Family-friendly holiday rentals in Chesterfield

Cottage on Main Street- Low Cleaning Fee

MESSAGE FOR SHORT STAY DISCOUNT Stay in the heart of Historic Downtown St. Charles! WALK EVERYWHERE at this beautifully updated 2BR/1BA blends modern comfort with charm just steps from Main Street. Walk to award-winning restaurants, unique boutiques, coffee shops, festivals, and riverfront views. Directly across from the Katy Trail, perfect for biking and morning strolls. Minutes to Ameristar Casino and 12 minutes to STL Airport. Fast Wi-Fi, cozy beds, and an unbeatable location. See you soon!

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

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.

Sweet Escape Near Historic Main St, 4BR, 2 Baths

Discover your Sweet Escape in this charming 4-bedroom bungalow, just a 3-minute drive (or 20-minute walk) to Historic Main Street’s cobblestone streets, boutique shops, dining, and events. Now featuring two full bathrooms, including a newly added second-floor bath for extra convenience. Enjoy a game-filled basement with pool table, ping-pong, foosball, and darts, plus yard games, a fire pit, and cozy nights with board games and DVDs. Sleep soundly on plush beds with room-darkening curtains.

St. Louis Home away from Home!

Our property is the perfect place for anyone looking for a peaceful stay in STL! This 4BR, 2.5 BA house gets amazing natural light throughout the day, and is nearly too cozy! Located 12 minutes from the airport, and near many of STL’s top attractions, our home is sure to leave you feeling refreshed after your stay! We’re a family that is dedicated to ensuring our guests enjoy the best experience possible. As local hosts, you can rest peacefully knowing that we are just a phone call away!

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.

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.

The HIPPO House! All 1950s Mini-Golf! MCM Lustron

Welcome to a unique 3-bedroom Lustron home in St. Louis, where retro charm and quirky details await! Greeted by Chelsea, our giant pink hippo, every guest steps into a rare mid-century gem—one of only 1,200 remaining Lustrons and even rarer with three bedrooms. Iconic steel walls, built-in cabinetry, and 1955 decor immerse you in history, while Wi-Fi ensures comfort. A backyard 9-hole mini-golf course adds some family fun. Book today to enjoy Chelsea’s welcome and a slice of history!

Spacious Home - Heated Pool Open Until November

Heated Pool is Open through end of October! Exceptionally updated sprawling home w/ 2400 sqft of living space inside with multiple entertainment areas and rooms well spread out. This is the perfect house for multiple families or generations to enjoy together! The house is amenity packed and offers a stunning kitchen, large backyard, pool house/detached office, and plenty of privacy! Located in the perfect central location within 5-15 minutes of the cities main attractions!

Hot Tub Gazebo | Game Room | 2 Kings | Sleeps 8

A spacious, fully stocked home with a hot tub beneath a private covered gazebo, a fire pit, a lower level game room, and a big fenced backyard. Send the kids downstairs to the arcade and indoor swing while the adults soak under the gazebo, or make it home base for a wedding at nearby Stone House. Two king beds, a bunk room kids love, and a kitchen ready for real cooking, all in a quiet St. Charles neighborhood near restaurants, wineries, and parks. Sleeps 8.

3+ acre, fast wi-fi, rustic timber frame, Koi pond

Rick’s Retreat is a charming rustic haven set on over three private acres, featuring a soothing Koi pond and waterfall. This spacious home is perfect for a memorable escape, blending rustic charm with modern comforts to make every guest feel at home. Whether you're seeking a relaxing weekend getaway, a family gathering, or a place to celebrate a special occasion, Rick’s Retreat offers everything you need for an unforgettable experience.

Great Location Fam Friendly Home w/Lrg Fenced Yard

Newly finished basement with 4th bedroom (King bed), large play/relaxation space & large 120-inch projector screen and separate large speaker for movie nights! Beds are all brand new comfortable memory foam! This house is in such a great and convenient area! Freshly renovated with all brand new beds and furniture, a fully stocked kitchen for cooking and baking and a fenced in pet friendly backyard! TONS of kids and baby items!