
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

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

Curl Up & Relax, Stylish Stay nr Woodstock

Spacious Catskills Farmhouse on over 5 acres!

Charming contemporary cottage with lap pool
Condo rentals with a pool

206 · Renovated Chic Premium 1 bdrm

Valley Overlook @ Mtn Creek Resort Park & Play

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

Comfy Studio at Mountain Creek Resort

Comfortable, chic, modern and sophisticated condo

✰ 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5

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

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

The Hilltop • Fenced 8-Acre Dog-Friendly Retreat

The Hudson Hideaway~Pool, Hot Tub, Sauna~1hr toNYC

Luxe Wooded Modern Getaway Retreat + Spa

Cold Spring Mountain Retreat: Autumn Oasis

The Perch, a luxe cottage 1h from NYC

A Lovely Cottage in the Woods

Hopewell House

Gorgeous Garrison Gem: Pool, Sauna, Hot Tub & More
Quick stats about vacation rentals with a pool in Highlands
Total rentals
10 properties
Nightly prices starting at
$98 CAD 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 pools Orange County
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- 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