A tropical beach with clear turquoise waters, lush green hills, and a small red building on a hill.

Caribbean Vacation Rentals

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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

Top Cities in Caribbean

A pier with kayaks and a sailboat.
Vacation HomesVacation Homes

Montego Bay

Montego Bay

Our top choices for Caribbean vacation 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, (190 reviews)
"Amazing stay"
United States
Stanley
The price is CA $132
CA $144 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $178
CA $229 total
includes taxes & fees
Oct 19 - Oct 20
150 Sol by Stay with Bear
A living room with a sofa, a TV, a lamp, and a painting on the wall.

3. 152 Sol by Stay with Bear

152 Sol by Stay with Bear
2.5 star property
Old San Juan
9.6 out of 10, Exceptional, (4 reviews)
"We had a great stay! The place was very clean, tidy, and exactly as expected. The location was perfect, and the host was very helpful and responsive. We really enjoyed our time here and would definitely stay again!"
Canada
Nicole
The price is CA $226
CA $247 total
includes taxes & fees
Oct 5 - Oct 6
152 Sol by Stay with Bear
A beach with clear turquoise water, a sandy shore, and wooden deck chairs under blue umbrellas.

4. Private Pool House By the Beach. 3 Min Walk to Grace Bay Beach • Sleeps 4

Private Pool House By the Beach. 3 Min Walk to Grace Bay Beach • Sleeps 4
Grace Bay
10.0 out of 10, Exceptional, (69 reviews)
"It was a great place to stay. It was very clean and had all the amenities that we needed. Loved to pool. Location was great and parking was available."
United States
Kellie C.
Private Pool House By the Beach. 3 Min Walk to Grace Bay Beach • Sleeps 4
A modern building with a staircase leading to a door, surrounded by greenery and white railings.

5. Alto Vista Hills

Alto Vista Hills
3.5 star property
Noord
8.8 out of 10, Excellent, (13 reviews)
"Good room, perfect for 2 people(the suite we got) Pretty clean, AC was nice No laundry at facility- I think maybe adding a drying rack would be nice :). Other than that everything went very smooth and it was very fun"
United States
Jacob
Alto Vista Hills
A covered outdoor seating area with a view of the ocean, a pool, and lounge chairs.

6. Ocean Front Property With Pool. - George Town

Ocean Front Property With Pool. - George Town
Exuma
9.4 out of 10, Exceptional, (50 reviews)
"Beautiful views, kayaks and paddle boards are provided to take advantage of the water. Quiet, peaceful area to unwind and relax."
United States
Jennifer P.
Ocean Front Property With Pool. - George Town
A compact kitchen with a microwave, sink, and washing machine. There is a small dining area with stools and a table.

7. Residence Nokoshima

Residence Nokoshima
Fort-de-France
9.6 out of 10, Exceptional, (4 reviews)
"The apartment was very clean, a good price, but much smaller than the pictures make it look."
Canada
Karen
Residence Nokoshima
A modern living room with a grey sofa set, a white coffee table, and a kitchen area in the background.

8. Coral Cove: Nearby Baha Mar, Pool & Patio, Gated, Beach Walkable

Coral Cove: Nearby Baha Mar, Pool & Patio, Gated, Beach Walkable
Cable Beach
9.6 out of 10, Exceptional, (9 reviews)
"Great stay! "
Canada
Locke D.
The price is CA $256
CA $550 total
includes taxes & fees
Oct 4 - Oct 5
Coral Cove: Nearby Baha Mar, Pool & Patio, Gated, Beach Walkable
A swimming pool with lounge chairs and palm trees, surrounded by buildings and a clear sky.

9. NÔA curacao

NÔA curacao
4.0 star property
Saliña
9.8 out of 10, Exceptional, (7 reviews)
"Beds were comfortable, a lot of kitchen utensils so cooking was easy there. Great location. Nice outdoor sitting area. You don't have a lot of privacy though."
United States
Stephanie
NÔA curacao
A beach with clear water, rocks, and a distant mountain.

10. OCEAN VIEW VILLA WITH PRIVATE POOL, STEPS FROM SECLUDED BEACH, GATED COMMUNITY!

OCEAN VIEW VILLA WITH PRIVATE POOL, STEPS FROM SECLUDED BEACH, GATED COMMUNITY!
Yabucoa
10.0 out of 10, Exceptional, (171 reviews)
"Amazing property with beach and pool amenities. This was our second time staying at this location. We love it. The only drawback, which is why we choose it, is it is located on the South side of the island and distant from most tourist items."
United States
Jason M.
OCEAN VIEW VILLA WITH PRIVATE POOL, STEPS FROM SECLUDED BEACH, GATED COMMUNITY!
A modern outdoor seating area with two blue wicker chairs, a small round table, and a potted plant.

11. Luxurious and Beautiful Isla Verde Beach house with private pool

Luxurious and Beautiful Isla Verde Beach house with private pool
Isla Verde
9.6 out of 10, Exceptional, (84 reviews)
"We loved the location and the house amenities. There are power and water struggles in San Juan, but the house had a generator and cistern."
United States
Jeannie W.
Luxurious and Beautiful Isla Verde Beach house with private pool
A pool with lounge chairs and palm trees, overlooking a clear blue ocean.

