Jamaica Holiday Rentals

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Our top choices for Jamaica holiday rentals

10.0 out of 10, Exceptional, (3 reviews)
"Couldn't be better! Outstanding! We had our family holiday ski trip from Dec 25-29th,2025. The amenities were second to none. The hot tub, sauna and fire pit made the winter warm! The house was clean comfortable and very cozy. The kitchen was extremely well appointed (sharp knives!). The staples available (coffee, tea, oil, spices etc.) were high quality and the best I've ever experienced in a short term rental. The beds and bedding were very comfortable! Most immortality the hosts were very...
United States
Laird N.
The price is AU$1,309
includes taxes & fees
12 Mar - 13 Mar
New Stratton Ski Haus: A-Frame Hot Tub Sauna EV Privacy 1Gbps Manchester Okemo
8.8 out of 10, Excellent, (8 reviews)
"Great location. House was recently updated but has some older charm in parts. Fun and cozy. Hot tub was great the first day but smell seemed off the next day. Perhaps more chlorine was needed. Great time , great trip. Pet friendly is a bonus and the house looks never used so the cleaning crew is doing great work. Will rent again next year perhaps !"
United States
Michael C.
The price is AU$997
includes taxes & fees
8 Apr - 9 Apr
Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods
9.6 out of 10, Exceptional, (167 reviews)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is AU$518
includes taxes & fees
12 Mar - 13 Mar
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is AU$349
includes taxes & fees
22 Mar - 23 Mar
Wellness Getaway with a Personal Sauna, and Private River Beach!
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is AU$338
includes taxes & fees
12 Mar - 13 Mar
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
10.0 out of 10, Exceptional, (50 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is AU$834
includes taxes & fees
16 Mar - 17 Mar
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
8.4 out of 10, Very good, (5 reviews)
"Very cozy and quiet. "
United States
Eric H.
The price is AU$391
includes taxes & fees
12 Mar - 13 Mar
Cozy cabin in charming Londonderry
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is AU$369
includes taxes & fees
1 Apr - 2 Apr
The Studio with a View. Bring your dog, too!
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is AU$410
includes taxes & fees
16 Mar - 17 Mar
Family Friendly Hilltop House In Putney Vermont
10.0 out of 10, Exceptional, (1 review)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is AU$434
includes taxes & fees
12 Mar - 13 Mar
Lake Whitingham & Mount Snow Area Village Apartment
9.2 out of 10, Wonderful, (22 reviews)
"Highly recommend clean beautiful stay!"
United States
Douglas D.
The price is AU$437
includes taxes & fees
31 Mar - 1 Apr
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
The price is AU$335
includes taxes & fees
29 Mar - 30 Mar
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
7.6 out of 10, Good, (56 reviews)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
The price is AU$433
includes taxes & fees
23 Mar - 24 Mar
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
7.4 out of 10, Good, (21 reviews)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
The price is AU$568
includes taxes & fees
17 Mar - 18 Mar
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
The price is AU$694
includes taxes & fees
15 Mar - 16 Mar
Cozy Private Cabin in Andover - Fireplace & Hot tub
9.0 out of 10, Wonderful, (78 reviews)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is AU$397
includes taxes & fees
9 Apr - 10 Apr
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
8.6 out of 10, Excellent, (32 reviews)
"Nice place close to mountain easy in easy out"
United States
Aaron B.
The price is AU$322
includes taxes & fees
16 Mar - 17 Mar
Efficient condo near slopes with kitchenette & great location
9.0 out of 10, Wonderful, (25 reviews)
"Great rate for a place with all the basics!"
United States
Macgregor
The price is AU$380
includes taxes & fees
12 Mar - 13 Mar
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
10.0 out of 10, Exceptional, (13 reviews)
"We enjoyed our stay."
United States
Anonymous traveller
The price is AU$806
includes taxes & fees
12 Mar - 13 Mar
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
9.2 out of 10, Wonderful, (28 reviews)
"Overall very clean and nice. Needs some updating like more spoons, only 2, bigger coffee cups. And a new coffee table that is very worn. "
United States
David A.
The price is AU$358
includes taxes & fees
8 Apr - 9 Apr
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
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

Everything you need to know about Jamaica 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 Jamaica holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Jamaica holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Jamaica holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jamaica. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jamaica 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 Jamaica holiday rentals we have selected for you start as low as AU$397 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Jamaica rentals

At Expedia, we put the best Jamaica 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 Jamaica 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 Jamaica 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 Jamaica. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms: This holiday home rental outside of Jamaica is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 12 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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. 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.