Family-friendly holiday rentals in Chickasha

4.97 out of 5 average rating, 340 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!

KitchenIndoor spacesLong stay

4.96 out of 5 average rating, 188 reviews

An A-Frame cabin is showcased, featuring a light green exterior and a triangular roof. A spacious wooden deck offers access to the entrance, surrounded by a grassy area and bare trees. The clear sky enhances the peaceful setting of the property.

Cabin in Noble

Secluded A-Frame Cabin near Lake Thunderbird & OU

Relax & unwind, this beautiful A-Frame cabin is nestled on 2.5 private acres of peace and quiet. Escape the city life in this immaculate cabin featuring a modern kitchenette with new furnishings. The spiral stairs lead to a comfortably sized loft and sleeping area. A short drive away you can experience local wineries, attractions, and the ever popular Lake Thunderbird State Park. Once back home it is time to enjoy the spacious deck with Chiminea along with spectacular views of the landscape.

FamilyIndoor spacesLayout

4.99 out of 5 average rating, 154 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!

Escape to your home away from home in the vibrant Wheeler District! Our beautiful three-story, three-bedroom retreat offers a relaxing oasis with a four-person outdoor hot tub that lights the water up in your choice of 5 different colors and with outdoor string lights for a nice chill vibe. Enjoy eating breakfast, lunch or dinner in the backyard built in seating area. Explore the neighborhood's charm, from strolling walkways, neighborhood park and playgrounds, eateries, and many boutique shops.

FamilyKitchenHospitality

4.86 out of 5 average rating, 159 reviews

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.

Home in Chickasha

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

FamilyKitchenGetting around

4.92 out of 5 average rating, 192 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.

FamilyKitchenCheckout

5.0 out of 5 average rating, 15 reviews

Home in Chickasha

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.

Indoor spacesKitchenGetting around

5.0 out of 5 average rating, 125 reviews

The exterior of a converted grain bin is displayed, featuring a large sunflower mural. A welcoming porch with rocking chairs is positioned to the side, surrounded by lush green grass and vibrant flower beds, enhancing the rural charm of the property.

Tiny home in Elgin

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.

KitchenFamilyHospitality

Place to stay in Medicine Park

Two charming cottages with colorful exteriors sit elevated on stilts beside a winding creek. Each cottage features a distinct color and a circular window. A pathway runs alongside the water, while ducks can be seen swimming in the foreground, enhancing the picturesque natural setting.

4.88 out of 5 average rating, 520 reviews

Hummingbird Birdhouse Cottage

The Hummingbird Cottage in the center of the Park has a covered elevated porch with table and chairs and a bonus area under the cottage with rocking chairs ideal for water and wildlife viewing. Sleep soundly on your Nectar mattress, watch television or use the wireless internet to stay connected. With a microwave, coffee maker and small fridge, you will have many amenities at your fingertips. You have a designated parking space with shops and restaurants a few steps away.

Indoor spacesFamilyValue

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.

KitchenFamilyPets

Superhost

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.

Home in Chickasha

4.8 out of 5 average rating, 102 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!

KitchenFamilyHeating

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.

4.99 out of 5 average rating, 183 reviews

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."

Indoor spacesFamilyHot tub

4.94 out of 5 average rating, 214 reviews

A private outdoor area features a circular in-ground pool surrounded by a stone patio. A grill is positioned near the pool house, complemented by potted plants and a wooden fence providing privacy. The space is shaded by overhanging trees, creating a serene atmosphere.

Home in Duncan

McNair Westgate House, Golf Oasis, Pool, Hot Tub

Experience the newly remodeled Westgate House, a private oasis in Duncan. This 3BR, 2.5 bath, 2472 sq ft, home features a HOT TUB, in-ground pool, pool house w/bar, high-end kitchen appliances, whiskey lounge with arcade table. The master bedroom offers exclusive access to a private patio and pool. Sleeps 6 guests comfortably. Conveniently located near Stephens County Fairgrounds, Casino, Brewery & Kiddieland Park.

KitchenIndoor spacesPool

Popular amenities for Chickasha family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 132 reviews

“Steele” only 3 miles to OU!

