
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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Popular amenities for Highlands rentals with a pool
House rentals with a pool

The Hudson Hideaway~Pool, Hot Tub, Sauna~1hr toNYC
This was a great home for our family trip. we ranged from 2 to 70 years old, and everyone was comfortable. The house is very nice and full of character and we loved the back yard with the pool, hot tub and sauna. It's very close to the trails too! Highly recommend!

Enchanted Escape | POOL, LAKE, Concierge Services
We had such a great experience staying at this Airbnb. The house was beautiful, super clean, and the view was just perfect honestly even better than the photos. What really made our stay stand out though was the host, Sunny. He was amazing so helpful, kind, and incredibly thoughtful. As a Muslim family, we really appreciated how respectful and considerate he was. He made sure we had our privacy and went out of his way to make everything as easy and comfortable as possible for us. It honestly felt like staying at a friend’s place. We’d definitely come back and highly recommend this spot to anyone looking for a peaceful, welcoming place to stay.

Summer Adventures in Cold Spring at Gilbo's
We were there for a USMA graduation, and the location / accommodations worked great. Handy having a decent grocery store two blocks away. The walking loop down to the Foundry and Cold Springs Park is delightful. Nice with our house guests (extended family and friends) to be able to spread out in the place. Kitchen was spacious and awesome for family meals. Pool wasn't open yet, but looked inviting to add to the outside BBQ area.

4Br Mountain Brook House on 130 acres w/ trails
It was a fantastic house with a beautiful view. Plenty of space and we really enjoyed our stay. The property itself is absolutely gorgeous. Would definitely come back.

The Barger Wixon House
Stayed for West Point graduation. House was awesome. Hosts were more awsomelierist….. Highly recommend. GO ARMY! BEAT navy!

Peaceful Light-Filled Guesthouse 1 Hour From NYC
Our family of 5 and pup had the best time on this gorgeous property! The photos do not do the artful design justice, it’s simply stunning and so thoughtful. Our kids swam ever day and loved the pool. We enjoyed Grace Farms, Prospect Movie Thester and a lovely Father’s Day meal at the Inn at Pound Ridge. The kitchen is incredibly well stocked for someone who likes to cook and DoorDash was also easy to use when we didn’t feel like cooking. We will definitely be back! Thank you, RJ and John!

Modern House with Private Pool, Hot-Tub, Fireplace
It was a beautiful stay and everything were just like the photos! We enjoyed our stayed!

Heated Pool On | Fenced Yard | Hot Tub | Lake View
Loved staying here, Fanny was very responsive. The house is so spacious. My girls and I had a blast!
Apartment rentals with a pool

One bedroom condo at Mountain Creek Resort
Kristof was an excellent communicator & his instructions were clear. He was responsive to my questions and the unit was as described. This location is very convenient for us to visit with family in the area

Valley Overlook @ Mtn Creek Resort Park & Play
I had a wonderful stay at this Airbnb in Vernon, New Jersey, right by Mountain Creek. The one-bedroom space was exactly as described in the photos—clean, cozy, and inviting. The accommodations, including the pool and hot tubs, and sauna were fantastic and easily accessible. The host was very responsive to messages, making the whole experience smooth and enjoyable. Highly recommend!

Cozy Retreat | Pool & Hot Tub | Mountain Creek Resort @ Appalachian
While having a vibe similar to the overlook hotel from the Shining, the place was amazing. Beautiful views and felt super cozy. Would recommend a stay here to anyone!

Appalachian Lodge Top Floor w/views
I enjoyed my stay here! Gorgeous condo with an absolutely breathtaking view. Decided to stay here for my friends wedding and it couldn’t have been a more perfect spot. Thank you to Paul and family for allowing me to stay at your home.

✰ 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5
Massimo was the absolute best and sweetest, honest, helpful, generous, considerate person I’ve ever worked with on here. His home was so beautiful, clean, and aesthetically pleasing. He even provided snacks, water, and mash mellows and graham crackers along with the sticks if we wanted to use the onsite bonfire. He thought of everything down to little candy in trays, chocolates , probably the best bed I’ve ever slept in. There was not 1 thing about this trip I could complain about. I bragged to my friends who came over how amazing he was even at responding when I got lost. I’ve recommended him to a few people already so I hope he gets an abundance of business. It was worth every penny. He is an exceptional host and person. I will make it back to stay again. If you’re looking for pure comfort and ease don’t waste a burger second and book ! His place is worth it. Thank you so much Massimo you made my birthday amazing!!!!

Modern Ski in/out/waterpark/King Bed/WIFI/Parking
It is a great location, with plenty of things to do in the immediate vicinity. The unit was quiet, clean, comfortable, and provided everything I needed for a week long stay. The owner was very responsive to any query, and I did not have any issues with the unit during my stay. I'd work with Henry again for a future stay in Vernon, NJ.

Resort Getaway @ Mtn. Creek -pool/hot tub/sauna
Kurk's place is updated nicely. Bed is comfy. The tub is amazing! The resort is very nice, the scenery and mountains surrounding it are beautiful, and the condo all made for a relaxing stay!

All New Chic Ski in/out King bed
Had a great stay at Joe’s place, it looks exactly like the description, completely spotless and clean. Very clear instructions and he’s always responsive. Felt right at home. I highly recommend staying at Joe’s place.
Quick stats about holiday rentals with a pool in Highlands
Total rentals
10 properties
Nightly prices starting at
$90 SGD before taxes and fees
Total number of reviews
1.1K 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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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Fairfield Beach
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Mountain Creek Resort
- United Nations Headquarters
- Statue of Liberty
- Central Park Zoo
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Radio City Music Hall
- Rye Playland Beach
- Bronx Zoo
- The Metropolitan Museum of Art
- Astoria Park
- Minnewaska State Park Preserve