Family-friendly vacation rentals in Chickasha

⭐️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.

The Cottage

Newly built in December 2025, this 3-bedroom, 2-bathroom home blends vintage touches and cozy details making it easy to settle into. Located in a quiet neighborhood on the edge of town but still only 5–10 minutes from downtown, restaurants, shopping, and local attractions. Inside, the home features a kitchen with plenty of room to cook and gather. Sleeping arrangements include 2 queen beds and 2 twin beds. Step outside to enjoy the large yard. The home also includes washer and dryer access.

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.

Bohemian Bungalow *no cleaning fee*

We have spent the last several years traveling the country & curating an eclectic collection of treasures: vintage National Park souvenirs, swag lamps, and unique art. We rotate art often, so every visit may yield a new treasure to discover! The kitchen table is a great place for your work-from-home needs, but there is a foldable desk in the bedroom closet if you need a private space. We can often accommodate a no-charge early check-in, so please do not hesitate to ask!

“Steele” only 3 miles to OU!

🌟 4BR | 2BA Home with Pool & Hot Tub! 🌟 Escape to comfort and style in Norman’s most desirable neighborhood! Perfect for singles, couples, or families, this home has everything you need for a relaxing stay. 💦 Private Pool & Hot Tub – unwind, relax, and soak your stress away (use at own risk) 🏡 Spacious & Modern – 4 bedrooms, 2 bathrooms, fully equipped kitchen📍 Prime Location – just 3 miles from OU— it’s ah Steele! Note: No parties, events, or gatherings permitted.

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.

Caroline's Suite

Relax with the whole family at this peaceful, cozy home. This completely updated home sleeps up to 6 people with a queen bed in one room, twin trundle beds in the other, and a sleeper couch, and a full kitchen. Stay comfortable anywhere in the house as each room has a mini split system with remotes. For your furry friends, a spacious, fenced back yard. Near USAO, Shanon Springs Park, and the Sports Complex. Quick drive to Grady Co Fairgrounds. Enjoy!

Powell Cabin Inside Turner Falls Park

This cozy (non-smoking) 2-bed/1-bath cabin at Turner Falls Park accommodates up to 4 people (2 adults, 2 kids). If you need more space or plan to host a party, please look elsewhere. The cabin is fully furnished and steps from picnicking, swimming, and the Falls. *Important Turner Falls Rules:* * Tickets required for all guests daily, including check-in/check-out days. * No re-entry after 10pm. * No pets. * Respond to all host messages.

Cardinal Birdhouse Cottage ADA friendly.

The Cardinal Birdhouse Cottage provides a barrier free entry with an elevated water-view deck. So close to shops and restaurants but restful and convenient with a Nectar mattress, wireless internet, large television, coffee maker, microwave, small fridge and many other amenities. This suite is ADA friendly with an oversized shower and close designated parking. The Cardinal shares a deck with the Bluebird and does NOT have a round window.

Serenity Cottage + hot tub in the country

Serenity Cottage at Red Hills Cottage Co. Slow down. Breathe deep. Make memories that last. Welcome to Serenity Cottage, a luxury shipping container retreat thoughtfully designed to help you escape the busyness of everyday life and rediscover the joy of simple moments. From the moment you arrive, you'll be greeted with fresh flowers and complimentary homemade cinnamon rolls—our way of saying, "We're so glad you're here."