Family-friendly vacation rentals in Olean

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Olean

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

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Top guest favorite
An inviting glamping tent interior features a spacious heated queen bed surrounded by vibrant patterned pillows and blankets. Colorful rugs cover the floor, creating a cozy atmosphere. Soft lighting is provided by a central fixture, enhancing the tent’s warm and welcoming environment.
Tent in Coudersport
4.99 out of 5 average rating, 127 reviews

Glamping Tent II in Stargazing Field

Olga Farm is an absolutely lovely place in the heart of the Pennsylvania Wilds. We're blessed to have this farm & love to share it with others. We have a private stargazing field where we host primitive campers...Glamping at Olga Farm is a step up from that in that you don't need to worry about a tent, but it still is essentially camping. Breath taking sunrises, a lovely organic vegetable garden & farm, & dark skies at night round out what makes Glamping at Olga Farm an unforgettable experience!

Top guest favorite
A cabin is nestled among tall pine trees, showcasing a rustic wooden exterior and a welcoming porch. The surrounding landscape reveals vibrant autumn foliage in hues of orange and red, creating a serene and secluded atmosphere.
Cabin in Ellicottville
4.96 out of 5 average rating, 168 reviews

Stylish & Secluded Hideaway, 5 mins to EVL

This private space is quietly tucked away in a stand of pines in the woods alongside Bryant Hill Creek. A wall of windows brings nature and natural light pouring into the space, and a fully-equipped kitchen and European bathroom provide modern comfort. Less than 4 miles outside of E-ville, it comfortably sleeps 2 adults and offers a chic and romantic setting for a couple to hide away with easy access to downtown. 4x4 a must in the snow, or simply park at the foot of the driveway. Tv & wifi.

Top guest favorite
A spacious living area is highlighted by green walls and natural light filtering through two windows. A stone fireplace serves as a focal point, with a television mounted above. Comfortable seating includes a dark sectional sofa and a leather armchair. A wooden coffee table occupies the center.
Loft in Olean
4.96 out of 5 average rating, 162 reviews

Joe's Cozy Loft

Joe's Cozy Loft is now under new management! Expect the same great accommodations and amenities as before but with seamless and Superhost service. Your stay with us includes wifi, off street parking after business hrs, a luxurious 2 person jet tub, laundry capabilities, a private deck with grill and more. We are a short walk or drive to many local restaurants and taverns. We are nestled in the heart of the the Enchanted Mountains with easy access to Ellicottville skiing, Buffalo and much more!

Top guest favorite
A spacious living area features a comfortable couch and armchair arranged around a coffee table. A stone fireplace anchors one wall, while a dining table is positioned nearby. The kitchen area, visible in the background, is equipped with modern appliances and wooden cabinetry.
Cottage in Great Valley
4.95 out of 5 average rating, 171 reviews

Country get away

Beautiful private country setting. Perfect spot to take in the fall foliage and count the stars as you sit around the fire. Newly remodeled cozy country cottage . Full kitchen and washer and dryer available . Perfect get away from the hustle and bustle of the city . Central location to all of the area attractions like Holiday Valley ski resort , Ellicottville shopping and restaurants and Seneca Allegany casino. WiFi and dish network provided in a clean and sanitized space. Gas grill available

Top guest favorite
A spacious living area is highlighted by a large brown leather sectional sofa adorned with decorative pillows. A vintage wooden trunk serves as a coffee table, topped with a lantern, a decorative orb, and a small plant. Soft light filters through sheer curtains.
Home in Allegany
4.96 out of 5 average rating, 176 reviews

Stylish 3-bedroom home near Ellicottville, NY

Stylish, entire residential 3 bedroom/ 1 bath home. Close to Ellicottville/skiing -30 mins., St. Bonaventure University, Cutco, Rock City Park, Allegany State Park, kayak launch, biking, and walking trail. Niagara Falls is a 1.5-hour drive, Zippo 30 minutes. Walmart and movie theater are 2 miles away. Many restaurants are nearby. A seasonal 2 screen drive-in movie theater-20 min. drive. 2 queen beds , 1 double bed, and a chair converts to a twin size bed. Fully equipped kitchen.

