A beach with clear turquoise water, white sand, and palm trees.

Caribbean Islands Holiday Rentals

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Our top choices for Caribbean Islands holiday rentals

1. BELL At The Airport Suites - No Smoking & Adults Only - Free Airport Transportation

BELL At The Airport Suites - No Smoking & Adults Only - Free Airport Transportation
3.5 star property
Nassau
9.6 out of 10, Exceptional, (542 reviews)
"Super friendly staff and very accommodating. I recommend staying here, especially if you have a last minute extra night you need to stay. I would come back!"
United States
William
The price is NZ$269
includes taxes & fees
17 Aug - 18 Aug
BELL At The Airport Suites - No Smoking & Adults Only - Free Airport Transportation

2. Aguadilla Surf Lodge

Aguadilla Surf Lodge
2.5 star property
Aguadilla
9.8 out of 10, Exceptional, (167 reviews)
"Excelent place! Excelent services!"
United States
Yaralis
The price is NZ$225
includes taxes & fees
19 Aug - 20 Aug
Aguadilla Surf Lodge

3. Aston Rubi City Suites

Aston Rubi City Suites
4.5 star property
Downtown Santo Domingo
9.2 out of 10, Wonderful, (291 reviews)
"The property was clean,staff was amazing and the rooms was modern ."
United States
Saiefa
The price is NZ$145
includes taxes & fees
4 Sept - 5 Sept
Aston Rubi City Suites

4. Glamping Ecolodge Cueva de las Águilas

Glamping Ecolodge Cueva de las Águilas
2.0 star property
Pedernales
8.6 out of 10, Excellent, (482 reviews)
"Amazing place definitely will come back"
United States
Yudelka
The price is NZ$189
includes taxes & fees
24 Aug - 25 Aug
Glamping Ecolodge Cueva de las Águilas

5. A 7 Minutos del Aeropuerto SDQ Apto.

A 7 Minutos del Aeropuerto SDQ Apto.
2.5 star property
La Caleta
9.4 out of 10, Exceptional, (22 reviews)
"Fausto is an amazing host- prompt, attentive. Bed is very comfortable and accommodations were perfect. Got us to the airport in good time and found us a local place to eat."
United States
Annette
The price is NZ$79
includes taxes & fees
16 Sept - 17 Sept
A 7 Minutos del Aeropuerto SDQ Apto.

6. Reserva Real by Harper

Reserva Real by Harper
4.5 star property
Bávaro
9.0 out of 10, Wonderful, (346 reviews)
"Lovely place"
United States
Valdo
The price is NZ$159
includes taxes & fees
4 Sept - 5 Sept
Reserva Real by Harper

7. Santa Fe Club

Santa Fe Club
3.5 star property
Sosúa
8.4 out of 10, Very good, (230 reviews)
"Wonderful stay"
United States
Jose Manuel FABIAN
The price is NZ$162
includes taxes & fees
18 Aug - 19 Aug
Santa Fe Club

8. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (740 reviews)
"The view, the accommodation, the staff were all superb. I always stay there when I visit the Island."
United States
Janice
The price is NZ$422
includes taxes & fees
14 Sept - 15 Sept
Bluebeard's Castle Resort

9. Residenciales H1 & H2

Residenciales H1 & H2
3.0 star property
Villa Olga
9.4 out of 10, Exceptional, (213 reviews)
"I enjoyed the bed and internet"
United States
Luz
The price is NZ$107
includes taxes & fees
17 Aug - 18 Aug
Residenciales H1 & H2

10. Green Land Bubble Glamping

Green Land Bubble Glamping
2.0 star property
Sosúa
9.4 out of 10, Exceptional, (98 reviews)
"Overall good experience"
United States
Jesus
The price is NZ$228
includes taxes & fees
1 Sept - 2 Sept
Green Land Bubble Glamping

11. Pineapple Fields Boutique Condo Hotel

Pineapple Fields Boutique Condo Hotel
3.0 star property
Governor's Harbour
9.8 out of 10, Exceptional, (15 reviews)
"A great location across the street from a gorgeous pink sand beach and Tippy’s. Rooms are clean and comfortable with a rustic chic feel to them and a well manicured set of grounds. A great place for a low-key getaway."
United States
Sean
The price is NZ$518
includes taxes & fees
18 Aug - 19 Aug
Pineapple Fields Boutique Condo Hotel

12. PALMERAS DE SOL CARIBE

PALMERAS DE SOL CARIBE
4.5 star property
Bávaro
9.4 out of 10, Exceptional, (35 reviews)
"We can recommend this hotel and we would book it again next time."
Mexico
carine
The price is NZ$238
includes taxes & fees
24 Aug - 25 Aug
PALMERAS DE SOL CARIBE

13. LINCOLN SUITE

LINCOLN SUITE
4.0 star property
Mata Hambre
9.4 out of 10, Exceptional, (136 reviews)
"Great location"
United States
Maritza
The price is NZ$136
includes taxes & fees
17 Aug - 18 Aug
LINCOLN SUITE

14. The Palms Resort

The Palms Resort
3.0 star property
Holetown
8.6 out of 10, Excellent, (228 reviews)
"A DELIGHTFUL STAY! Can’t wait to return!"
United States
Zoe
The price is NZ$205
includes taxes & fees
17 Aug - 18 Aug
The Palms Resort

15. Playa icacos

Playa icacos
2.0 star property
Cabezas
9.2 out of 10, Wonderful, (103 reviews)
"Love it 100% recomendated!!!!"
United States
Diaris
The price is NZ$218
includes taxes & fees
17 Aug - 18 Aug
Playa icacos

16. Hotel Costa Love Aeropuerto PUJ

Hotel Costa Love Aeropuerto PUJ
4.0 star property
Verón
8.8 out of 10, Excellent, (405 reviews)
"The breakfast, the staff, clean room excellent"
United States
Massiel Altagracia
The price is NZ$121
includes taxes & fees
23 Aug - 24 Aug
Hotel Costa Love Aeropuerto PUJ

17. Garden Suite near the Beach and restaurants!

Garden Suite near the Beach and restaurants!
Ucares
10.0 out of 10, Exceptional, (95 reviews)
"Great thanks to Adam and his wife for everything thank again had an amazing time and the dogs "
United States
Sabrina S.
The price is NZ$344
includes taxes & fees
17 Aug - 18 Aug
Garden Suite near the Beach and restaurants!

18. Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
St. Thomas
9.4 out of 10, Exceptional, (252 reviews)
"Enjoyed our stay "
United States
Jason A.
The price is NZ$451
includes taxes & fees
3 Sept - 4 Sept
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

19. Lameshur Cottage's Guest House

Lameshur Cottage's Guest House
St John
10.0 out of 10, Exceptional, (141 reviews)
"Amazing place! Great host!!Close to Salt Pond."
United States
Shawn C.
The price is NZ$593
includes taxes & fees
23 Aug - 24 Aug
Lameshur Cottage's Guest House

20. Golden Beach by Otium

Golden Beach by Otium
3.5 star property
Isla Verde
9.4 out of 10, Exceptional, (10 reviews)
"Super clean room, amazing area, very comfortable and communication was excellent "
United States
Leslee
The price is NZ$460
includes taxes & fees
14 Sept - 15 Sept
Golden Beach by Otium
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Caribbean Islands holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Caribbean Islands. 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 Caribbean Islands. 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 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 holiday 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 Caribbean Islands short-term rentals, that won’t be hard to do.