Caribbean Islands Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Caribbean Islands holiday rentals

The Place at the Sea

The Place at the Sea
2.0 star property
Ponce
9.4 out of 10, Exceptional, (262 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 NZ$171
includes taxes & fees
16 Feb - 17 Feb
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 NZ$2,545
includes taxes & fees
2 Mar - 3 Mar
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, (488 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 NZ$289
includes taxes & fees
16 Mar - 17 Mar
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 NZ$2,001
includes taxes & fees
13 Mar - 14 Mar
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 NZ$484
includes taxes & fees
16 Feb - 17 Feb
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 NZ$258
includes taxes & fees
18 Feb - 19 Feb
Anne's Apartments

Hotel Juan Dolio

Hotel Juan Dolio
4.0 star property
Juan Dolio - El Pueblo
The price is NZ$104
includes taxes & fees
16 Feb - 17 Feb
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 NZ$990
includes taxes & fees
16 Feb - 17 Feb
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, (177 reviews)
"Wonderful "
United States
Pedro
The price is NZ$197
includes taxes & fees
22 Feb - 23 Feb
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 NZ$1,263
includes taxes & fees
25 Feb - 26 Feb
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 NZ$1,500
includes taxes & fees
23 Feb - 24 Feb
H2O LifeStyle Resort

Reserva Real by Harper

Reserva Real by Harper
4.0 star property
Bávaro
9.2 out of 10, Wonderful, (221 reviews)
"Awesome place"
United States
Yasmany
The price is NZ$197
includes taxes & fees
16 Mar - 17 Mar
Reserva Real by Harper

Residenciales H1 & H2

Residenciales H1 & H2
4.0 star property
Villa Olga
9.8 out of 10, Exceptional, (146 reviews)
"Great, not a fancy place, but cozy, feels like home."
United States
Solsiret
The price is NZ$97
includes taxes & fees
16 Feb - 17 Feb
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, (1,180 reviews)
"Great staff, location and amenities."
United States
Deon Oliver
The price is NZ$826
includes taxes & fees
20 Feb - 21 Feb
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 NZ$2,003
includes taxes & fees
16 Feb - 17 Feb
Galleon Villas by Hello Cayman Vacation

Playa Colorá

Playa Colorá
3.0 star property
Cabezas
9.2 out of 10, Wonderful, (220 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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Caribbean Islands Hotel Reviews

Find out more about Caribbean Islands

Everything you need to know about Caribbean Islands holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Caribbean Islands holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Caribbean Islands holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Caribbean Islands holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Caribbean Islands. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Caribbean Islands holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Caribbean Islands holiday rentals we have selected for you start as low as NZ$197 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Caribbean Islands rentals

At Expedia, we put the best Caribbean Islands holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Caribbean Islands rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Caribbean Islands holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Caribbean Islands. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.