Family-friendly holiday rentals in Chesterfield

4.94 out of 5 average rating, 342 reviews

A spacious sleeping area features a large bed adorned with plush white pillows. Shelves display vintage cameras and decorative items, while ambient lighting is created by lamps on side tables. The walls are painted a soft blue, adding to the room's calm ambiance.

Tiny home in Pacific

Route 66 Railroad Shanty, a cozy artsy small space

This 536 s.f. house, believed to have once been a sleeping shanty for railroad crews switching shifts for the night. Fully renovated and updated in 2021 by a local artist, you will find custom metal art throughout, granite countertops and a very warm cabin feel featuring a kitchen and bathroom finished with locally sourced Missouri dark red cedar, 10 minutes from six flags, Purina farms 15 min from hidden valley and 45 min from downtown this place is in a great location and will not disappoint!

4.97 out of 5 average rating, 105 reviews

BEAUTIFUL Historic 3 Bedroom Upscale Guesthouse!!

Spacious luxury three bedroom home in historic St. Charles. Minutes away from Main Street, Frenchtown, Streets of St. Charles, shopping, and more. The bright, fully equipped chef's kitchen features a gas range, spacious counters, and upscale appliances for all your dining and entertainment needs. Bedrooms include luxury DreamCloud Mattresses and upscale bedding. Full size washer/dryer, walk in closet, and Roku. Dream bathrooms with soaker tub. Backyard features outdoor relaxation and playhouse.

4.99 out of 5 average rating, 121 reviews

Home in Ballwin

Pet & Child Friendly*Great Location*Ideal 4 Groups

Stay Awhile is more than a place to stay—it’s a memory maker! This spacious St. Louis vacation rental is tucked in a fantastic neighborhood & less than 30 minutes from top St. Louis attractions-like the Zoo & Arch! Designed for families, groups & pets, it offers cozy beds, a well-stocked kitchen & plenty of space for everyone. A one-of-a-kind Eye Spy game is hidden throughout the décor, making the home part of the adventure. Perfect for those who love comfort, convenience & a touch of whimsy.

4.91 out of 5 average rating, 221 reviews

The exterior of the Pacific Palace showcases a unique wooden design with ornate decorations. Brightly colored adirondack chairs invite relaxation on the porch, while a stone pathway leads to the front door beneath a gabled awning. Lush greenery frames the playful architecture.

Home in Pacific

Pacific Palace, super unique!

The Pacific Palace is unlike any other Airbnb! Located in the heart of downtown Pacific, Missouri - only 2 minutes from Highway 44 and 10 minutes from Purina. This house is an incredible one of a kind treasure with lots of unique features including: outdoor gazebo, fish pond, all original cedar interior design, two second story balconies, two large bat tubs (one located in the main bedroom) and so much more!!! Private parking and a gate for added privacy. Just minutes from Six Flags. Book today

The charming front porch features a white wicker chair and a decorative wreath, inviting relaxation. Greenery surrounds the entryway, complemented by a well-maintained lawn. A gravel pathway leads from the porch to the driveway, creating a welcoming entrance to the guest house.

4.97 out of 5 average rating, 732 reviews

301 Guesthouse- Historic Main street-Katy Trail

Our 301 Guest House is new and completely remodeled in 2018! It’s ideal for one or two people with beautiful furnishings, great queen bed, lots of amenities, full kitchen, with big back yard and patio to enjoy outdoors too! Cable and FAST WiFi! Enjoy light Breakfast! BEST location, Great events year round within walking distance, with being only about 2 blocks from S. Main St, where there are about 100 gift shops n restaurants! Katy Trail is so close, with Spring, Summer, Fall and Xmas events!

Apartment in St. Charles Historic District

A modern kitchen area features white cabinetry and a kitchen island with three cushioned stools. Pendant lights hang above the island, illuminating the space. A doorway leads to another room, with a glimpse of additional kitchen appliances visible in the background.

