
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.

⭐️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!

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

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.

Come visit the Happy House!
The Happy House is not just a place to sleep, its a colorful, magical, whismsical and Happy experience! Happy decor, art, flowers, mushrooms, and mythical creatures brighten every smile. Enjoy the outdoors with the privacy fenced XL backyard, trampoline, swing set, grill, and patio table or enjoy the snacks, drinks, toys, board games, and TV den inside. Bring your pets big or small, we'll be happy to welcome them all! Just 5 min to Tinker AFB, 15 min to Paycom, Bricktown, OKC Zoo.

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.

★ ★ ★ ★★Thunderbird Farmhouse OU/Lake/Hike-5acres
☆ Excellent Family 3 bdrm home on quiet 5 acres off hwy 9. Farmhouse decor family amenities. Games, books, WIFI, horse shoe pit, corn hole game, outdoor fire pit, and plenty of room to explore. Circle drive for easy boat pull through. Located 15 minutes East from OU Campus. Easy Access to Football Stadium, Lloyd Noble Arena & Norman. 1 minute West to Lake Thunderbird entrance and Calypso Cove Marina. ThunderBird Lake also has Hiking, Biking & Horse Trails.

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.

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.

*2 KINGS* Clean & Comfortable* Home Away From Home
Bring the whole family to this great place with lots of room for fun. Walking distance to a park. Less than 2 miles to Mustang Town Center which offers affordable day passes to community zero entry pool (seasonal), fitness, rock wall, disc golf and more! Easy commute to FAA, armory, airport, restaurants, Bricktown, convention center and Scissor Tail Park. All new furniture and beds as of 4/2022. Level 2 electric vehicle charging available.

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.

Sooner Suite - Private Entry & Close to OU!
Come and go as you please from this completely remodeled private entry suite. Quiet neighborhood less than 1 mile to south campus. Enjoy a queen size platform bed and walk-in shower. Cozy and clean. Your space shares a wall with our home’s den. (with newly installed insulation and a solid core door to deter sound though we can’t guarantee you won't hear our small children.)

Secluded country living, but easily accessible!
If you're looking for a nice, quiet and relaxing time in the country, this place is for you! Whether you are in town for business or a family vacation - this will be your home-away-from home. Plenty of parking available and tons of privacy. Close to I-40 and the new Kickapoo Turnpike.
Popular amenities for Chickasha family-friendly rentals
Family-friendly home rentals with a hot tub

6 min to Airport | HOT TUB | POOL TABLE | Arcade

“Steele” only 3 miles to OU!

Heart of Norman | Your Local Stay Hot tub & Arcade

Pet Friendly, Hot Tub/Sauna/Cold Plunge/Weights!

Enchanting Log Cabin

Game room and hot tub!

The Rustic Spot Open now for booking. See u soon!

L-Town Retreat (Hot tub, full kitchen) Ft Sill
Family- and pet-friendly home rentals

Tinker AFB OKC I-40 Maverick Themed Getaway!

Fun 3 bedroom home with extras. Good vibes await!

The Roost, No pet fees, fenced yard

Modern Stay Near Fort Sill + 75” TV & Shopping

EDO Bungalow

Retreat On 14th | Fenced Backyard | Highspeed WiFi

Open skies Fresh air Great times- Modern Farmhouse

Peaceful pet friendly home near OKC and more!
Family-friendly home rentals with a pool

Home Away From Home, 1b get-away & more!

Clean & Comfy Home in Lawton

Norman Bliss: Spacious Home for 8+

1 BR Close to OU & Downtown/Indoor Pool & Hot Tub!

The Prancing Pony

The Oasis - A Relaxed 5 Bedroom Home with a Pool

No Cleaning Fee. Home near Post and the Refuge.

FarmHouse Acreage POOL&Outdoor Kitchen near OU
When is the best time to visit Chickasha?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ386 | ﺩ.ﺇ356 | ﺩ.ﺇ378 | ﺩ.ﺇ356 | ﺩ.ﺇ386 | ﺩ.ﺇ386 | ﺩ.ﺇ386 | ﺩ.ﺇ353 | ﺩ.ﺇ356 | ﺩ.ﺇ356 | ﺩ.ﺇ382 | ﺩ.ﺇ378 |
| Avg. temp | 3°C | 6°C | 11°C | 15°C | 20°C | 25°C | 28°C | 27°C | 23°C | 16°C | 10°C | 4°C |
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 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!
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- Frontier City
- Oklahoma City Museum of Art
- Fairgrounds
- Science Museum Oklahoma
- Plaza District
- University of Oklahoma
- National Cowboy & Western Heritage Museum
- Oklahoma Memorial Stadium
- Quail Springs Mall
- Paycom Center
- Oklahoma City University
- Martin Park Nature Center
- Myriad Botanical Gardens
- Oklahoma City National Memorial & Museum
- Remington Park
- Sam Noble Oklahoma Museum of Natural History
- Oklahoma City Zoo
- The Criterion
- The Zoo Amphitheatre
- Civic Center Music Hall
- Chickasaw Bricktown Ballpark-SE
- Mount Scott
- Will Rogers Park
- iFly Indoor Skydiving





