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Family-friendly vacation rentals in Monticello

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Monticello family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Home in East Stroudsburg
4.92 out of 5 average rating, 189 reviews

Big House On The Hill - Hot Tub, Sauna, Fireplace!

NatielaRating, 5 stars2 months ago
From the beginning Ting and Ning had excellent communication that made the booking experience at their rental extremely easy. My questions were answered in a timely manner and the instructions were clear. The home was beautiful and the comfort was so manageable that my guests and i were so sad for it to end. The fruit when we walked in was much needed because we were starving. The home was such a great experience and i would definitely book with Ting and Ning again. Thank you for such an amazing weekend!!!
Top guest favorite
Home in Rhinebeck
4.91 out of 5 average rating, 230 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

AudreyRating, 5 stars1 month ago
Michael and Enrique were excellent hosts, and left me and my girlfriends ice cream in the freezer to enjoy! They responded quickly when we had any questions. The view from the hottub looking out onto the woods is beautiful and the hottub was just what we needed to relax. A beautiful, cozy getaway, and so close to Rhinebeck!
Superhost
The exterior of a spacious two-story home is shown, featuring a light exterior with decorative stone accents. Multiple large windows provide ample natural light. A circular gravel driveway surrounds the house, set within a green landscape and bordered by trees and open space.
Home in Long Pond
4.81 out of 5 average rating, 258 reviews

Fantastic Luxury home 6 Bed room *HOT TUB* *LINEN

PydonnaRating, 5 stars4 days ago
We were a family of 13 and the kids loved the game room and hottub. We will be definitely be back. Carry the host was awesome in communicating to us
Superhost
A bright living area features large windows that allow natural light to illuminate a pink sectional sofa adorned with colorful cushions. A white coffee table sits atop a light wooden floor, complemented by a decorative rug. Art pieces in warm hues are displayed on the wall.
Home in Olivebridge
4.92 out of 5 average rating, 455 reviews

Mountain-Top Catskills Getaway Cabin w/hot tub

LindsayRating, 5 stars2 weeks ago
We had such a nice stay in Olivebridge. Wray’s home is beautifully decorated and extremely private, and just a half hour drive to Woodstock, where there are plenty of shops and restaurants to explore. The hot tub was a bonus, as was the very eclectic DVD collection. Highly recommend! Thanks again for having us!
Guest favorite
The kitchen features an open layout with bright natural light illuminating modern appliances, a spacious island with seating, and rustic shelving displaying various kitchen essentials. A solid wood dining table sits in the background, complemented by a patterned rug beneath.
Chalet in Jewett
4.97 out of 5 average rating, 182 reviews

Private Catskills Home w. Hot Tub, near Ski Mnt

Gina-LouiseRating, 5 stars2 months ago
Great place that was clean, comfortable and cozy. There were excellent instructions for everything and my family loved the hot tub!
Superhost
A bright living area features expansive floor-to-ceiling windows offering views of the autumn foliage outside. Comfortable seating includes a green sofa and modern chairs. A textured area rug and a decorative coffee table complete the space, enhancing a warm and inviting atmosphere.
Cabin in Swan Lake
4.83 out of 5 average rating, 201 reviews

Stunning Sullivan County Cabin w/HotTub/Spa &Pool

CarolineRating, 5 stars3 weeks ago
Our group had a great time at Anna’s place. Spacious and comfortable with great views. Anna is very responsive and gave clear check in instructions. Little communication needed given her detailed instructions, and the little communication needed- she was very responsive.
Guest favorite
A hot tub is illuminated with soft blue light, situated on a deck. Snow-covered ground surrounds the area, providing a tranquil setting in the evening. The hot tub features a spacious design, accommodating several guests for relaxation.
Cabin in Bushkill
4.9 out of 5 average rating, 188 reviews

Bushkill Falls Cabin

DannyRating, 5 stars2 months ago
The place was secluded. the hot tub was perfect. The basement was real chill to hang out on a snowy icy evening
Superhost
A welcoming living area features high ceilings and natural light from two windows. A comfortable sofa is positioned opposite a coffee table, with a dining space visible in the background. A front door opens to the outdoors, surrounded by tasteful decor and plants.
Home in Albrightsville
4.8 out of 5 average rating, 379 reviews

Lake House w/Large HOT TUB Towamensing Trails

MirandaRating, 5 stars3 weeks ago
Loved the home, it was beautiful! Perfect for the girls trip I planned! Rooms were spacious and had all that we needed! Would definitely book this home again! Loved that there were instructions everywhere for things to be cautious of so that nothing gets broken! The only thing I would say is, I wish the porch & hot tub area had a bit more lighting to it, other than that this home was amazing!

