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 €69 per night before taxes and fees

  • Verified guest reviews

    Over 1,240 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • 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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Superhost
Guesthouse in Olean
4.86 out of 5 average rating, 202 reviews

Cozy Country Get Away Suite

If you're passing through town on your travels or a local looking for a private get away, this is the perfect place to kick back, relax and enjoy some peace and quiet. You can sit by the fire, look across to see fireflies in the field or tilt your head back to have an amazing star-gazing experience. A one of a kind property to make memories with friends, family, or for a special romantic get away. Access to 93 acres with trails to walk or mountain bike on, fields to wander through and wildlife.

Top guest favorite
Farm stay in Cattaraugus
5.0 out of 5 average rating, 166 reviews

The Guest House at Burdick Blueberries Farm

Share the peaceful beauty of our working family blueberry and flower farm with organic and sustainable practices. Located in East Otto, New York. During the blueberry season experience the joyful bustle of the pick-your-own blueberries and flowers, Mid-July - August. Private guest house attached to farmhouse. Enjoy our patio and spacious lawns plus in-ground pool. Walk along the blueberry bushes, farm roads and woodland trails. Guest space has a simple & natural aesthetic, a relaxing haven.

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, 166 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!

Guest favorite
The cottage exterior features a stone façade, complemented by a welcoming porch and large windows. Greenery surrounds the entrance, with potted plants adding a touch of life. The front door, framed by glass panels, offers a glimpse into the cozy interior.
Cottage in Olean
4.83 out of 5 average rating, 193 reviews

Artists cottage - mid century

The perfect spot to relax, read, write meditate. View birds, wildlife in an old forest along the Allegany River from the porch, deck or large picture windows. Take a walk. (fast Wi Fi, 32 inch TV and echo dot) Families and dog owners will like the large yard (no fence, warning ticks and Lyme disease in the area). My grandmother designed the cottage around a vintage house trailer (tiny house)1956. There are many unique and cleaver features. Family mementos through history are on display.

Top guest favorite
An open floor plan showcases a spacious living area, featuring a large sectional sofa and a dining table surrounded by several chairs. A central kitchen island with granite countertops provides additional seating. Natural light filters through large windows, enhancing the warm, inviting atmosphere.
Guesthouse in Great Valley
4.98 out of 5 average rating, 113 reviews

Pole Barn Base Camp-Near Ellicottville/Casino/ASP

Centrally located .This space is a 40 by 32 two story new build. Features 3 bedrooms- 3q, 2f, 1t. One bathroom with tile shower. Open floor plan with full kitchen , living room, dining room highlighted by a 16ft concrete bar and 16 ft high ceilings Locker/ cubby room with washer and dryer. Outdoor fire pit with firewood provided. 60 inch smart TV -WiFi -Radiant floor heat. Self check in. Holiday Valley 6.9 mi Seneca Allegany casino 8.1 mi. Ellicottville 7.9 mi Allegany State Park 12 mi

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, 185 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
4.96 out of 5 average rating, 114 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

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, 272 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.

Guest favorite
Camper/RV in Machias
4.91 out of 5 average rating, 115 reviews

The Buzzy Bee

Escape to the Buzzy Bee, a charming vintage camper nestled in the heart of our 50-acre farm. Wake up to breathtaking sunrises, enjoy peaceful sunsets over the pastures and watch horses, donkeys, cows, ducks and other farm animals just steps away. Sleeping up to 6 guests with 4 beds. The Bee is perfect for families, coupes or friends seeking a unique farm stay experience. End your day stargazing by the campfire and enjoying the quiet beauty of country life.

Top guest favorite
The chalet stands amidst lush greenery, showcasing a large wrap-around deck with outdoor seating and an umbrella. A stone fire pit surrounded by red Adirondack chairs is positioned on the lawn, offering a welcoming space for gatherings.
Chalet in Ellicottville
4.99 out of 5 average rating, 133 reviews

Pines Chalet in Ellicottville ~ Hot Tub~Fireplace

Located just two miles from the Village of Ellicottville, The Pines on Maples offers stunning views & a variety of amenities for relaxation and entertainment. Tucked away in the rolling hills of Western New York, this chalet features a large wood deck with a Weber grill & sitting area, as well as a walk-down path to an eight-person hot tub & an unilock fire pit with Adirondack chairs. State of the art Stuv indoor fireplace for cozy cabin days!!

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, 231 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
The newly constructed cabin glows warmly against the night sky, lit by strings of soft lights. A fire pit surrounded by seating offers a cozy gathering space. Nearby, trees provide a natural backdrop, enhancing the tranquil forest surroundings.
Cabin in Marshburg
5.0 out of 5 average rating, 113 reviews

Allegheny National Forest and Kinzua Reservoir

The Lost Woods Cabin is a newly constructed timberframed gem located in the heart of the Allegheny National Forest. This secluded, majestic cabin sits on 25 private acres that are bordered by the Allegheny National Forest and is only ten minutes away from three different boat launches on the 50-mile-long Kinzua Reservoir. It is truly a quintessential forest getaway with all the modern conveniences, including Star Link's internet.

Popular amenities for Olean family-friendly rentals

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