Family-friendly holiday rentals in Rolla

A charming white cottage is set against a backdrop of greenery, featuring dark shutters and a welcoming front porch. A flowering bush with soft pink blooms is situated in the foreground, adding a touch of natural beauty to the scene.

5.0 out of 5 average rating, 109 reviews

Get Cozy in the Country - The Cottage on Luca Hill

A rural stay just 4 miles from the increasingly popular town of St. James. On the farm, you’ll enjoy gorgeous sunsets by the firepit, view the cattle grazing just feet away, and get cozy inside the newly furnished Cottage. Well known for its award winning wineries and dining, STJ also offers various specialty shops and lets not forget the gorgeous Meramec Springs and surrounding rivers. MO S&T and Fort Leonard Wood are just a short drive along I-44 as well. It would be our pleasure to host you!

FamilyKitchenTV

4.95 out of 5 average rating, 578 reviews

A bright red tiny house is reflected in the calm water, surrounded by lush greenery. The property includes a private dock, equipped with a water slide and lounge chairs, enhancing the serene lakeside setting.

Tiny home in Rolla

Tiny Paradise on the Quarry

Come and enjoy the Tiny Paradise on the Quarry, as seen on HGTV's "Tiny Paradise" in 2017. House Beautiful Magazine's listed it as one of the TOP 50 Tiny Houses in the USA. Featured in People Magazine's HGTV special edition magazine. Missouri Life Magazine listed it as one of the top 9 gems in Missouri. Also featured as one of the four fall get-a-ways in 417 Magazine's. St. Louis Magazine listed it as the coolest Airbnb in their Aug/Sept 2019 issue. You are welcome to have more than two guest

KitchenFamilyPool

The kitchen features modern appliances, including a stainless steel refrigerator and a gas stove. White cabinetry and open shelving are accented by yellow decor. A central island offers additional workspace, while natural light enters through a window above the sink, highlighting the clean, inviting layout.

4.94 out of 5 average rating, 128 reviews

BKC Ranch

Welcome to BKC Ranch! You will have the entire place to yourself. There is a keypad for entry. A stocked coffee bar & comfy bedding! There is a nice screened in porch with a patio set, gas fire pit & a barbecue grill with fenced in yard. Just a couple miles outside of Rolla, just minutes from Fugitive Beach & MS and T, A 36 mile drive to Fort Leonard Wood. Trout Parks, beautiful Meremec Springs Park and many local wineries, Very close to shopping, restaurants and only about 5 miles off of I-44.

KitchenIndoor spacesAmenities

4.84 out of 5 average rating, 179 reviews

A charming cabin exterior is framed by trees showing autumn leaves. A welcoming porch features wooden steps, outdoor seating, and decorative lighting. The cabin's natural wood siding and metal roof blend harmoniously with the surrounding landscape.

Cabin in St. James

Hawks Ridge Cabin

Hawk Ridge is a stunning custom 1.5 story with 3 bedrooms and 2.5 baths, handicap accessible situated on 14 private acres. It is minutes from St. James, Meramec Springs State Park with trophy trout fishing, wineries, hiking and golfing. Canoeing, kayaking, rafting, zip-lining and horseback riding are only 10 short miles away. This location has something for every. 41 miles from Ft. Leonard Wood 17 miles from Fugitive Beach 17 miles from Steelville (floating) 3 miles from Maramec Springs Park

KitchenIndoor spacesTV

4.94 out of 5 average rating, 338 reviews

A modern farmhouse is set against a backdrop of lush trees, featuring a metal roof and a welcoming front entrance. A wooden path leads to the door, surrounded by well-maintained greenery and stones, creating an inviting approach to the home.

Home in Newburg

The Retreat at Merry Meadows: Cheerful 4-Bed home

Bring the family to The Retreat with lots of room for fun. Located on a quiet country road, surrounded by woods and fields. I am sure you will find this spacious farm house built in 2019, to be the perfect retreat. We are about 10 miles south of rolla. Fugitive Beach is only a 20 minutes drive away. Kabekona Hills Retreat Center is practically next door. Lane Springs is another popular destination. The large living room and kitchen, makes this a perfect location to bring the whole family.

