Family-friendly holiday rentals in Maryland Heights

4.96 out of 5 average rating, 112 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.

Indoor spacesKitchenBackyard

A light-filled seating area is showcased, featuring a soft gray sofa adorned with several pillows. In front, a glass-topped coffee table rests on a textured area rug. A decorative cabinet with shelves creates a focal point, highlighted by ambient lighting.

4.83 out of 5 average rating, 181 reviews

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

FamilyKitchenLong stay

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.

4.96 out of 5 average rating, 769 reviews

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!

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Apartment in Maryland Heights

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.

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!

Indoor spacesFamilyValue

4.87 out of 5 average rating, 206 reviews

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.'

4.88 out of 5 average rating, 147 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!

KitchenIndoor spacesBathroom

A cozy living room features a large gray sectional sofa, complemented by two wooden chairs. Natural light enters through sheer window coverings, illuminating the space. A light-colored rug adds texture underfoot while artwork decorates the walls, enhancing the room's comfortable atmosphere.

4.78 out of 5 average rating, 186 reviews

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 spacesFamilyQuiet

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.

4.95 out of 5 average rating, 445 reviews

*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 spacesKitchenCondition

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, 327 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.

KitchenFamilyValue

The exterior of a light blue Lustron home is featured, complemented by a vibrant yellow trim and front door. A large pink hippo sculpture stands prominently in the front yard, alongside green grass and white fencing, creating a playful and welcoming entry.

4.94 out of 5 average rating, 101 reviews

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!

Indoor spacesKitchenHospitality

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.

4.93 out of 5 average rating, 122 reviews

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.

KitchenIndoor spacesLong stay

4.98 out of 5 average rating, 389 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! 🚲

KitchenFamilyCheckout

4.92 out of 5 average rating, 129 reviews

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!

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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

4.87 out of 5 average rating, 101 reviews

Getaway House | St Charles 4BR Sleeps 11 Game Room

KitchenFamilyCondition

4.97 out of 5 average rating, 115 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

KitchenFamilyAccess

4.95 out of 5 average rating, 154 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!

KitchenFamilyAccess

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

Indoor spacesFamilyBackyard

4.92 out of 5 average rating, 106 reviews

A spacious living area features a vibrant teal sectional sofa facing a large flat-screen television mounted on a dark wall. A glass coffee table sits in front of the sofa, while a modern ceiling fan provides overhead lighting. The open layout leads to a dining area visible in the background.

Home in Soulard

The Soulard Atelier- Hot Tub!

KitchenFamilyAccess

An outdoor space is presented with a spacious layout, featuring a gas fire pit at the center, surrounded by seating for six. An oversized hot tub is visible nearby, with decorative string lights overhead illuminating the area. A barbecue pit and a seating area enhance the space.

4.87 out of 5 average rating, 347 reviews

Private Oasis w/hot tub

KitchenFamilyLaundry

An outdoor pool area features a circular pool with clear blue water, surrounded by a textured stone patio. Comfortable seating is available under a covered gazebo, and the house displays large glass doors with multiple windows, allowing natural light to brighten the space.

4.87 out of 5 average rating, 191 reviews

Heated Saltwater Pool+Hot Tub! Great location!

KitchenFamilyBeach

Home in Tower Grove South

A charming bedroom features a spacious bed layered with colorful pillows and a textured throw. Brightly painted walls are adorned with an array of artwork and photographs. Natural light filters in through large windows, while a ceiling fan adds a touch of elegance to the vibrant decor.

Elevated Retreat | Concierge + Hot Tub | Historic

KitchenIndoor spacesGetting around

4.97 out of 5 average rating, 157 reviews

Family- and pet-friendly home rentals

4.91 out of 5 average rating, 246 reviews

The exterior of the Pacific Palace showcases a unique wooden design with ornate decorations. Brightly colored adirondack chairs invite relaxation on the porch, while a stone pathway leads to the front door beneath a gabled awning. Lush greenery frames the playful architecture.

Home in Pacific

Pacific Palace, super unique!

Indoor spacesKitchenView

A vibrant green wall adorned with various plants serves as a backdrop for a glowing neon sign reading 'Cheers!' A stylish bar cart with glasses is placed in front, enhancing the welcoming atmosphere of the living space.

4.96 out of 5 average rating, 110 reviews

2bed/2bath Walk Main St Shops Eateries & Bars!

Indoor spacesFamilyParks

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, 155 reviews

Cozy Mid-Century Modern Townhome

Indoor spacesKitchenGetting around

4.83 out of 5 average rating, 162 reviews

Spacious Home - Heated Pool Open Until November

Indoor spacesKitchenLong stay

A living area is presented with two blue armchairs positioned beside a small coffee table adorned with a plant and decor items. Natural light filters through sheer curtains, highlighting the wooden floor. A wall-mounted circular decor piece adds a subtle touch to the space.

4.87 out of 5 average rating, 752 reviews

The Benton House - With fenced yard!

FamilyKitchenWi-Fi

4.78 out of 5 average rating, 119 reviews

A light-filled bedroom features a spacious bed layered with a soft blanket and decorative pillows. A vase with flowers sits on the nightstand next to a wall-mounted lamp. Windows dressed with floral curtains provide views of the neighborhood.

Home in St. Ann

Cozy Cottage in the City

Indoor spacesFamilyGetting around

4.96 out of 5 average rating, 147 reviews

Great Location Fam Friendly Home w/Lrg Fenced Yard

KitchenFamilyDecor

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, 1085 reviews

The Little House.

FamilyIndoor spacesValue

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 159 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

KitchenIndoor spacesWalkability

Apartment in University City

A spacious kitchen features white cabinetry and granite countertops, complemented by stainless steel appliances. An island with two black stools provides additional seating. A window allows natural light to brighten the area, while modern fixtures enhance the kitchen's functionality.

Large U. City Apt 4 BR, 2 Bath, Pool, near Wash U.

Indoor spacesKitchenCondition

4.99 out of 5 average rating, 168 reviews

4.88 out of 5 average rating, 222 reviews

Home in Gray Summit

Sunset Mountain Privacy

FamilyKitchenParking

4.92 out of 5 average rating, 108 reviews

Tower Grove Oasis #1 + King Bed + Queen Bed+ Patio

KitchenFamilyLocation

Apartment in Maryland Heights

T Sweet St. Louis Airport 2 bedrooms Apartment

FamilyKitchenQuiet

5.0 out of 5 average rating, 10 reviews

4.76 out of 5 average rating, 90 reviews

The basement game room features a foosball table in the foreground with colorful player figures. A cozy fireplace is displayed on a large screen mounted on the wall, while bar stools are positioned around a counter. The room is brightly lit with a modern design.

Home in Maryland Heights

Home with Game Retreat, 8 min STL Airport/Westport

Indoor spacesKitchenNearby

5.0 out of 5 average rating, 3 reviews

Clark Manor

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