
Family-friendly holiday 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.

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!

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

Christmas Getaway 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.

Groovy in the Grove 5 min to SSM
Welcome to Groovy in the Grove - your hip 1 bedroom hideaway with a parking pad in vibrant St. Louis! Situated a mere 5 minutes from SSM Hospital, this retro retreat combines '60s flair with modern comfort. Dive into the spirited local scene brimming with eclectic eateries, quirky shops, and electric nightlife. Your colorful getaway stands as a nostalgic haven in the heartbeat of the Grove, promising a unique and unforgettable stay. Let the groove get in and discover the charm of St. Louis!

Historic loft living. Safe, central neighborhood
FULLY FURNISHED, cozy private studio apartment on the 3rd FL in the Southwest Gardens neighborhood next to the famous "Hill" area of South St. Louis. This elephant themed unit is walking distance from dozens of the best restaurants the area has to offer. Queen bed and love seat/fold out portable sleeps 3. *****we have 3 other private 5-star listings with the same amenities within our building. Go to my profile and scroll down to see them. We would love to host you in any of them.

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.

Bright & Cozy Shotgun DPX 1 Block from Historic DT
Admire this unique historic home's design with brand new amenities and antique details that give a fresh and charming feel. Built in the late 1800's, this half of the duplex has a typical shotgun layout with ten-foot ceilings giving a spacious feel. The front door leads directly to the living room, then into the bedroom, both of which have the original hard wood floors. The back of the house has the kitchen, with exposed brick, a dining area, and a bathroom with a washer and dryer.

ArtBnB: Enjoy the Curated Comforts of Home
With easy highway access, and conveniently situated equidistance from Soulard, Lafayette Square, Tower Grove South, and Cherokee St, this custom designed space is not only an experience on its own, but a perfect base for exploring The Gateway City. Surround yourself with art, literature, and the homie comforts that set ArtBnB aside from staunch hotel chains. A lightly stocked kitchen, library, garden, patio, deck, grill, fire pit, wine rack, kennel, and toiletries are all included.
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☆

White Lotus Hideaway | Hot Tub on Main Street

Roomy Oasis with hot tub on the Hill!

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

Secluded Lakeside Lodge Minutes from St. Louis

Romantic tiny home w/ hot tub

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

Forest Edge Tiny House | 8 Min to Airport

Family friendly 3bd home! Longer stays available

Trendy Soulard area One Bedroom Apartment

New: Cozy Cottage Near The Hill

The Ladybug Inn

Beautiful Cottage on Large Private Lot

Sunset Mountain Forest Privacy

Stylish Retreat | Cozy Apt. near Top Attractions!
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

Spacious 4BED Home for Holidays - Central Location

Innsbrook Luxe Escape (5 bedrooms)
Quick stats about holiday rentals that are family-friendly in Chesterfield

Total holiday rentals
Explore 20 holiday rentals in Chesterfield

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

Verified guest reviews
Over 60 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Chesterfield holiday rentals include wifi 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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- Central West End
- Six Flags St. Louis
- Busch Stadium
- Enterprise Center
- Saint Louis Zoo
- City Museum
- Missouri Botanical Garden
- St. Louis Aquarium at Union Station
- Cuivre River State Park
- Pere Marquette State Park
- Castlewood State Park
- Hidden Valley Ski Resort
- Meramec State Park
- The Winery at Aerie's Resort
- Grafton Winery the Vineyards
- Cathedral Basilica of Saint Louis
- Bellerive Country Club
- Norwood Hills Country Club
- Raging Rivers WaterPark
- Saint Louis Science Center
- St. Louis Country Club
- Adventure Valley Zipline Tours and Paintball Park
- Missouri History Museum
- Noboleis Vineyards




