Vacation rentals with a pool in Monticello

Find and book unique homes with a pool on Airbnb

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Popular amenities for Monticello rentals with a pool

House rentals with a pool

Top guest favorite
A spacious pool area is surrounded by lounge chairs and patio tables under umbrellas. A large house stands in the background, providing a welcoming setting. The outdoor kitchen area includes seating and appliances, while a small lawn game is visible in the foreground.
Home in Narrowsburg
5 out of 5 average rating, 21 reviews

Farm House with Built in pool/jacuzzi open in May

JennRating, 5 stars1 week ago
We came for a quick girls weekend and were pleasantly surprised by how comfortable and homey we felt here. We loved going to the nearby Woodstock museum and a couple of great restaurants in the area. Sadly, the weather wasn’t great but we hope to come back sometime to enjoy all of the amenities that this home and property have to offer!
Guest favorite
The outdoor space features a stone fire pit surrounded by a paved area, providing a cozy gathering spot. A fenced-in pool area is visible in the background, accompanied by lounge chairs, a gazebo, and a shaded dining area, all set against a natural green landscape.
Home in Saugerties
4.98 out of 5 average rating, 60 reviews

Upstate Family-Friendly House w/ Pool Pets Allowed

NasimRating, 5 stars3 months ago
We had a great time at Natalia house, a very big house with a lot to do for my three years old daughter. Will definitely stay here again.
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 Albrightsville
4.89 out of 5 average rating, 120 reviews

Woodland Mountain Summer Vacation Getaway

MaureenRating, 5 stars2 months ago
We had a great time. Plenty of space for everyone. The house was very comfortable and clean. Would definitely recommend especially if you are vacationing with a large group.
Guest favorite
An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.
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
A wooden deck surrounds a round above-ground pool, offering seating for four on metal lounge chairs. Lush green grass and trees provide a natural backdrop, while the beige siding of the house adds a cozy touch to the outdoor space.
Home in Albrightsville
4.93 out of 5 average rating, 110 reviews

Big House, Private pool, Hot tub & Lots of privacy

VivianeRating, 5 stars2 months ago
I highly recommend a family home, it makes you feel at home 🏠
Guest favorite
An outdoor swimming pool is surrounded by a spacious stone patio, featuring six lounge chairs in vibrant colors. Lush greenery and trees border the area, creating a private setting. The pool reflects the clear sky above, inviting for a refreshing swim.
Home in Kingston
4.83 out of 5 average rating, 70 reviews

Beaver | Pool, Firepit, Secluded, 10 acres

GraemeRating, 5 stars2 months ago
We had an absolutely wonderful stay at Hava’s Airbnb! From the moment we booked, Hava was an incredible host—warm, welcoming, and unbelievably reachable. She responded to every question we had almost instantly, whether it was about check-in details or local recommendations, making the entire experience seamless and stress-free. The place itself was spotless, cozy, and exactly as described, with thoughtful touches that made us feel right at home. Hava’s communication stood out—she checked in to ensure everything was perfect without ever being intrusive. Her suggestions for nearby spots were spot-on, and it’s clear she genuinely cares about her guests’ comfort. We couldn’t have asked for a better host, and we’d love to stay here again. Highly recommend Hava to anyone looking for a fantastic Airbnb experience!
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!

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.
Guest favorite
A sparkling outdoor pool is depicted, with lounge chairs placed around its perimeter. Shade is provided by a large umbrella, while a picturesque lake and green hills are visible in the background. Several people can be seen enjoying the water.
Condo in Lake Harmony
4.79 out of 5 average rating, 144 reviews

Cozy Lake Front Condo on Big Boulder Lake.

DanielleRating, 5 stars3 months ago
Jackie's condo is spacious and welcoming. Beautiful lakefront property, minutes from Big Boulder. Close to all the local restaurants. Layout is larger than it appears on the listing. Felt right at home!
Top guest favorite
The vibrant exterior of The Appalachian building is showcased, featuring colorful wooden siding and multiple balconies. A sparkling outdoor pool is visible in the foreground, surrounded by lounge chairs and shaded by umbrellas. Lush greenery lines the area, contributing to a welcoming environment.
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
An illuminated salt-water pool reflects soft light at night, surrounded by a well-maintained patio. The backdrop features a multi-story building with balconies and warm lights glowing from the windows, creating a serene atmosphere.
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!
Superhost
A landscaped pool area features a large swimming pool surrounded by lounge chairs and umbrellas. A small building houses amenities, with a peaceful lakeside view in the background. Greenery enhances the setting, creating an inviting environment for relaxation.
Condo in Lake Harmony
4.84 out of 5 average rating, 116 reviews

Lakefront 2 Bedroom Condo Lake Harmony

ChristineRating, 5 stars2 months ago
We really enjoyed our stay. The place was very clean and comfortable with great views
Guest favorite
The exterior of The Appalachian Lodge is displayed, showcasing a multi-story building with a combination of warm colors and architectural details. A heated outdoor pool and lounging area are visible in the foreground, surrounded by landscaped grounds and comfortable seating options.
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!
Top guest favorite
A spacious living and dining area features a large wooden table surrounded by chairs, with a cozy seating arrangement across from a fireplace. Large windows offer natural light and a view of the outdoors, enhancing the inviting ambiance of the space.
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!
Guest favorite
A clear swimming pool is enclosed by a fence, featuring a ladder for easy access. Lush greenery and the mountains are visible in the background, with lounge chairs positioned nearby. The scene is set under a bright blue sky with wispy clouds.
Condo in East Jewett
4.97 out of 5 average rating, 121 reviews

Gorgeous Views Sunny Bright Near Lakes Near

LyubomyrRating, 5 stars2 months ago
We spend our family weekend in this place and it truly felt like home! Very neat, cozy, with a beautiful view, it was truly relaxing and made our weekend very comfortable and allowed us to rest away from the loud city and enjoy the nature and quiet of the area. Everything was working, everything was clean and the host was very welcoming and answered all our request and replied very quickly! Great family weekend!

Quick stats about vacation rentals with a pool in Monticello

  • Total rentals

    30 properties

  • Nightly prices starting at

    $300 before taxes and fees

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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