Search Holiday Homes in Caribbean Islands

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Sept - 21 Sept
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Browse Select Caribbean Islands Holiday Homes

Our top choices for Caribbean Islands holiday homes

1120 Vieques by Stay with Bear
Apartment, 2 Bedrooms, Corner | Living area | 40-inch flat-screen TV with digital channels, streaming services

1120 Vieques by Stay with Bear

4.0 star property
9.6 out of 10, Exceptional, (36)
"Such a great stay! The place was clean, cozy, and exactly as described. The host was super responsive and made everything easy. Would definitely book again!"
1120 Vieques by Stay with Bear
Playa Nueva Romana
Private beach, white sand, free beach cabanas, sun-loungers

Playa Nueva Romana

3.5 star property
9.4 out of 10, Exceptional, (26)
"I enjoyed the privacy, kindness of people around and overall the calm culture. "
Playa Nueva Romana
The Cottage at Villa Indigo
Interior

The Cottage at Villa Indigo

3.0 star property
8.8 out of 10, Excellent, (15)
"We love St. Thomas This property was in a safe location as long as you are willing to drive on the left side of the road."
The price is ₹23,722
₹40,078 total
includes taxes & fees
9 Sept - 10 Sept
The Cottage at Villa Indigo
Residencia Katya
Full-sized fridge, oven, toaster, blender

Residencia Katya

3.0 star property
9.8 out of 10, Exceptional, (6)
"Perfect location and beautiful house "
The price is ₹4,034
₹4,760 total
includes taxes & fees
9 Sept - 10 Sept
Residencia Katya
4BR 14 pax Twin Villa-Bbq & private pool
14 outdoor pools

4BR 14 pax Twin Villa-Bbq & private pool

3.0 star property
10.0 out of 10, Exceptional, (1)
"A+ is my assesment of this accomidation. The owner/renter went through great lengths to make my stay comfortable. Communication was excellent, the property condition was excellent. It has a full kitchen with every appliance needed! The bedrooms were excellent with a tv in every room, AC in every room and comfortable linens. It is in a gated community not far from shopping or restaurants. Plaza San Juan 5 minutes, Los Corales beach was 20 minutes. I am running out of room so I will add that I...
4BR 14 pax Twin Villa-Bbq & private pool
Casa Parcha
Exclusive Tent, River View | 1 bedroom, Egyptian cotton sheets, premium bedding

Casa Parcha

3.5 star property
9.8 out of 10, Exceptional, (30)
"Very nice place to stay."
The price is ₹13,487
₹15,754 total
includes taxes & fees
23 Sept - 24 Sept
Casa Parcha
Gorgeous Hideout
Private beach nearby

Gorgeous Hideout

3.0 star property
10.0 out of 10, Exceptional, (1)
"Host was very on top on things great safe area "
Gorgeous Hideout
The White House TCI Guest House
Front of property

The White House TCI Guest House

3.5 star property
8.0 out of 10, Very good, (8)
"Very clean, stayed there for my birthday with my sisters. Looking to visit soon again. "
The White House TCI Guest House
Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach
Outdoor pool, open 7:00 AM to 9:00 PM, pool loungers

Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach

4.0 star property
9.8 out of 10, Exceptional, (18)
"The hosts were expecting pleasant caring and fantastic service, very professional but made sure I was okay with everything. I would recommend the Jahadno Villa I get it a 10 clean rooms are extremely nice and every room had they own bathroom I love it. I thank u for accommodating me an my girls we enjoyed our stay."
The price is ₹4,575
₹17,935 total
includes taxes & fees
11 Sept - 12 Sept
Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach
RVR Rentals
Deluxe House, Garden View | Private kitchen

RVR Rentals

2.5 star property
RVR Rentals
Imperial Topaz At Richmond
Outdoor pool

Imperial Topaz At Richmond

3.5 star property
9.0 out of 10, Wonderful, (4)
"Nice upscale property with very comfortable accommodations. "
Imperial Topaz At Richmond
Drax Hall Country Club's Sweet Escape
Terrace/patio

Drax Hall Country Club's Sweet Escape

3.5 star property
8.0 out of 10, Very good, (3)
"The AC is not working there is only two beds, not three beds that was stated by the host!!! She had another guest at the house at 11am on us which is very unprofessional I rate it a 5 out of 10 "
The price is ₹9,344
₹13,893 total
includes taxes & fees
14 Sept - 15 Sept
Drax Hall Country Club's Sweet Escape
Primaveral 2
Exterior

Primaveral 2

3.5 star property
5.2 out of 10, (5)
Primaveral 2
Taste of Paradise
Exterior

Taste of Paradise

4.0 star property
8.4 out of 10, Very good, (37)
"Great stay"
The price is ₹9,780
₹24,450 total
includes taxes & fees
9 Sept - 10 Sept
Taste of Paradise
Eagle Vacation Home
Exterior

Eagle Vacation Home

4.0 star property
9.6 out of 10, Exceptional, (8)
"Nice quiet area easy walk to beach"
Eagle Vacation Home
Sunshine Lodge- Your Home Away From Home
Land view from property

Sunshine Lodge- Your Home Away From Home

4.0 star property
7.4 out of 10, Good, (3)
"It was beautiful on the inside and had an amazing view of Montego Bay."
The price is ₹5,656
₹6,592 total
includes taxes & fees
21 Sept - 22 Sept
Sunshine Lodge- Your Home Away From Home
Palm Beach Vacation Villa
Exterior

Palm Beach Vacation Villa

3.0 star property
7.4 out of 10, Good, (3)
"Don’t know a thing. Property manager did not respond to ANY messages, including ones sent weeks in advance; manager sent check-in instructions 17 minutes before our flight landed. Let me repeat that: property manager did not send check-in instructions until 17 minutes before a flight arrived in a different country, with their customers not knowing where to go or what to do, with spotty Internet connection at best. Absolute garbage. Awe nan a hode cu Arubiano."
The price is ₹26,214
₹29,756 total
includes taxes & fees
7 Sept - 8 Sept
Palm Beach Vacation Villa
Caprice 7 Ocean Front Villa private Pool
On the beach

Caprice 7 Ocean Front Villa private Pool

3.5 star property
10.0 out of 10, Exceptional, (2)
"The staff was amazing and the property was gorgeous . "
Caprice 7 Ocean Front Villa private Pool
Soleil Sea Renity
Beach

Soleil Sea Renity

3.0 star property
10.0 out of 10, Exceptional, (1)
"House was clean and comfy. Lots of tvs but was not able to watch them. I didn’t like the idea that a 3 bedroom was booked, but had to pay for each per beside the rental…. Hidden costs"
The price is ₹20,274
₹32,219 total
includes taxes & fees
28 Sept - 29 Sept
Soleil Sea Renity
Casa Cielo
Porch

Casa Cielo

3.5 star property
9.6 out of 10, Exceptional, (20)
"Very welcome I love it "
Casa Cielo
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Caribbean Islands Hotel Reviews

Fairmont El San Juan Hotel

Fairmont El San Juan Hotel

10/10 Excellent
"Nice setup, nice view. Beautiful place! "
Lisa Cijin 4-night trip
Posted 2 days ago
Fairmont El San Juan Hotel

Find out more about Caribbean Islands

Find out more about Caribbean Islands

Caribbean Islands Holiday Homes information

Number of reviews
Accommodation
51 Holiday Homes
Lowest Price
₹4,034
Highest Price
₹26,214

Explore a world of travel with Expedia

Explore a world of travel with Expedia