Vacation rentals with a pool in Highlands
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Highlands
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 Highlands rentals with a pool
House rentals with a pool
Home in Pound Ridge
5.0 out of 5 average rating, 126 reviewsPeaceful Light-Filled Guesthouse 1 Hour From NYC
Home in West Milford
4.99 out of 5 average rating, 114 reviewsOn The Rocks In The Hot Tub
Home in Middletown
4.94 out of 5 average rating, 101 reviewsSummer Farm Country Escape with Pool and Hot tub.
Home in Bushkill
4.96 out of 5 average rating, 297 reviewsEntire House One Bedroom Hot Tub Barrel Sauna
Home in Woodstock
4.98 out of 5 average rating, 101 reviewsWoodstock Historic Artist Estate- The Museum House
Home in Yorktown Heights
4.88 out of 5 average rating, 120 reviewsCozy winter getaway 1 hr from NYC!
Home in Putnam Valley
4.93 out of 5 average rating, 182 reviewsPutnam Valley Escape
Home in Woodstock
4.91 out of 5 average rating, 214 reviewsJapanese Teahouse & Onsen, outside shower, tennis
Condo rentals with a pool
Condo in Vernon Township
4.97 out of 5 average rating, 146 reviewsComfy Studio at Mountain Creek Resort
Condo in Vernon Township
4.95 out of 5 average rating, 241 reviewsNYC Escape 1 hr away
Condo in Vernon Township
4.95 out of 5 average rating, 738 reviewsAppalachian Lodge Top Floor w/views
Condo in Vernon Township
4.76 out of 5 average rating, 138 reviews1 Bedroom Condo @ Appalachian Resort Hotel
Condo in Vernon Township
4.94 out of 5 average rating, 104 reviewsResort Getaway-Mtn Creek Ski/Pool/Hot Tub/Sauna
Condo in Vernon Township
4.87 out of 5 average rating, 178 reviewsNewly renovated bright and open 1 bedroom
Condo in Vernon Township
4.9 out of 5 average rating, 207 reviewsUpscale Condo Ski-In/Out Mountain Creek 1 hr NYC
Condo in Vernon
4.94 out of 5 average rating, 126 reviewsMtn front Resort Pool Hot Tub Sauna Best View 340
Home rentals with a private pool
Home in Lagrangeville
4.84 out of 5 average rating, 121 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
Home in Kerhonkson
4.94 out of 5 average rating, 326 reviewsCountry House: Rustic Charm With Modern Feel
Farm stay in Fleischmanns
4.91 out of 5 average rating, 11 reviewsEscape to a Dreamy 1857 Farmhouse in Fleischmanns
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
Home in Lanesville
4.77 out of 5 average rating, 205 reviewsGo Hiking and Skiing from a Family-Friendly Farmhouse
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
Quick stats about vacation rentals with a pool in Highlands
Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
990 reviews
Nightly prices starting at
$60 before taxes and fees
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