Family-friendly holiday rentals in Maryland Heights

Top Guest favourite

Guest favourite

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!

Kitchen · Indoor spaces · Value

BEAUTIFUL Historic 3 Bedroom Upscale Guesthouse!!

Spacious luxury three bedroom home in historic St. Charles. Minutes away from Main Street, Frenchtown, Streets of St. Charles, shopping, and more. The bright, fully equipped chef's kitchen features a gas range, spacious counters, and upscale appliances for all your dining and entertainment needs. Bedrooms include luxury DreamCloud Mattresses and upscale bedding. Full size washer/dryer, walk in closet, and Roku. Dream bathrooms with soaker tub. Backyard features outdoor relaxation and playhouse.

Family · Indoor spaces · Access

Main Street Hideaway

This house is located on historic Main Street in Saint Charles, Missouri. This means we are within walking distance of dozens of restaurants and boutique shops. We are in the wedding district and three wedding venues are within a 5 minute walk: The Old Stone Chapel & LaBelle Couer. This is the perfect spot for bridal parties and families. This unique house, is a perfect spot for a bridal party to get ready and prepare for the big day. Brand new bath added in 2024. Outdoor patio new in 26

Kitchen · Indoor spaces · Pets

301 Guesthouse- Historic Main street-Katy Trail

Our small 301 Guest House was 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!

Family · Kitchen · Location

Stunning Modern Apt| King bed 5 min CreveCoeurLake

Experience luxury and style in our St. Louis home. This second-floor residence features 2 modern bedrooms, a cozy living room, a fully equipped kitchen, a stylish bathroom, and a dedicated workspace with high-speed WiFi- blending comfort and elegance. Located in a secure Maryland Heights community, just minutes from Creve Coeur Lake, Westport Plaza, Hollywood Casino & Amphitheatre, and historic St. Charles. With plush bedding, premium amenities, and ample parking, we promise a seamless stay!

Kitchen · Family · Decor

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!

Kitchen · Family · Backyard

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.

Indoor spaces · Kitchen · Access

Top Guest favourite

Guest favourite

*NEW HotTub* The Jewel on 5th-2br2b-near 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.

Indoor spaces · Kitchen · Condition

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.

Indoor spaces · Family · Hospitality

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!

Family · Indoor spaces · Accuracy

Top Guest favourite

Guest favourite

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! 🚲

Kitchen · Family · Hiking

The Frenchtown Inn | 2BR Charmer

Welcome to the Frenchtown Inn on the corner of Third and French! Experience the best of St. Charles in this charming 2-bedroom, 2-bathroom house situated in the heart of Frenchtown. This delightful space offers a perfect blend of comfort, convenience, and a touch of history, ideal for an unforgettable stay. We are dog friendly, complete with a fenced in yard. The Frenchtown Inn awaits you. Come experience a memorable, relaxing getaway with family or friends in our inviting home!

Family · Kitchen · Wi-Fi