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!

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.

Country Oasis 5 minutes from Chickasha

Escape to this peaceful countryside barndominium, just 5 minutes from the Chickasha Sports Complex, Grady County Fairgrounds, and historic downtown Chickasha. Whether you’re here for a tournament, business, or a relaxing getaway, you’ll enjoy the perfect blend of comfort and convenience. The home is fully accessible and equipped with grab bars in the shower and bedroom. Enjoy the convenience of a full-size washer and dryer, well Equipped kitchen, comfortable furnishings, and ample space.

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.

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.

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!

“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!

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."

Historic 4 bedroom Craftsman 3 Blocks from OU

- ONLY three blocks from the University of Oklahoma! - Four spacious bedrooms, comfortably sleeps 8 - Plenty of parking for up to 5 cars - Clean house kept pet-free, smoke-free for you! - Beautifully restored historic craftsman enclosed yard, and a delightful patio for dining al fresco. Out of caution for our guests with respiratory sensitivities, we are a no pet, no smoking home. Quiet hours from 10 pm-8 am.