Kid-friendly vacation rentals in Olive

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Olive

Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Cottage in West Shokan

4.95 out of 5 average rating, 155 reviews

Cozy Catskills Getaway on 3 Acres—Updated ‘24

You have the whole house and three acres to enjoy. The two bedrooms are upstairs, with skylights and a bright, airy feel to them. The wood burning stove is an awesome way to make things cozy. There's also a firepit and grill you're welcome to use. Guests have complete access to the home and three-acre property. The garage on the property is inaccessible by guests. We're available to contact anytime. Hike, ski, swim, bike, do yoga, or whatever comes to mind— all is possible in the Catskills. The Ashokan reservoir bike/walk path is a few miles down the road. Not far the other way is Marty's Mercantile for coffee, lunch, and basic supplies. There's plenty of parking in the driveway. Don't expect to Uber while up here. Walk, bike, or ride a horse instead. :) There's plenty of parking in the driveway.

Guest favorite

Guesthouse in Accord

4.94 out of 5 average rating, 138 reviews

Studio in Private Forest; Peace and Solitude

Set in a hemlock forest on a quiet country road, this newly redone and separate guest studio is a perfect getaway. Set on 30 private wooded acres, the property is bisected by a Class A trout stream. Guests have access to the shared pool Mon-Fri, but not Sat-Sun. The second floor studio has a queen size bed and a queen size sofa bed along with a private bathroom. There is Wifi, a television (ROKU). There is no kitchen, however, we do provide a microwave, dorm fridge and Keurig coffee machine.

Guest favorite

Guesthouse in Mount Tremper

4.97 out of 5 average rating, 325 reviews

Artful and Serene Woodstock Getaway

Please read description thoroughly before booking. Relax with a comfortable mix of rustic and elegant in this colorful studio with loft bedroom in the Catskill Mountains of NY. Midway between lovely towns, Woodstock and Phoenicia. Full kitchen and bath, cathedral ceiling, sleeps two adults comfortably. Due to allergies, we do not allow pets. This includes service animals. We use fragrance free laundry detergent. No smoking or vaping. This listing is not suitable for children or infants.

Guest favorite

Home in Kingston

4.97 out of 5 average rating, 319 reviews

This New House

Unique custom built new home constructed purposefully for Airbnb quests. This house offers a distinctive design with a large loft bedroom and a fully tiled bathroom. The loft overlooks the downstairs living area which has an open living room, dinning area, and kitchen. The second bedroom and bath are located on the first floor. Granite, slate, and soapstone accentuate the countertops, vanities, and floors. You will also see plenty of natural pine, hickory, and local cedar throughout the house.

Guest favorite

Guesthouse in Olivebridge

4.93 out of 5 average rating, 120 reviews

The Ashokan Guest House

This newly renovated guest house is attached to a 120 year-old former Boarding House which housed the workers building the Ashokan Reservoir. This quiet refuge sits on a lovely 3-acre lot in Catskill Park within .5 mile of Ashokan Reservoir. An outdoor adventure in our beautiful Catskill Mountains awaits any direction you go. This is the perfect location for couples or individuals looking for a retreat (it is not child-proofed/child friendly!). Near Kingston, Woodstock and Stone Ridge.

Guest favorite

Cabin in Kerhonkson

4.92 out of 5 average rating, 431 reviews

Home Alone Woods

Small and charming cabin in a quiet place surrounded by woods and nature with the hiking trails half a mile away. There is an easy access to Hunter Mountain, Minnewaska State Park, and Shawangunks. This is a perfect getaway for nature and outdoor enthusiasts, bikers, hikers, climbers, and skiers or people who look for peace and tranquility in the woods.The kitchen is equipped with cooking essentials such as pots, pans, and utensils. WE DO NOT GUARANTEE THAT THE HOT TUB WILL BE AVAILABLE.

Guest favorite

Chalet in Olivebridge

4.99 out of 5 average rating, 145 reviews

Spruced Moose Lodge & Treehouse w. Hot Tub & Pool!

Secluded log home on 5 acres, beautifully situated at the top of a no outlet road on a mountainside in the Catskills. The home has 4 bedrooms + 3.5 baths, with the 4th bedroom being a finished basement that has built-in full size bunk beds. There is also a sunroom, screened porch, pool, hot tub, and a treehouse that resembles a floating pirate ship 30 feet up in the trees, oh, and now a Projector TV in the basement! Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

Guest favorite

Cabin in Kerhonkson

5 out of 5 average rating, 347 reviews

The Metsämökki - A Finnish Cabin in the Woods

The Metsämökki is a small Finnish cabin in the foothills of the Catskill Mountains. Originally a sauna that was shipped here from Finland. We renovated it to a tiny house that offers complete privacy. Enjoy the babbling brook while sitting on the deck and taking in the surrounding nature. We're not offering high-tech or glamour but this cabin is a beautiful retreat from the busy city. **Check out our new midweek discounted rates and enjoy a little extra time for a great price!!

Guest favorite

Home in West Shokan

4.92 out of 5 average rating, 345 reviews

1850 Carriage House, Creek

Sunny Carriage House near the Ashokan Rail Trail and Catskill high peaks, with the beautiful sound of the nearby Bushkill Creek. Spacious, clean, peaceful. Fast reliable WIFI, woodstove. Two bedrooms, marble bathroom, AC, fire pit. A comfortable mix of handmade wooden mid-century minimalism. The house is in a beautiful natural setting while a short drive to town, restaurants. If The Carriage House is booked for your dates, check out Watson House, a 150-year-old house next door.

Guest favorite

Guest suite in Woodstock

4.98 out of 5 average rating, 128 reviews

Woodstock retreat with hot tub and deck with view

Guest suite in home of long-time Woodstock artist and resident. Separate entrance off 2nd story deck with meadow and mountain views. Space has everything you need for a retreat away from it all – a meditation nook for 2, yoga mats to use inside or out on the deck, hot tub to soak cares away and relax after a day out and about in the beautiful Catskill mountains. Hot tub is in 3-acre backyard with privacy enclosure, so bathing suits are optional (we provide bathrobes.)

Guest favorite

Guesthouse in Mount Tremper

4.93 out of 5 average rating, 107 reviews

Esopus Creek Hideaway

Summer spectacular on the Esopus! Clean remodeled 1 BDRM vintage cabin with modern amenities and sleek design interior. You will not want to leave this waterfront property with exquisite mountain views, both Hunter and Bellayre are just 15 miles away. All new kitchenette and bath easy no fuss mountain livin' situated on 2 private acres. Minutes to Phoenicia, Kingston and Woodstock. 3 Minutes to the infamous Phoenicia Diner! Cozy cute simple perfect getaway

Guest favorite

Cottage in West Shokan

4.92 out of 5 average rating, 169 reviews

Relaxing Cottage in the Catskill Mountains

1000 sq ft. cottage located on a 7 acre partially wooded property in the Catskills. Two bedrooms (one queen, one full), one bath, open floor plan with vaulted ceilings and sliding glass doors opening to a deck in the back yard. Cook and eat on the deck with both gas and charcoal grills, plus large dining table with umbrella. Fire pit outside and wood burning stove inside for extra warmth and ambience. Dogs considered, just ask.