4.93 out of 5 average rating, 412 reviews

Pop Lucks Guest Suite in Historic Old St Charles

Welcome to Pop Luck's Guest Suite! This adorable gem represents everything you love about Old St. Charles. This cozy suite is just steps away from the heart of Main Street, restaurants, and all the action St. Charles has to offer. Pop Luck's is a charming one-bedroom, with an open and airy living room and kitchen. It has natural light and high ceilings throughout. It's farmhouse cottage decor makes for a relaxing place to rest. Also, check out our sister suite The Ella Rose, right next door.

Guest suite in Dardenne Prairie

A treehouse-style rental is nestled among vibrant autumn foliage, with wooden steps leading up to the entrance. The structure features a private front porch, framed by surrounding trees and a gravel path, conveying a natural and serene atmosphere.

4.88 out of 5 average rating, 327 reviews

Treehouse Spa Suite

Treehouse Day Spa is nestled on 3 wooded acres in St.Charles County. There is a subdivision next to me but I have my trees!!! Get away from it all while being close to it all at the same time. Augusta wineries, Main Street St. Charles and the Streets of Cottleville are all within minutes of the location! There are two rental units in the treehouse: The spa suite and the penthouse. They each have a separate entrance and are private spaces. Recharge your battery! Regroup Relax Refresh

Superhost

A grey sectional sofa is positioned next to a circular glass table, creating a comfortable seating area. Natural light floods the space through large glass doors leading to the outside. A potted plant adds greenery, while wall decor spells out 'HOME.'

Home in St. Louis

4.9 out of 5 average rating, 134 reviews

St. Louis Home away from Home!

Our property is the perfect place for anyone looking for a peaceful stay in STL! This 4BR, 2.5 BA house gets amazing natural light throughout the day, and is nearly too cozy! Located 12 minutes from the airport, and near many of STL’s top attractions, our home is sure to leave you feeling refreshed after your stay! We’re a family that is dedicated to ensuring our guests enjoy the best experience possible. As local hosts, you can rest peacefully knowing that we are just a phone call away!

The exterior of a charming century home showcases a covered front porch with white railings and a welcoming entrance. Lush greenery and flower beds line the stone steps leading to the porch, enhancing the inviting character of the property.

4.94 out of 5 average rating, 417 reviews

*HotTub* The Jewel on 5th-2br2b-near Historic Main

A true gem only a 15 min drive from the STL Airport. Enjoy a well equipped, century home a short 12 min walk to Historic Main and a HOTTUB. The large stocked kitchen is great for entertaining. Master bedroom w/luxurious, king sized, 4 poster bed and ensuite bathroom awaits you. In the private, queen suite you’ll find its own bathroom and another door leading onto the deck. The chair off the kitchen folds out to a standard twin and bedding is provided for the sofa as well. Can sleep 6.

A cozy living room features a large gray sectional sofa, complemented by two wooden chairs. Natural light enters through sheer window coverings, illuminating the space. A light-colored rug adds texture underfoot while artwork decorates the walls, enhancing the room's comfortable atmosphere.

4.85 out of 5 average rating, 171 reviews

Family/4bd/2bth/Huge Yard/Playset/Ping-Pong/Arcade

Our freshly updated and furnished house is ready for the family with kids, the adult getaway, and wedding parties from Stone House event venue across the street! Boasting tons of privacy, a huge yard with a playset and games, a fully stocked kitchen with everything you could want for a Thanksgiving dinner, and a large basement with arcade boxes, ping pong, weights, and seating areas. A very safe and secluded location that is close to amazing parks, restaurants, wineries, and shopping.

A well-organized kitchen features dark cabinetry and a light countertop, providing ample workspace. A comfortable couch is positioned in the living area, absorbing natural light from the window. Decorative elements, including a round wall mirror and soft furnishings, add a touch of warmth to the space.