12. Oceanfront Paradise in Exuma: Pool, Kayaks & Stunning Views Await You!

Oceanfront Paradise in Exuma: Pool, Kayaks & Stunning Views Await You!
Ramsey
10.0 out of 10, Exceptional, (153 reviews)
"This was our 4th trip and this house was our favorite. Amazing…"
United States
Lisa A.
Oceanfront Paradise in Exuma: Pool, Kayaks & Stunning Views Await You!
A balcony with a view of the beach, a table with chairs, and a hammock.

13. Ocean Front-Great Location

Ocean Front-Great Location
Playa Fortuna
9.8 out of 10, Exceptional, (69 reviews)
"Wonderful apartment and great beach. Close to everything. Highly recommend;"
United States
Heidi
The price is CA $159
CA $362 total
includes taxes & fees
Oct 21 - Oct 22
Ocean Front-Great Location
A dining area with a wooden table, white chairs, and a ceiling fan.

14. 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 CA $184
CA $197 total
includes taxes & fees
Oct 8 - Oct 9
Blue House Joyuda
A pool area with lounge chairs and umbrellas, a stone wall, and a view of the ocean.

15. Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!

Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!
Cayman Islands
9.8 out of 10, Exceptional, (68 reviews)
"Everything was perfect for our family."
United States
Nancy N.
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!
A swimming pool with lounge chairs, a thatched-roof structure, and a white building in the background.

16. 7BR Oasis in Paradise on One Happy Island

7BR Oasis in Paradise on One Happy Island
Palm Beach
9.8 out of 10, Exceptional, (18 reviews)
"Amazing place to stay. The hostess was wonderful and very caring. We hd a great time."
United States
Michelle’s World Travel & Cruises
7BR Oasis in Paradise on One Happy Island
A bedroom with a large bed, a view of the beach, and a wooden deck.

17. The Sandbar Luxury Oceanfront Home, 5 Bedroom 5 Bath, Infinity Pool/Hot Tub

The Sandbar Luxury Oceanfront Home, 5 Bedroom 5 Bath, Infinity Pool/Hot Tub
Exuma
10.0 out of 10, Exceptional, (129 reviews)
"The Sandbar is a beautiful beachfront home. We were there this past week and it was the perfect place for our family. The location is perfect and plenty of beach which some houses don’t have much. I think I saw 3 people on the beach. The pool and hot tub are very enjoyable. Great for a big family. Communication with the host was excellent as well. There was not a negative with this house. Love the sandbar!"
United States
Gwen M.
The Sandbar Luxury Oceanfront Home, 5 Bedroom 5 Bath, Infinity Pool/Hot Tub
A pool with a view of a beach and ocean.

18. Blue Hues! Secluded Exuma Beachfront + Private Pool / Whole-House Generator

Blue Hues! Secluded Exuma Beachfront + Private Pool / Whole-House Generator
George Town
10.0 out of 10, Exceptional, (248 reviews)
"Outstanding rental…we loved every minute in this beautiful house with its stunning views. Would highly recommend!"
United States
Samantha C.
Blue Hues! Secluded Exuma Beachfront + Private Pool / Whole-House Generator
A bedroom with a large bed, a chair, a small table, and a view of the beach through a sliding door.

19. BeauSoleil Beach House, Luxury Private Ocean Front with Infinity Pool/Hot Tub

BeauSoleil Beach House, Luxury Private Ocean Front with Infinity Pool/Hot Tub
Exuma
10.0 out of 10, Exceptional, (128 reviews)
"Fantastic property on an absolutely gorgeous stretch of beach! We loved our stay and would highly recommend to anyone looking for a 5 star experience in Exuma. "
United States
Michael P.
BeauSoleil Beach House, Luxury Private Ocean Front with Infinity Pool/Hot Tub
A resort with a white building, outdoor seating, and palm trees.

20. Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.

Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.
North Side
10.0 out of 10, Exceptional, (12 reviews)
"Really enjoyed it. Couldn’t have been happier."
United States
James L.
Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.
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 Hotel Reviews

La Concha Resort, Puerto Rico, Autograph Collection

La Concha Resort, Puerto Rico, Autograph Collection

10/10 Excellent
"Beautiful resort, and wonderful personnel, kind and professional. Best of the best"
Oscar 3-night trip
Posted 2 hours ago
La Concha Resort, Puerto Rico, Autograph Collection

Price trends for hotels in Caribbean

Less expensive
More expensive
This month
Next month
July
May
CA $216
CA $208
Month
Price
January
CA $207
February
CA $207
March
CA $188
April
CA $195
May
CA $223
June
CA $191
July
CA $173
August
CA $186
September
CA $195
October
CA $216
November
CA $208
December
CA $217
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed Vacation Homes in Caribbean. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Caribbean

Caribbean Vacation Homes information

Number of reviews
1,091
Accommodation
11306 Vacation Homes
Lowest Price
CA $144
Highest Price
CA $550