Family-friendly holiday 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!

Kitchen · Family · Quiet

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

Family · Kitchen · Cleanliness

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.

Kitchen · Indoor spaces · Comfort

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.

Kitchen · Family · Amenities

Book the Lodge-Pool-hot tub 4 king,14 bed, dine 24

Family & Group-Friendly Escape-5BR lodge on 9 secluded, park like acres w/ pool, hot tub, fireplaces, gourmet kitchen, & dining & sleeping for 22. 4 king beds, billiards, darts, games, & more. Walk to trails, drive 5 min to Medicine Park & Old Fort Sill. Great for reunions, nature lovers, & family fun. Pets welcome w/ fee. Priced # of guests. > 30 people venue fees apply - Event 1 $1,500, Event 2 +$500: tables, chairs, linens, etc. Barn, Air Stream, 2 night rental required for events.

Indoor spaces · Family · Bathroom

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

Kitchen · Family · Accuracy

Roomy two Story, Cozy w/ private pool

PLEASE READ AND TAKE NOTE OF POOL OPEN AND CLOSED DATES Two story house in an established neighborhood. Quiet and roomy place close to many attractions in Oklahoma City. Pool open from April 15th to September 30th ATTENTION all exercise equipment and swimming pool area is "USE AT YOUR OWN RISK" we are not responsible for any injury or death caused by use of these items. there is no life gaurd on duty, so gate must be closed at all times and kids should never be unsupervised!

Kitchen · Family · Hospitality

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.

Indoor spaces · Family · Hot tub

“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.

Indoor spaces · Kitchen · Hot tub

Farm Guest House 7 mi. from O.U.- Pet Friendly!

📍Centrally located near: 🏈O.U. 7miles 🎓SE Norman 4miles 🐟T.Bird Lake 10miles 🎰RiverwindCasino 13miles 🚬Smoking Permitted Outdoors 🍁(includes legal medicinal privilege) 📢No noise restrictions 🐶Fully fenced yard/safe 4 unsupervised pets 🏕️Covered Porch🌭GRILL⛱️ patio furniture 🔥Gas Firepit 🚚 Surveillanced Parking (covered & uncovered) 🛏️LUXURY KING BED 📺TWO 75” T.V.s. 🌡️TWO A.C. Units 🔐Safe/Secure/ZERO Crime🚫 🚸Expect personal space seclusion & privacy

Indoor spaces · Family · Layout

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.

Family · Indoor spaces · Amenities

Suite Caroline’s

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!

Family · Kitchen · Walkability