Family- and pet-friendly home rentals

Guest favorite
The modern barn-style home is surrounded by lush greenery, featuring large windows that highlight its spacious interior. A wraparound deck with railings invites outdoor relaxation, while an inviting facade includes a prominent gabled entry. Soft lighting enhances the welcoming ambiance as dusk approaches.
Home in Mount Tremper
4.9 out of 5 average rating, 224 reviews

Stunning Modern Barn minutes from Woodstock 21N195

Tracy,JRating, 5 stars2 weeks ago
A beautiful and thoughtfully reconstructed house. It has everything you could need to enjoy a very chill time at the house indoors and outdoors or even cook a meal in. Kid friendly.Beautiful light. Beautiful views. Very convenient location. Kind hosts. We have stayed at a few places around town but this was by far our favorite house.
Top guest favorite
The two-story home features a red-brick facade with white trim and a covered front porch supported by white columns. A seasonal decoration with a pumpkin is visible on the porch. Large windows allow natural light, and the surrounding yard displays green grass and trees.
Home in Saugerties
4.97 out of 5 average rating, 126 reviews

Welcome to Malden Manor, in a prime location!

OrionRating, 5 stars2 months ago
Lovely place in Saugerties, close to lots of great hiking and restaurants.
Guest favorite
A charming wooden house is set among trees with green leaves and a gently landscaped pathway. Warm light emanates from the windows, illuminating the porch area. The seasonal fallen leaves create a natural carpet on the ground, enhancing the serene woodland surroundings.
Cabin in Woodstock
4.97 out of 5 average rating, 148 reviews

Pet Friendly Cabin Doh-Ray up at 1450 ft

JosephRating, 5 stars2 months ago
Beautiful location...nice and quiet. 7 or 8 mins to woodstock. Decorated seemingly professionally. All the appointments (convennces) you could ask for.
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
A well-maintained private yard features lush green grass, a vibrant hammock for relaxation, and a stone path leading through flower beds. A cozy seating area with woven chairs and a decorative rug is positioned near the apartment, surrounded by trees for added privacy.
Apartment in Carmel-by-the-Sea
4.87 out of 5 average rating, 296 reviews

Private space, with yard

IanRating, 5 stars4 days ago
My partner and I were very familiar with the area as we were traveling to go to a memorial and celebrate Easter with the family. We wanted to pick a place that was private and quiet. This fit the bill in spades. We would stay there again. For those who are traveling for hiking and exploration this is an ideal location as there are many state parks nearby. They have everything mapped out and lots of information at your fingertips.
Superhost
Home in West Kill
4.93 out of 5 average rating, 121 reviews

Catskill Mountain Cabin Waterfall Retreat

TatyanaRating, 5 stars3 months ago
I enjoyed my stay at Gavin and Alison's house in the Catskills. It was a great place to spend a snowy winter weekend in January with my son and two grandchildren. The house is a short drive from various skiing and winter-sports resorts. We were satisfied with the kitchen and other amenities, played board games, and generally had a relaxing time. The hosts were very responsive when we had questions.
Guest favorite
A person is paddling on a calm, reflective pond surrounded by lush greenery and hills in the background. The water's surface mirrors the landscape, enhancing a serene atmosphere. The scene is framed by trees and a gently sloping area, showcasing nature's beauty.
Cabin in Prattsville
4.83 out of 5 average rating, 169 reviews

Modern Cabin w/Swimming, Boats, HOT TUB & VIEWS!

SaraRating, 5 stars2 months ago
We had an amazing weekend stay at Catherine and Diego’s modern cabin! The property is exactly as described—beautiful, cozy, and perfect for a group getaway, with charming wood paneling and all the comforts of home. The hot tub and stunning views of the snow-covered landscape were highlights, creating a peaceful and relaxing atmosphere after a day out. The location was ideal, offering both privacy and proximity to skiing and other activities, and the hosts provided clear instructions for check-in, making the experience stress-free. We’d highly recommend this cabin to anyone looking for a quiet, cozy escape in the mountains!
Guest favorite
A rustic log cabin is framed by lush greenery, featuring a stone chimney and two inviting front doors with diamond-shaped windows. A private hot tub is situated next to the cabin, hinting at a cozy outdoor space for relaxation.
Cabin in Barrett Township
4.95 out of 5 average rating, 554 reviews

Pocono Rustic Log Cabin

JeannieRating, 5 stars3 weeks ago
Walter and Florence’s cabin was so cozy and clean. The Hot tub was so relaxing. They are great hosts. We enjoyed our stay and would definitely come back.

