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Family-friendly vacation rentals in Chickasha

Find and book unique family-friendly homes on Airbnb

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 G$14,622 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,120 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!

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, 334 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
4.85 out of 5 average rating, 153 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 rustic cabin exterior showcases a covered porch with comfortable seating for four, complemented by vibrant stools. The natural surroundings feature greenery, and a hammock is draped nearby. A stone chimney adds to the cabin's charm, highlighting its inviting outdoor space.
Cabin in Medicine Park
4.99 out of 5 average rating, 164 reviews

Eagles Nest (Hot Tub)

This cabin is rustic yet elegant, rock interior wall in kitchen with apron sink, butcher block cabinet tops and stainless appliances. There is a grand rock wood fireplace, stained concrete floors, deep soaking tub in master bath. The cabin has a bedroom and bath downstairs and bedroom and bath upstairs. Features a 4-seater hot tub in private covered patio. Eagles Nest sits in the foothills of the Wichita Mountains which gives it that amazing "cabin feel." Eagles Nest is a home away from home.

Top guest favorite
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.
Guesthouse in Newcastle
4.94 out of 5 average rating, 187 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.

Guest favorite
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
4.88 out of 5 average rating, 320 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 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, 122 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
Campsite in Lawton
4.89 out of 5 average rating, 112 reviews

Airstream w flush toilet, city water, hot tub

Glamping for Two or a Small Crew (Couples + family) Enjoy a scenic Airstream getaway with hot tub, firepit, patio lights, and space to sleep 4. Includes queen bed, sofa double, flush toilet, shower, and AC. Grill dinner, swing under the stars, or play cornhole. Just 5 minutes to Medicine Park, Old Fort Sill, and the Refuge. Perfect for couples or small families. Price varies based on # of guests, weekday or weekends, season, local festivals, and holidays.

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, 147 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.

Superhost
A spacious living area features a soft rug underfoot, complemented by a green sofa and two upholstered chairs. A wooden bench sits against the wall, while a decorative wreath adds a touch of color. A coffee table occupies the center, and natural light fills the space.
Home in Chickasha
4.81 out of 5 average rating, 101 reviews

Caroline's Suite

Relax with the whole family at this peaceful, cozy home. This completely updated home sleeps up to 6 people with a queen bed in one room, twin trundle beds in the other, and a sleeper couch, and a full kitchen. Stay comfortable anywhere in the house as each room has a mini split system with remotes. For your furry friends, a spacious, fenced back yard. Near USAO, Shanon Springs Park, and the Sports Complex. Quick drive to Grady Co Fairgrounds. Enjoy!

Top guest favorite
A scenic view of the river and its surroundings is captured, highlighting the shimmering water under the sunlight. Rocks line the riverbank, and trees are visible in the background, framing the landscape. A bridge can be seen crossing the river, connecting the two banks.
Home in Medicine Park
4.93 out of 5 average rating, 249 reviews

Creekside Cabin

Medicine Park OK, the Jewel of the Southwest! This little resort town is situated at the forefront of the Wichita Wildlife Refuge and around the corner from recreational Lake Lawtonka! Enjoy the beautiful view of the bona fide cobblestone community with its artistic landscaping and rich history while overlooking Medicine Creek/Bath Lake Swimming Hole. Just minutes from Lawton/Ft.Sill to enjoy shopping, movies and entertainment for the whole family!

Guest favorite
A warm kitchen space features rich wooden cabinetry with a central island and stone countertops. Stainless steel appliances are included, and a vintage rug adds a cozy touch. Natural light streams in from windows, illuminating the decorative elements and well-organized workspace.
Guesthouse in Medicine Park
4.98 out of 5 average rating, 331 reviews

Harper's Landing Medicine Park Ft Sill Refuge

Beautiful Guesthouse (1 BR 1 BA) nestled between the base of Mt. Scott in the Wichita National Wildlife Refuge and Gondola Lake. King Size Bed & A Queen Size Sofa Sleeper Fireplace Well stocked Kitchen Walk-In Shower Cozy Living Area Screened patio Large Screen Smart Television with Direct TV, Netflix, and other streaming options. Fire Pit Steps to Hiking and Biking Trails Minutes to town Minutes to Ft Sill Gate (Apache)

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, 179 reviews

Serenity Cottage + hot tub in the country

Serenity Cottage at Red Hills Cottage Co. Slow down. Breathe deep. Make memories that last. Welcome to Serenity Cottage, a luxury shipping container retreat thoughtfully designed to help you escape the busyness of everyday life and rediscover the joy of simple moments. From the moment you arrive, you'll be greeted with fresh flowers and complimentary homemade cinnamon rolls—our way of saying, "We're so glad you're here."

Popular amenities for Chickasha family-friendly rentals

When is the best time to visit Chickasha?

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Avg. priceG$21,933 GYDG$20,262 GYDG$21,515 GYDG$20,262 GYDG$21,933 GYDG$21,933 GYDG$21,933 GYDG$20,053 GYDG$20,262 GYDG$20,262 GYDG$21,724 GYDG$21,515 GYD
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