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

Caribbean Islands Private Home Rentals

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Check prices for these dates

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

Our top choices for Caribbean Islands holiday 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 S$143
includes taxes & fees
2 Nov - 3 Nov
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 S$232
includes taxes & fees
25 Oct - 26 Oct
150 Sol by Stay with Bear
A poolside area with lounge chairs, a wooden deck, and a view of the ocean.

3. 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 S$431
includes taxes & fees
16 Oct - 17 Oct
Watermark Luxury Oceanfront All Suite Hotel
A beach with clear turquoise water, palm trees, and a few people.

4. 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 S$259
includes taxes & fees
25 Oct - 26 Oct
Colinas del Atlantico Vacational House 1st Floor
Property grounds

5. 3BR 3BA Home w/ Pool & Tropical Garden

3BR 3BA Home w/ Pool & Tropical Garden
4.0 star property
Papaya
The price is S$681
includes taxes & fees
18 Oct - 19 Oct
3BR 3BA Home w/ Pool & Tropical Garden
A beach with clear water, a sandy shore, and a rocky outcrop in the distance.

6. 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 S$283
includes taxes & fees
13 Oct - 14 Oct
Casa vacacional en Arenales Isabela
A beach scene with two people running.

7. 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 S$265
includes taxes & fees
20 Oct - 21 Oct
Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach
An outdoor bar area with a pool, covered seating, and a view of the pool.

8. BTS8

BTS8
3.0 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
The price is S$206
includes taxes & fees
23 Oct - 24 Oct
BTS8
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

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

10/10 Excellent
"We had an amazing time at the hotel, the restaurants were great and the staff was amazing. The only thing I thought is the housekeeping staff need to be more consistent in the rooms and around the hotel. We really recommend this hotel to anyone. We stayed the first week of October."
Norma 5-night trip
Posted less than an hour ago
Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

Find out more about Caribbean Islands

Caribbean Islands Private Holiday Homes information

Number of reviews
412
Accommodation
30 Private Holiday Homes
Lowest Price
S$143
Highest Price
S$681