Vacation rentals with a pool in Highlands

Find and book unique homes with a pool on Airbnb

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Popular amenities for Highlands rentals with a pool

House rentals with a pool

Top guest favorite
Home in Warwick
4.98 out of 5 average rating, 60 reviews

4 bedroom house with pool (Kids & Dog Friendly)

KerriRating, 5 stars6 days ago
Our stay was wonderful, and the host was great from beginning to end! Highly recommend
Guest favorite
Home in Newburgh
4.83 out of 5 average rating, 81 reviews

Entire Home (private pool), Event Friendly

ChannyRating, 5 stars1 week ago
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.
Guest favorite
Home in Bushkill
4.92 out of 5 average rating, 201 reviews

Entire House Hot tub Barrel Sauna Private Backyard

PietroRating, 5 stars3 months ago
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
Guest favorite
Home in New Paltz
4.93 out of 5 average rating, 133 reviews

Harrison Field Pool 10Acres BikeRailTrail 2Town

AlannaRating, 5 stars6 months ago
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!
Superhost
Home in Grahamsville
4.89 out of 5 average rating, 92 reviews

Spacious Catskills Farmhouse w/ In-Ground Pool!

AnnRating, 5 stars2 months ago
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.
Guest favorite
Home in Saugerties
4.86 out of 5 average rating, 86 reviews

Unique Contemporary on 40 Pvt Ac, Enclosed Hot Tub

NadineRating, 5 stars2 months ago
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!
Guest favorite
Home in Clinton Corners
5 out of 5 average rating, 8 reviews

Family home in the country

CeciliaRating, 5 stars6 months ago
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.
Superhost
Home in Highland
4.78 out of 5 average rating, 18 reviews

Classic Hudson Valley Riverfront House with Pool

GeraldineRating, 5 stars3 months ago
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

Superhost
Condo in Vernon Township
4.79 out of 5 average rating, 123 reviews

Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

JasonRating, 5 stars4 days ago
Henry’s place was exactly as described . The place was clean and perfect for 2 people. I would recommend staying there again.
Top guest favorite
Condo in Vernon Township
4.96 out of 5 average rating, 165 reviews

One bedroom condo at Mountain Creek Resort

MelissaRating, 5 stars1 month ago
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!
Guest favorite
Condo in Vernon Township
4.92 out of 5 average rating, 111 reviews

Valley Overlook @ Mtn Creek Resort Park & Play

MollyRating, 5 stars2 months ago
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!
Guest favorite
Condo in Vernon Township
4.94 out of 5 average rating, 835 reviews

Appalachian Lodge Top Floor w/views

Jahari LeeRating, 5 stars5 days ago
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!
Guest favorite
Condo in Vernon Township
4.96 out of 5 average rating, 51 reviews

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

CherylynRating, 5 stars1 month ago
Had a great weekend at Chris’s place! 10/10 recommend! Can’t wait to be back next ski season!
Guest favorite
Condo in Vernon Township
4.92 out of 5 average rating, 64 reviews

Comfortable, chic, modern and sophisticated condo

KerryRating, 5 stars3 weeks ago
wonderful stay and will definitely be booking again:)
Top guest favorite
Condo in Vernon Township
4.96 out of 5 average rating, 107 reviews

✰ 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5

GregRating, 5 stars1 month ago
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!
Top guest favorite
Condo in Vernon Township
5 out of 5 average rating, 33 reviews

Luxury Romantic Hideaway

LisaRating, 5 stars2 months ago
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

Destinations to explore

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