Family-friendly home rentals with a pool

Top guest favorite
A spacious backyard is highlighted, featuring a volleyball net between two trees and a hammock hanging nearby. Sunlight filters through the leaves of the surrounding trees, illuminating the well-maintained grassy area. A small shed is visible in the background, offering additional outdoor storage.
Home in Saugerties
4.98 out of 5 average rating, 160 reviews

Spacious Staycation near HITS & the Hudson

McKennaRating, 5 stars6 months ago
My group loved our stay at Alan and Cara’s place for the Sheep & Wool festival. Great space for a large group; we especially loved how comfortable the living room couches were and how there was space for everyone there to gather. The place was immaculately clean. We’d love to come back again!
Top guest favorite
An aerial view of a spacious property showcasing a round, 33-foot swimming pool surrounded by lush greenery. The house features a patio area and gazebo, offering a serene outdoor setting. Guests can be seen enjoying the pool, emphasizing the space's recreational potential.
Home in Tobyhanna
4.8 out of 5 average rating, 129 reviews

Cozy home for 10 ~ Private pool, BBQ, fire pit

EsteeRating, 5 stars2 months ago
We had a wonderful stay at this house. It was clean, spacious, very warm despite the cold, and had a terrific pool table and air hockey table. Our family relaxed and spent good time together.
Guest favorite
A modern kitchen area features stainless steel appliances, including an oven and microwave, alongside a spacious dining table with seating for four. Natural light is filtered through large windows, illuminating the open concept living space that connects to a cozy sitting area.
Townhouse in Tannersville
4.81 out of 5 average rating, 115 reviews

Aquatopia & Camelbeach Waterparks,Pool,Pickleball

ChristopherRating, 5 stars1 week ago
muy lindo alojamiento, zona tranquila y el anfitrión muy amable y pendiente de cualquier cosa que necesites 😉 definitivamente recomendable 😄👍
Guest favorite
A modern farmhouse exterior is visible beside a crystal-clear swimming pool surrounded by grassy areas. Colorful pool floats are placed in the water, while a wooden fence and tall trees frame the peaceful setting.
Home in Saugerties
4.95 out of 5 average rating, 108 reviews

MODERN FARMHOUSE in the WOODS

BenjaminRating, 5 stars6 months ago
We had a terrific stay. The house was exactly as advertised.
Guest favorite
A large heated swimming pool is surrounded by lush greenery, with several lounge chairs arranged on a concrete deck. A float in blue and white lies on the water's surface, and an umbrella provides shade nearby.
Apartment in Saugerties
4.97 out of 5 average rating, 111 reviews

Lovely Creekside w pool/sauna near Woodstock

MelissaRating, 5 stars8 months ago
We spent three nights at Rich and Sheila's place and it was an amazing getaway. Our apartment was perfect-clean and comfy. We loved the proximity to the creek and the pool was a huge bonus! Rich and Sheila were both responsive and welcoming. We look forward to a return trip.
Guest favorite
A wooden deck is featured, equipped with a patio umbrella, overlooking a seasonal swimming pool. Surrounding trees provide privacy and a natural setting. A gravel pathway leads to the cabin, enhancing the serene ambiance of the forested area.
Cabin in East Stroudsburg
4.88 out of 5 average rating, 129 reviews

Pocono cabin with POOL at Shawnee Mtn

Yossi Rating, 5 stars4 weeks ago
If you're after something warm and cozy, this is your spot! It easily fits a family of four and comes with everything you need. The views around the cabin are stunning, and the outdoor space is perfect! there’s a hot Jacuzzi always ready, a fire pit, two chill sitting areas, a big deck, and a massive pool. really recommend!
Guest favorite
A serene salt-water pool reflects the surrounding greenery and blue sky. The natural stone edge frames the pool, while two lounge chairs are positioned nearby, creating a peaceful outdoor retreat.
Home in Cold Spring
4.95 out of 5 average rating, 167 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

ChristopherRating, 5 stars1 month ago
We had a peaceful and relaxing stay at Shawna’s beautiful Cold Spring country-style home. We were in town for a family gathering and accommodations, cleanliness and Shawn’s communication were five star. We absolutely recommend the house and Shawna as a host for you to stay with!
Guest favorite
A clear, blue saltwater swimming pool is surrounded by lush greenery and tall trees. Lounge chairs are positioned by the poolside, with a stone path leading to the water. The tranquil setting provides a sense of privacy and relaxation.
Home in Hudson
4.93 out of 5 average rating, 243 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

JakeRating, 5 stars7 months ago
Amazing amazing for a birthday weekend. Good proximity to Hudson while still feeling in the woods. So clean and cozy.

Quick stats about vacation rentals that are family-friendly in Monticello

  • Total rentals

    30 properties

  • Nightly prices starting at

    $80 before taxes and fees

  • Total number of reviews

    360 reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore