A road flanked by dense bamboo groves.

Jamaica Holiday Rentals

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Our top choices for Jamaica holiday rentals

1. Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is NZ$636
includes taxes & fees
16 Aug - 17 Aug
Long Trail House at Stratton Mountain Resort

2. 3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
3.0 star property
West Dover
The price is NZ$1,111
includes taxes & fees
24 Aug - 25 Aug
3 Mi to Mount Snow: Spacious West Dover Home

3. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
Charming Wilmington Cabin, 8 Mi. to Mt Snow!

4. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is NZ$3,255
includes taxes & fees
16 Aug - 17 Aug
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
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 Jamaica Hotel Reviews

Find out more about Jamaica

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 Jamaica 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 Jamaica. 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 Jamaica. Seeing all the best attractions is bound to make you fall in love with Jamaica. 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 Jamaica short-term rentals, that won’t be hard to do.

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.

What are some of the best holiday rentals that Jamaica has to offer?

Okemo Mountain Lodging by Vail Resorts: This holiday home rental outside Jamaica is in the mountains and offers cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

How many holiday rentals are there in Jamaica?

With 45 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. Jamaica State Park and Ball Mountain Dam are other places to visit while you're in town.

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.