Indoor spacesFamilyOutdoor spaces

4.96 out of 5 average rating, 109 reviews

A cozy seating area is featured with a floral patterned loveseat and a blue checked armchair, complemented by a decorative pillow. Two windows framed with plaid curtains allow natural light to fill the space, while wooden flooring adds warmth to the room.

Guesthouse in Rolla

Charming Hummingbird Cottage

Welcome to Hummingbird Cottage, a picturesque countryside retreat in Rolla, Missouri! Nestled in a beautiful landscape, our English-style cottage offers rustic charm with a cozy aesthetic. Surrounded by wildlife, yet close to attractions like Fugitive Beach and local wineries. The cottage sleeps two. There is a full kitchen, a bathroom with a walk-in shower, and beautiful outdoor pavilion. Experience the perfect summer getaway in this cozy cottage surrounded by a lovely natural landscape.

Indoor spacesFamilyParks

4.82 out of 5 average rating, 104 reviews

Midnight Manor, New back deck/Rocked fire pit/ramp

Enjoy a stay at this modern industrial/ farmhouse style 3 bedroom home, tucked in the middle of what used to be called “ The old shoe factory addition “ of Rolla. Fully renovated from the inside out in 2024, this house welcomes you with warmth, earth tones, an open concept, a towering fireplace, exposed beams, and a relaxing environment to getaway to. Centrally located and in walking distance to the water park, gym, rec center, movie theater, and more! Fugitive beach is about 7 miles away!

FamilyKitchenHospitality

A quaint home with a vibrant red exterior and cedar accents is highlighted. A wooden ramp leads to the entrance, with a charming staircase visible. Lush greenery surrounds the house, enhancing the natural setting. The entrance features a welcoming front porch area.

4.95 out of 5 average rating, 173 reviews

Cedar Haven Rolla

Welcome to Cedar Haven Rolla. In a quiet neighborhood centrally located in the heart of Rolla. Unwind after a long day in the relaxing warmth of this newly renovated home. Located only 6 blocks from historic downtown Rolla and old route 66, 9 blocks from the University of Missouri Science and Technology (MST), and only 3 blocks from Rolla's largest park - Ber Juan (fitness complex, splash zone, walking trails, frisbee golf). Just 3 minutes driving from Interstate 44, Hwy 63, + Hwy 72.

Indoor spacesKitchenLocation

A comfortable living area is highlighted by a large leather sofa and armchair, complemented by a wooden coffee table. A television is situated on a rustic stand, and natural light fills the space from the windows, creating a welcoming environment.

4.99 out of 5 average rating, 113 reviews

Double B Ranch Guest House

Welcome to the Double B Ranch Guest House. Bordering three sides of Rolla city limits, you’re on the ranch with just a rock throw from town! The calming quietness of country living within steps of our city. Walking distance to Missouri MS&T, 30 minutes from Ft. Leonard Wood. You may enjoy the entire 1600 square foot sparkling clean home that is also handicap accessible. View the meadow from the back deck while watching the wildlife play. A stocked lake is available for fishing!

FamilyKitchenQuiet

A living room area is furnished with a gray sofa and loveseat, accented by decorative pillows. Natural light filters through sheer white curtains, illuminating the patterned area rug. A small table and a wall mirror add to the inviting feel of the space.

4.88 out of 5 average rating, 107 reviews

Peaceful Southbrook

Welcome to Peaceful Southbrook! You will have the entire place to yourself. There is a keypad for entry. Recently remodeled with tasteful decor, a stocked coffee bar and comfy bedding!! There is a nice little area in the back yard with a patio set and a barbecue grill. In the heart of Rolla just a couple miles from Fugitive Beach, MS and T, Fort Leonard Wood, Trout Parks and beautiful Meremec Springs Park. Very close to shopping and restaurants and only about 1 mile off of I-44.

Indoor spacesKitchenLaundry

4.93 out of 5 average rating, 255 reviews

The kitchen features wooden cabinetry with a modern finish, complemented by stainless steel appliances including a refrigerator and microwave. A spacious countertop offers ample preparation space, while a glass dining table is surrounded by white chairs, creating a bright and functional atmosphere.

Apartment in St. James

James Stay at the Old Opera House

Nestled in the heart of the Ozarks, this completely renovated 1900s property has been restored into a charming AirBNB stay. This property is perfect for business travel, couples, and small families. Guests will enjoy their stay at this two bedroom apartment located in Historic St. James, adjacent to Route 66. This property is within walking distance to local favorites including Rich's Famous Burgers, Historic Johnnie’s Bar, and a short drive to Sybil’s for fine dining.