4.91 out of 5 average rating, 104 reviews

Cottage on Main Street- Low Cleaning Fee

MESSAGE FOR SHORT STAY DISCOUNT Stay in the heart of Historic Downtown St. Charles! This beautifully updated 2BR/1BA blends modern comfort with charm just steps from Main Street. Walk to award-winning restaurants, unique boutiques, coffee shops, festivals, and riverfront views. Directly across from the Katy Trail—perfect for biking and morning strolls. Minutes to Ameristar Casino and 12 minutes to STL Airport. Fast Wi-Fi, cozy beds, and easy access to everything. WALK EVERYWHERE!

4.98 out of 5 average rating, 379 reviews

The exterior of a historic log cabin features a welcoming yellow door and a decorated porch with a small table and chairs. Lush greenery surrounds the cabin, while vibrant flowers add a touch of color. The structure is complemented by the clear blue sky.

Cabin in Saint Charles

Camp Mill Pond: Historic Cabin Near Main Street

*St. Louis Magazine A-List Winner!* ***PRESS: DESIGN STL, STL MAG, AND FOX2NEWS*** Camp Mill Pond is a throwback to the slow and easy rhythm of hot summer days. This circa 1835 cabin offers easy access to our historic area, including Main Street, Katy Trail for biking, and Frenchtown, without sacrificing modern comforts! This 180-year-old historic cabin sits on a beautiful lot, shared with our 1865 three-story home and a two-story carriage house. Ask about renting bikes! 🚲

Popular amenities for Chesterfield family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.84 out of 5 average rating, 105 reviews

A comfortable living area is furnished with a dark green leather sofa and patterned chair. A wooden entertainment unit holds a television, while a lamp provides warm light. Natural wood accents are visible in the ceiling and decorative elements, enhancing a cabin-like ambiance.

Home in Wright City

Country home L Level, private, kitchen, hot tub

A wooden deck is surrounded by trees, featuring a Western Red Cedar hot tub and a barrel sauna. The hot tub is positioned next to a wooden bench, with a wooden privacy wall enhancing the cabin's natural setting. A round table and chairs are visible on the deck.

4.97 out of 5 average rating, 115 reviews

Cedar Hot Tub & Cedar Sauna, Chalet at Innsbrook

4.96 out of 5 average rating, 609 reviews

Home in Dittmer

Honeymoon Suite at Camp Skullbone In The Woods

4.9 out of 5 average rating, 116 reviews

A private hot tub is illuminated with soft blue lights, surrounded by a wooden fence. String lights hang overhead, enhancing the evening ambiance. The area offers seating options, creating a cozy space for relaxation.

Cottage in Augusta

Romantic Augusta Cottage-Relax & get away!

4.93 out of 5 average rating, 101 reviews

A well-lit kitchen features grey cabinetry and stainless-steel appliances. A wooden dining table with black stools is positioned centrally, adorned with a vase of sunflowers. Natural light floods in through a large window, providing a view of the outdoor landscape.

Home in Des Peres

Cul De Sac - next to the best shopping in STL

4.95 out of 5 average rating, 131 reviews

A fenced outdoor space features two red Adirondack chairs positioned on a grassy area, creating a cozy spot for relaxation. String lights are visible above, adding a warm ambiance to the backyard.

Home in Marthasville

Katy Haus: Hot tub, Wineries, Fenced yard, Dog-fri

4.97 out of 5 average rating, 350 reviews

A modern studio cabin is elevated on pillars, surrounded by lush greenery. The exterior features dark wood siding and multiple windows, allowing natural light to illuminate the interior. A deck is visible, indicating outdoor space for relaxation.

Farm stay in Grafton

Pere Ridge Tree Escape with private hot tub

4.89 out of 5 average rating, 230 reviews

A living area features a stylish gray sofa and a patterned armchair. A modern console table stands against a textured wall, accented by a wavy light installation. A green plant adds a touch of nature to the space, alongside decorative items on the table.

Tiny home in Alton

Romantic tiny home w/ hot tub

Family- and pet-friendly home rentals

A living area is presented with two blue armchairs positioned beside a small coffee table adorned with a plant and decor items. Natural light filters through sheer curtains, highlighting the wooden floor. A wall-mounted circular decor piece adds a subtle touch to the space.

