
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$14,644 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.

⭐️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!

Secluded A-Frame Cabin near Lake Thunderbird & OU
Relax & unwind, this beautiful A-Frame cabin is nestled on 2.5 private acres of peace and quiet. Escape the city life in this immaculate cabin featuring a modern kitchenette with new furnishings. The spiral stairs lead to a comfortably sized loft and sleeping area. A short drive away you can experience local wineries, attractions, and the ever popular Lake Thunderbird State Park. Once back home it is time to enjoy the spacious deck with Chiminea along with spectacular views of the landscape.

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

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.

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 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.

Route 66 Oklahoma City 1925 Red Caboose
Enjoy a wonderful night in our 1925 CB&Q wooden caboose. As you pull into the driveway of our little farm, you won’t believe you’re only 20 minutes from downtown Oklahoma City and less than 10 minutes from Edmond. You may encounter deer, turkeys, road runners and much more. Enjoy the lonesome howl of distant coyotes in the evening as you step outside this old waycar. If you’re looking for a unique experience and you’re a romantic fool such as I, come stay a night in 13744.

★ ★ ★ ★★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.

Hidden Treasure Pool House Near I-40
If you like a little extra in your travels, you're welcome to our 1300 sq. ft. Guest Home on a 17 acre setting just 35 minutes from downtown OKC or 20 minutes from Weatherford OK. Secure location with a gated entry and some quiet scenic country but just a short drive away from the action in OKC. Great place for couples, solo adventurers, business travelers, and a family with children. NO parties or large groups. No more than 6 people on the premises.
Popular amenities for Chickasha family-friendly rentals
Family-friendly home rentals with a hot tub

Private Lakefront | POOL TABLE | Fishing | HOT TUB

“Steele” only 3 miles to OU!

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

Lake Oasis w/pool, Hot tub, Gym

Family Home + Back Guest Home

Apache Retreat- 1 mile to OU Campus with Hot Tub

Hogwarts house: hot tub, massage, kitchen, sleep6

Cute poolhouse with amenities
Family- and pet-friendly home rentals

Cozy Studio Apartment

Creekside Cabin

Entire Barndominium located on 5 acres!

Relax & Recharge | Hot Tub | Sauna | Cold Plunge

Rails & Trails at Moore

Modern & historic - Amazing Studio near State Fair

The Prancing Pony

The Oasis - A Relaxed 5 Bedroom Home with a Pool
Family-friendly home rentals with a pool

Roomy two Story, Cozy w/ private pool

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

Clean & Comfy Home in Lawton

Beautiful Large Group Retreat w/Private Pool

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

No Cleaning Fee. Home near Post and the Refuge.

Warm Getaway with a Poolside Patio in Norman, OK

Carmen Campus-close 2bed luxury-4
When is the best time to visit Chickasha?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$21,965 GYD | G$20,292 GYD | G$21,547 GYD | G$20,292 GYD | G$21,965 GYD | G$21,965 GYD | G$21,965 GYD | G$20,083 GYD | G$20,292 GYD | G$20,292 GYD | G$21,756 GYD | G$21,547 GYD |
| 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 |
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- Frontier City
- Fairgrounds
- Plaza District
- University of Oklahoma
- Science Museum Oklahoma
- Paycom Center
- Oklahoma City Museum of Art
- Quail Springs Mall
- National Cowboy & Western Heritage Museum
- Oklahoma Memorial Stadium
- Oklahoma City University
- Martin Park Nature Center
- Oklahoma City National Memorial & Museum
- Sam Noble Oklahoma Museum of Natural History
- Remington Park
- Oklahoma City Zoo
- Civic Center Music Hall
- Myriad Botanical Gardens
- Bricktown
- Chickasaw Bricktown Ballpark-SE
- Museum Of Osteology
- iFly Indoor Skydiving
- Regal Warren Moore
- Will Rogers Park





