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

Search Vacation Homes in Caribbean Islands

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Caribbean Islands vacation homes

1. Blue House Joyuda

Blue House Joyuda
3.5 star property
Cabo Rojo
9.6 out of 10, Exceptional, (55 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 21 - Oct 22
Blue House Joyuda

2. 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 21 - Oct 22
Slice of Paradise- 2 mins from Spotts Beach!

3. 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 ¥15,378
¥16,762 total
includes taxes & fees
Nov 2 - Nov 3
1120 Vieques by Stay with Bear

4. Villa Mar

Villa Mar
2.5 star property
Punta Cana
The price is ¥11,969
¥14,124 total
includes taxes & fees
Oct 21 - Oct 22
Villa Mar

5. 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 ¥20,086
¥25,835 total
includes taxes & fees
Nov 3 - Nov 4
150 Sol by Stay with Bear

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 ¥42,027
¥56,957 total
includes taxes & fees
Oct 31 - Nov 1
Watermark Luxury Oceanfront All Suite Hotel

7. 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
¥44,977 total
includes taxes & fees
Oct 21 - Oct 22
Sophisticated Beach Condo-Ocean View-Sapphire

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 ¥15,851
¥28,611 total
includes taxes & fees
Oct 21 - Oct 22
"Garden" Suite near the beach and restaurants!

9. 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 ¥23,777
¥99,862 total
includes taxes & fees
Oct 31 - Nov 1
Amazing Beachfront home the calm side of the island. Swimming & kayaking

10. 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)
"Cute property. Walking distance to town and a little market. Nice to have the beach chairs and beach towels. Washer and dryer were a must with beach days and snorkeling. Host was very responsive. Would stay again."
United States
Oona C.
The price is ¥27,077
¥49,065 total
includes taxes & fees
Oct 25 - Oct 26
Spacious Home with Beach Gear and Outdoor Space

11. Hermosa Villa - Piscina Privada

Hermosa Villa - Piscina Privada
Verón
9.0 out of 10, Wonderful, (22 reviews)
"Very nice and comfortable"
United States
Guillermo R.
The price is ¥12,800
¥19,933 total
includes taxes & fees
Oct 21 - Oct 22
Hermosa Villa - Piscina Privada

12. 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 21 - Oct 22
SPECTACULAR Ensenada View @ Villa Ilusion Villa 3 - Punta Aloe #1

13. 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 ¥11,482
¥31,315 total
includes taxes & fees
Oct 25 - Oct 26
Casa vacacional en Arenales Isabela

14. Cozy Beach Apartment

Cozy Beach Apartment
Aguadilla Pueblo
10.0 out of 10, Exceptional, (15 reviews)
"Very clean and close to the beach"
United States
Rendiluis
The price is ¥9,701
¥22,030 total
includes taxes & fees
Oct 21 - Oct 22
Cozy Beach Apartment

15. BTS5

BTS5
3.0 star property
Montego Bay
The price is ¥18,863
¥29,778 total
includes taxes & fees
Oct 25 - Oct 26
BTS5

16. 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 ¥14,064
¥32,051 total
includes taxes & fees
Oct 27 - Oct 28
La Casita del Este

17. 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 23 - Oct 24
Casa Paradise Palms! Beautiful views from the rooftop. Walk to ferry/beach.

18. 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 26 - Oct 27
Modern vacation home with private yard, steps to the beach and centrally located

19. Casita Chiquita #1

Casita Chiquita #1
Aguadilla
9.2 out of 10, Wonderful, (49 reviews)
"The house was perfect. It’s a great place to stay if you have an early flight, as it’s conveniently located close to the airport."
United States
Maria
The price is ¥12,168
¥16,180 total
includes taxes & fees
Oct 21 - Oct 22
Casita Chiquita #1

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
¥30,340 total
includes taxes & fees
Oct 26 - Oct 27
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Caribbean Islands Hotel Reviews

Find out more about Caribbean Islands

Caribbean Islands Vacation Homes information

Number of reviews
989
Accommodation
172 Vacation Homes
Lowest Price
¥14,124
Highest Price
¥99,862