Family-friendly holiday rentals in Maryland Heights

4.97 out of 5 average rating, 105 reviews

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.

The charming front porch features a white wicker chair and a decorative wreath, inviting relaxation. Greenery surrounds the entryway, complemented by a well-maintained lawn. A gravel pathway leads from the porch to the driveway, creating a welcoming entrance to the guest house.

4.97 out of 5 average rating, 731 reviews

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!

4.88 out of 5 average rating, 195 reviews

A well-lit living area features a dark leather sofa adorned with colorful cushions, complemented by a wooden coffee table and a blue area rug. Artwork and decorative accents enhance the space, with sunlight filtering through the windows, creating a warm, inviting atmosphere.

Flat in Maryland Heights

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!

The exterior view of a charming brick house highlights a traditional design with two dormer windows and a bright blue front door. An American flag hangs proudly from the porch, surrounded by well-maintained landscaping that enhances the welcoming appearance.

4.91 out of 5 average rating, 295 reviews

Tompkins Street Retreat

Relax in this two-bedroom, two-bath house with a backyard patio and firepit with a privacy fence. Walk to unique shopping and entertainment on Historic St. Charles Main Street. Local wineries and St. Louis attractions are a short drive away. Enjoy a comfortable living room with a large TV and a fully equipped kitchen for special meals. Unwind after an active day with a meal, drinks under the pergola, and a great night's sleep in our king-size bed. We also offer FREE off-street/garage parking.

Flat in St. Charles Historic District

A modern kitchen area features white cabinetry and a kitchen island with three cushioned stools. Pendant lights hang above the island, illuminating the space. A doorway leads to another room, with a glimpse of additional kitchen appliances visible in the background.

4.93 out of 5 average rating, 412 reviews

Pop Lucks Guest Suite 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.

The living room showcases a blend of seating options, including a black futon and a brown leather sofa, complemented by a colorful area rug. Natural light filters through patterned curtains, illuminating the space which features a television and decorative touches.

4.95 out of 5 average rating, 139 reviews

Cozy Mid-Century Modern Townhome

This comfy 2 bedroom, 1.5 bath townhome is perfect for up to 5 guests. Luxury King bed in bedroom 1 and luxury Queen bed in bedroom 2. A futon in the living room can be used for a 5th guest. A pack-n-play is available upon request. This dynamic location is 5 minutes from bars, restaurants, shopping, Lindenwood University, and Ameristar Casino. It's only 2 miles from St. Charles, historic, Main Street, and it's only 15 minutes from the airport, and about 30 minutes from downtown St. Louis.

A grey sectional sofa is positioned next to a circular glass table, creating a comfortable seating area. Natural light floods the space through large glass doors leading to the outside. A potted plant adds greenery, while wall decor spells out 'HOME.'

4.9 out of 5 average rating, 133 reviews

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!

Bungalow in St. Charles Historic District

A well-appointed bedroom is featured, with a spacious bed adorned with soft linens and a decorative accent pillow. Two bedside lamps are positioned on either side, providing additional lighting. A window allows natural light to filter in, while a wall-mounted air conditioning unit enhances comfort.

4.97 out of 5 average rating, 270 reviews

Patio House, secluded in heartbeat of Main Street

The Patio is nestled in the heart of historic St. Charles a few steps from Main Street, Katy Trail, Missouri River, Antique and Boutique Shopping, Restaurants Bars and More, Several Wedding venues are within walking distance of the property as well. In addition to your well appointed unit, this property has as much outside as it does in. Take your coffee, wine, water and enjoy our patio, complete with fire table, dining table edged with lush plantings for privacy. PLEASE NOTE NO SMOKING

The exterior of a charming century home showcases a covered front porch with white railings and a welcoming entrance. Lush greenery and flower beds line the stone steps leading to the porch, enhancing the inviting character of the property.

4.94 out of 5 average rating, 417 reviews

*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.

A living room features exposed brick walls, a comfortable gray couch, and a black wicker chair. A flat-screen television is mounted on one wall, while natural light fills the space through two windows. A vibrant area rug adds color to the hardwood floor.

4.96 out of 5 average rating, 317 reviews

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.

A well-organized kitchen features dark cabinetry and a light countertop, providing ample workspace. A comfortable couch is positioned in the living area, absorbing natural light from the window. Decorative elements, including a round wall mirror and soft furnishings, add a touch of warmth to the space.

4.91 out of 5 average rating, 104 reviews

Cottage on Main Street- Low Cleaning Fee

MESSAGE FOR SHORT STAY DISCOUNT Stay in the heart of Historic Downtown St. Charles! 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 easy access to everything. WALK EVERYWHERE!

4.98 out of 5 average rating, 379 reviews

The exterior of a historic log cabin features a welcoming yellow door and a decorated porch with a small table and chairs. Lush greenery surrounds the cabin, while vibrant flowers add a touch of color. The structure is complemented by the clear blue sky.

Cabin in Saint Charles

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! 🚲

Popular amenities for Maryland Heights family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in Tower Grove South

4.88 out of 5 average rating, 121 reviews

Hot Tub * New Renovated * Massage Shower * Yard

4.99 out of 5 average rating, 112 reviews

Spacious home with entertainment room and hot tub

An oversized concrete patio features a hot tub surrounded by wooden privacy panels. Comfortable seating is arranged nearby, illuminated by string lights overhead against a backdrop of trees and a twilight sky.

