Family-friendly vacation rentals in Chickasha

Clean, Modern Luxury on Western- New Build in OKC!

Welcome to Western Ave dining and entertainment district! Minutes from Classen Curve, Nichols Hills, and the Paseo, this brand new custom home is nestled in the absolute best part of OKC. Walk to dining and drinks, shop at Whole Foods and all the wonderful shops in Nichols Hills plaza, hop downtown in minutes or just park in the two car garage and enjoy a staycation in this safe clean and quiet modern home. Truly a wonderful area... you can't beat the quality, convenience and value. Just Listed!

⭐️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

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.

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.

Mountain Boomer

Nestled among the trees in Medicine Park is a cozy cabin with all the comforts you could desire. The cabin has two bedrooms, two bathrooms perfectly placed for maximum privacy. Medicine Park adjoins the Wichita Mountains and offers ; hiking, biking, fishing, kayaking, and bird watching. Sit back, relax and take in the fresh air or explore nearby trails for new adventures. This is the perfect place to unwind from your everyday routine and make lasting memories that you’ll treasure forever

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.

“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.

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.

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!