
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

Adams Farm-"The Little Farmhouse"

The Brick House on Washington Street

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Historic Home on 17 acres of land. Go escape!

Historic 1850’s Renovated Farmhouse w/ Pool!
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)

Renovated Stratton Mtn Studio | Walk to Lifts

Luxury Condo | 2 Ensuites | Peak Foliage Retreat

One Bedroom Suite Near Okemo

Mountainside Condo- 3bed/3Bath with amazing views.
Other vacation rentals with a pool

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

Cozy Bear- 1 mile to Mt Snow Ski Home

Clean cozy Stratton chalet

Modern Cottage between Mount Snow and Stratton

Goose Crossing

Winter Skiing @ Mt Snow! Ski off trail sleeps 8.

Blue Bird Cabin at Brattleboro KOA

Luxury Mid-Century Modern Vermont Home, Okemo View
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- 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