
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.

The Ella Rose Guest Suite ~Historic Old St Charles
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

The Luxury Lodge in St. Charles
The Luxury Lodge is a Private Residence at Rear of Property with Private Keypad Door Entrance, Private Parking, Outdoor Deck, Dog Run Line and 1/2 acre Fenced Backyard. Kick back & relax in this serene, spotlessly clean, stylish luxury & country living in St. Charles, MO w/ Great Scenic View. Dog friendly, comfy Queen Size Bed, Love Seat, Queen Sleeper Sofa, Large Stone Fireplace, Huge Bathroom, Rain Shower, Private Powder Room, Large Screen TV, Cable & Streaming, Kitchenette, Fridge & Dresser.

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!

Historic Victorian comfort, great area
First, check out all 4 of our private 5 Star listings that creatively combines the old with the new. If one is unavailable, check the others by going to “My Profile” and scrolling down until you see all 4. This Historic building; built in 1896 has changed missions through the years; From church, to merc. Trade, to grocery store; quite the history have graced these walls. You’ll love our safe, Southwest Gardens area; next to the famous “Hill” offers unmatched restaurant, shops, bakeries

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.

*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.

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

Ravishing 1-Bedroom Apartment with Street Parking
Beautiful unit in St.Louis Hills. The apartment is spacious, when you walk in the living room opens up to the dining room and kitchen. The unit is beautifully furnished and has a modern style with all the amenities you could ask for. The building is centrally located, Francis Park is within walking distance. Downtown is about a 10/15 minute drive. Food places in area include Salt and Smoke, Donut Drive In, Mom's Deli, Legrands, Rockwell Beer Garden in Francis park and much more.

Sunset Mountain Forest Privacy
Nowhere else will you find a jacuzzi tub, private pool with an amazing view, gas fireplace, 3 bedrooms and 2 full bathrooms on the main floor with private entrance, spacious living room, kitchen, and covered deck, plus free laundry for this price! Host stays in separated lower level and the only places shared are the laundry room and outdoors. Great for dog owners attending Purina Farms, 3 individuals, 3 couples, or a couple and 2-5 kids. Great for weekend getaways!
Popular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

Private Suite w/ Washer & Dryer

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

Private Oasis w/hot tub

Roomy Oasis with hot tub on the Hill!

The St. Louis Jewel Box- Backyard W/ Hot Tub!

The House Next Door

Pere Ridge Tree Escape

Blair's House in St. Charles - Game Room - Hot Tub
Family- and pet-friendly home rentals

Sunny Modern Farmhouse - Pet Friendly Purina Farms

Deluxe Barndominium | King bed + Pkg

The Little House.

New: Cozy Cottage Near The Hill

Route 66 Railroad Shanty, a cozy artsy small space

The Ladybug Inn

Spacious Family Home w/ Pool & Amazing Spaces

KingBed Comfort-Prime Location Near CreveCoeurLake
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

Peaceful Lakefront Chalet w/Dock and Boats!

Pura Vida Chalet - Lakefront on Lake St. Gallen

Innsbrook Luxe Escape (5 bedrooms)

Entire home! Sleeps 8, Pool, Hot tub, Lake, 52 AC
Quick stats about vacation rentals that are family-friendly in Chesterfield
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ110 before taxes and fees
Total number of reviews
60 reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Destinations to explore
- Chicago Vacation rentals
- Nashville Vacation rentals
- Downtown Chicago Vacation rentals
- Indianapolis Vacation rentals
- St. Louis Vacation rentals
- Branson Vacation rentals
- Louisville Vacation rentals
- Harpeth River Vacation rentals
- Platteville Vacation rentals
- Kansas City Vacation rentals
- Southern Indiana Vacation rentals
- Lake of the Ozarks Vacation rentals
- Busch Stadium
- Six Flags St. Louis
- Central West End
- 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
- Cathedral Basilica of Saint Louis
- Grafton Winery the Vineyards
- Norwood Hills Country Club
- Raging Rivers WaterPark
- Saint Louis Science Center
- Adventure Valley Zipline Tours and Paintball Park
- Bellerive Country Club
- Missouri History Museum
- Boone Valley Golf Club
- Old Warson Country Club