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, 319 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 favorite
A spacious studio apartment features a cozy sleeping area with a comfortable bed, a seating area with stylish chairs, and an electric fireplace beneath a wall-mounted smart TV. A mini fridge and coffee maker are located near a small dining space, creating a functional layout.
Guesthouse in Oklahoma City
4.92 out of 5 average rating, 219 reviews

Chic and Central Studio in Plaza District

Private studio garage apartment in the historic Gatewood neighborhood, steps from the plaza district where you'll find local restaurants, bars, & shops. Private w/ free off street parking. Additional features include WiFi, HBO, smart TV, electric fireplace, mini split, fridge, coffee maker, cozy linens, & more. Centrally located less than 10 min. from downtown, midtown, paseo. Book today to stay good in Gatewood! Please note, the unit is a studio garage apartment & the bathroom is quite small.

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, 144 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 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, 169 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.

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
4.87 out of 5 average rating, 294 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, 303 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
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, 1,133 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
The living room features a green leather sofa adorned with colorful cushions, complemented by a rustic wooden coffee table. A large, art-adorned wall offers a glimpse into the dining area beyond, where vibrant blue walls and a pink area rug create a lively atmosphere.
Home in Crestwood
4.97 out of 5 average rating, 466 reviews

Cool Bungalow near the Plaza, Paseo, & Fairgrounds

This unique blue Bungalow features art that highlights the area including Midtown, Paseo, the Plaza and all the great things 23rd St. has to offer. Built in 1924, this home has all the charm of an older home with all the modern amenities of a new one. The ground floor features a living room, dining room, a closet turned into a place to "get ready", bathroom, bedroom with a queen bed, kitchen, and laundry room. The upstairs houses a second bedroom with a queen and twin bed.

Guest favorite
A living room area features a blue-gray sectional sofa with decorative pillows, complemented by a cozy armchair. A flat-screen TV is mounted on the wall opposite a light rug. Natural light enters through a window adorned with light curtains, and a ceiling fan adds a functional touch.
Townhouse in Edmond
4.88 out of 5 average rating, 176 reviews

Redbud Cottage #1

This tastefully decorated duplex is situated in the heart of Edmond, within walking distance to shopping, grocery stores and restaurants. Conveniently located to great local shopping, delicious eateries and quick interstate access to downtown OKC. Comfortably sleeps 4. With high speed wifi, smart TVs, cozy beds and a well-stocked kitchen, you’ll feel right at home! Need double the space? Book both sides of this duplex! Inquire with host if you need assistance.

Top guest favorite
A welcoming living area features a vibrant yellow sofa, complemented by a cozy pink chair and a round coffee table. Natural light enters through large windows, highlighting the contemporary decor. A television is positioned on a wooden console, and a soft rug adds comfort to the floor.
Guesthouse in Norman
4.97 out of 5 average rating, 280 reviews

Cozy Mid Century Modern Loft Near Campus

Nestled in the historic Southridge District of old Norman, this cozy loft is within walking distance of the University of Oklahoma campus and one block from The Mont, well known restaurant and home of the Sooner Swirl . You will fall in love with the views overlooking this beautiful neighborhood and its midcentury-modern boho vibe. Located in the heart of Norman so within minutes you can be at your event. We are a premier home away from home for OU parents!

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, 127 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, 160 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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Avg. priceG$20,279 GYDG$19,652 GYDG$20,279 GYDG$20,279 GYDG$21,951 GYDG$21,951 GYDG$21,951 GYDG$20,070 GYDG$20,279 GYDG$20,279 GYDG$21,742 GYDG$21,533 GYD
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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 G$14,634 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,030 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!