
Vacation rentals with a pool in Highlands
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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

4 bedroom house with pool (Kids & Dog Friendly)
Our stay was wonderful, and the host was great from beginning to end! Highly recommend

Entire Home (private pool), Event Friendly
Faisal was extremely responsive throughout our stay. we loved the indoor pool and the game tables. there was a nice selection. The rooms were nice. It was great that the bedrooms were on the same floor as the living room, dining room and kitchen. We came with an elderly person and they were able to make their way around the house. my son asked if he can use the fire pit out in back and he was able to. he collected wood from the side of the house. nice location. we really enjoyed our stay.

Entire House Hot tub Barrel Sauna Private Backyard
I have been to many places but this house was top notch I'm glad I got to stay there with my family. everyone was very happy with the property. I would like to stay in the summer as well

Harrison Field Pool 10Acres BikeRailTrail 2Town
We had a great weekend celebrating our parents anniversary. The house was plenty big for all of us and the grounds are beautiful. Nathan was quick to respond when we had trouble navigating the AC and made sure we enjoyed our stay!

Spacious Catskills Farmhouse w/ In-Ground Pool!
This is a beautiful old house with huge windows and tons of light, beautiful views, and lots of bedrooms and hang out areas so everyone has space. The kitchen had everything we needed, the beds were comfortable and the entire place was super clean and tidy. There was a good selection of games we could play and music that our family enjoyed. It was also so nice that the house was pet friendly. The only downside was that the house was quite close to the road and my kids really wanted to sled down the hill in the backyard, but there was nothing to stop them from sliding into the road. There is hardly any traffic on the road, though, so noise was not an issue. We really enjoyed our stay here! Definitely recommend for big groups or families. We are a 7 person family - teenage kids, parents, grandparents.

Unique Contemporary on 40 Pvt Ac, Enclosed Hot Tub
Such a great experience that reaffirms how hard hosts work! Robyn communicated the weather problems in advance and let us know things might be iffy getting in because of a winter storm. Instead of just making sure the home itself was pristine, relaxing, and totally picturesque, she made sure our arrival was perfect. Snow plowed, everything iced, bag of goodies hung up on our arrival. It was such incredible, flexible caretaking of the property and the guests! Besides that, onto the regular stuff- awesome kitchen, hot tub, bedrooms, everything super clean. Was a perfect winter stay!

Family home in the country
We loved staying at Craig’s house. Very warm and inviting with everything you need. Very quiet and peaceful wooded area which we enjoyed very much at the end of the day.

Classic Hudson Valley Riverfront House with Pool
We had a wonderful time at Dan’s house! The peaceful surroundings made it the perfect getaway after the hectic holiday season. The house itself was clean, cozy, and thoughtfully equipped with all the amenities we could need. The fireplace and piano added such lovely, warm touches to our stay, and we especially enjoyed the stunning view of the river. With multiple rooms to spread out, everyone had their own space to relax, which made our stay even more comfortable. The kitchen was fully stocked with everything we needed, and the central location was ideal for exploring nearby towns like Kingston, Poughkeepsie, and New Paltz. On top of everything, Dan was incredibly responsive and provided clear, thoughtful instructions. He is a great host. This home was exactly what we needed to unwind, recharge, and enjoy some quality time together. We highly recommend and would love to return in the future (and enjoy the pool!).
Condo rentals with a pool

Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Henry’s place was exactly as described . The place was clean and perfect for 2 people. I would recommend staying there again.

One bedroom condo at Mountain Creek Resort
We really enjoyed our stay! The condo was VERY clean, full stocked with all of the needed essentials and in a great location right by the ski slope. Both the bed and pull-out coach were SUPER comfortable. All instructions were super clear, and the recommendations were perfect. Thank you for letting us stay at your place, we love Mountain Creek!

Valley Overlook @ Mtn Creek Resort Park & Play
My family and I had a wonderful weekend at Joe’s place. The unit was just as he described, and perfect for our needs. My older son enjoyed going snowboarding and it was great to have a space to hang out with my infant while the others were on the slopes. Joe was even able to accommodate a late checkout for us so we had a place to be with the baby while my other son was out snowboarding which was so appreciated! We will definitely be back!

Appalachian Lodge Top Floor w/views
My children and I had a wonderful time! The unit was immaculate, the views were lovely, and there was plenty to do at the hotel. Paul was the best host! We had a car issue and had to extend our stay. He was polite, quick to respond, accommodating, and he took excellent care of us whenever we had any questions or concerns. We are looking forward to visiting again!

Deluxe 1 Bdr | Walkout Patio to Pool & Hot Tub! | Mountain Creek Resort @ Appalachian
Had a great weekend at Chris’s place! 10/10 recommend! Can’t wait to be back next ski season!

Comfortable, chic, modern and sophisticated condo
wonderful stay and will definitely be booking again:)

✰ 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5
Massimo was so communicative, place was great, and the little extras provided -- snacks, beverages, and the set up for old time arcade games -- totally awesome! Thanks!

Luxury Romantic Hideaway
Asko’s home was a dream to stay in for a week. Spacious living areas, high-quality furnishings and well stocked kitchen and bathrooms made my family and I immediately feel at home from the first moment. Asko was kind and very responsive to a few questions that I had upon arrival. Walking distance to Mountain Creek. Highly recommend and will stay there again! Would give six stars if I could!
Quick stats about vacation rentals with a pool in Highlands
Total rentals
10 properties
Nightly prices starting at
ﺩ.ﺇ257 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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- Radio City Music Hall
- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Tenement Museum
- Riverside Park
- Mountain Creek Resort
- Comedy Cellar
- Apollo Theater
- St. Nicholas Park
- Citi Field
- Yankee Stadium
- Inwood Hill Park
- MetLife Stadium
- United Nations Headquarters
- Bronx Zoo
- Astoria Park
- Rockefeller Center
- Statue of Liberty
- Minnewaska State Park Preserve