Holiday Rentals in Caribbean Islands

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Our top choices for Caribbean Islands holiday rentals

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, (466)
"Room was clean and very nice. Micah is a very accommodating host. "
United States
Clark
Bell At The Airport Suites - Adults Only

Manderley Villas

Manderley Villas
3.0 star property
Mangrove
9.6 out of 10, Exceptional, (93)
"The property was perfect! Maureen was lovely and very accommodating. Staying at Manderley made my quick overnight in Barbados a seamless and stress-free experience. Very clean and spacious unit. "
United States
Sydney
The price is €87
includes taxes & fees
3 Jan - 4 Jan 2026
Manderley Villas

Turtles Nest Beach Resort 

Turtles Nest Beach Resort 
3.0 star property
West End Village
9.4 out of 10, Exceptional, (166)
"Great place on one of the best beaches in Anguilla."
Canada
John
The price is €410
includes taxes & fees
5 Jan - 6 Jan 2026
Turtles Nest Beach Resort 

Glamping Ecolodge Cueva de las Águilas

Glamping Ecolodge Cueva de las Águilas
2.0 star property
Pedernales
8.6 out of 10, Excellent, (345)
"Love this place"
United States
marcia
Glamping Ecolodge Cueva de las Águilas

Phoenix Park Villas Portmore

Phoenix Park Villas Portmore
4.0 star property
Portmore
10.0 out of 10, Exceptional, (4)
"I will definitely recommend that you stay here is so peaceful security are strictly on point with everything and the comfort of the home is great will be staying back for sure ."
United States
Kimoya
The price is €233
includes taxes & fees
28 Dec - 29 Dec
Phoenix Park Villas Portmore

Playa Escondida

Playa Escondida
3.5 star property
Cabezas
9.4 out of 10, Exceptional, (105)
"Room was ready and clean. No problem to find the place and parking was convenient "
United States
Joel
Playa Escondida

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, (222)
"Clean, quiet, convenient location. Perfect stay!!!"
United States
Glenda
The price is €173
includes taxes & fees
30 Dec - 31 Dec
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

Ceblue Luxury Villas

Ceblue Luxury Villas
5.0 star property
The Valley
10.0 out of 10, Exceptional, (7)
"My husband and I absolutely loved our time at CeBlue! Latoya our concierge was amazing and the beach is beautiful! Only negative would be there isn’t much options for food when you go beginning of August as most places close for hurricane season. Latoya was able to help us find some amazing restaurants throughout the island though. We will be back "
United States
Brooke Renee
The price is €3,324
includes taxes & fees
28 Dec - 29 Dec
Ceblue Luxury Villas

Hotel Panoramic

Hotel Panoramic
3.0 star property
Trois-Ilets
8.6 out of 10, Excellent, (321)
"Staff was nice - we had arrived a few days after Carnival so it was a busy time for everyone on the island "
Canada
Marco
The price is €218
includes taxes & fees
15 Jan - 16 Jan 2026
Hotel Panoramic

Estudio centrico

Estudio centrico
3.0 star property
Los Jardines
10.0 out of 10, Exceptional, (1)
"Estaba todo limpio zona trankila.."
Mexico
Jorge
The price is €50
includes taxes & fees
26 Dec - 27 Dec
Estudio centrico

Green Land Bubble Glamping

Green Land Bubble Glamping
2.0 star property
Sosúa
9.4 out of 10, Exceptional, (87)
"Clean room…welcoming staff. Beautiful landscape. Amazing bubble."
United States
Rosalinda
The price is €143
includes taxes & fees
30 Dec - 31 Dec
Green Land Bubble Glamping

Garden Suite near the Beach and restaurants!

Garden Suite near the Beach and restaurants!
Ucares
10.0 out of 10, Exceptional, (76)
"The bed is very comfortable "
United States
Wei g.
The price is €148
includes taxes & fees
5 Jan - 6 Jan 2026
Garden Suite near the Beach and restaurants!

Old San Juan Rentals

Old San Juan Rentals
3.5 star property
Old San Juan
8.6 out of 10, Excellent, (681)
"Amazing stay and staff was always available for us"
United States
Dominique
The price is €228
includes taxes & fees
6 Jan - 7 Jan 2026
Old San Juan Rentals

Mare 1660

Mare 1660
4.0 star property
Isla Verde
8.6 out of 10, Excellent, (83)
"Great room. Excellent beach access. Great building!"
United States
peter
Mare 1660

SELVA by DW

SELVA by DW
4.0 star property
Pitahaya
10.0 out of 10, Exceptional, (2)
"This was our 1st experience in PR. This house was AMAZINGLY beautiful and really show cased the outdoor space!! It was VERY clean, high quality linens. Had a nice cook space. The space it self was STUNNING!! The outdoor space was PERFECTION!!!! We actually booked for the lounge net area, and it did not disappoint!! **Downfalls [we understand that somethings are out of anyones control so more of a FYI] -There was nothing "comfy" about the house. It is all cement: bed frame, entire bathroom so...
United States
Jamie leigh
SELVA by DW

Boca residence

Boca residence
2.0 star property
Boca Chica
The price is €47
includes taxes & fees
26 Dec - 27 Dec
Boca residence

The Somerset on Grace Bay

The Somerset on Grace Bay
5.0 star property
Grace Bay
9.6 out of 10, Exceptional, (182)
"Property was just right for our family loved the staff very friendly "
United States
Elias
The price is €1,406
includes taxes & fees
5 Jan - 6 Jan 2026
The Somerset on Grace Bay

Prado Suites Las Terrenas

Prado Suites Las Terrenas
3.5 star property
El Callejón
10.0 out of 10, Exceptional, (1)
"Sí, todo super "
Mexico
Oliver
The price is €90
includes taxes & fees
6 Jan - 7 Jan 2026
Prado Suites Las Terrenas

Drift Hotels

Drift Hotels
3.5 star property
Historic Center
9.6 out of 10, Exceptional, (10)
"This place is immaculate.  Well maintained by the staff as well as the owner. Free street parking was not a problem on a November. Not sure though how things are during the peak summer season.  Location is excellent, there's a local grocery store close by and the hotel is less than 10-minute walk from the downtown tourist area. There are well equipped shared kitchens in every floor and coffee is always available. Highly recommend. "
Canada
Raymond
The price is €114
includes taxes & fees
13 Jan - 14 Jan 2026
Drift Hotels

Fountain Anguilla

Fountain Anguilla
3.5 star property
Shoal Bay
9.0 out of 10, Wonderful, (62)
"It was very nice property to stay it "
United States
Felicia
Fountain Anguilla
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

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, apart-hotels, 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 €79 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.