4.87 out of 5 average rating, 732 reviews

The Benton House - With fenced yard!

4.95 out of 5 average rating, 142 reviews

The exterior of a contemporary single-story house is displayed, featuring a light-colored facade with dark accents. A two-car garage is visible, along with a small front garden. Clear skies and green trees surround the property, suggesting a peaceful residential setting.

Home in O'Fallon

Family friendly 3bd home! Longer stays available

4.94 out of 5 average rating, 1,240 reviews

An artistic space features vibrant murals and wall art, including a striking circular installation illuminated by blue and purple lights. The decor showcases a blend of abstract designs, providing a unique atmosphere. A polished pole stands at the center, complemented by geometric patterns on the wall.

Home in St. Louis

ArtBnB: Enjoy the Curated Comforts of Home

A light-filled seating area is showcased, featuring a soft gray sofa adorned with several pillows. In front, a glass-topped coffee table rests on a textured area rug. A decorative cabinet with shelves creates a focal point, highlighted by ambient lighting.

4.83 out of 5 average rating, 169 reviews

Main Street Hideaway

Home in Tower Grove South

A wooden bookshelf is filled with an assortment of dog-themed figurines and decorations, arranged alongside a framed portrait of a dog. Pink wallpaper with a dog print serves as the backdrop, while small lace doilies add a decorative touch. A collection of DVDs is neatly displayed below.

4.96 out of 5 average rating, 178 reviews

Granny's DOG House - KING BED - One of a Kind!

4.91 out of 5 average rating, 166 reviews

A living area is arranged with a light beige couch and two dark blue armchairs. A small table with a lamp is positioned nearby. The space features natural light filtering through sheer curtains, and artwork adorns the walls, adding a touch of color.

Home in Wentzville

The Ladybug Inn

4.83 out of 5 average rating, 148 reviews

Home in St. Louis

Spacious Home - Heated Pool Open - Amenity Packed

4.95 out of 5 average rating, 111 reviews

The living room features a sectional sofa in a soothing blue hue, accompanied by decorative pillows. A round coffee table sits at the center, surrounded by a vibrant area rug. Artworks adorn the wall, and a desk with a chair is positioned near a window.

Home in Dogtown

Paw-some Retreat: Fenced Yard, Near Hospitals, W/D

Family-friendly home rentals with a pool

Superhost

5 out of 5 average rating, 3 reviews

T | Pool · Hot Tub · Arcade · 4BR Luxury Retreat

4.96 out of 5 average rating, 205 reviews

A spacious hot tub is positioned on a wooden deck, featuring bubbling water and ergonomic seating. The surrounding fence offers privacy, while the brick wall of the house is visible in the background. A cover is partially closed above the hot tub.

Guesthouse in Lebanon

Pool, Hot Tub and Dog Paradise

4.95 out of 5 average rating, 56 reviews

Place to stay in Pacific

First floor pet friendly family suite near Purina

An open living space is highlighted by vaulted wooden ceilings and large windows allowing natural light to flood in. A stone fireplace acts as a focal point, complemented by modern furniture. A staircase leads to a loft area, while polished wooden flooring adds warmth.

4.98 out of 5 average rating, 138 reviews

Early Check-in, Late Check-out on Weekends 8AM-8PM

A deck area is visible, featuring a wooden table with two glasses of wine and a candle. Lounge chairs in shades of blue are positioned nearby, while large windows reveal the interior space of the chalet surrounded by trees.

4.93 out of 5 average rating, 168 reviews

Peaceful Lakefront Chalet w/Dock and Boats!

4.99 out of 5 average rating, 164 reviews

Pura Vida Chalet - Lakefront on Lake St. Gallen

5 out of 5 average rating, 30 reviews

The outdoor pool area features a serene pool surrounded by a spacious deck. Lounge chairs are positioned around the pool, and a large umbrella provides shade over seating areas. Lush greenery borders the space, creating a peaceful atmosphere.

Home in Augusta

"The Villa" at Villa Augusta in MO wine country