
Vacation rentals with a pool in Jamaica
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Jamaica
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Jamaica rentals with a pool
House rentals with a pool

Hot Tub, Game Room, Minutes to Mt. Snow & Stratton

Magical Farm Getaway - a must visit!

The 1770 House

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Stratton; 8 min. Walk to food/drink. Pet friendly!

Historic Home on 17 acres of land. Go escape!

Historic 1850’s Renovated Farmhouse w/ Pool!

Hollywood Bungalow in the Berkshires #C0191633410
Condo rentals with a pool

Mount Snow Ski Chalet

Slopes N Seasons | Trailside Condo at Mount Snow

Cozy Updated 2 Bedroom Corner Condo

Seasons Condo @ Mt Snow (Ski-in/out, hike, bike)

Ski in/out - 2BR Condo - Indoor Pool/Spa

Perfect 3 Br. Getaway Condo in Stratton, Vermont!

One Bedroom Suite Near Okemo

Jiminy Peak Country Inn - ski in/out condo MT view
Other vacation rentals with a pool

MtSnow/Stratton Ski Lodge-Hot Tub-Game Room-Pool

The Manor-Stunning Modern Farmhouse with Hot Tub

SnowTree Chalet- Summer monthly discount 50%

Clean cozy Stratton chalet

Mountain Blossom Retreat by Evergreen Home

Sundance Village- Ski-on/off, Hot tub, clubhouse

Wandering Moose: Four Season Pool, Hot Tub & Sauna

Blue Bird Cabin at Brattleboro KOA
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- Rentals with pools Windham County
- Rentals with pools Vermont
- Rentals with pools United States
- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Six Flags Great Escape Lodge & Indoor Water park
- Berkshire East Mountain Resort
- Magic Mountain Ski Resort
- Pats Peak Ski Area
- West Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Sugarloaf State Reservation
- Dorset Field Club
- The Shattuck Golf Club
- Northern Cross Vineyard
- Hooper Golf Course
- Crotched Mountain Ski and Ride
- Pico Mountain Ski Resort
- Autumn Mountain Winery
- Whaleback Mountain
- Mount Snow Ski Resort
- Hildene, The Lincoln Family Home
- Ekwanok Country Club
- Fox Run Golf Club