Family-friendly vacation rentals in Chickasha

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Chickasha

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

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Top guest favorite
A spacious living area features soft carpeting and neutral-toned walls. A comfortable sofa is positioned near a wooden TV stand, which holds a Smart Roku TV. Two upholstered chairs are placed beside a floor lamp, with natural light streaming through the adjacent windows.
Cottage in Tuttle
4.97 out of 5 average rating, 311 reviews

⭐️Backyard Bungalow⭐️Work Travel Friendly

Our Backyard Bungalow is cozy with country charm. Enjoy a peaceful morning on the porch with a hot cup of coffee. Located only 13 miles from Will Rogers Airport and the FAA Academy, this bungalow will give you the comfort of home as you're traveling. The bungalow is located adjacent to the owners home within a quiet neighborhood and just 20 miles from both Oklahoma City and Norman. Internet access will be provided, along with ample space for work-related needs. We look forward to your stay!

Guest favorite
A single-story home with a light-colored exterior and a black front door is situated under a clear blue sky. A concrete pathway leads to the entrance, and a grassy area is visible in front of the house, complemented by a large tree providing shade.
Home in Chickasha
4.84 out of 5 average rating, 135 reviews

The Adventure Home

Relax with the whole family at this peaceful place to stay. Our home is located two blocks from USAO and a seven minute to downtown Chickasha, where you can find the Leg Lamp. It is also a three minute drive to Shannon Springs Park, home of the Festival Lights. The home offers a spacious back yard and out door dinning area. Our kitchen is fully equipped to cook in. About this space. It is a two bedroom that can comfortably sleep 5 with a queen and a twin over full bunk bed. *New* Washer/dryer

Top guest favorite
A spacious living area is presented with a gray sofa and a blue armchair, complemented by colorful throw pillows. A round coffee table sits at the center, and large sliding doors lead to a sleeping area. Kitchen amenities and laundry facilities are visible in the background.
Guesthouse in Newcastle
4.98 out of 5 average rating, 124 reviews

Adorable Private Guest House, Quiet, Clean, Wi-Fi!

Guests will love staying at this entire guest house that features tons of amenities to make their stay memorable. This place features a private entrance, coffee, snacks, beverages, Fast Wifi, free parking, and more! Located close to University of Oklahoma & Riverwind Casino! This place also has a covered pavilion that is great for hanging out and cooking on our outdoor grill. Our beautiful swing set located in the back yard is perfect for photoshoots or enjoying the weather. May be shared.

Guest favorite
A spacious living area showcases a comfortable brown sofa with decorative cushions, paired with a rustic coffee table on a patterned rug. The open kitchen features dark cabinetry and stainless steel appliances, with natural light brightening the space through a nearby window.
Farm stay in Wanette
4.98 out of 5 average rating, 103 reviews

Exotic Animal Hotel

Come stay in your very own unique safari room! Come stay the night with over 100 exotic animals from around the world! We are an exotic animal encounter experience! Your windows from your room are connected to the ringtail lemur and ruffed lemur enclosures! There is also a fire pit, playground, and a ton of hiking! You can even see a lot of the animals from outside your Airbnb! This is a very family oriented environment! You are encouraged to just relax and spend time with your family!

Superhost
A small rustic cabin is situated on a wooden deck, surrounded by lush greenery. Two donkeys and a horse are seen near the entrance. A single chair is positioned on the porch, and a vehicle is parked nearby, complementing the country setting.
Tiny home in Lawton
4.86 out of 5 average rating, 288 reviews

Tiny Cabin at the DonkeyRanch

It's a 200sqft Cabin in the middle of a 20 acre Pasture with views of the Slick Hills and Mt Scott.Minutes from lake Lawtonka and Medicine Park. Donkeys and horses roam free,as do normal country bugs and critters Plenty of room for family events and reasonable parties,,, I deleted the rest of this message.. Rent or Don't I could've sold the cabin ,but argued with Mom that people need to get off their ass and experience a different life. Safe place,except Oklahoma weather and Donkey shit

Top guest favorite
The image features the iconic Ferris wheel illuminated with vibrant colors, set against a twilight sky. Nearby, a grassy area offers an open view, while rustic structures are visible in the foreground, contributing to the lively atmosphere of the Wheeler District.
Guesthouse in Oklahoma City
4.99 out of 5 average rating, 287 reviews

The Scissortail, a Downtown Wheeler District Stay

🎡 DOWNTOWN RIVERFRONT DISTRICT🎡 Wheeler District is OKC’s newest downtown community showcasing the original historic Santa Monica Pier Ferris Wheel as the gateway for its riverfront plaza. Unique homes built with appealing architectural designs, retail shophomes, fabulous eateries, and a national award winning brewery set this district apart. With the scenic view of its ferris wheel and the downtown skyline, this urban escape provides perfect relaxation amid your Oklahoma City stay!

