Holiday Rentals in Jamaica

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Our top choices for Jamaica holiday rentals

Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.
Jamaica
8.8 out of 10, Excellent, (8 reviews)
"Beautiful home, we enjoyed our stay!"
United States
Luke B.
The price is €625
includes taxes & fees
27 May - 28 May
Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester
Townshend
The price is €326
includes taxes & fees
14 May - 15 May
Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (169 reviews)
"3rd year at this listing, absolutely love it. Close to okemo and mount snow. Host got back to me very quickly when reached out to. "
United States
Jake D.
The price is €307
includes taxes & fees
19 May - 20 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is €273
includes taxes & fees
14 May - 15 May
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
3.0 star property
West Dover
The price is €443
includes taxes & fees
14 May - 15 May
Outdoor Adventure Hub! Family Home in West Dover

Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
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 €246
includes taxes & fees
28 May - 29 May
Wellness Getaway with a Personal Sauna, and Private River Beach!

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
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 €272
includes taxes & fees
26 May - 27 May
Family Friendly Hilltop House In Putney Vermont

Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Location location location!"
United States
Britt H.
The price is €347
includes taxes & fees
14 May - 15 May
Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.6 out of 10, Exceptional, (12 reviews)
"The best stay ever!!! Very clean, great location, super cozy, all the amenities you would need. 5/5 stars, we will be coming back :)"
United States
Carolina I.
The price is €279
includes taxes & fees
14 May - 15 May
Cozy Bromley Retreat

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
The price is €191
includes taxes & fees
19 May - 20 May
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"Great proximity to mountain and Ludlow downtown area."
United States
Yasmine O.
The price is €259
includes taxes & fees
14 May - 15 May
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.6 out of 10, Good, (56 reviews)
"The place was very dirty. The linens were dirty, the pots/pans and all of the cooking utensils were dirty. There was a rubber band on the floor in bathroom that didn't belong to us.There was only 3 forks and a few spoons. Very little silverwear."
United States
Leigh-Ellen F.
The price is €320
includes taxes & fees
15 May - 16 May
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is €235
includes taxes & fees
14 May - 15 May
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

LUXE Forest Retreat

LUXE Forest Retreat
Chester
The price is €407
includes taxes & fees
21 May - 22 May
LUXE Forest Retreat

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
Londonderry
10.0 out of 10, Exceptional, (10 reviews)
"Great location, well-designed house, and a beautiful view."
United States
Marcel P.
The price is €538
includes taxes & fees
18 May - 19 May
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (108 reviews)
"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."
United States
Hannah M.
The price is €259
includes taxes & fees
14 May - 15 May
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
7.4 out of 10, Good, (21 reviews)
"Poor management company. Great lodge. "
United States
Billy W.
The price is €330
includes taxes & fees
15 May - 16 May
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Clock Tower Base Area
9.4 out of 10, Exceptional, (27 reviews)
"This condo is a true ski-in, ski-out experience! Literally walked out the back door and skied to the lift. (A/B lifts) The kitchen was well appointed, the bed comfortable, and was perfectly set up for a ski vacation. The entire space had a comfortable, rustic vibe. Would definitely stay here again when returning to Okemo."
United States
Patricia D.
The price is €331
includes taxes & fees
14 May - 15 May
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

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

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
9.0 out of 10, Wonderful, (80 reviews)
"Unit was as advertised. Clean and comfortable."
United States
Ralph D.
The price is €217
includes taxes & fees
16 May - 17 May
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (33 reviews)
"Nice place close to mountain easy in easy out"
United States
Aaron B.
The price is €183
includes taxes & fees
14 May - 15 May
Efficient condo near slopes with kitchenette & great location
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 €246 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?

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna: This holiday home rental outside of Jamaica is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 11 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 balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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. 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.