Family-friendly holiday rentals in Springfield

4.97 out of 5 average rating, 236 reviews

A charming log cabin is embraced by lush greenery, with a welcoming front porch featuring wooden steps. A gravel driveway leads to the cabin, framed by soft, grassy areas dotted with colorful flowers and trees, creating a peaceful natural setting.

Cottage in Ash Grove

Stonecrest Cottage - Country Farmhouse Style

Experience Ozark country life just minutes from a city. Explore our 1/4-mile wooded trail. Look for deer, wild turkey, and a variety of songbirds. Sit around the fire pit admiring a canopy of stars. Take advantage of the picnic and play area adjacent to the cottage. Fall asleep listening to the echo of a distant train whistle. Stonecrest Cottage was built in 2020 on 5 picturesque acres with AirBNB guests in mind. Come and experience this serene setting surrounded by Missouri Conservation Land.

Earthen home in Springfield

A modern underground home features a unique architectural design, with sloped green roofs and large windows. An outdoor area is seen with a circular arrangement of wooden stumps surrounding a fire pit and a dining table set for six, all against a backdrop of lush greenery.

4.92 out of 5 average rating, 111 reviews

Unique 'Earthouse' Retreat w/ Spring-Fed Creek

Enjoy living at its finest with an unforgettable stay at this modern underground 3-bed, 3-bath home! Earthouse offers unique architectural design providing guests with an open inviting interior complete with high-end furnishings, modern decor, and abundant natural light. Whether you're exploring Springfield, visiting local colleges, making your way to Branson for the day, or getting away, this luxurious, one-of-a-kind abode will be your ideal home base! NO PARTIES, EVENTS, OR LARGE GATHERINGS.

4.99 out of 5 average rating, 113 reviews

*Hot Tub Retreat • Fire Pit • Arcade + Peloton Gym

Escape to your private Springfield retreat. Unwind in the hot tub beneath glowing string lights, gather around the fire pit for drinks and s’mores, or relax in the cozy living room with a classic arcade game. Start mornings with fresh espresso from the Breville coffee bar, then recharge in the Peloton fitness studio. Perfect for couples, friends, and weekend getaways—just a short drive to Branson and local attractions! 14 min MSU 15 min Downtown 9 min Airport 15 min 3 Hospitals 13min Bass Pro

Loft in Downtown Springfield

An open living area features a charcoal sectional sofa arranged around a circular wooden coffee table. A flat-screen television is mounted on the exposed brick wall, and a sleek kitchen area with modern bar seating is visible in the background.

4.87 out of 5 average rating, 196 reviews

Beautiful historic Loft

Come stay with us in this beautifully restored historic loft with upscale amenities. Located in the heart of Downtown Springfield. This luxury loft was once a historic building dating back to 1920’s and still boasts the exposed brick and original hardwood floors. This loft will sleep 4 with a king bed, futon, and pull out couch. There is one bathroom and a wash room with washer and dryer. The loft is Walking distance from fine dining, breweries, night clubs, coffee shops, and so much more!

A cozy living area is highlighted by a comfortable brown leather sofa adorned with soft throw pillows. Natural light filters through sheer curtains, illuminating a neutral area rug. A small dining table and chairs are positioned nearby, while a framed artwork adds a decorative touch to the wall.

4.96 out of 5 average rating, 219 reviews

The Kickapoo Cottage - Close to JQH & Mercy

*Bike or electric scooter available upon request for longer stays!* Loads of natural light pours into this wonderful little space. Small, but very cozy and in the heart of Springfield! Enjoy a Tempur-Pedic queen mattress, twin trundle daybed, fully stocked kitchen & outdoor fire-pit. Less than a mile to JQH Arena and Missouri State. Walking distance (0.4 miles) to the charming Pickwick Place Historic District including Tie & Timber Beer Co, Tea Bar and Bites, and Cherry Picker coffee!

4.9 out of 5 average rating, 213 reviews

A modern container unit is set within a lush outdoor space, surrounded by trees. The covered patio features a stone seating area with a table and chairs, complemented by a wooden deck. Large glass doors offer a view into the interior, inviting natural light.

