Family-friendly holiday rentals in Chickasha

4.97 out of 5 average rating, 343 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!

Indoor spacesKitchenAccess

4.84 out of 5 average rating, 162 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

Indoor spacesKitchenWalkability

4.92 out of 5 average rating, 196 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.

Indoor spacesKitchenParking

5.0 out of 5 average rating, 18 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 spacesFamilyCleanliness

4.94 out of 5 average rating, 133 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.

FamilyIndoor spacesHeating

4.88 out of 5 average rating, 337 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

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

Indoor spacesKitchenAccuracy

4.93 out of 5 average rating, 476 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!

Indoor spacesFamilyHeating

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.

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.

KitchenIndoor spacesLayout

4.91 out of 5 average rating, 140 reviews

“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.

KitchenIndoor spacesQuiet

5.0 out of 5 average rating, 102 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!

📍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 spacesKitchenGetting around

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.

FamilyIndoor spacesSleep quality

4.81 out of 5 average rating, 104 reviews

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

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!

KitchenIndoor spacesCheckout

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

4.92 out of 5 average rating, 137 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

FamilyIndoor spacesParking

4.99 out of 5 average rating, 164 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!

Indoor spacesKitchenAir conditioning

4.97 out of 5 average rating, 171 reviews

Home in Medicine Park

Align New Private Indoor Hot Tub & Sauna Retreat

KitchenFamilyAccuracy

4.9 out of 5 average rating, 304 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

FamilyKitchenCondition

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!

Indoor spacesKitchenCheckout

4.93 out of 5 average rating, 188 reviews

Apache Retreat- 1 mile to OU Campus with Hot Tub

KitchenFamilyHeating

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

Indoor spacesFamilyTV

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

Indoor spacesKitchenCondition

Family- and pet-friendly home rentals

4.85 out of 5 average rating, 960 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 spacesKitchenCheckout

4.95 out of 5 average rating, 102 reviews

Simmerin’ Down in Sooner Town

Indoor spacesFamilyCleanliness

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

Indoor spacesKitchenCheckout

4.85 out of 5 average rating, 325 reviews

An open living space features modern lighting with colorful pendant lamps. A large television displays vibrant visuals, while a cozy seating area is arranged around a central coffee table. A wall adorned with greenery and a neon sign adds a contemporary touch.

Home in Moore

Fun 3 bedroom home with extras. Good vibes await!

FamilyIndoor spacesHospitality

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

Indoor spacesKitchenNearby

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

FamilyIndoor spacesBackyard

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, 272 reviews

Sleeps 6 in Prime Location

KitchenIndoor spacesPets

4.86 out of 5 average rating, 223 reviews

Convenient house near OU campus

Indoor spacesKitchenLocation

Family-friendly home rentals with a pool

4.93 out of 5 average rating, 316 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

KitchenFamilyLaundry

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.

4.91 out of 5 average rating, 117 reviews

Poppy's Place - Campus Home w/ Pool

FamilyIndoor spacesOutdoor spaces

4.98 out of 5 average rating, 126 reviews

Guest suite in Moore

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

Indoor spacesKitchenAccuracy

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.

KitchenFamilyTV

4.85 out of 5 average rating, 128 reviews

An open-concept living area is featured, showcasing a light-colored couch positioned near a contemporary shelving unit. A hallway is visible, leading to private rooms. Decorative plants are included, adding a touch of greenery. The warm wood flooring enhances the inviting atmosphere.

Apartment in Norman

1145-2 OU-2 bed 2 bath apartment close to OU-2

KitchenFamilyPool

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, 161 reviews

Charming, one room Carriage House w/pool

FamilyIndoor spacesCondition

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.

4.88 out of 5 average rating, 156 reviews

The Oasis - A Relaxed 5 Bedroom Home with a Pool

Indoor spacesKitchenGetting around

An aerial view depicts a mapped route from a sports stadium to a residential area. Streets and greenery are visible, with buildings and structures highlighted in proximity to the university, providing a sense of the neighborhood layout and nearby amenities.