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 Stormville
4.94 out of 5 average rating, 176 reviewsPrivate Hudson Valley Country Retreat
Home in Highland Mills
4.83 out of 5 average rating, 52 reviewsPerfect for families and large groups
Home in Rhinebeck
4.87 out of 5 average rating, 116 reviews4Br Mountain Brook House on 130 acres w/ trails
Home in Putnam Valley
5 out of 5 average rating, 20 reviewsThe Barger Wixon House
Home in Woodstock
4.92 out of 5 average rating, 239 reviewsLittle owl Japanese teahouse: pool and tennis
Home in Kerhonkson
4.94 out of 5 average rating, 109 reviewsModern Lux 5-Bed, Catskill view, Dog Friendly!
Home in woodstock
4.86 out of 5 average rating, 504 reviewsCABIN WITH HOT TUB OUTDOOR FIREPLACE PIZZA OVEN
Home in Narrowsburg
4.95 out of 5 average rating, 177 reviewsMid-Century Modern House with Fireplace & Hot-Tub
Condo rentals with a pool
Condo in Vernon Township
4.92 out of 5 average rating, 107 reviewsValley Overlook @ Mtn Creek Resort Park & Play
Condo in Vernon Township
4.9 out of 5 average rating, 51 reviewsComfortable, chic, modern and sophisticated condo
Condo in Vernon Township
4.99 out of 5 average rating, 71 reviewsCozy Condo at the Base of Mountain Creek Resort
Condo in Vernon Township
4.95 out of 5 average rating, 259 reviewsNYC Escape 1 hr away
Condo in Vernon Township
4.96 out of 5 average rating, 99 reviews✰ 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5
Condo in Vernon Township
5 out of 5 average rating, 47 reviewsLittle Getaway at the Black Creek Sanctuary
Condo in Vernon Township
4.95 out of 5 average rating, 130 reviewsResort Getaway @ Mountain Creek-Pool/Hot Tub/Sauna
Condo in Vernon Township
4.91 out of 5 average rating, 331 reviewsAppalachian TOP 4TH FLOOR Studio+ w/amazing views!
Home rentals with a private pool
Home in Woodstock
5 out of 5 average rating, 9 reviewsLuxury Retreat in the Catskills
Home in Rhinebeck
5 out of 5 average rating, 69 reviewsRhinebeck Country Living with a Modern Twist
Home in Bearsville
5 out of 5 average rating, 22 reviewsMagnificent Designer Home - Close To Skiing
Home in Kerhonkson
4.95 out of 5 average rating, 346 reviewsCozy Country Cabin for Dogs, Families & Friends
Home in Lagrangeville
4.84 out of 5 average rating, 133 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
Quick stats about vacation rentals with a pool in Highlands
Total rentals
10 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
950 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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