Caribbean Islands Vacation Rentals

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Our top choices for Caribbean Islands vacation rentals

The Place at the Sea

The Place at the Sea
2.0 star property
Ponce
9.4 out of 10, Exceptional, (263 reviews)
"awesome place to stay"
United States
CHRISTOPHER A
The Place at the Sea

Manderley Villas

Manderley Villas
3.0 star property
Mangrove
9.6 out of 10, Exceptional, (99 reviews)
"The place is spacious, clean and quiet. Checked in is quick and easy."
Canada
Michael
The price is CA $117
CA $141 total
includes taxes & fees
Feb 17 - Feb 18
Manderley Villas

The Somerset on Grace Bay

The Somerset on Grace Bay
5.0 star property
Grace Bay
9.6 out of 10, Exceptional, (183 reviews)
"Property was just right for our family loved the staff very friendly "
United States
Elias
The price is CA $1,735
CA $2,215 total
includes taxes & fees
Mar 15 - Mar 16
The Somerset on Grace Bay

Glamping Ecolodge Cueva de las Águilas

Glamping Ecolodge Cueva de las Águilas
2.0 star property
Pedernales
8.6 out of 10, Excellent, (372 reviews)
"Clean rooms food the view "
United States
Nelsy
Glamping Ecolodge Cueva de las Águilas

Bell At The Airport Suites - Adults Only

Bell At The Airport Suites - Adults Only
2.5 star property
Nassau
9.6 out of 10, Exceptional, (489 reviews)
"Very clean, nice place to stay close to the airport. The owner was really helpful, going out of his way to make our stay pleasant. Strongly recommend."
United States
Lee Anne
The price is CA $172
CA $243 total
includes taxes & fees
Feb 18 - Feb 19
Bell At The Airport Suites - Adults Only

The Park at Grace Bay

The Park at Grace Bay
4.0 star property
Grace Bay
The price is CA $1,296
CA $1,645 total
includes taxes & fees
Mar 13 - Mar 14
The Park at Grace Bay

Great Cistern Beach Village

Great Cistern Beach Village
2.5 star property
Marsh Harbour
9.6 out of 10, Exceptional, (37 reviews)
"We had the best time here! Allen was so helpful and nice. Great location near restaurants and right on the beach. We wish we could have stayed longer and hope to be back soon. "
United States
gregory
The price is CA $329
CA $398 total
includes taxes & fees
Feb 17 - Feb 18
Great Cistern Beach Village

Pineapple Fields Boutique Condo Hotel

Pineapple Fields Boutique Condo Hotel
3.0 star property
Governor's Harbour
9.8 out of 10, Exceptional, (12 reviews)
"Great place to stay"
United States
Warren DeWayne
Pineapple Fields Boutique Condo Hotel

Anne's Apartments

Anne's Apartments
2.0 star property
Osbourn
The price is CA $161
CA $212 total
includes taxes & fees
Feb 18 - Feb 19
Anne's Apartments

Hotel Juan Dolio

Hotel Juan Dolio
4.0 star property
Juan Dolio - El Pueblo
The price is CA $72
CA $85 total
includes taxes & fees
Feb 17 - Feb 18
Hotel Juan Dolio

Playa icacos

Playa icacos
2.0 star property
Cabezas
9.4 out of 10, Exceptional, (83 reviews)
"Room was perfect. Location was great, nice , cozy and super clean."
United States
Mitchell J
Playa icacos

Marina Garden Cap Cana by Beach Homes PC

Marina Garden Cap Cana by Beach Homes PC
4.5 star property
Cap Cana
10.0 out of 10, Exceptional, (5 reviews)
"The condo was just like the photos, beautiful spot, convenient check-in and location! We will be back! "
Canada
Anthony
The price is CA $588
CA $814 total
includes taxes & fees
Feb 17 - Feb 18
Marina Garden Cap Cana by Beach Homes PC

Aston Rubi City Suites

Aston Rubi City Suites
4.5 star property
Downtown Santo Domingo
9.4 out of 10, Exceptional, (178 reviews)
"Wonderful "
United States
Pedro
The price is CA $96
CA $124 total
includes taxes & fees
Mar 9 - Mar 10
Aston Rubi City Suites

Fountain Anguilla

Fountain Anguilla
3.5 star property
Shoal Bay
9.0 out of 10, Wonderful, (67 reviews)
"The friendly and wonderful staff made this stay really comfortable. I am not used to having hotel staff as helpful and friendly as this hotel has and I mean anywhere in the Caribbean! "
Canada
Andrew
The price is CA $677
CA $1,038 total
includes taxes & fees
Feb 25 - Feb 26
Fountain Anguilla

H2O LifeStyle Resort

H2O LifeStyle Resort
4.0 star property
Long Bay
9.4 out of 10, Exceptional, (96 reviews)
"The place was very neat, clean and excellent service. Perfect for family vacation. One of the best experiences. "
United States
Vishal
The price is CA $910
CA $1,247 total
includes taxes & fees
Feb 28 - Mar 1
H2O LifeStyle Resort

Reserva Real by Harper

Reserva Real by Harper
4.0 star property
Bávaro
9.0 out of 10, Wonderful, (222 reviews)
"Awesome place"
United States
Yasmany
The price is CA $107
CA $138 total
includes taxes & fees
Mar 10 - Mar 11
Reserva Real by Harper

Residenciales H1 & H2

Residenciales H1 & H2
4.0 star property
Villa Olga
9.8 out of 10, Exceptional, (147 reviews)
"Great, not a fancy place, but cozy, feels like home."
United States
Solsiret
The price is CA $68
CA $80 total
includes taxes & fees
Feb 17 - Feb 18
Residenciales H1 & H2

Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten
4.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (1,182 reviews)
"Great staff, location and amenities."
United States
Deon Oliver
The price is CA $613
CA $679 total
includes taxes & fees
Feb 20 - Feb 21
Hilton Vacation Club Royal Palm St. Maarten

Galleon Villas by Hello Cayman Vacation

Galleon Villas by Hello Cayman Vacation
3.5 star property
Seven Mile Beach
10.0 out of 10, Exceptional, (204 reviews)
"This place is always good especially the ground floor walk out to the beach. Even though our Umit could be renovated it was still fine. "
United States
Yaman
The price is CA $1,396
CA $1,647 total
includes taxes & fees
Feb 17 - Feb 18
Galleon Villas by Hello Cayman Vacation

Playa Colorá

Playa Colorá
3.0 star property
Cabezas
9.2 out of 10, Wonderful, (221 reviews)
"Great place for a single person on a budget "
United States
Ryan
Playa Colorá
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

Find out more about Caribbean Islands

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Caribbean Islands. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.