Tiny home in Springfield

Modern Glamping Container Close To Springfield

Create a new fun getaway experience in the air conditioned modern converted container on 3 private acres just minutes from food, shopping, and the Wilson’s Creek civil war battlefield. Enjoy the sunset views from the covered porch or curl up next to a fire under a blanket while you taste our gourmet s’mores options. The Greenway trail is an easy walk or rent our bikes for a fun ride on the Ozark trail. The unit has a private bath house with a shower and compost toilet. King bed.

The charming exterior of the cottage is framed by vibrant seasonal blooms and well-maintained greenery. A yellow front door adds a pop of color, while a brick chimney rises against a backdrop of lush trees. The inviting pathway leads to the entrance, enhancing the home's curb appeal.

4.98 out of 5 average rating, 329 reviews

Yellow Door Cottage, Quiet St., Near Downtown/MSU

Welcome to our 1931 Bissman yellow door cottage close to downtown, cafes and local micro-brewery just 1 block away. Theaters, restaurants, galleries and nightlife very close. Enjoy a cozy vintage charm and the location can't be beat. The house has been lovingly maintained and boasts many original details- featured as Home of the Week In Springfield paper. It has easy access to MSU, Drury, Evangel, Hammond’s Cardinals baseball field, WOW, Bass Pro, Mercy, hwy access and the mall.

Loft in Downtown Springfield

An open-concept living space features exposed brick walls and wooden beams. A spiral staircase leads to the upper level. The kitchen showcases stainless steel appliances, while a large couch occupies the lounging area, inviting relaxation. Ample natural light floods through the large windows.

4.94 out of 5 average rating, 810 reviews

WestBrick Luxury Loft

A gem in the heart of downtown Springfield. Designed by award winning architect Matthew Hufft. Conveniently located on McDaniel Street directly across from the parking garage, this rental is walking distance from all that downtown Springfield has to offer. Superior finishes include: granite counters, exposed brick walls, exposed beam ceiling, stainless steel commercial grade appliances with 6 burner gas range and wine fridge, marble mosaic floors and glass shower.

Guest house in Springfield

A spacious sleeping area features a queen-size bed with soft linens and several decorative pillows. Light walls are complemented by warm brown accents. A wardrobe and a small basket are positioned nearby, with a soft glow from recessed lighting enhancing the cozy atmosphere.

4.93 out of 5 average rating, 371 reviews

Dry Creek Cottage | Fire Pit · Wooded Views

Some places make you forget what day it is. Dry Creek Cottage is one of them. Tucked into a quiet neighborhood just outside Springfield, this private guesthouse backs up to a wooded dry creek, and the moment you step onto the back patio, the pace of everyday life just falls away. Whether you're here for a work trip, in town visiting an MSU student, ready to unplug, reconnect, or just finally slow down, Dry Creek Cottage is ready for you. We'd love to have you.

4.96 out of 5 average rating, 1,052 reviews

The stone exterior of the home is highlighted by lush greenery and mature trees surrounding the property. A well-maintained lawn extends in front, with colorful plants at the entrance. The inviting facade features a central door flanked by smaller windows.

Cottage in Springfield

Historic Fieldstone Cottage on Weller

NO CLEANING FEE! This architectural Bissman home is nestled in an iconic, older neighborhood and is within a SHORT WALK to Starbucks and Cherry Street Corridor with restaurants, bars, tea room and coffee house.Just come for a night through town, a cozy destination get-away or an extended stay! Close to Downtown, MSU, flea markets, Route 66, Cardinals stadium, WOW museum, Mercy Hospital, and EXPO.Fast QUANTUM FIBER Internet, DISNEY+and smart TV in master bedroom

4.98 out of 5 average rating, 313 reviews

A modern cabin features a wooden deck with a railing, set against a backdrop of trees. A six-seater UTV is parked in front, showcasing its utility for outdoor activities. The exterior is designed with a combination of dark wood and large windows, enhancing natural light.

Cabin in Strafford

River Cabin/UTV/Trails/Kayaks/HotTub/OutD Shower

The James River Cabin is a luxurious secluded cabin nestled among the trees on 90 acres of river front property. It is just 10 short miles from Springfield, MO (Buc-ee’s and Bass Pro) less than an hour from Branson, MO. On-site activities are numerous and include bicycling, trail hiking, utv trail riding, kayaking, fishing, hot tubbing, and swimming in your own personal paradise. The river access is a short but fun two minute utv drive from the cabin.