
Family-friendly vacation rentals in Chesterfield
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chesterfield
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Sunny South City Guest House
Newly-rehabbed & cozy guest house. Everything you need is located here in the historic Bevo Mill neighborhood. In the heart of south St. Louis city, you’re steps away from local businesses, including the picturesque, historical Das Bevo. Step into a vintage-styled oasis, featuring large windows with plenty of natural light, tall vaulted ceilings, comfy queen bed, unique fridge, breakfast bar, sizable bathroom with a large walk-in shower. Hang outside at the picnic table under cute string lights.

Christmas Getaway ~ Old St Charles, Missouri
Welcome to The Ella Rose 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. The Ella Rose 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. Come sit and listen to the music of our outdoor bubbler rock.

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

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!

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.

Home Suite Home
A NEIGHBORHOOD home with a small town vibe. NO PARTIES tolerated!!!!! OPEN ALL PHOTOS TO READ PHOTO DETAILS. A PRIVATE BASEMENT SUITE with: PRIVATE Entry, Living Room, Bedroom, Full Bath, Kitchenette, Yard/Patio; walk to Historic Route 66, restaurants, coffee shops, shopping, churches, parks/playgrounds/trails; 10-20 minutes from Lambert Airport, Downtown STL, historic neighborhoods, and major attractions; and major US Highways. *SEARCH from 3915 Watson Rd, 63109 for travel distances.

Sparkling Vintage Charmer, King Bed, Quiet Comfort
The Fairview is a vintage modern 2BR home in desirable North Hampton (south StL city). We've taken special care to offer a unique, memorable experience while providing the convenient, clean comfort you expect in an overnight stay. You'll have easy access to two major highways which means most StL attractions will be minutes away. (The drive to Barnes Hospital is less than 10 min.) The Fairview is nearby restaurants, coffee shops and shopping––it's the perfect place to live like a local!

Entire lower level of our home w/Paris Theme
Our home is located in a quiet West St. Louis County neighborhood. The lower/walkout of this place is your home away from home. It has a private entrance from a walk around sidewalk to the backyard. You will have the entire lower level of our home. We live in the upstairs or first floor of this home. Our place is best suited for one couple, solo adventurers, business travelers, and one family (with kids). This space has been recently remodeled with a French Parisian theme!

Large Fenced Yard & Deck-Cozy Fam Friendly Home
**FAMILY FRIENDLY** (See details for the items avail for families) This 2 bedroom home has everything you need for a relaxing trip! Fully updated with stylish and comfortable furniture and decor. Fully equipped kitchen and an amazing backyard/deck. Quiet street by one of the best Mexican restaurants in St. Louis - Hacienda - (can walk 2 min there) Close to everything! 13 minutes to the St. Louis Zoo 10 minutes to The Magic House 15 minutes to Busch Stadium & Union Station

Lady Asha Yurt/Treehouse!
Hummingbird Hollow Outdoors Lady Asha Yurt/Treehouse. Experience an authentic, rustic and secluded glamping experience on a beautiful Farm Animal Sanctuary with horses, donkeys, sheep, goats and potbellied pigs grazing beneath you, a true animal lover's heaven on earth. There is an comfortably sized and uniquely designed bell tent on an elevated platform nestled in the trees. Cozy futon beds with linens, and multiple cooking options for convenient camping fun.

Route 66 Cozy Cottage
* Fast Wifi (Spectrum) * Keypad entry (no keys to keep track of) * Private driveway by the front door for easy access to carry luggage in and out * Huge yard for dogs, kids or even adults to play * Lovely outdoor patio with plenty of comfortable seating and beautiful landscaping * For the kiddos- toys, books, and games (puzzles and games for adults too) * Essentials for your furbabies as well - treats, leashes, food & water bowls, waste bags, towels

Treehouse Spa Suite
Treehouse Day Spa is nestled on 3 wooded acres in St.Charles County. 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
Popular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

Pet friendly second floor duplex with large yard

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

Private Suite w/ Washer & Dryer

☆ Hot Tub ☆ New Renovated ☆ Massage Shower ☆Yard☆

Roomy Oasis with hot tub on the Hill!

Secluded Lakeside Lodge Minutes from St. Louis

Innsbrook Luxe Escape (5 bedrooms)

The House Next Door
Family- and pet-friendly home rentals

Forest Edge Tiny House | 8 Min to Airport

Historic Bungalow

ArtBnB: Enjoy the Curated Comforts of Home

New: Cozy Cottage Near The Hill

The Ladybug Inn

Beautiful Cottage on Large Private Lot

Pet & Child Friendly*Great Location*Ideal 4 Groups

Elegant apt w king bed! walk to brewery & eats!
Family-friendly home rentals with a pool

Private indoor pool & sauna

Clark Brick House w/ Pool | Historic St. Charles

Welcoming Downtown West Suite- King w/ Patio (223)

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

Spacious Family Home w/ Pool & Amazing Spaces

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

Entire home! Sleeps 8, Pool, Hot tub, Lake, 52 AC

Heated Saltwater Pool+Hot Tub! Great location!
Quick stats about vacation rentals that are family-friendly in Chesterfield

Total vacation rentals
Explore 20 vacation rentals in Chesterfield

Nightly prices starting at
Chesterfield vacation rentals start at € 26 per night before taxes and fees

Verified guest reviews
Over 60 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Chesterfield vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chesterfield rentals

4.6 Average rating
Chesterfield stays receive an average rating of 4.6 out of 5 from guests
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- Six Flags St. Louis
- Central West End
- Busch Stadium
- Saint Louis Zoo
- Enterprise Center
- City Museum
- Missouri Botanical Garden
- Cuivre River State Park
- St. Louis Aquarium at Union Station
- Pere Marquette State Park
- Meramec State Park
- Castlewood State Park
- The Winery at Aerie's Resort
- Hidden Valley Ski Resort
- Grafton Winery the Vineyards
- Cathedral Basilica of Saint Louis
- Norwood Hills Country Club
- Raging Rivers WaterPark
- Saint Louis Science Center
- Bellerive Country Club
- St. Louis Country Club
- Adventure Valley Zipline Tours and Paintball Park
- Missouri History Museum
- Old Warson Country Club