Jamaica Holiday Rentals

  • 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
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Jamaica holiday rentals

Exterior

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 HK$2,584
HK$5,730 total
includes taxes & fees
17 May - 18 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.
Smart TV, fireplace, books, stereo

Stratton Ski Haus | A-Frame Hot Tub Sauna EV Sleeps 10

Stratton Ski Haus | A-Frame Hot Tub Sauna EV Sleeps 10
Jamaica
10.0 out of 10, Exceptional, (3 reviews)
"Great peaceful stay. Hosts were always in communication with us. Close to Stratton. Hot tube & sauna were a great top off to a day of skiing. "
United States
fran g.
The price is HK$4,072
HK$8,805 total
includes taxes & fees
20 May - 21 May
Stratton Ski Haus | A-Frame Hot Tub Sauna EV Sleeps 10
Interior

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 HK$1,198
HK$4,083 total
includes taxes & fees
21 May - 22 May
Outdoor Adventure Hub! Family Home in West Dover
Indoor pool

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Okemo Village
10.0 out of 10, Exceptional, (64 reviews)
"The host is extremely friendly and accommodating! The place is large and didn’t feel cramped with two adults and five male teenagers! Perfect in every way, clean, well stocked, and easy access to the slopes!"
United States
Nina
The price is HK$3,523
HK$6,573 total
includes taxes & fees
22 May - 23 May
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Living room

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 HK$2,322
HK$2,887 total
includes taxes & fees
1 Jun - 2 Jun
Long Trail House at Stratton Mountain Resort
Exterior

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 HK$1,331
HK$2,797 total
includes taxes & fees
18 May - 19 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Smart TV, fireplace

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (13 reviews)
"great location easy access to the mountain and the pool was outstanding."
United States
jim f.
The price is HK$3,629
HK$9,231 total
includes taxes & fees
15 May - 16 May
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Outdoor pool, a heated pool

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (23 reviews)
"Great communication without host. The property is clean, well stocked and well maintained. Would definitely stay again! Thanks for letting us share your space."
United States
Steve G.
The price is HK$2,349
HK$4,200 total
includes taxes & fees
15 May - 16 May
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Exterior

Brand New Luxury “Tiny” House, Immersed In Nature

Brand New Luxury “Tiny” House, Immersed In Nature
Athens
10.0 out of 10, Exceptional, (1 review)
"This is by far the most beautiful home I’ve ever stayed! So clean and amazing views of nature. We can’t wait to come back."
United States
Mia G.
The price is HK$2,153
HK$3,490 total
includes taxes & fees
15 May - 16 May
Brand New Luxury “Tiny” House, Immersed In Nature
Interior

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Whitingham
8.8 out of 10, Excellent, (3 reviews)
"This apartment is very efficient and really wowed everyone based on the automotive inspired design. It was an impeccable space, well stocked, and the beds were even extremely comfortable. We enjoyed the bar/grill within walking distance, too. Would stay here again. "
United States
Ben B.
The price is HK$2,850
HK$5,050 total
includes taxes & fees
16 May - 17 May
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Exterior

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is HK$4,689
HK$8,119 total
includes taxes & fees
1 Jun - 2 Jun
Cozy Vermont Cabin · Mountain Views · Near Okemo
Smart TV, fireplace, stereo

LUXE Forest Retreat

LUXE Forest Retreat
Chester
The price is HK$2,372
HK$3,770 total
includes taxes & fees
17 May - 18 May
LUXE Forest Retreat
Front of property

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is HK$7,664
HK$12,671 total
includes taxes & fees
17 May - 18 May
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
Interior

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 HK$939
HK$2,979 total
includes taxes & fees
15 May - 16 May
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
TV, books

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 HK$2,018
HK$2,402 total
includes taxes & fees
17 May - 18 May
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Dining

New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow
10.0 out of 10, Exceptional, (16 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is HK$2,100
HK$4,682 total
includes taxes & fees
15 May - 16 May
New Ludlow Village Home with Stunning Okemo Mountain View
Interior

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Londonderry
9.6 out of 10, Exceptional, (24 reviews)
"Great communication and very welcoming."
United States
Marcy Y.
The price is HK$1,598
HK$4,575 total
includes taxes & fees
17 May - 18 May
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Smart TV, fireplace

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 HK$1,938
HK$5,020 total
includes taxes & fees
18 May - 19 May
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
Smart TV, fireplace, video games, DVD player

Walk To Town, Hottub, Firepit, Games, Mt Snow

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (59 reviews)
"Hosts were organized and helpful"
United States
Michael C.
The price is HK$2,153
HK$5,662 total
includes taxes & fees
17 May - 18 May
Walk To Town, Hottub, Firepit, Games, Mt Snow
Exterior

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

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester
Townshend
The price is HK$1,761
HK$3,007 total
includes taxes & fees
19 May - 20 May
Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester
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

6/10 Okay
"Room was clean. "
Kathleen 1-night trip
Posted 3 hours ago
Comfort Inn & Suites Brattleboro I-91

Find out more about Jamaica

Search for holiday rentals in Jamaica on Expedia! You can easily find your home rentals, villas, holiday apartments in Jamaica using one of the methods below:

  • View our selection of featured holiday rentals in Jamaica
  • Use the map to find apartments and other holiday homes in the Jamaica neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Jamaica while they last

Look no further and take a look at our great range of rental properties in Jamaica!

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.