
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.

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

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!

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.

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.

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.

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.

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.

Tiny Home with Private Patio
Tucked back behind the main house, this private newly remodeled studio creates a space to retire for rest and relaxation. Located less than a mile north of the University of Oklahoma campus and just a short walk to downtown Norman's restaurants and bars. This Bright and open-plan layout features a queen-size murphy bed, a sliding barn door, a kitchenette, 42 inch TV with Apple Play, and a private patio.

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.)
Popular amenities for Chickasha family-friendly rentals
Family-friendly home rentals with a hot tub

Monthly rental Romantic | Hot tub | Rainshower

GUEST HOUSE 1.5 miles to OU CAMPUS

Arcade + Hot Tub for a perfect stay

Perfect vacation home! Pool/jacuzzi/pooltable

Stay on Historic Route 66! OKC Nest: Guesthouse

Eagles Nest (Hot Tub)

New Align Hot Tub & Sauna Retreat Wichita Mountain

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

Entire Barndominium located on 5 acres!

Modern & historic - Amazing Studio near State Fair

Old School - A rustic, peaceful getaway

A Cozy Yukon Getaway off I40!

Cozy Retreat Near Downtown OKC, OU Medical Dist.

Come visit the Happy House!

Respite Retreat Capitol

〰️The Nomad | Walk to Western Ave District
Family-friendly home rentals with a pool

Roomy two Story, Cozy w/ private pool

Clean & Comfy Home in Lawton

Villa On 45th-Gorgeous 3 bedroom w/pool & hot tub!

Tiny log cottage, Woods, Creek, Mountains, Hot Tub

The Oasis - A Relaxed 5 Bedroom Home with a Pool

No Cleaning Fee. Home near Post and the Refuge.

The Chartreuse Moose, apartment w/pool for 4

La casa Linda: Beautiful Pool and Hot Tub
When is the best time to visit Chickasha?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $134 CAD | $130 CAD | $134 CAD | $134 CAD | $145 CAD | $145 CAD | $145 CAD | $133 CAD | $134 CAD | $159 CAD | $145 CAD | $145 CAD |
| 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 $97 CAD 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

Wifi availability
30 of Chickasha vacation 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!
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