
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

Lakefront, Indoor Pool, Pvt Hot Tub, Pickleball

Autumn Leafing in Cold Spring

4Br Mountain Brook House on 130 acres w/ trails

The Barger Wixon House

Farmhouse w/ Sauna & Hot Tub near Storm King

Upstate Modern Scandinavian Barn in the Catskills

Spacious Catskills Farmhouse on over 5 acres!

Charming contemporary cottage with lap pool
Condo rentals with a pool

Valley Overlook @ Mtn Creek Resort Park & Play

Cozy Retreat | Pool & Hot Tub | Mountain Creek Resort @ Appalachian

Comfy Studio at Mountain Creek Resort

Deluxe 1 Bdr | Walkout Patio to Pool & Hot Tub! | Mountain Creek Resort @ Appalachian

Comfortable, chic, modern and sophisticated condo

Modern Ski in/out/waterpark/King Bed/WIFI/Parking

Little Getaway at the Black Creek Sanctuary

Resort Getaway @ Mtn. Creek -pool/hot tub/sauna
Other vacation rentals with a pool

Cold Spring Village Maisonette with Pool

Luxe Wooded Modern Getaway Retreat + Spa

Country Retreat | Last Call for The Pool!

BoHo Scandi Farm Retreat, Fireplace, Dogs Welcome

Cold Spring Mountain Retreat: Autumn Oasis

Catskills Retreat: 4Br l Fire-pit l Hot Tub l Hike

Cold Spring Gem

The Perch, a luxe cottage in the woods 1h from NYC
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
1.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
Destinations to explore
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- Rentals with a washer and dryer Highlands
- Waterfront rentals Highlands
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- Rentals with pools Orange County
- Rentals with pools New York
- Rentals with pools United States
- Times Square
- Rockefeller Center
- Bryant Park
- Madison Square Garden
- Empire State Building
- Columbia University
- MetLife Stadium
- Central Park Zoo
- Yankee Stadium
- Mountain Creek Resort
- Citi Field
- Fairfield Beach
- United Nations Headquarters
- Rye Beach
- Grand Central Terminal
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- Radio City Music Hall
- Canarsie Beach
- The Metropolitan Museum of Art
- Astoria Park
- Bronx Zoo
- Minnewaska State Park Preserve
- Walnut Public Beach