KitchenFamilyTV

4.99 out of 5 average rating, 235 reviews

The cozy bedroom features a large bed with a checkered blanket and natural wood walls. A fan provides airflow, while a window allows soft light to enter. A dark wooden dresser stands nearby, contributing to the rustic charm of the space.

Cabin in St. James

Cedar Cabin-Angler’s Catch

Cedar Cabin w/King Bed, Fully Stocked Kitchen, Washer/Dryer, Walk-In Shower, Ramp Access, 2 Decks, Fire Pit, Grill, Free Parking, and 1.3 miles from Beautiful Maramec Spring Park. A trout fisherman’s catch or a couple’s cozy getaway. Close to several Ozark attractions including Maramec Springs Park, Montauk State Park, Current River, Huzzah River, and more. The cabin also has a love seat twin sofa sleeper and is 5 miles from town. Hope to see you soon 😉

Indoor spacesFamilyParking

Popular amenities for Rolla family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 168 reviews

A modern cabin exterior is shown, featuring warm outdoor lighting and a combination of wood and metal materials. A spacious deck is accessible via steps, while a covered area with a grill and outdoor movie projector is visible on the side. Lush greenery surrounds the property.

Cabin in Leasburg

Luxury Cabin Sleeps 6 w/ Hot Tub and Outdoor Movie

Indoor spacesFamilyBathroom

4.94 out of 5 average rating, 120 reviews

A spacious hot tub is illuminated by soft blue lighting, surrounded by a wooden gazebo. Two wine glasses are placed on the edge, inviting relaxation. A grill is visible in the background, and strands of light fill the area, creating a serene evening ambiance.

Cabin in Owensville

Guest Cabin at R & J Ranch

Indoor spacesKitchenValue

4.98 out of 5 average rating, 298 reviews

Tiny home in Waynesville

Tiny Home with Hot Tub Near Ft. Leonard Wood!

Indoor spacesFamilyAccuracy

The exterior view of the farmhouse highlights a two-story wooden structure with a green metal roof and welcoming entryway. Surrounding landscaping features a pebbled area with decorative elements, and lush greenery includes trees that enhance the tranquil rural setting.

4.98 out of 5 average rating, 131 reviews

Reel-e Rustic Roost

Indoor spacesKitchenWalkability

4.95 out of 5 average rating, 140 reviews

A covered patio area is illuminated by soft twinkle lights, creating a welcoming ambiance for evening gatherings. Comfortable seating and a dining table provide space for relaxation and meals. The surrounding lawns and trees offer a tranquil rural setting.

Cabin in Steelville

Cabin with Private River Access and Hot Tub

KitchenFamilyWalkability

4.99 out of 5 average rating, 228 reviews

The exterior of a rustic cabin showcases a red metal roof and wooden log siding, framed by a spacious yard. Seating is provided by two red chairs arranged on a stone patio, surrounded by manicured bushes and a few trees with autumn foliage in the background.

Cabin in Devils Elbow

Tombstone Cabin with Hot Tub!

Indoor spacesFamilyWalkability

Superhost

A rustic cabin features red exterior walls and a metal roof, situated on a well-manicured lawn. The entrance is framed by bushes, with a covered porch and a small seating area visible on one side. Lush trees provide a natural backdrop.

Cabin in Bourbon

4.76 out of 5 average rating, 371 reviews

Cabin In The Woods 2

FamilyIndoor spacesCheck-in

4.94 out of 5 average rating, 192 reviews

A fire pit area is surrounded by six wooden Adirondack chairs, positioned on a gravel bed. Nearby, colorful flowers add a touch of nature to the landscape, which gently slopes towards a serene body of water reflecting the sky above. Tall trees provide a natural backdrop.

Home in Steelville

Willie Acres: Hot Tub•Pool•Walking Trails

KitchenIndoor spacesLocation

Family- and pet-friendly home rentals

A cozy bedroom features a spacious bed draped with a textured yellow blanket. Natural light filters through sheer white curtains, illuminating a comfortable armchair and a desk with a lamp. A mirror reflects the room's inviting atmosphere, while neatly stacked towels are displayed nearby.