4.87 out of 5 average rating, 155 reviews

Modern Oasis fire pit and hot tub

4.97 out of 5 average rating, 102 reviews

The exterior of a single-story house is illuminated by soft evening light, showcasing a manicured lawn and a paved driveway. Trees line the background, and the front porch is accented by neatly trimmed shrubs, creating an inviting entrance.

Home in St. Peters

Blair's Jungle House w/ Hot Tub - Game Room

4.9 out of 5 average rating, 116 reviews

A private hot tub is illuminated with soft blue lights, surrounded by a wooden fence. String lights hang overhead, enhancing the evening ambiance. The area offers seating options, creating a cozy space for relaxation.

Cottage in Augusta

Romantic Augusta Cottage-Relax & get away!

4.95 out of 5 average rating, 140 reviews

A well-lit bedroom features a spacious bed with soft bedding and decorative pillows. Two nightstands flank the bed, each with a lamp. A stylish rug lies beneath the bed, and artwork adorns the wall. Natural light filters in through the window, covered by navy curtains.

Home in The Hill

Roomy Oasis with hot tub on the Hill!

4.94 out of 5 average rating, 142 reviews

A serene lake scene is presented, reflecting vibrant colors of a sunset. Trees line the shore, silhouetted against the sky, while their shapes are mirrored in the still water, creating a peaceful ambiance.

Cottage in Millstadt

Secluded Lakeside Lodge Minutes from St. Louis

4.93 out of 5 average rating, 101 reviews

A well-lit kitchen features grey cabinetry and stainless-steel appliances. A wooden dining table with black stools is positioned centrally, adorned with a vase of sunflowers. Natural light floods in through a large window, providing a view of the outdoor landscape.

Home in Des Peres

Cul De Sac - next to the best shopping in STL

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 270 reviews

A charming two-story house features a gray exterior, framed by vibrant trees in autumn hues. Large windows allow natural light to enter, and a welcoming entrance hints at the cozy space within. A stone pathway leads up to the home, surrounded by a rustic landscape.

Tiny home in Saint Ann

Forest Edge Tiny House | 8 Min to Airport

Bungalow in Saint Charles

4.85 out of 5 average rating, 320 reviews

Historic Bungalow

The exterior of the house is shown, featuring a white facade with black shutters. A bright yellow door serves as a focal point, complemented by two windows on either side. The sloped roof adds character to the two-story structure.

4.87 out of 5 average rating, 1,046 reviews

The Little House.

Colorful flowers and greenery line the flower bed in front of the cottage. Several flowering plants are visible, accompanied by neatly trimmed boxwood shrubs. The pathway is paved, leading up to the home's entrance, with a mix of sunlight and shade enhancing the natural landscape.

4.95 out of 5 average rating, 159 reviews

New: Cozy Cottage Near The Hill

4.92 out of 5 average rating, 151 reviews

A spacious bathroom features a freestanding bathtub surrounded by natural stone walls. A walk-in shower with a glass panel is visible alongside a modern sink. Warm lighting hangs above, and a potted plant adds a touch of greenery, enhancing the serene atmosphere.

Home in University City

Tranquil three-bedroom home in central St. Louis

4.99 out of 5 average rating, 164 reviews

A light-filled living room features a comfortable sofa adorned with decorative pillows, complemented by two yellow accent chairs. A glass coffee table sits atop a textured rug, with natural light entering through windows dressed with blinds. The open layout leads to a dining area in the background.

Home in Dogtown

Dogtown Century home near Forest Park & Maplewood

A comfortable living room is showcased, featuring a large sectional sofa and a decorative stone fireplace. Colorful stained glass windows allow natural light to filter in, while a patterned area rug adds warmth to the hardwood floor.

4.99 out of 5 average rating, 242 reviews

Sparkling Vintage Charmer, King Bed, Quiet Comfort

4.96 out of 5 average rating, 116 reviews

A well-maintained, single-story home is shown from an aerial view. The brick exterior is complemented by a neatly trimmed lawn and mature trees surrounding the property. A small covered porch with seating is visible, along with a driveway leading to a single-car garage.

Home in O'Fallon

Family friendly 4bd home! Longer stays available!

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 150 reviews

An indoor pool is illuminated by soft blue lighting, showcasing the inviting water. The pool is surrounded by large glass panels, creating a sense of openness. A handrail is visible at one end for easy access, and various pool floats can be seen in the water.

Home in Ballwin

Private indoor pool & sauna

5 out of 5 average rating, 3 reviews

T | Pool · Hot Tub · Arcade · 4BR Luxury Retreat

4.81 out of 5 average rating, 27 reviews

Home in Fairview Heights

Arch View Luxury: Hottub-Pool-Sauna-Wine &Brkfst

4.95 out of 5 average rating, 56 reviews

Place to stay in Pacific

First floor pet friendly family suite near Purina

5 out of 5 average rating, 30 reviews

The outdoor pool area features a serene pool surrounded by a spacious deck. Lounge chairs are positioned around the pool, and a large umbrella provides shade over seating areas. Lush greenery borders the space, creating a peaceful atmosphere.

Home in Augusta

"The Villa" at Villa Augusta in MO wine country

4.83 out of 5 average rating, 147 reviews

Spacious Home - Heated Pool Open - Amenity Packed

4.88 out of 5 average rating, 8 reviews

A cozy cabin is set among trees, featuring a wooden porch with a railing. A gentle ramp leads to the entrance, and picnic tables are positioned nearby on gravel. Grilling stations are visible in the outdoor space, enhancing the sense of nature.

Cabin in Villa Ridge

Redbud Cabin S-8