Holiday Rentals in Jamaica

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Holiday Rentals in Jamaica

Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi

Mountain Acres
9.6 out of 10, Exceptional, (4)
"Inside of home was awesome! Slept eight adults and three children very comfortably. We brought two chairs for extra seating for meals. A large pasta pot and cutting board would be great. Overall lovely home thank you for sharing it with us!"
United States
William A.
Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi

Long Trail House at Stratton Mountain Resort

3.0 star property
Stratton
8.6 out of 10, Excellent, (77)
"Nice, clean room in prime location"
United States
Kristin
The price is €374
includes taxes & fees
17 Nov - 18 Nov
Long Trail House at Stratton Mountain Resort

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Clock Tower Base Area
9.0 out of 10, Wonderful, (74)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
The price is €224
includes taxes & fees
17 Nov - 18 Nov
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Ludlow
9.8 out of 10, Exceptional, (127)
"Enjoyed our stay immensely"
United States
jim m.
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Winhall
9.6 out of 10, Exceptional, (30)
"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "
United States
Virginia A.
The price is €557
includes taxes & fees
13 Nov - 14 Nov
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Townshend
10.0 out of 10, Exceptional, (5)
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Sunderland
10.0 out of 10, Exceptional, (126)
"I stayed here with 8 people and the house was great for all of us. It was clean and comfortable and the hot tub was an extra plus. I would recommend staying here!"
United States
Alexa S.
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Andover
9.0 out of 10, Wonderful, (29)
"The property was beautiful with a gorgeous view. The cleanliness of the house was less than expected. Cobwebs, stained bedspread, dirty cabinets, and handprints all over the loft windows gave the impression that it hadn't been thoroughly cleaned in a while. There were also several lightbulbs that were burned out on arrival. If it were cleaned up properly, it would be a great place to stay."
United States
Stephen T.
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton
9.6 out of 10, Exceptional, (166)
"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 €323
includes taxes & fees
13 Nov - 14 Nov
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Winhall
9.6 out of 10, Exceptional, (241)
"What a wonderful place to stay! My boyfriend and I too advantage of the beautiful deck and had coffee and dinner on it every day. We also used the charcoal grill to cook dinner and the wood stove outside, for a beautiful outside dining expereince! We would love to come back again!"
United States
Katherine B.
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

Londonderry
8.6 out of 10, Excellent, (8)
"My husband and I stayed at the treehouse cabin for two nights. It was so adorable and had so many fun amenities from the hot tub, to the fire place and record player. They even had snow shoes for us to borrow and we were able to use them and had a fun morning snow shoeing. Easy check in, and just a nice clean fun place to stay."
United States
Meghan C.
The price is €502
includes taxes & fees
17 Nov - 18 Nov
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Ludlow
8.0 out of 10, Very good, (41)
"This Vrbo has been housing people since the 1960's, and we're so glad to be a part of this place's history It is truly a timeless home within a beautiful area with great outdoor activites, generous people and good food (we recommend The Hatchery). Both showers (the top floor shower and the middle floor) did have a leak, but our hosts responded quickly to our concerns and addressed them within a timely manner :) "
United States
John Q.
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Wilmington
10.0 out of 10, Exceptional, (227)
"Great house, fantastically well equipped (kayaks, bikes etc). Excellent, very responsive host. View out over the lake is amazing. Really enjoyed our stay. "
United Kingdom
Lucian L.
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Winterplace at Okemo

4.0 star property
Clock Tower Base Area
8.8 out of 10, Excellent, (25)
"I think it needs some wall touch ups and new shower liners , other than that is was a pleasant stay. "
United States
Jocelin
Winterplace at Okemo

Long Trail House Studio at Stratton Mountain Resort

Stratton
10.0 out of 10, Exceptional, (64)
"Our stay was incredible. The location was perfect, room and facility was clean. Thank you for being a great host, 10/10!"
United States
Tyler M.
Long Trail House Studio at Stratton Mountain Resort

Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

Dover
9.6 out of 10, Exceptional, (5)
"Property was clean, well presented and very comfortable. We had a great time, checking out nearby waterfalls and history of such places as Bennington. We would stay again and recommend to friends and family.."
United States
Stephen T.
The price is €388
includes taxes & fees
13 Nov - 14 Nov
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

Beautiful Lodging at Mount Snow with Hot Tub on Deck

Wilmington
9.4 out of 10, Exceptional, (42)
"This cabin is geared more for Winter and skiing since there is no air conditioning. Our family of 5 guys stayed here on 7/25/2025 because it was not that far from our rafting location, hiking and other attractions in southern VT. The cabin is very clean and the kitchen is stocked for all one's needs. We spent several nights after dinner around the firepit. We very much enjoyed staying here."
United States
Richard D.
Beautiful Lodging at Mount Snow with Hot Tub on Deck

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Windham
10.0 out of 10, Exceptional, (54)
"Consistently great time at this place (3rd time there)"
United States
Chad B.
Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Dover
10.0 out of 10, Exceptional, (9)
"This place is somehow better than it looks online. It is truly spectacular. And incredibly easy ski in ski out. Ski in is right to the door and ski out is about 10 foot walk to the magic carpet in the backyard. Tina of room. First class appliances. Tons of parking. We had a big group. Also two great places to hang out upstairs in the great room then the kids needed up hanging out a lot on the main floor. Checking in was a piece of cake and Todd was very responsive if we needed anything. Can’t...
United States
Marc G.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Beautiful Custom Built Timber Frame Home, Sleeps 11

Wilmington
10.0 out of 10, Exceptional, (108)
"The house is beautiful and has a gorgeous view, especially at night of the stars. Michael was super responsive with a couple of questions we had on logistics and supplies to bring. We would highly recommend staying there and will probably book again in the future."
United States
Jeff L.
Beautiful Custom Built Timber Frame Home, Sleeps 11
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, 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 Jamaica holiday rental for you by simply entering your desired dates. Then check your favorite 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 depends 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 €224 per night. Entering your travel dates in the search wizard you might find 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?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: 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 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Jamaica?

With 39 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.