Family-friendly vacation rentals in Chesterfield

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, 707 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!

4.97 out of 5 average rating, 241 reviews

A comfortable living area features a gray sofa, patterned chairs, and a round coffee table on a natural fiber rug. Light streams through sheer curtains, highlighting the artwork of bicycles on the wall, creating a relaxed setting for guests.

Home in Kirkwood

A Kirkwood Cottage, Quaint Suburb of St Louis

Quaint cozy cottage on a “No Thru Street”. The best place to stay in Kirkwood.This was my childhood home. Only 1/2 mile to downtown Historic Kirkwood with its many shops & restaurants,Farmers Market, Kirkwood Park & Pool & Train Depot. A couple of miles to Museum of Transport,Powder Valley Nature Center & Magic House Museum is a MUST if you have children. Home has steps to entry & is 4th house from railroad tracks that are up on the hill at end of street.Close easy access to all major highways

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, 368 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!

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.

4.94 out of 5 average rating, 400 reviews

Charming Pop Lucks Guest Suite in 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, 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

Bungalow in St. Charles Historic District

A well-appointed bedroom is featured, with a spacious bed adorned with soft linens and a decorative accent pillow. Two bedside lamps are positioned on either side, providing additional lighting. A window allows natural light to filter in, while a wall-mounted air conditioning unit enhances comfort.

4.97 out of 5 average rating, 259 reviews

Patio House, secluded in heartbeat of Main Street

The Patio is nestled in the heart of historic St. Charles a few steps from Main Street, Katy Trail, Missouri River, Antique and Boutique Shopping, Restaurants Bars and More, Several Wedding venues are within walking distance of the property as well. In addition to your well appointed unit, this property has as much outside as it does in. Take your coffee, wine, water and enjoy our patio, complete with fire table, dining table edged with lush plantings for privacy. PLEASE NOTE NO SMOKING

4.99 out of 5 average rating, 220 reviews

Charming Bungalow in Historic St. Charles, MO

This charming bungalow is located in the heart of Historic St. Charles, Missouri. Just blocks from Historic Main Street where you can enjoy dining & shopping from a variety of local businesses, as well as Frontier Park & the Katy Trail which are perfect for a stroll or bike ride! The bungalow is steps away from Lindenwood University, a short drive to Streets of St. Charles & Ameristar Casino, a 15 minute drive to St. Louis Lambert Airport, and a 30 minute drive to 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, 397 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, 156 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.

4.95 out of 5 average rating, 182 reviews

Home in Villa Ridge

Serenity Valley (No Cleaning Fee- No pets please)

Discover Serenity in this 675 sq ft Studio cottage on a private wooded lot. Cozy space with 1 queen bed & optional inflatable queen bed for up to 4 guests. Relax on the patio, enjoy a bubble bath in the vintage clawfoot tub, or take in the panoramic woods view on the couch. Amenities include WIFI, washer/dryer, fully stocked kitchen, pack&play. Just 60 mins from downtown STL, 15 mins from Washington, 20 minutes from Six Flags. Your tranquil escape awaits! No pets allowed.

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, 194 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

Superhost

An inviting outdoor space is showcased, featuring a wooden deck with a dining area, lounge chairs, and a hot tub. String lights create a warm ambiance, while a fire pit adds a cozy element to the setting. The surrounding fence ensures privacy.

Bungalow in Carondelet

4.83 out of 5 average rating, 607 reviews

“HOT TUB” Oasis in the heart of the city!

Guest suite in Wright City

A comfortable leather futon is positioned in the living area, complemented by a wooden coffee table with storage. Decorative pillows add a touch of charm, while a wall clock and bicycle artwork provide visual interest. Warm lighting enhances the inviting atmosphere.

4.83 out of 5 average rating, 132 reviews

Private Suite w/ Washer & Dryer

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, 107 reviews

Cedar Hot Tub & Cedar Sauna, Chalet at Innsbrook

4.96 out of 5 average rating, 134 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, 108 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

Family- and pet-friendly home rentals

Bungalow in Saint Charles

4.85 out of 5 average rating, 317 reviews

Historic Bungalow

Apartment in North Hampton

The living room features a cozy arrangement with a dark gray sectional couch adorned with cushions and a throw blanket. A wooden console table holds a table lamp, while natural light filters in through large windows, illuminating the textured area rug and simple decor.

5 out of 5 average rating, 250 reviews

Centrally Located Mid-Century Modern Retreat

4.94 out of 5 average rating, 1,210 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

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, 162 reviews

Main Street Hideaway

4.97 out of 5 average rating, 118 reviews

An open floor plan features a comfortable grey couch adorned with patterned throw pillows. A spacious kitchen showcases dark cabinetry and stainless-steel appliances, while a rustic wooden dining table accommodates six. Natural light fills the area, highlighting the modern decor and wooden beams.

Home in St. Peters

Family Friendly Home Near Parks and Dining

4.94 out of 5 average rating, 327 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

4.91 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!

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

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 37 reviews

A serene outdoor area features a solar-heated salt-water pool, flanked by two lounge chairs and vibrant red seating. Surrounding greenery enhances the natural setting, with large windows revealing the interior space. The patio is designed for relaxation and enjoyment of the tranquil environment.

Home in Union

Willow Creek: Mid-Century Oasis

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

Superhost

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)

Superhost

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.