Family-friendly holiday rentals in Chickasha

4.97 out of 5 average rating, 344 reviews

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

⭐️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!

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.

4.84 out of 5 average rating, 163 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

4.92 out of 5 average rating, 198 reviews

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

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.

5.0 out of 5 average rating, 20 reviews

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.

4.96 out of 5 average rating, 52 reviews

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.

4.94 out of 5 average rating, 135 reviews

A swimming pool features clear blue water, surrounded by a spacious concrete deck. Several lounge chairs provide seating, arranged to allow sunbathing. A fenced area offers privacy, with green trees visible in the background, enhancing the outdoor setting.

Villa in Lawton

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.

4.85 out of 5 average rating, 961 reviews

A cozy sleeping area features a spacious bed adorned with floral-patterned bedding. Soft lighting is provided by wall-mounted lamps on either side of the bed. A light-filled door offers access to the outdoor space, while cabinetry is visible to the right.

Guesthouse in Norman

The Prancing Pony

The Prancying Pony is a short walk to the University of Oklahoma Campus, Historic Downtown Arts District, restaurants, and dining. The Pony is a quiet and secluded cabana with beautiful garden and pool. The ambiance, the outdoor space, and neighborhood make this the ideal location for exploring the best of Norman. This apartment is good for couples, solo adventurers, and business travelers. The apartment has one, gated parking spot. Also included is the use of an outdoor grill.

4.94 out of 5 average rating, 479 reviews

A guest room is presented with two spacious beds, each covered in white bedspreads. A light gray floral artwork is mounted on the wall, and a lamp sits on a dark wood bedside table. Natural light enters through a window with sheer curtains, illuminating the welcoming space.

Home in Midwest City

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!

4.95 out of 5 average rating, 149 reviews

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

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.

4.91 out of 5 average rating, 140 reviews

OU 4 Miles | Private Pool + Hot Tub | 4BR

4BR | 2BA | Private Pool & Hot Tub | 4 Miles to OU! Welcome to your Norman home away from home! Perfect for families, couples, OU visits, game weekends, graduations, or a relaxing getaway. 💦 Private Pool & Hot Tub – Relax, cool off, and unwind. (Use at own risk.) 🏡 Spacious & Comfortable – 4 bedrooms, 2 baths, fully equipped kitchen… ❤️ Enjoy Norman — it’s ah Steele! Come make your memories here! No parties, events, or gatherings permitted.

A spacious living area features a soft rug underfoot, complemented by a green sofa and two upholstered chairs. A wooden bench sits against the wall, while a decorative wreath adds a touch of color. A coffee table occupies the center, and natural light fills the space.

4.81 out of 5 average rating, 104 reviews

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!

Shipping container in Chickasha

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.

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."

4.99 out of 5 average rating, 188 reviews

Popular amenities for Chickasha family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 188 reviews

Apache Retreat- 1 mile to OU Campus with Hot Tub

4.97 out of 5 average rating, 173 reviews

Home in Medicine Park

Align New Private Indoor Hot Tub & Sauna Retreat

4.92 out of 5 average rating, 138 reviews

A freshly renovated two-story house features a white exterior with wooden accents. The front porch is adorned with a welcoming balcony above, while the manicured lawn is complemented by a decorative lamp post. Nearby, a clear sign indicates the property name.

Home in Duncan

McNair Golf Front, Hot Tub, Poker Room, Ping Pong

A tranquil backyard scene is illuminated by string lights as dusk settles. The saltwater pool glows in inviting blue, surrounded by comfortable lounge chairs. A firepit is positioned nearby on a manicured lawn, with a cozy seating arrangement creating an inviting outdoor space for relaxation.

4.97 out of 5 average rating, 102 reviews

Sooner Oasis-Pool, Hot Tub, Arcade, 3 miles to OU!

4.99 out of 5 average rating, 166 reviews

The exterior of a three-story home is showcased, featuring a light blue facade with multiple large windows. A welcoming front porch is visible, framed by greenery and landscaping, and steps lead up to the entrance, creating an inviting appearance.

Home in Oklahoma City

Home Away From Home with hot tub!

4.9 out of 5 average rating, 305 reviews

A single-story brick house is presented, featuring a well-maintained lawn and a driveway leading to a garage. The front porch is modestly adorned, with small shrubs flanking the entrance. Windows are framed neatly, offering a welcoming appearance.

Home in Lawton

L-Town Retreat (Hot tub, full kitchen) Ft Sill

4.99 out of 5 average rating, 170 reviews

A rustic cabin exterior showcases a covered porch with comfortable seating for four, complemented by vibrant stools. The natural surroundings feature greenery, and a hammock is draped nearby. A stone chimney adds to the cabin's charm, highlighting its inviting outdoor space.

