Holiday 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.

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Guest favourite

Home in Narrowsburg

4.95 out of 5 average rating, 197 reviews

Modern House with Private Pool, Hot-Tub, Fireplace

A modern 3BR/2BA Catskills retreat on 6 private acres with heated pool, hot-tub, and fireplace. Perched on a hill, this single-level home offers scenic views, mid-century modern decor, and comfort—ideal for girls' trips, couples and families. Amenities: Private Heated Pool Fireplace High-speed Wi-Fi Modern kitchen Grill A/C Narrowsburg offers: -Restaurants & Shops -Luxury Spas & Yoga -Alpaca Farm -Hiking -Farmer's Markets -Delaware Valley Arts Alliance Experience the best of the Catskills!

Guest favourite

Home in West Milford

4.98 out of 5 average rating, 150 reviews

On The Rocks In The Hot Tub

Unique home featuring a large deck with an enclosed hot tub, indoor/outdoor bars, game room and seasonal pool (pool is not heated) Fall-Winter:Minutes away from the town of Warwick. Pennings, Heaven Hill Farm for apple-pumpkin picking, Peter Mountain, Mountain Creek for skiing. Many vineyards/cideries Summer: Boating on Greenwood Lake, kayak rentals, hiking (Appalachian Trail), drive-in theater, family activities at Wawanique State Park, Crystal Springs Golf and ice cream at Bellvale Creamery

Guest favourite

Home in North Branch

4.89 out of 5 average rating, 114 reviews

Indoor Heated Pool + Sauna + Creek, Spacious 4Bdrm

This one-of-a-kind property nestled in the quiet village of North Branch has all the makings of a dream vacation. This cozy home in the woods has 3 stunning acres with creek access towards the end of the property! Enjoy a full-size heated indoor pool + an infrared sauna open year-round combined with breathtaking scenery. If you're looking for a vacation for kids + adults, this peaceful home is for you! Enjoy a relaxing vacation in a comfortable home with all the beauty that nature has to offer.

Superhost

Cabin in Swan Lake

4.83 out of 5 average rating, 202 reviews

Stunning Sullivan County Cabin w/HotTub/Spa &Pool

This designer home is in the western Catskills, 2hrs away from NYC on 10 acres of hillside property. 20 mins from the Kartrite indoor water park. Perfect family getaway for hiking, canoeing, fishing , water sports. Quiet, secluded, fully stocked kitchen, 360 degree views , patio deck seating private heated pool from May 20- Sept 30 cabana, hammock, loungers Starting March 1st 2021, we are offering our newly installed Hot Tub/ Spa ( 5-6 seater) set into the side of hill w/ magnificent views

Guest favourite

Home in Hudson

4.93 out of 5 average rating, 243 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

CASA LUNA Perfect peaceful upstate NY country retreat. An all year round escape. 2 hours from NYC driving or Amtrak. 15 mins to downtown Hudson with great restaurants and shopping. 20 mins to water skiing on Copake Lake and 25 mins snow skiing at Catamount, Berkshires. Private & secluded. Columbia County, New York. 4 bedrooms, 2.5 bathrooms, salt water swimming pool, koi pond, claw foot bath tub, steam room. If CASA LUNA is booked check CASA SOL https://www.airbnb.com/rooms/1627143

Guest favourite

Home in Bushkill

4.91 out of 5 average rating, 112 reviews

Lakefront, Pool, Hot Tub, Arcade, Pickleball

Recently highlighted by Pocono Television Network, Old Mallard opens its doors to spring at this inviting lakefront retreat—perfect for couples, families, or anyone craving a nature-packed getaway. The Private Heated Pool opens May 15, 2025. Enjoy the private hot tub, kayaks, arcade, ping pong, or unwind at the indoor community pool, open weekends 12-4 PM. A quick 5-minute trip to Bushkill Falls lets you explore the vibrant spring. Book now for a lakeside stay you won’t forget!

Guest favourite

Home in Woodstock

4.91 out of 5 average rating, 199 reviews

Woodstock Romantic Mountain Studio w/ Pool

Come escape to the cozy Woodstock studio . Swim, hike, bike, BBQ and experience peace & serenity. Our large studio is a vacation gem and home away from home on 10 mountain top acres with large shared pool. 5 star. (Pool is shared with us, & we try to respect our guests privacy.) High-speed wifi Work remotely. The studio is on a private road just 5 mins from the center of Woodstock. Perfect for a couple, small family or single. 30 day rentals available October-May

Top Guest favourite

Condo in Vernon Township

4.94 out of 5 average rating, 145 reviews

Ski-In/Ski-Out @ Mountain Creek-Pool/Hot Tub/Sauna

NEWLY Renovated! Top floor 1 bedroom Condo with Mountain/Pool View at Mountain Creek Resort. Steps away from ski mountain & gondola ! Swim in the outdoor heated saltwater pool, relax in the sauna or soak in the hot tub while taking in mountain views, Catch the sunset from your private top floor balcony or cozy up by your gas fireplace. Visit award-winning spas, golf, breweries, wineries, farms, and fine dining at Crystal Springs & Warwick, NY--only 10 min away.

Guest favourite

Home in Woodstock

4.86 out of 5 average rating, 133 reviews

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!

**POOL OPENING MAY 9, 2025** Our beautiful Villa has amazing mountain views, a clean, modern design and is the perfect getaway to socialize & relax. It is ideally located for hiking & has a gorgeous, private salt water pool (mid May- mid Oct) and a wonderful hot tub which is open year round! In addition to the main house there is also a spacious studio cottage (with bathroom) & heat that can be used as a WFH private office. It has it's own high speed internet.

Guest favourite

Home in East Stroudsburg

4.97 out of 5 average rating, 120 reviews

Stylish 4Bdr Mountain Retreat, Hot Tub, Pool

Welcome to Serenity Falls! A true gem mountain house with its own private waterfall! Large deck with a private hot tub, dining area, and magical atmosphere with entertainment for all. This retreat also offers a full-size billiards table and a game room with PS4, darts, and other toys for all ages. Enjoy delicious meals with loved ones on the spacious deck with a BBQ grill and take in the breathtaking Poconos scenery. What else can you ask for?

Superhost

Villa in Port Murray

4.86 out of 5 average rating, 137 reviews

Mountaintop Villa w amazing view, pool

Welcome to the Mountain Villa! Nestled on 13 acres of picturesque landscape, this Airbnb property boasts breathtaking views that will leave you in awe. Relax and unwind by the private in-ground pool while taking in the stunning scenery. When the nights get chilly, cozy up by the wood burning fireplace for a perfect evening. Please read the house rules prior to requesting to book.