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, 332 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!

Guest favorite
An A-Frame cabin is showcased, featuring a light green exterior and a triangular roof. A spacious wooden deck offers access to the entrance, surrounded by a grassy area and bare trees. The clear sky enhances the peaceful setting of the property.
Cabin in Noble
4.96 out of 5 average rating, 180 reviews

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.

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
4.85 out of 5 average rating, 153 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, 186 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.

Guest favorite
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
4.88 out of 5 average rating, 315 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 exterior of a converted grain bin is displayed, featuring a large sunflower mural. A welcoming porch with rocking chairs is positioned to the side, surrounded by lush green grass and vibrant flower beds, enhancing the rural charm of the property.
Tiny home in Elgin
5 out of 5 average rating, 121 reviews

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.

Top guest favorite
The outdoor space features a swimming pool surrounded by a fenced yard, with a covered patio area equipped with chairs and a grill. The house has a rustic brick exterior, complemented by trees and a scenic view of the nearby hills.
Guesthouse in Lawton
5 out of 5 average rating, 292 reviews

No Cleaning Fee. Home near Post and the Refuge.

Furnished 1,000 sq ft. home, recently re-modeled and includes conveniences designed to meet the needs of families looking for a quiet and relaxing get-away with their Soldier, busy professionals, or those enjoying a vacation. I want this house to be your "home away from home" . So you do not need to bring your iron, bath, or kitchen items! This home is located 10 miles from Lake Lawtonka, Ft. Sill and Wichita Mountains Wildlife Refuge. Pool is open. Pool closed October.

Top guest favorite
The exterior of a red wooden caboose is presented, featuring windows and steps that lead to a small porch area. Surrounding greenery enhances the rustic setting, while a sign on the side indicates the caboose's name. A few chairs are visible nearby on a concrete surface.
Train in Jones
4.95 out of 5 average rating, 534 reviews

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.

Superhost
The exterior of a single-story brick home is displayed, featuring a well-maintained pathway leading to a front entrance. Flower beds filled with yellow blooms and soft greenery border the walkway. Large windows allow natural light to enhance the inviting façade under a clear blue sky.
Home in Norman
4.9 out of 5 average rating, 257 reviews

★ ★ ★ ★★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.

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, 140 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
Guesthouse in Hinton
4.97 out of 5 average rating, 215 reviews

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.

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, 175 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$21,963 GYDG$20,290 GYDG$21,545 GYDG$20,290 GYDG$21,963 GYDG$21,963 GYDG$21,963 GYDG$20,081 GYDG$20,290 GYDG$20,290 GYDG$21,754 GYDG$21,545 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$14,642 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!