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

Holiday Homes in Caribbean Islands

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Caribbean Islands holiday 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, (65 reviews)
"Great location !Parking sucks , if you drive park on one of the parking garage"
United States
Amy
The price is AU$228
includes taxes & fees
20 Oct - 21 Oct
150 Sol by Stay with Bear
A dining area with a wooden table, white chairs, and a ceiling fan.

2. Blue House Joyuda

Blue House Joyuda
3.5 star property
Cabo Rojo
9.4 out of 10, Exceptional, (53 reviews)
"Excelent place in front of the ocean, beautiful property"
United States
Samary
The price is AU$197
includes taxes & fees
8 Oct - 9 Oct
Blue House Joyuda
A swimming pool with a waterfall feature, surrounded by stone tiles and potted plants.

3. Villa Carmin I Apt with Private Pool

Villa Carmin I Apt with Private Pool
3.5 star property
Aguadilla
8.8 out of 10, Excellent, (3 reviews)
"This place was perfect, dog friendly, convenient and close enough to beaches. The place was clean and well supplied."
United States
Elba
The price is AU$392
includes taxes & fees
5 Oct - 6 Oct
Villa Carmin I Apt with Private Pool
A balcony with two chairs, a tiled floor, and a view of a blue-roofed building and green hedges.

4. Montones Beach Apartment C-3

Montones Beach Apartment C-3
3.0 star property
Jobos
8.2 out of 10, Very good, (54 reviews)
"Excellent, awesome 👌 The best place to go vacations "
United States
Felix
The price is AU$305
includes taxes & fees
6 Oct - 7 Oct
Montones Beach Apartment C-3
A modern kitchen with a central island, stainless steel appliances, and two bar stools.

5. Home away II

Home away II
Cangrejo Arriba
9.0 out of 10, Wonderful, (31 reviews)
"Everything was wonderful at the property. The entire place was clean. I would definitely recommend this place."
United States
Delroy
The price is AU$317
includes taxes & fees
26 Sept - 27 Sept
Home away II
A dining area with a table, chairs, and a mirror.

6. 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 AU$282
includes taxes & fees
25 Sept - 26 Sept
La Casita del Este
An outdoor kitchen with a gas stove, sink, and stone counter.

7. 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 AU$294
includes taxes & fees
25 Sept - 26 Sept
Garden Suite near the Beach and restaurants!
A swimming pool with lounge chairs and a signboard.

8. This is a three bedrooms three bathrooms house that is fully furnihsed

This is a three bedrooms three bathrooms house that is fully furnihsed
Florence Hall
9.0 out of 10, Wonderful, (13 reviews)
"Quick check in and great communications and house was very clean will definitely be staying again."
United States
Ava
The price is AU$267
includes taxes & fees
25 Sept - 26 Sept
This is a three bedrooms three bathrooms house that is fully furnihsed
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

9. Anchor's Away, Russell Island

Anchor's Away, Russell Island
Russell Island
10.0 out of 10, Exceptional, (43 reviews)
"Beautiful home, location and hosts were flexible and fantastic. "
United States
Allan
The price is AU$497
includes taxes & fees
28 Sept - 29 Sept
Anchor's Away, Russell Island
An outdoor bar area with a pool, covered seating, and a view of the pool.

10. BTS8

BTS8
3.0 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
The price is AU$230
includes taxes & fees
25 Sept - 26 Sept
BTS8
A bedroom with a bed, a bedside table, a lamp, and a wardrobe.

11. Villa Mar

Villa Mar
2.5 star property
Punta Cana
The price is AU$127
includes taxes & fees
25 Sept - 26 Sept
Villa Mar
A kitchen with white cabinets, a granite countertop, a refrigerator, a stove, and a microwave.

12. Cozy Tropical Vacation home 10 minutes away from beaches and attractions

Cozy Tropical Vacation home 10 minutes away from beaches and attractions
Soufriere
10.0 out of 10, Exceptional, (8 reviews)
"We had such a wonderful stay in Saint Lucia with Jenelle! Her place was very clean and spacious with a nice terrace. We had everything we need! She was incredibly kind, welcoming and generous throughout our visit. One of the sweetest touches was when she generously shared fresh fruits and vegetables with us (avocados, bananas, lemons, oranges, coconut) a thoughtful gesture that made us feel right at home. Oh I almost forgot the eggs from her farm 😊 We truly appreciated her hospitality and...
Canada
Antonio
The price is AU$200
includes taxes & fees
25 Sept - 26 Sept
Cozy Tropical Vacation home 10 minutes away from beaches and attractions
A covered outdoor area with a wooden table and chairs, surrounded by lush greenery and a view of the landscape.