Cabin in Medicine Park

Eagles Nest (Hot Tub)

4.91 out of 5 average rating, 110 reviews

A hot tub is prominently featured, surrounded by natural elements, providing a space for relaxation. An outdoor seating area with colorful chairs encircles a firepit, while a welcoming entrance features steps leading up to the home. A cozy bedroom is detailed in vibrant colors, enhancing its inviting ambience.

Cabin in Medicine Park

Isn't She Lovely Waterfront-HotTub

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 338 reviews

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

Tiny Cabin at the DonkeyRanch

4.88 out of 5 average rating, 192 reviews

A spacious outdoor area features a circular fire pit surrounded by four sturdy chairs. The modern farmhouse with a metal roof is viewed in the background, with lush green fields and a clear blue sky creating a serene setting.

Home in Oklahoma City

Open skies Fresh air Great times- Modern Farmhouse

4.93 out of 5 average rating, 136 reviews

A spacious living area features a brick fireplace and a large wall-mounted television. Two comfortable gray sofas and a glass coffee table create a welcoming seating arrangement. Light streams in from a nearby entrance, illuminating the room's neutral tones.

Home in Mustang

*2 KINGS* Clean & Comfortable* Home Away From Home

5.0 out of 5 average rating, 104 reviews

A collage of accommodations is presented, featuring a spacious king bed with modern decor, a comfortable seating area highlighted by decorative throw pillows, an outdoor patio with seating, a well-equipped bathroom, and the stylish exterior of the rental house.

Guesthouse in Noble

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

4.95 out of 5 average rating, 104 reviews

Simmerin’ Down in Sooner Town

4.88 out of 5 average rating, 120 reviews

The front exterior of the home is showcased, featuring a red-trimmed brick facade. A well-maintained lawn surrounds the driveway, which leads to a two-car garage. A decorative mailbox stands at the edge of the property, complementing the welcoming entrance.

Home in Duncan

Dottie's and Joe's Gorgeous Family Friendly Home

4.98 out of 5 average rating, 237 reviews

The farmhouse exterior features a welcoming front patio with comfortable seating arranged around a fire pit. A charming chiminea and a grill are visible, accompanied by decorative planters and greenery. The structure showcases a blend of rustic appeal with modern simplicity.

Farm stay in Comanche

Hidden Hills Properties llc

The kitchen is equipped with modern stainless steel appliances and features grey countertops with a sleek design. Open shelving displays dishware, and a window allows natural light to illuminate the space. Tiles on the floor provide a clean and functional appearance.

4.87 out of 5 average rating, 273 reviews

Sleeps 6 in Prime Location

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 307 reviews

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

No Cleaning Fee. Home near Post and the Refuge.

4.98 out of 5 average rating, 231 reviews

An inviting living area is presented, featuring a comfortable brown sofa and a decorative area rug. A coffee table occupies the center, while a television is positioned against one wall. Natural light enhances the space through a nearby window, framed by simple curtains.

Guesthouse in Mustang

Home Away From Home, 1b get-away & more!

4.92 out of 5 average rating, 319 reviews

A private outdoor space features an in-ground pool, surrounded by lush greenery. The house above showcases spacious glass doors leading to a balcony, with seating areas and a built-in slide for enjoyment. Warm wood accents create a welcoming atmosphere.

Guesthouse in Norman

Warm Getaway with a Poolside Patio in Norman, OK

4.88 out of 5 average rating, 195 reviews

A private backyard features a newly remodeled pool, surrounded by green grass and mature trees. A storage shed sits at the back, and the space is enclosed by a wooden fence, providing privacy and a tranquil outdoor environment.

Home in Lawton

Ft Sill house big enough for everyone.

4.98 out of 5 average rating, 127 reviews

Guest suite in Moore

1 BR Close to OU & Downtown/Indoor Pool & Hot Tub!

A covered patio features comfortable seating arranged around a round table, with a view of a large pool in the background. Soft natural light filters through the patio's overhead design, and lush greenery lines the property, creating a serene outdoor space.

4.92 out of 5 average rating, 118 reviews

Poppy's Place - Campus Home w/ Pool

Townhouse in Midwest City

The exterior of a single-story home is displayed, featuring a combination of brick and wood paneling. A light-colored door and windows with blinds are visible, along with a landscaped yard and a driveway leading to the entrance.

Cozy Condo

5.0 out of 5 average rating, 187 reviews

An inviting backyard pool area features a wooden deck with multiple seating options, surrounded by lush greenery. The clear blue water of the pool reflects the sunlight, creating a calm and relaxed outdoor atmosphere.