Top guest favorite
The exterior of a converted grain bin is displayed, featuring a large sunflower mural. A welcoming porch with rocking chairs is positioned to the side, surrounded by lush green grass and vibrant flower beds, enhancing the rural charm of the property.
Tiny home in Elgin
5 out of 5 average rating, 103 reviews

The Painted Silos - The Sunflower Bin

Nestled in Elgin, Oklahoma, this converted grain bin offers a unique experience. A short drive from Ft. Sill, Medicine Park and the Wichita Mountain Wildlife Refuge. Featuring modern amenities with a rustic charm, this silo has been tastefully decorated and outfitted with all the luxuries you need for a cozy stay. This charming silo sleeps up to four and includes a stylish living area, fully equipped kitchen, dining area, one spacious bedroom, cozy built in bunk beds, and 1.5 bath.

Guest favorite
A covered back patio features seating arranged around a small table, complemented by decorative cushions. Brick walls add warmth, and a welcoming door is visible in the background, enhancing the inviting outdoor space.
Guest suite in Oklahoma City
4.93 out of 5 average rating, 1,109 reviews

Centrally Located Guest Suite On 2 Acres

Centrally Located, Less than 5 mins drive to the Adventure District ( Okc Zoo, Science Museum and Tinseltown) 4 miles from Downtown Bricktown This is a Converted in law room with private separate entrance. It also includes a covered back patio with seating The guest suite is attached to the main house. Access to guest suite via Keypad Lock All living areas are treated with BIOSWEEP® SURFACE DEFENSE it provides a safe and effective defense against germs, bacteria, and viruses.

Guest favorite
A cozy sleeping area features a spacious bed adorned with floral-patterned bedding. Soft lighting is provided by wall-mounted lamps on either side of the bed. A light-filled door offers access to the outdoor space, while cabinetry is visible to the right.
Guesthouse in Norman
4.85 out of 5 average rating, 876 reviews

The Prancing Pony

The Prancying Pony is a short walk to the University of Oklahoma Campus, Historic Downtown Arts District, restaurants, and dining. The Pony is a quiet and secluded cabana with beautiful garden and pool. The ambiance, the outdoor space, and neighborhood make this the ideal location for exploring the best of Norman. This apartment is good for couples, solo adventurers, and business travelers. The apartment has one, gated parking spot. Also included is the use of an outdoor grill.

Top guest favorite
The exterior of a red wooden caboose is presented, featuring windows and steps that lead to a small porch area. Surrounding greenery enhances the rustic setting, while a sign on the side indicates the caboose's name. A few chairs are visible nearby on a concrete surface.
Train in Jones
4.95 out of 5 average rating, 503 reviews

Route 66 Oklahoma City 1925 Red Caboose

Enjoy a wonderful night in our 1925 CB&Q wooden caboose. As you pull into the driveway of our little farm, you won’t believe you’re only 20 minutes from downtown Oklahoma City and less than 10 minutes from Edmond. You may encounter deer, turkeys, road runners and much more. Enjoy the lonesome howl of distant coyotes in the evening as you step outside this old waycar. If you’re looking for a unique experience and you’re a romantic fool such as I, come stay a night in 13744.

Top guest favorite
A cozy sleeping area features a spacious bed with decorative pillows and a green comforter. Wall art depicting an Italian scene complements the calming atmosphere. Nightstands are positioned on either side, and a mounted television is visible, alongside a small electric fireplace for ambiance.
Cabin in Blanchard
4.95 out of 5 average rating, 119 reviews

Italian Cabin

At Lori’s Country Cabins you can kick back and relax at this unique and peaceful getaway in the country but still close to town. The Italian cabin offers a private porch with seating, charcoal grill and a fire pit right outside your duplex style cabin. Fix a snack or a full meal with a kitchenette. More than two staying, no worries there is a loft with a movable ladder for easy access with a floor mattress. Pets are welcome with a non-refundable pet fee.

Top guest favorite
A modern shipping container retreat is framed by lush greenery, showcasing a spacious porch with seating and large windows. The exterior is accented by well-maintained landscaping and a gravel driveway leading up to the entrance.
Shipping container in Chickasha
4.99 out of 5 average rating, 155 reviews

Serenity Cottage + hot tub in the country

Relax. Refocus. Write a special moment into your story. Our thoughtfully designed shipping container is where comfort and elegance intertwine. We want your stay to be filled with simple pleasures. No TV but fast WiFi for your devices. Find solace on the porch, sipping coffee with a fresh cinnamon roll. Immerse yourself in relaxation in the hot tub. As evening falls, gather around the fire pit under the starlit sky.

Popular amenities for Chickasha family-friendly rentals

When is the best time to visit Chickasha?

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

  • Total vacation rentals

    Explore 30 vacation rentals in Chickasha

  • Nightly prices starting at

    Chickasha vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

  • Verified guest reviews

    Over 940 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Chickasha vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chickasha rentals

  • 4.9 Average rating

    Chickasha stays are highly rated by guests—averaging 4.9 out of 5!