Family-friendly holiday rentals in Chesterfield

4.94 out of 5 average rating, 109 reviews

A comfortable living room features a sectional couch, light hardwood flooring, and a patterned area rug. A flat-screen TV is mounted above a brick fireplace. Natural light enters through windows adorned with light curtains, while a dining area with chairs is visible in the background.

Home in Wentzville

Cozy Home in Wentzville Sleeps 6 + Game Room

Welcome to your home away from home in Wentzville, Missouri! Families and furry friends are welcome to our cozy, centrally located home. Sleeps 6- 1 King , 1 Queen, and 1 Sleeper Sofa Full sized bed Fully equipped Kitchen with everything you need to create a delicious meal, or a cup of coffee Game room and Laundry located in the basement- 60 game free play arcade machine and foosball! Roku friendly TV located in both bedrooms, living room and on the Patio Fully Fenced Yard with Fire Pit

4.99 out of 5 average rating, 113 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, 209 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, 704 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!

4.99 out of 5 average rating, 132 reviews

A log cabin with a dark metal roof is featured, accompanied by a covered porch area containing two chairs. Surrounding landscaping includes a well-maintained lawn and decorative stones, providing a natural setting that complements the cabin's rustic design.

Cabin in Pacific

Catch The Dream:; An Immersive Equestrian Escape

Welcome to the most serene and immersive equine retreat in the area! We are so happy you decided to stay with us. We want you to feel relaxed and at home as you enjoy the equine activities as well as the cozy log cabin and all its features and amenities! Enjoy views of the lush property and relax as you watch the horses graze and roam. We offer customized horsemanship opportunities that accommodate each person's level of comfort and ability. Cost: $75 for two hours, maximum of two lessons/day

4.98 out of 5 average rating, 366 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 and a golf cart!

4.99 out of 5 average rating, 195 reviews

A view from the living area into the bedroom, showcasing a serene space with a queen-size bed dressed in crisp white linens and accented by earthy throw pillows. Natural light illuminates the room, complemented by a ceiling fan and light-toned wooden flooring.

Flat in North Hampton

The Zen Den - Centrally Located, Calm and Tranquil

The Zen Den was conceptualized out of a desire to create a calm and peaceful oasis centrally located in the North Hampton neighborhood of St. Louis where parks, cafés, restaurants, and entertainment are only minutes away. The space features modern appliances, contrasted with soft light features and natural building materials, such as reclaimed lumber, to convey a sense of calm and tranquility. Ideal for those guests seeking to retreat at the end of a busy day exploring or remote working.

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, 316 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

The living room showcases a blend of seating options, including a black futon and a brown leather sofa, complemented by a colorful area rug. Natural light filters through patterned curtains, illuminating the space which features a television and decorative touches.

4.95 out of 5 average rating, 131 reviews

Cozy Mid-Century Modern Townhome

This comfy 2 bedroom, 1.5 bath townhome is perfect for up to 5 guests. Luxury King bed in bedroom 1 and luxury Queen bed in bedroom 2. A futon in the living room can be used for a 5th guest. A pack-n-play is available upon request. This dynamic location is 5 minutes from bars, restaurants, shopping, Lindenwood University, and Ameristar Casino. It's only 2 miles from St. Charles, historic, Main Street, and it's only 15 minutes from the airport, and about 30 minutes from downtown St. Louis.

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, 394 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, 155 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.

The exterior of the house features a well-maintained lawn with shrubbery and a covered porch. A cozy seating area with a modern coffee table is shown, complemented by a sectional sofa. A well-equipped kitchen with appliances and a dining table set for six are also visible. A serene bedroom showcases a spacious bed with soft linens.

4.99 out of 5 average rating, 193 reviews

Little House By Main St -5 4K TV's- 1-75 Inch -1GB

Little House By Main St -5 4K TV's- 1-75 Inch -1GB Internet- No location has better access to so much. All the best amenities on both sides of Main Street St Charles! Walking distance from the Ameristar Casino, Texas Road House, Main Street (Honky Tonk, Big A's, Q, Thirstys), Starbucks, Taco Bell, Buffalo Wild Wings, McDonald's and the Bars / Restaurants on Main. An Awesome Location for all of the Festivals in St Charles! And secured parking in the 1 car garage!

