoor kitchen with a gas stove, sink, and stone counter.

9. "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 ￥15,802
￥28,681 total
includes taxes & fees
Oct 19 - Oct 20
"Garden" Suite near the beach and restaurants!
A beach with a wooden pier, lounge chairs, and jet skis.

10. 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 ￥23,703
￥99,553 total
includes taxes & fees
Oct 31 - Nov 1
Amazing Beachfront home the calm side of the island. Swimming & kayaking
A clear view of Canuck Palms beach with turquoise waters and a rocky outcrop.

11. 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 ￥43,456
￥75,692 total
includes taxes & fees
Oct 19 - Oct 20
Modern vacation home with private yard, steps to the beach and centrally located
A hotel room with a bed, desk, chair, and an air conditioning unit.

12. Cozy Beach Apartment

Cozy Beach Apartment
Aguadilla Pueblo
10.0 out of 10, Exceptional, (14 reviews)
"Very clean and close to the beach"
United States
Rendiluis
The price is ￥9,671
￥21,962 total
includes taxes & fees
Oct 21 - Oct 22
Cozy Beach Apartment
A coastal landscape with a rocky cliff and a beach.

13. 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 ￥27,077
￥49,382 total
includes taxes & fees
Oct 19 - Oct 20
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.

14. 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 ￥31,604
￥64,080 total
includes taxes & fees
Oct 19 - Oct 20
Casa Paradise Palms! Beautiful views from the rooftop. Walk to ferry/beach.
A beach with clear turquoise water, rocky shoreline, and palm trees.

15. 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 ￥23,491
￥30,965 total
includes taxes & fees
Oct 20 - Oct 21
Kas di Amor: Ocean Views, Walk Downtown, Amazing House Reef, 2 Bedroom House
A table with two glasses of champagne and a flower, overlooking a body of water and a grassy area.

16. 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 ￥21,279
￥39,684 total
includes taxes & fees
Oct 19 - Oct 20
Romantic Beachfront Paradise Villa with Incredible Ocean Views & Outdoor Event Space
An aerial view of a beach resort with a clear blue sea, a sandy beach, and a building with a blue roof.

17. 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 ￥27,654
￥118,595 total
includes taxes & fees
Oct 22 - Oct 23
Great Location, beautiful home on the water,beach, pool and top amenities
A modern kitchen with a built-in oven, a refrigerator, and a dining area with a table set for four.

18. Phoenix Park Villas Portmore

Phoenix Park Villas Portmore
4.0 star property
Portmore
9.2 out of 10, Wonderful, (7 reviews)
"I will definitely recommend that you stay here is so peaceful security are strictly on point with everything and the comfort of the home is great will be staying back for sure ."
United States
Kimoya
The price is ￥42,665
￥70,491 total
includes taxes & fees
Oct 19 - Oct 20
Phoenix Park Villas Portmore
A patio area with a table and chairs, surrounded by large banana plants and a white wall.

19. 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 ￥10,666
￥21,337 total
includes taxes & fees
Oct 20 - Oct 21
Isla Verde Walk To Beach -Bars-Restaurants Near Airport Good for a Stop-N-Go
A stone-walled outdoor shower area with a metal rain showerhead.

20. 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 ￥22,123
￥30,656 total
includes taxes & fees
Oct 21 - Oct 22
Cozy one bedroom studio
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

Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

10/10 Excellent
"Beautiful view and excellent service"
Stuart Donald 7-night trip
Posted 1 hour ago
Princess Grand Jamaica Resort - All Inclusive

Find out more about Caribbean Islands

Caribbean Islands Vacation Homes information

Number of reviews
1,095
Accommodation
172 Vacation Homes
Lowest Price
￥14,079
Highest Price
￥118,595