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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (194 reviews)
"Amazing stay"
United States
Stanley
The price is CA $126
CA $138 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 $192
CA $247 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 $240
CA $261 total
includes taxes & fees
Oct 20 - Oct 21
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, (70 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)
"Very clean place The host and his Mom were very very helpful and very kind people Very fast response time with any help needed Would definitely stay there again"
United States
Douglas
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)
"This house was perfect for us! The AC was cool, the beds were comfy, there was a washer and dryer, and the water jug connecting to the fridge was so convenient and provided ICE! The property manager was quick to respond and everything was exactly as pictured. Had a great stay and would highly recommend!"
United States
Amber R.
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, (10 reviews)
"Great stay! "
Canada
Locke D.
The price is CA $319
CA $624 total
includes taxes & fees
Oct 19 - Oct 20
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, (172 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, (86 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, (156 reviews)
"We can’t say enough about how amazing our vacation was! We will definitely be back to this house! It’s perfectly situated in the middle of everywhere you want to go! The beach at the house is absolutely gorgeous. The kitchen is well equipped with everything you might need. The home was so clean and comfortable! The outdoor sitting area was perfect for afternoons!"
United States
Sabrina 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, (72 reviews)
"This was an amazing location. Through apartment was clean and well appointed. We had a wonderful stay!"
United States
Amanda L.
The price is CA $159
CA $366 total
includes taxes & fees
Oct 23 - Oct 24
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
9.6 out of 10, Exceptional, (54 reviews)
"Excelent place in front of the ocean, beautiful property"
United States
Samary
The price is CA $167
CA $178 total
includes taxes & fees
Oct 19 - Oct 20
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)
"Great house that was able to accommodate our family and each room having its own on suite bathroom was a plus."
United States
Michelle C.
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 pool with a view of a beach and ocean.

17. 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)
"This is our second time staying at Blu Hues for two weeks and it is paradise. The house is wonderful, the pool perfect and the "private beach" is the best. Rick is the perfect host who provides the best island information and communicates everything you need to travel to Exuma. We look forward to our next visit !"
United States
shellee h.
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.

18. 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)
"This property is amazing. Owners and property manager were fantastic. Would very highly recommend for anyone coming to the Bahamas."
United States
Chad G.
BeauSoleil Beach House, Luxury Private Ocean Front with Infinity Pool/Hot Tub
A resort with a white building, outdoor seating, and palm trees.

19. 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.
A poolside area with a clear pool, white lounge chairs, and a covered patio with steps leading to the pool.

20. 2bedroom beach front house in soothing Río Grande with AC and salt swimming pool

2bedroom beach front house in soothing Río Grande with AC and salt swimming pool
Zarzal
9.6 out of 10, Exceptional, (16 reviews)
"Wonderful property, great host. Our family truly enjoyed our stay."
United States
Carly M.
2bedroom beach front house in soothing Río Grande with AC and salt swimming pool
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

Hotel Rumbao, a Tribute Portfolio Hotel

Hotel Rumbao, a Tribute Portfolio Hotel

10/10 Excellent
"The hotel was very nice and it was convenient since you were able to find a lot of local restaurants. The only think is the pool was too small."
Jose 2-night trip
Posted 4 hours ago
Hotel Rumbao, a Tribute Portfolio Hotel

Price trends for hotels in Caribbean

Less expensive
More expensive
Next month
July
May
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
1,030
Accommodation
11306 Vacation Homes
Lowest Price
CA $138
Highest Price
CA $624