Indoor spacesFamilyBackyard

4.99 out of 5 average rating, 169 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)

KitchenFamilyCondition

A modern farmhouse exterior features a spacious covered porch with wooden support beams. The front door is framed by two windows, and the yard is manicured with lush green grass. The sloped roof and white siding complement the natural surroundings.

4.99 out of 5 average rating, 137 reviews

Welcome to the Ranch at OU. * HOT TUB *

Indoor spacesKitchenCheck-in

4.94 out of 5 average rating, 132 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

Indoor spacesFamilyAmenities

Superhost

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

4.9 out of 5 average rating, 301 reviews

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

Indoor spacesKitchenHot tub

4.93 out of 5 average rating, 131 reviews

A serene pool area is surrounded by lush greenery and well-maintained landscaping. The spacious casita features large windows and a distinctive roof design, while flower pots add subtle color along the pool's edge. The inviting spa and comfortable seating create a relaxed atmosphere.

Guesthouse in Norman

GUEST HOUSE 1.5 miles to OU CAMPUS

FamilyKitchenNearby

4.93 out of 5 average rating, 184 reviews

Apache Retreat- 1 mile to OU Campus with Hot Tub

Indoor spacesKitchenAmenities

4.91 out of 5 average rating, 107 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

KitchenFamilyGetting around

Family- and pet-friendly home rentals

4.85 out of 5 average rating, 944 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

Indoor spacesKitchenHospitality

4.98 out of 5 average rating, 234 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

Indoor spacesKitchenParking

4.88 out of 5 average rating, 329 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

KitchenFamilyValue

Guesthouse in Medicine Park

A warm kitchen space features rich wooden cabinetry with a central island and stone countertops. Stainless steel appliances are included, and a vintage rug adds a cozy touch. Natural light streams in from windows, illuminating the decorative elements and well-organized workspace.

4.98 out of 5 average rating, 333 reviews

Harper's Landing Medicine Park Ft Sill Refuge

KitchenFamilyCheckout

4.94 out of 5 average rating, 148 reviews

A cozy living area features a comfortable sofa and an armchair, accented by decorative cushions. A round coffee table is placed centrally, and a standing lamp provides warm light. Two windows with plantation shutters allow natural light to filter in.

Home in Duncan

Sugarberry Cottage

FamilyKitchenCleanliness

4.93 out of 5 average rating, 134 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

KitchenFamilyHeating

4.87 out of 5 average rating, 215 reviews

Convenient house near OU campus

FamilyIndoor spacesHospitality

4.96 out of 5 average rating, 408 reviews

A red barn-style building is set within a green lawn, offering ample outdoor space. The structure features multiple windows and a large roll-up door. A military vehicle is parked alongside, with trees lining the background, creating a serene setting.

Farm stay in McLoud

Entire Barndominium located on 5 acres!

KitchenIndoor spacesParking

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 223 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!

KitchenFamilyHospitality

4.93 out of 5 average rating, 472 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

FamilyKitchenAccess

Guesthouse in Pauls Valley

The pool area is softly illuminated by string lights overhead, creating a serene ambiance at dusk. Comfortable lounge chairs line the poolside, and the inviting water reflects the twinkling lights, while lush greenery surrounds the space, enhancing the peaceful atmosphere.

4.96 out of 5 average rating, 158 reviews

Charming, one room Carriage House w/pool

KitchenFamilyWalkability

5.0 out of 5 average rating, 302 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.

Indoor spacesKitchenNearby

4.98 out of 5 average rating, 120 reviews

Guest suite in Moore

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

Indoor spacesKitchenAccuracy

4.88 out of 5 average rating, 194 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.

FamilyIndoor spacesAccess

Superhost

A cozy living area is portrayed with a tan sofa and two armchairs surrounding a dark wooden coffee table. A neutral rug lies on the floor, while natural light enters through sliding glass doors adorned with vertical blinds. A decorative piece hangs on the wall above.

Condo in Norman

4.8 out of 5 average rating, 227 reviews

Carmen Campus-close 2bed luxury-4

KitchenFamilyCheckout

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.