Guest favorite
A covered deck is seen with a wooden railing, featuring a white bench and a dark door. The yard stretches beyond, highlighted by grass and surrounding trees, while sunlight filters in, creating a bright and open atmosphere.
Apartment in Olean
4.97 out of 5 average rating, 103 reviews

Henley Hideaway

Centrally located to downtown Olean, this 2 bedroom unit is sure to make you feel at home! Enjoy easy access to local restaurants, Four Mile Brewery, and the Allegheny River Trail for a bike ride or scenic walk. Includes free Wi-Fi, off-street parking, a fenced in yard, on site laundry, a full kitchen and more. Close to St. Bonaventure University, 30 min drive to Ellicottville & Holiday Valley. This is the back unit and will share a driveway with any guests staying in the front unit

Superhost
The exterior of a charming two-story house is showcased, featuring light yellow siding and dark brown shutters. A wide front porch with white railings invites relaxation, while neatly trimmed green bushes line the walkway. Lush grass enhances the welcoming appearance of the property.
Home in Olean
4.83 out of 5 average rating, 120 reviews

Olean Ny 4 bedrms. entire house. St. Bonaventure

One 58 inch tv. 1940's home . Location is perfect! 2 miles from St. Bonnies.Rock City is close.Niagra Falls 1.5hr,Ellicotville, You can walk everywhere Pizza place across the street Grocery store is 3 blocks away and the movies &Walmart only a mile.Great restaurants stones throw away.We have a fire pit/ grill. Price depends on how many people. $15 per person per night over 5&must tell owner about extra day visitors and they are 5.00 per person. dog fee 35. a nt

Top guest favorite
The exterior of a modern chalet is shown, featuring a striking wooden facade with large triangular windows. Surrounded by lush greenery, the building is complemented by a stone walkway and simple outdoor seating, creating a peaceful entryway to the inviting natural surroundings.
Chalet in Ellicottville
4.97 out of 5 average rating, 264 reviews

Firefly Chalet

Ideal private chalet getaway in Ellicottville NY. The property is located at the top of a hill on a private drive, giving you a beautiful overlook of the valley. The location is a 5 min drive to downtown Ellicottville and 3min drive to Holiday Valley. There are many state land hiking trails off of the private drive. Convenient location for families looking to ski for the weekend, hike locally/at Allegany State Park, and visit the beautiful town of Ellicottville NY.

Top guest favorite
A charming cottage is surrounded by lush green grass and trees, featuring a gabled roof and multiple windows. The structure is painted in light colors, with dark shutters providing a subtle contrast. A peaceful, natural setting complements this inviting home.
Cottage in Fillmore
4.97 out of 5 average rating, 126 reviews

The Ridge Airbnb and Campground

Grandma‘s cottage (1250 sq ft) with some modern necessities and upgrades! Welcome to “The Ridge.” Enjoy a large creek a two minute walk away. Minutes to Houghton college. Letchworth State Park 21 min🏔️ 11 min Rushford Lake, there is public beach. 15 min to Arcade . We are Dog friendly! We always aim for five star service 🙂 I do ask that you list the number of guests .And if it’s one, it’s 1 and if it’s six it’s 6 🙃. P.S. We have 16 new ducklings! 🦆

Top guest favorite
A small log cabin is presented featuring an inviting front porch with a railing. Solar panels are visible on the roof. The surrounding area includes greenery and a gravel pathway, contributing to the rural setting.
Cabin in Great Valley
4.91 out of 5 average rating, 339 reviews

The Porcupine, featuring fiber optic internet

* Get Away From it all The Porcupine is a small, comfortable and private log cabin. And and we are proud to be solar powered! Great for a couple or a family with small children. Rural setting great for hikes or bikes. 3 miles to the village of Ellicottville. 8 miles to the Seneca Allegany Casino. And 2 miles to the slopes of Holiday Valley

Top guest favorite
A light-filled living area features large windows framed by soft curtains, revealing views of the surrounding forest. A comfortable sofa and a fold-out couch provide seating, while a low coffee table holds a decorative bowl and a magazine. Warm, neutral tones enhance the serene atmosphere.
Apartment in Great Valley
4.88 out of 5 average rating, 298 reviews

Cozy apartment tucked into the forest (with sauna)

Nestled in the forest only seven minutes’ drive from Holiday Valley, this contemporary style self-contained apartment is the perfect weekend getaway for skiing and nature-loving couples. With every luxury and convenience including a sauna, you can home cook meals or barbecue on the deck, with nothing but forest beyond, relax and watch a movie on our LCD screen or use high speed internet on cable.

Top guest favorite
Tiny home in Ellicottville
4.93 out of 5 average rating, 401 reviews

Tiny House in the heart of Ellicottville

5 1/2 Park Square is an adorable tiny house property located in the heart of Ellicottville. It is walking distance to restaurants and bars. Holiday Valley Ski Resort and Holimont within 2 minute drive. Hiking trails abound. Summer and Fall Seasons provide a fantastic weekend adventure! *as featured in StepOutBuffalo as a must rent Tiny Space!

Popular amenities for Olean family-friendly rentals

When is the best time to visit Olean?

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

  • Total vacation rentals

    Explore 20 vacation rentals in Olean

  • Nightly prices starting at

    Olean vacation rentals start at €52 per night before taxes and fees

  • Verified guest reviews

    Over 1,200 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Olean vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Olean rentals

  • 4.8 Average rating

    Olean stays are highly rated by guests—averaging 4.8 out of 5!