4.98 out of 5 average rating, 112 reviews

Charming 2 bedroom home - The Winchester.

KitchenFamilyBathroom

4.98 out of 5 average rating, 172 reviews

The exterior of the house features a covered carport with space for two vehicles. Lush green grass surrounds the driveway, complemented by a small evergreen shrub. The well-maintained front yard is lined with trees, enhancing the welcoming appearance of the home.

Home in Newburg

Raven House, 3 bedroom, Rolla 5 mi, Ft Wood 22 mi

FamilyKitchenBeach

4.98 out of 5 average rating, 171 reviews

A rustic home built of natural wood is framed by blooming pink trees and lush green grass. The structure features a spacious porch with seating, while large windows allow views into the inviting interior.

Farm stay in Steelville

Yeary Farms Milt's Place with Private Beach!

Indoor spacesKitchenAccess

A modern kitchen features gray cabinetry, a sink with a stylish faucet, and granite countertops. Open shelving displays dishes and glassware above a microwave and coffee maker. A stove and oven are visible on the right, with a towel hanging on the wall, providing convenience for cooking.

4.96 out of 5 average rating, 191 reviews

Route 66 Stay•Fenced Yard• Fire pit & Pet Friendly

FamilyIndoor spacesDecor

4.94 out of 5 average rating, 212 reviews

A single-story home features a light grey exterior and a gabled roof. Two large windows allow natural light, and a small porch is flanked by flower planters. A well-maintained lawn with scattered shrubs and flowers surrounds the house.

Home in Cuba

Cozy Corners

KitchenFamilyHeating

4.95 out of 5 average rating, 216 reviews

A wooden cabin with a metal roof is set on a gravel area, surrounded by trees. A spacious porch features several black chairs arranged for seating. Windows framed in wood allow natural light to fill the interior. The entrance is marked by a simple door.

Cabin in Leasburg

Peaceful Cabin

Indoor spacesKitchenLayout

4.99 out of 5 average rating, 115 reviews

A spacious green lawn spreads across the foreground, bordered by trees. A two-story farmhouse, renovated and modernized, stands to the left, while a red barn is visible to the right, creating a harmonious rural scene under a clear blue sky.

Farm stay in Owensville

Modern Country Farm House with beautiful views

FamilyIndoor spacesHospitality

4.97 out of 5 average rating, 108 reviews

Hideaway B | 2bed 2bath | 1 Car Garage

FamilyKitchenDecor

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 85 reviews

A modern bathroom is shown, featuring a freestanding soaking tub illuminated by a pendant light. A spacious vanity with a marble countertop is visible, along with clean lines and minimalistic design elements. The door slides open to reveal additional space, contributing to a bright, airy atmosphere.

Farm stay in Rolla

Charming King&Queen Studio-Soaking Tub-Farm Views

FamilyKitchenBarbecue

4.87 out of 5 average rating, 23 reviews

Home in Saint Robert

Sista’s Home ‘Suite’ Home

Indoor spacesKitchenHospitality

5.0 out of 5 average rating, 18 reviews

Home in Belle

Family Fun Summer-Gym, Pool, Hot Tub, Playhouse

FamilyKitchenDecor

5.0 out of 5 average rating, 7 reviews

Cabin in Steelville

Cabin 7 on Meramec River

FamilyQuietComfort

Superhost

Home in Licking

5.0 out of 5 average rating, 4 reviews

Perfect Location! 3BR Home Near the Park

Hospitality

Superhost

A cozy living space features a red patterned couch adorned with yellow throw pillows, positioned near a wooden side table. A potted plant sits on the table, while a decorative cabinet stands against the wall. Soft light illuminates the warm hardwood floors.

Cottage in Steelville

4.83 out of 5 average rating, 53 reviews

Cozy 4-Bedroom - Annex to Wildwood Springs Lodge

Indoor spacesFamilyCondition

4.97 out of 5 average rating, 75 reviews

A log cabin is framed by greenery, showcasing a welcoming front porch with an American flag. The cabin is surrounded by lush grass and trees, with a stone chimney visible, indicating a cozy and rustic character in a private wooded setting.

Cabin in Bourbon

Real Log Cabin with Pool or Hot Tub +River Access

Indoor spacesFamilyCleanliness