
Vacation rentals with a pool in Monticello
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Top-rated rentals with a pool in Monticello
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Popular amenities for Monticello rentals with a pool
House rentals with a pool

Private Hudson Valley Country Retreat
Place was perfect! Clean & made our Holiday stay in the beautiful Hudson Valley a wonderful experience. We loved the personal touches the house offered and we will be back

Hilltop Hideaway | Hot Tub • Heated Pool • Golf
My friends and I were looking forward a relaxing weekend getaway and we found it! This house has incredible amenities with ample space for a large group. We loved the hot tub, fire pit and the projector in the basement allowed us to have a home theater!

NEW: Large Cabin w/ Hot Tub & Game Room!
This place was an absolute gem. clean, incredibly cozy, and somehow even better in person than in the photos. It’s the perfect spot for stargazing and an amazing escape from the city to fully unplug and soak in the fresh air and natural beauty. Perfect for get together!

Summer Retreat! Amazing Pool, Playground, 7 acres!
This property is large and roomy with plenty beds to go around including the basement with the pool and ping pong tables plus a home gym with various equipments. The outdoors were fantastic with a very nice temperature controlled pool, Jacuzzi, swings set for the little ones and enough acreage to have a soccer match. The neighborhood was nice and quiet in a great country setting with lots of wildlife to enjoy to include lots of singing birds. Our family reunion was a great success due in part to the before mentioned surroundings. Douglas was always available to resolve minor issues, very responsive and accommodating, thanks for making our stay at this property a great one.

Scenic River View Escape | New Paltz
I spent my birthday at this beautiful house and couldn’t have asked for a better experience. The place was spotless and full of natural light, with lovely views that made the stay even more special. The atmosphere was peaceful and clean, and the house had everything we needed for cooking and relaxing. I truly felt at home and appreciated all the thoughtful touches. Highly recommend for anyone looking for a cozy, well-equipped getaway!

Little owl Japanese teahouse: pool is OPEN
My husband and I had a wonderfully relaxing time at the Little Owl Teahouse. It’s a cozy and well-outfitted cabin with a super comfy bed and a great leather reading chair. Drank lots of the delicious mountain well water. Made breakfast in kitchen — love the pans and electric cooktop. Short drive to Woodstock for dinner. And oh the beauty of the surroundings - scenic views everywhere. Our two little doggies were happy to romp in the fenced in yard. Little too chilly when we were there but pool looks so appealing. Lisa is a proactive and super responsive host.

Spacious, Cozy Catskills Getaway with Heated Pool
Two-family get-together over a holiday weekend; one from Boston, the other Baltimore, meeting in the middle. Tyson was a terrific host. The property was lovely and exactly as expected. Everyone had a great time. Success all around!

Lake Front Retreat in the Poconos * King Bed*
We loved this Airbnb. It was beautiful there and Michael was quick to answer any questions. We did manage to get on the water with the kayaks, so that was great. We will definitely be back.
Condo rentals with a pool

Cozy Hideaway Windham, Hunter ,Pool,Pickleball.
Beautiful gem, fantastic hosts. Wouldn’t change a thing. Thank you!

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!

Lakefront 2 Bedroom Condo Lake Harmony
An amazing lakefront property. Great for hiking, adventuring, and skiing in the winter. I would stay again.

Appalachian Lodge Top Floor w/views
Paul’s condo was PERFECT for our family of 4. The condo is in pristine condition. Highlights include beautiful balcony over the view with a surrounding view, HUGE bathroom and very comfortable king bed. The amenities also made the stay tip-notch, including very large pool, hot tub, outdoor play areas and pool/games downstairs. The building was well-kept as a resort. Highly recommend: 10/10!

✰ 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!
Quick stats about vacation rentals with a pool in Monticello
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ1,102 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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- Hunter Mountain
- Mountain Creek Resort
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Bushkill Falls
- Minnewaska State Park Preserve
- The Kartrite Resort & Indoor Waterpark
- Sunset Hill Shooting Range
- Delaware Water Gap National Recreation Area
- Windham Mountain
- Ringwood State Park
- Promised Land State Park
- Elk Mountain Ski Resort
- Resorts World Catskills
- Walkway Over the Hudson State Historic Park
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- Sterling Forest State Park
- Villa Roma Ski Resort
- Hunter Mountain Resort
- Wawayanda State Park
- Mount Peter Ski Area
- Opus 40
- Campgaw Mountain Ski Area