Popular amenities for Chesterfield family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 102 reviews

Home in North Hampton

Spacious home with entertainment room and 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.

4.96 out of 5 average rating, 105 reviews

Cedar Hot Tub & Cedar Sauna, Chalet at Innsbrook

4.96 out of 5 average rating, 580 reviews

The exterior of a chalet is illuminated at night by warm string lights. Large windows reflect soft interior light, revealing a cozy atmosphere. The wooden deck is accessed by a railing, creating a welcoming entry. Trees are visible in the background, adding natural charm.

Home in Dittmer

Honeymoon Suite at Camp Skullbone In The Woods

4.96 out of 5 average rating, 133 reviews

A well-lit bedroom features a spacious bed with soft bedding and decorative pillows. Two nightstands flank the bed, each with a lamp. A stylish rug lies beneath the bed, and artwork adorns the wall. Natural light filters in through the window, covered by navy curtains.

Home in The Hill

Roomy Oasis with hot tub on the Hill!

4.89 out of 5 average rating, 106 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!

4.95 out of 5 average rating, 135 reviews

A serene lake scene is presented, reflecting vibrant colors of a sunset. Trees line the shore, silhouetted against the sky, while their shapes are mirrored in the still water, creating a peaceful ambiance.

Cottage in Millstadt

Secluded Lakeside Lodge Minutes from St. Louis

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

Cozy winter ranch on wooded land near shopping

4.88 out of 5 average rating, 216 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

4.87 out of 5 average rating, 1,013 reviews

The exterior of the house is shown, featuring a white facade with black shutters. A bright yellow door serves as a focal point, complemented by two windows on either side. The sloped roof adds character to the two-story structure.

Home in Holly Hills

The Little House.

4.94 out of 5 average rating, 1,206 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 McKinley Heights

ArtBnB: Enjoy the Curated Comforts of Home

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, 165 reviews

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

4.92 out of 5 average rating, 145 reviews

A spacious bathroom features a freestanding bathtub surrounded by natural stone walls. A walk-in shower with a glass panel is visible alongside a modern sink. Warm lighting hangs above, and a potted plant adds a touch of greenery, enhancing the serene atmosphere.

Home in University City

Tranquil three-bedroom home in central St. Louis

4.99 out of 5 average rating, 152 reviews

A light-filled living room features a comfortable sofa adorned with decorative pillows, complemented by two yellow accent chairs. A glass coffee table sits atop a textured rug, with natural light entering through windows dressed with blinds. The open layout leads to a dining area in the background.

Home in Dogtown

Dogtown Century home near Forest Park & Maplewood

4.9 out of 5 average rating, 142 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

4.94 out of 5 average rating, 325 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

4.96 out of 5 average rating, 108 reviews

Home in O'Fallon

Family friendly 4bd home! Longer stays available!

Family-friendly home rentals with a pool

A patio area features a small in-ground pool with gentle water features. Surrounding the pool are wooden lounge chairs and a table set that invite relaxation. Lush greenery and potted plants enhance the outdoor space, while a large umbrella offers shade.

4.93 out of 5 average rating, 164 reviews

Clark Brick House w/ Pool | Historic St. Charles

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, 135 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, 167 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

4.88 out of 5 average rating, 202 reviews

Home in Gray Summit

Sunset Mountain Forest Privacy

4.99 out of 5 average rating, 136 reviews

A spacious living area features high ceilings and large windows, allowing natural light to fill the room. Comfortable seating is arranged around a central coffee table, with a dining table present in the background. The wooden floor complements the soft blue walls and decorative accents.

Home in Innsbrook

Innsbrook Luxe Escape (5 bedrooms)

4.98 out of 5 average rating, 128 reviews

An outdoor seating area features red Adirondack chairs set on a gravel surface, framed by trees. Soft glowing string lights are suspended above, illuminating the serene lakefront view, where lush greenery reflects on the calm water.

Chalet in Wright City

Peaceful chalet - *new* private beach, WIFI, kayak

The exterior of an A-frame cabin features large glass windows and an expansive wooden deck surrounded by lush greenery. Multiple seating areas are visible on the deck, providing space for relaxation. The architectural design highlights sharp angles and natural elements.