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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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, (197 reviews)
"Amazing stay"
United States
Stanley
The price is CA $137
CA $177 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 $186
CA $240 total
includes taxes & fees
Oct 28 - Oct 29
150 Sol by Stay with Bear
A modern interior with a large window, a potted plant, and a door leading outside.

3. Miramar by PMI Puerto Rico

Miramar by PMI Puerto Rico
3.0 star property
Santurce
9.4 out of 10, Exceptional, (3 reviews)
"This property was 10/10!!!! Easy check in , awesome location and fast communication with host!!! Will definitely be booking again"
United States
Anthony
The price is CA $119
CA $326 total
includes taxes & fees
Oct 28 - Oct 29
Miramar by PMI Puerto Rico
A compact kitchen with a microwave, sink, and washing machine. There is a small dining area with stools and a table.

4. 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 sofa, chairs, and a coffee table. There is a view of a swimming pool through the glass door.

5. 5BR Private Pool Sleeps 10 Walk to Ocean Park Beach

5BR Private Pool Sleeps 10 Walk to Ocean Park Beach
Santurce
10.0 out of 10, Exceptional, (1 review)
"The property was amazing, clean, and extremely convenient. The host was very responsive and helpful"
United States
Carl C.
The price is CA $666
CA $1,287 total
includes taxes & fees
Oct 28 - Oct 29
5BR Private Pool Sleeps 10 Walk to Ocean Park Beach
A clear blue pool with lounge chairs and umbrellas, surrounded by tropical vegetation and a view of the ocean.

6. Escape to Exhale at a modern style villa with breathtaking views of chalk sound

Escape to Exhale at a modern style villa with breathtaking views of chalk sound
Providenciales
9.4 out of 10, Exceptional, (39 reviews)
"Beautiful view, comfortable breezy patio, great pool."
United States
Vivian T.
Escape to Exhale at a modern style villa with breathtaking views of chalk sound
A swimming pool with lounge chairs and palm trees, surrounded by buildings and a clear sky.

7. 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
An outdoor patio with a wooden roof, wicker furniture, and a bar area.

8. New pool and generator

New pool and generator
Boquerón
9.2 out of 10, Wonderful, (91 reviews)
"Excellent place! Very clean, close to the beach and quiet. We really enjoyed our stay!"
United States
Celso A
New pool and generator
A room with a sofa, a chair, a small table, and a view of the outside.

9. Villa mares.

Villa mares.
Sabana Abajo
9.2 out of 10, Wonderful, (16 reviews)
"Comfort, clean, good location"
United States
Daisy
The price is CA $159
CA $331 total
includes taxes & fees
Nov 2 - Nov 3
Villa mares.
A modern kitchen with a central island, stainless steel appliances, and two bar stools.

10. Home away II

Home away II
Cangrejo Arriba
9.2 out of 10, Wonderful, (35 reviews)
"Clean"
United States
Damian
The price is CA $139
CA $304 total
includes taxes & fees
Oct 28 - Oct 29
Home away II
A poolside area with a clear pool, white lounge chairs, and a covered patio with steps leading to the pool.

11. 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
A spacious living area with a dining table, sofas, and a chandelier.

12. Bright, big, pool, 5 min 2 beach

Bright, big, pool, 5 min 2 beach
Isla Verde
9.8 out of 10, Exceptional, (19 reviews)
"Perfect location and stay"
United States
Chris L.
The price is CA $883
CA $1,172 total
includes taxes & fees
Oct 28 - Oct 29
Bright, big, pool, 5 min 2 beach
A bedroom with a bed, a hanging plant, a shelf with jars, and a unique light fixture.

13. Detached lodge on the property with a swimming pool (shared) located 5 minutes from the beach

Detached lodge on the property with a swimming pool (shared) located 5 minutes from the beach
Les Trois-Îlets
10.0 out of 10, Exceptional, (32 reviews)
"We stayed at this property for seven nights, and it was absolutely magical. The sunsets and sounds of the tropical forest were amazing. Phillips and his wife were so very welcoming and showed us a map of what to do and where we should visit on the island. The kitchen area has everything you’d need to prepare small meals and enjoy them from your private deck. The location is perfect for setting out to explore the island and its stunning beaches. I would absolutely recommend staying here, and hope...
United States
Samantha G.
Detached lodge on the property with a swimming pool (shared) located 5 minutes from the beach
A balcony with a round table and chairs, a potted plant, and a view of a sunset over a body of water.

14. Sunset Hideaway Suite - Oceanview/central to Cruz Bay

Sunset Hideaway Suite - Oceanview/central to Cruz Bay
St John
9.8 out of 10, Exceptional, (20 reviews)
"Clean and spacious! Great location, proximity to Cruz Bay!"
United States
Laina M.
The price is CA $335
CA $583 total
includes taxes & fees
Oct 28 - Oct 29
Sunset Hideaway Suite - Oceanview/central to Cruz Bay
A covered outdoor seating area with a view of the ocean, a pool, and lounge chairs.

15. 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 beach view with palm trees and a white fence leading to the sand.

16. On the beach, a private pool, a house all to yourself.

On the beach, a private pool, a house all to yourself.
Bravos de Boston
9.8 out of 10, Exceptional, (210 reviews)
"Our extended family stayed here the 2nd week and enjoyed this Cottage even more than we did if that is possible!!!! What a slice of island heavenSweet lifetime memories made."
United States
Susan R.
On the beach, a private pool, a house all to yourself.
A modern outdoor seating area with two blue wicker chairs, a small round table, and a potted plant.

17. 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 beach with clear turquoise water, a sandy shore, and wooden deck chairs under blue umbrellas.

18. 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, (71 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 swimming pool with lounge chairs and a canopy.

19. Private Pool*Full Solar*Secluded Rainforest Setting*1 Mile from PR3*20 From SJU

Private Pool*Full Solar*Secluded Rainforest Setting*1 Mile from PR3*20 From SJU
Rio Grande
10.0 out of 10, Exceptional, (172 reviews)
"Our stay was remarkable and enjoyed it so much we are looking forward to coming back, the host is friendly, the house clean and cool, and the dogs are missed. We will definitely book another stay here"
United States
Cheryl W.
Private Pool*Full Solar*Secluded Rainforest Setting*1 Mile from PR3*20 From SJU
A balcony with wicker chairs and a table, overlooking a coastal landscape with houses and the sea.

20. New 2BR villa w/ balcony near Cruz Bay

New 2BR villa w/ balcony near Cruz Bay
St John
8.0 out of 10, Very good, (27 reviews)
"We had an amazing stay! Highly recommend!"
United States
Jennifer
New 2BR villa w/ balcony near Cruz Bay
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

The Reef at Atlantis

The Reef at Atlantis

10/10 Excellent
"Todo excelente. Yo hablo inglespero por momentos no se entiende lo que dicen y no hacen mucho esfuerzo en entender y nadie habla español . El lugar esta lleno de extranjeros. Personas que no hablen inglés no pueden ir. Eso no solamente en el hotel es general en todo Bahamas."
Leandro 5-night trip
Posted 2 hours ago
The Reef at Atlantis

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
864
Accommodation
10957 Vacation Homes
Lowest Price
CA $177
Highest Price
CA $1,287