Family-friendly vacation rentals in Olean

Find and book unique family-friendly homes on Airbnb

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 R 994 ZAR 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!

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
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, 166 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, 170 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.

Top guest favorite
The cabin's exterior is framed by vibrant autumn foliage, with a wooden facade and a welcoming porch. A neatly landscaped yard features lush green grass and ornamental plants, inviting visitors to enjoy the natural surroundings. A paved path leads up to the entrance.
Cabin in Lewis Run
5 out of 5 average rating, 100 reviews

Timberdoodle Lodge: Grammy's Cottage

Grammy's Cottage at Timberdoodle Lodge is on a quiet road in the heart of Trail Central in the Allegheny National Forest. Your cabin is near many of the best hiking and biking trails and fishing spots the Allegheny National Forest has to offer. A few miles away you can visit Pine Acres Golf Club, Jake's Rock, Morrison's Trail, Rimrock, Kinzua Bridge State Park and Kinzua Reservoir. Visit the Zippo Museum in Bradford; Holiday Valley Ski Resort in Ellicottville, NY; and much much more.

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

Guest favorite
The living area features wooden walls and flooring, creating a rustic ambiance. A comfortable seating arrangement includes a sofa and chairs. A wooden table sits nearby. A staircase leads to the upper level. Wall-mounted decorations enhance the natural theme, including mounted animal displays.
Cabin in Almond
4.94 out of 5 average rating, 315 reviews

The Country Cabin

Quiet, peaceful, and private cabin in the woods. Explore 4000 acres of State Land nearby. Hiking, nature walks, or birdwatching. Enjoy cross-country skiing on the nearby state land. Relax by the pond, fish, or take a refreshing swim. Tall Pines ATV Park (11 miles) offers off-road adventures. Hit the slopes at Swain Ski Resort (22 miles) for winter sports. Located near SUNY Alfred and AU (2 Miles), ideal for parents visiting. Perfect for a family vacation or a weekend getaway.

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
A charming cabin with a wooden exterior is set against a green lawn. The structure features multiple windows, allowing natural light to enter. A small staircase leads to the entrance, while a fenced yard surrounds the property, offering a sense of privacy and space.
Barn in Cuba
4.98 out of 5 average rating, 219 reviews

Stylish & Inviting, Close to lake, 1BR-Sleeps 2

This unique place has a style all its own. This 1BR space "delivers" when it comes to comfort and convenience. Comes with a fully equipped kitchen and all the amenities to make your stay as comfortable and easy as possible. Has a deck if you would like to just relax or enjoy a meal. This cozy space is on the second story so if you have a hard time with stairs sadly we aren't the place for you. Try us out, you won't be disappointed!!

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

Guest favorite
A wooden deck is presented, surrounded by towering trees and lush greenery. A small table with two folding chairs is visible, offering a tranquil spot to enjoy nature. Sunlight filters through the leaves, creating a serene outdoor setting.
Guest suite in Great Valley
4.92 out of 5 average rating, 429 reviews

Comfy studio nestled in the woods (New Listing)

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

Top guest favorite
A log cabin features a spacious front porch supported by wooden posts. Vibrant pink flowers are arranged along the porch steps, while a manicured lawn surrounds the cabin. Large windows allow natural light to enter, and an outdoor seating area is visible on the porch.
Cabin in Salamanca
4.98 out of 5 average rating, 152 reviews

Papa's Cabin is just 5 minutes from Ellicottville

We welcome you to visit Papa's Cabin in the Woods, which was built with love for family and friends to enjoy, summer, winter, spring and fall. Our beautiful 2 bedroom 2 bath cabin is just minutes from the town of Ellicottville, NY which is known for its 2 ski resorts, including Holiday Valley, with cross-country trails and summer adventure park. It is a playground for outdoor fun and adventure.

Popular amenities for Olean family-friendly rentals

When is the best time to visit Olean?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 2,337 ZARR 2,121 ZARR 2,469 ZARR 2,237 ZARR 2,635 ZARR 2,154 ZARR 2,552 ZARR 2,436 ZARR 2,320 ZARR 2,403 ZARR 2,486 ZARR 2,105 ZAR
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