
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.

⭐️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.

Boutique Retreat w Private Deck! La Sombra Studio
This modern studio garage apartment is a quiet retreat on 2.5 acres within 15 minutes of Downtown Oklahoma City! If you are looking for boutique experience away from the noise but still accessible to everything the city has to offer the La Sombra Studio is the spot. Perfect for the couple looking to get away, business travelers, or a solo retreat. You will have a private deck with perfect sunset views, fire-pit, outdoor shower for warmer weather, & a table for meals or even working outside.

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.

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.)

Game room/ kids play room/4bdr/7mins dnwtownokc
Perfectly located in Nicholas Hills, OKC, this property is minutes from dining, cafes, sports venues, offices, the zoo, museums, malls, Classen Curve, Plaza District, and more. Just 7 mins to downtown OKC and 16 mins to Will Rogers Airport. Ideal for vacations, business, or family trips, this unique property offers all you need. Discover Oklahoma City's charms here!!
Popular amenities for Chickasha family-friendly rentals
Family-friendly home rentals with a hot tub

Ultimate Game Night Getaway |Hot Tub, Arcade & Fun

Monthly rental Romantic | Hot tub | Rainshower

GUEST HOUSE 1.5 miles to OU CAMPUS

Private Lakefront | POOL TABLE | Fishing | HOT TUB

Beautiful 3 bedroom house/ pool table/ jacuzzi

Stay on Historic Route 66! OKC Nest: Guesthouse

Monthly rental

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

The Pavo - Walkable To OU Campus

*2 KINGS* Clean & Comfortable* Home Away From Home

Cozy Retreat Near Downtown OKC, OU Medical Dist.

Big Pine Cottage: Pets & Family Friendly, Garage

〰️The Nomad | Walk to Western Ave District

Open skies Fresh air Great times- Modern Farmhouse

Chic 50s Time Capsule Downtown/OU Med/OK Capitol

Historic Bungalow Walkable District
Family-friendly home rentals with a pool

Clean & Comfy Home in Lawton

1 BR Close to OU & OKC with heated Pool & Hot Tub!

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

Lake Oasis w/pool, Hot tub, Gym

Enchanted Amish Log Cabin Cedar Springs Ranch, OK

Instaworthy condo on ground floor in gated complex

No Cleaning Fee. Home near Post and the Refuge.

Modern 1BR w/ Pool & Balcony
When is the best time to visit Chickasha?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $126 SGD | $122 SGD | $126 SGD | $126 SGD | $137 SGD | $137 SGD | $137 SGD | $125 SGD | $126 SGD | $150 SGD | $137 SGD | $137 SGD |
| 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 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 $91 SGD per night before taxes and fees

Verified guest reviews
Over 940 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!