13. 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)
"We stayed one night and it was perfect for what we needed! The property is great, the location is a bit out of the way from everything, but getting a taxi to take us to and from was no issue at all. "
United States
Ashley H.
The price is AU$505
includes taxes & fees
25 Sept - 26 Sept
Casa Paradise Palms! Beautiful views from the rooftop. Walk to ferry/beach.
A modern kitchen with a built-in oven, a refrigerator, and a dining area with a table set for four.

14. Phoenix Park Villas Portmore

Phoenix Park Villas Portmore
4.0 star property
Portmore
9.8 out of 10, Exceptional, (6 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 AU$470
includes taxes & fees
23 Oct - 24 Oct
Phoenix Park Villas Portmore
A bedroom with a bed, bedside lamps, a ceiling fan, a mirror, a wooden door, and a potted plant.

15. Vacation Family Home-5min from STI airport sleep 6 WiFi +Netflix

Vacation Family Home-5min from STI airport sleep 6 WiFi +Netflix
Ortega
9.8 out of 10, Exceptional, (7 reviews)
"This house is sooo nice. AC In every room,quality furniture, clean. It’s much more cared for than most rentals, and I’ve done ALOT!"
United States
Matthew
The price is AU$152
includes taxes & fees
28 Sept - 29 Sept
Vacation Family Home-5min from STI airport sleep 6 WiFi +Netflix
A small, well-lit room with a bed, a desk, and a window.

16. The YellowButterfly Tiny House

The YellowButterfly Tiny House
Nassau
9.4 out of 10, Exceptional, (21 reviews)
"Very clean, safe environment."
United States
Warren
The price is AU$183
includes taxes & fees
29 Sept - 30 Sept
The YellowButterfly Tiny House
A living room with a sofa, a glass coffee table, and red patterned curtains.

17. Charming 2-bedroom house in Portmore with WiFi, AC

Charming 2-bedroom house in Portmore with WiFi, AC
Portmore
10.0 out of 10, Exceptional, (8 reviews)
"Room was spotless, very caring host."
United Kingdom
Sophia
The price is AU$132
includes taxes & fees
25 Sept - 26 Sept
Charming 2-bedroom house in Portmore with WiFi, AC
A modern bedroom with a large bed, bedside tables with lamps, a wardrobe, and an air conditioning unit.

18. 1120 Vieques by Stay with Bear

1120 Vieques by Stay with Bear
3.5 star property
Santurce
9.2 out of 10, Wonderful, (188 reviews)
"Amazing stay"
United States
Stanley
The price is AU$187
includes taxes & fees
27 Sept - 28 Sept
1120 Vieques by Stay with Bear
An aerial view of a coastal area with a beach, clear blue waters, and buildings along the shore.

19. Colinas del Atlantico Vacational House 2nd Floor

Colinas del Atlantico Vacational House 2nd Floor
3.5 star property
Isabela
8.0 out of 10, Very good, (34 reviews)
"Quiet place, very clean, modern Apt. "
United States
Gerardo
The price is AU$251
includes taxes & fees
30 Sept - 1 Oct
Colinas del Atlantico Vacational House 2nd Floor
A sunset over the ocean with string lights above a beach.

20. Casa Seael- Beach House

Casa Seael- Beach House
Aguadilla Pueblo
8.6 out of 10, Excellent, (18 reviews)
"Location and Conform"
United States
Luis
The price is AU$331
includes taxes & fees
4 Oct - 5 Oct
Casa Seael- Beach House
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

Hyatt Vacation Club at Hacienda del Mar, Dorado

Hyatt Vacation Club at Hacienda del Mar, Dorado

10/10 Excellent
"Everything"
Melissa 3-night trip
Posted less than an hour ago
Hyatt Vacation Club at Hacienda del Mar, Dorado

Find out more about Caribbean Islands

Caribbean Islands Holiday Homes information

Number of reviews
546
Accommodation
166 Holiday Homes
Lowest Price
AU$127
Highest Price
AU$505