Family-friendly holiday 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.

%{current} / %{total}1 / 1
Top guest favourite
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, 324 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!

Top guest favourite
A cozy living room features a large area rug with a rustic design, a comfortable sofa, and a wooden cabinet. A bedroom showcases a queen bed with light blue accents, complemented by soft natural light filtering through window treatments. Highland cattle and outdoor seating with scenic views are also pictured.
Home in Sulphur
4.99 out of 5 average rating, 100 reviews

The Highland Hideout- 2 Bed/2 Bath/Firepit

Looking for peace and quiet, you can’t beat this farmhouse. Located just 4 miles north of Broadway Ave in Sulphur, nestled at the end of a long private driveway this home is the perfect location to getaway from it all. With 2 bedrooms and 2 bathrooms. It has a view overlooking a beautiful pond and you can be sure to see some of the most beautiful sunsets Oklahoma has to offer. If you love farm life without the hassle, this is the place to be. You’ll also get to see and enjoy our Highland cattle

Guest favourite
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, 147 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

Guest favourite
A single-story home features a light-colored exterior with a metal roof, surrounded by lush green grass. A spacious porch with seating overlooks a well-maintained yard, while a black fence encloses the outdoor area. The long driveway offers ample parking space.
Home in Luther
4.95 out of 5 average rating, 312 reviews

Peaceful 2 bedroom home in the country with pool

Relax with the whole family at this peaceful place to stay in the country. The master bedroom has a king size bed, TV and full size closet. The second bedroom has a Queen size bed and a Twin size bed Bathroom has shower/tub The laundry room equipped with a washer, dryer, iron and ironing board Fully equipped kitchen Enjoy swimming in the pool, walking trails in the woods 10 min drive to the famous Chicken Shack for some good food and great atmosphere •Queen air mattress available

Top guest favourite
A bright living area features light blue walls and hardwood flooring. A comfortable armchair and a small ottoman provide seating options. An entertainment unit displays a large television, and wall art adds color. A lamp stands next to the chair, providing additional light.
Guest house in Newcastle
4.94 out of 5 average rating, 176 reviews

Modern, Clean, Cute Private Apartment close to OU!

Guests will love staying at this entire above-home apartment that features tons of amenities to make their stay memorable. This place features a private entrance, coffee, snacks, beverages, Fast Wifi, & free parking! 15 minutes to OU & Riverwind Casino! This place also has a private, covered pavilion that is great for hanging out and cooking on our outdoor grill. Outdoor area may be shared. Our beautiful swing set located in the back yard is perfect for photoshoots or enjoying the weather.

Top guest favourite
The exterior of a wooden house is visible alongside a tranquil, spring-fed pond. Large windows adorn the structure, revealing a friendly atmosphere. Green grass and trees surround the property, providing a natural setting, while a wooden fishing pier extends into the calm water.
Home in Shawnee
4.97 out of 5 average rating, 168 reviews

Oak Spring Retreat! Rest, Hike, Fish and Explore!

Relax with the whole family at this peaceful getaway . This 3 bedroom 2 bathroom home sleeps 6 and is located on 20 secluded acres with private wooded hiking trails and a 3 acre spring fed stocked pond! Enjoy exploring our one of a kind property and seeing all the wildlife! We have a row boat available so bring your poles! Our game shop has ping pong, basketball and other games. Located 45 minutes from OKC and 10 minutes from OKlahoma Baptist University! REST ADVENTURE PLAY EXPLORE UNPLUG

Top guest favourite
A charming entrance to the cottage is framed by wooden steps leading up to a covered porch. Flower boxes adorn the windows, adding greenery. A grill sits to the side, surrounded by natural landscaping, creating a serene outdoor environment.
Tiny home in Wanette
4.98 out of 5 average rating, 800 reviews

Sage Guest Cottage! Your Own Very Private HotTub!

Sage Cottage is located in the beautiful Pottawatomie County in our own Oaklore Forest. The cottage sleeps two on our queen size bed, Has a mini-kitchen and 3-piece bathroom with stand-up shower. The kitchen is equipped with a small bar sink, double hot plate, toaster, microwave, coffee pot, kuerig, toaster oven, small fridge and cooking essentials. There is a bistro table, picnic table, grill & breakfast table inside! Free Wi-Fi, Hot tub open all year, robes, see "other things to note"

Guest favourite
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
4.97 out of 5 average rating, 124 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!

Guest favourite
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
4.87 out of 5 average rating, 302 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 favourite
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.
Guest house in Oklahoma City
4.99 out of 5 average rating, 326 reviews

The Scissortail, a Downtown Wheeler District Stay

🎡 RIVERFRONT DOWNTOWN 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 favourite
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, 113 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.

Top guest favourite
The spacious living area features a high ceiling with wood beams and large windows that provide natural light. Comfortable seating arrangements include a light-colored sofa and small dining table. A cozy fireplace is positioned along one wall, creating a welcoming focal point.
Farm stay in Arcadia
5 out of 5 average rating, 283 reviews

Relaxing Farm retreat on 40 acres in Arcadia

Come and relax on a 40 acre farm in Arcadia, OK! The beautiful two story wood barn features a newly built out 2,000 sq.ft. apartment with all the amenities for a comfortable stay. This includes a full kitchen, 85 inch TV with surround sound, two loft bedrooms with three beds each, a Weber Grill, & plenty of relaxing space. The property includes hiking trails, kayaks, multiple animals, and Kenny the Clydesdale! Please no parties, we live on site and enjoy the quiet relaxing farm too.

Popular amenities for Chickasha family-friendly rentals

When is the best time to visit Chickasha?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price£71£69£71£71£77£77£77£71£71£71£77£76
Avg. temp3°C6°C11°C15°C20°C25°C28°C27°C23°C16°C10°C4°C

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

  • Total holiday rentals

    Explore 30 holiday rentals in Chickasha

  • Nightly prices starting at

    Chickasha holiday rentals start at £52 per night before taxes and fees

  • Verified guest reviews

    Over 1,120 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Chickasha holiday rentals include wifi 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!