Search Holiday Rentals in Jamaica

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Jamaica holiday rentals

Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, pool loungers
Long Trail House at Stratton Mountain Resort

Aparthotel in Stratton

Long Trail House at Stratton Mountain Resort
3.0 star property
8.6 out of 10, Excellent, (77)
"Nice, clean room in prime location"
United States
Kristin
The price is 10.661.220 ₫
13.251.896 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Long Trail House at Stratton Mountain Resort
Solitude Village Two Bedroom Suite Mountainside | Private kitchen | Fridge, microwave, stovetop, toaster
Solitude Village at Okemo by Vail Resorts

Aparthotel in Clock Tower Base Area

Solitude Village at Okemo by Vail Resorts
4.0 star property
8.0 out of 10, Very good, (32)
"Great location!"
United States
DIEN
Solitude Village at Okemo by Vail Resorts
Property grounds
Winterplace at Okemo, A Vail Resorts Property

Aparthotel in Clock Tower Base Area

Winterplace at Okemo, A Vail Resorts Property
4.0 star property
8.8 out of 10, Excellent, (26)
"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place "
United States
Kathia
Winterplace at Okemo, A Vail Resorts Property
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Jamaica Hotel Reviews

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"I arrived far before published check-in time and only had to wait a reasonable amount of time to get into my room. Desk clerks were efficient and friendly. Clean, comfortable room. "
Wick 1-night trip
Posted 1 day ago
Comfort Inn & Suites Brattleboro I-91

Frequently asked questions

Can I find holiday rentals in Jamaica?

Yes, there are holiday rentals close to the most popular sights in Jamaica, or you can select a more secluded option if you're looking for a relaxing stay. Jamaica is known for its mountain views and art. Make sure you have time to check out the monuments while you're in the area.

How many holiday rentals are there in Jamaica?

With 43 Expedia holiday rentals, you're guaranteed to find just the right place for your Jamaica stay.

What can I see and do in Jamaica?

Cultural attractions include Hot Glass Works and Margie's Muse Handweaving & Gallery, whereas Green Mountain National Forest and Winhall River are a couple of picturesque spots to enjoy the outdoors. You’ll find favourite places to visit such as Stratton Mountain Resort and Mount Snow in the wider area.

What are holiday rentals like in Jamaica?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Jamaica. Holiday rentals offer extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for family gatherings.