Holiday houses in Overland

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Top-rated holiday rentals in Overland

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Top Guest favourite

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.

Home in Saint Charles

4.97 out of 5 average rating, 704 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!

Top Guest favourite

A log cabin with a dark metal roof is featured, accompanied by a covered porch area containing two chairs. Surrounding landscaping includes a well-maintained lawn and decorative stones, providing a natural setting that complements the cabin's rustic design.

Cabin in Pacific

4.99 out of 5 average rating, 132 reviews

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

Guest favourite

A bright living room features large windows draped in sheer curtains, allowing natural light to fill the space. A comfortable gray sofa is complemented by an accent chair and a decorative rug, with a coffee table at the center adorned with minimal decor and greenery.

Apartment in University City

4.88 out of 5 average rating, 136 reviews

Renovated U. City/Clayton Luxe Condo

Welcome to my apt in the U. City/Clayton area! We own the building and renovated this 3BR, 1BA spacious, airy and bright space for you. An attached garage space underneath the building w/ direct connection to the apt . Enjoy the benefits & skip the hassle, in a quiet building w/ modern furniture. Sleeps 6 but book w/ 2 other listing in this building for up to 18 total. Looking for a vehicle to rent? Link: https://turo.com/us/en/minivan-rental/united-states/st-louis-mo/toyota/sienna/1169950

Superhost

A well-lit interior space features warm wooden flooring and a soft area rug. Natural light filters in from a nearby window, enhancing the inviting atmosphere of the room. The layout suggests a cozy and functional space suitable for relaxation or entertaining.

Home in Pasadena Park

4.8 out of 5 average rating, 244 reviews

Cheerful 1-bedroom, red brick, historic home

Keep it simple at this peaceful, historic, and centrally-located place. This red brick home is a piece of long-standing history (built in 1928), on a quiet one way street. It is just 5 minutes away from the airport & University of Missouri Saint Louis, and just 15 minutes from down town and central west end. It is literally central to just about any place you wish to visit in the Saint Louis area! There’s convenient and free on-street parking too! Come enjoy your time at The Ruby Brick Stay!

Guest favourite

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

4.88 out of 5 average rating, 259 reviews

Forest Edge Tiny House | 8 Min to Airport

Welcome to a private hidden gem 8 minutes from the airport with an oasis of an acre of woods surrounding the property! It’s a quiet getaway from the hustle and bustle of the city but only 8 min to the Airport, 15 miles to down town. 15 min to St. Charles area and 10 min to Hollywood Casino Amphitheatre. Perfect for couples, small family or single visitor to St. Louis! Dogs are welcome to stay for an additional fee. Early checkin/checkout available for $15/hour as availability allows.

Guest favourite

An artistic space features vibrant murals and wall art, including a striking circular installation illuminated by blue and purple lights. The decor showcases a blend of abstract designs, providing a unique atmosphere. A polished pole stands at the center, complemented by geometric patterns on the wall.

Home in McKinley Heights

4.94 out of 5 average rating, 1,210 reviews

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.

Guest favourite

A cozy seating area is seen with a black leather couch positioned beside a small table. A lamp provides illumination, while vertical blinds allow filtered light to enter through the window. The flooring is light-colored, enhancing the room's spacious feel.

Home in Hanley Hills

4.88 out of 5 average rating, 112 reviews

2 Bdrm Home Less than 6 miles from Lambert Airport

Your family will have easy commute to surrounding restaurants and other eye catching places such as: -Less than 6 miles to St Louis Zoo -Less than 17 miles to Gateway Arch -Less than 15 miles to Bush Stadium -Less than 14 miles to STL Soccer Stadium -Less than 15 miles to Enterprise Center -Less than 13 miles to Hollywood Casino -Less than 9 miles to Walmart -Less than 1 mile to Save a Lot (Grocery) -Less than 6 miles to Lambert Airport -Less than 6 miles to Wholes Food Market

Guest favourite

Home in Rock Hill

4.95 out of 5 average rating, 172 reviews

Family Friendly Cozy Home w/ Lrg Fenced Yard

**FAMILY FRIENDLY** (See details for the items avail for families) This 2 bedroom home has everything you need for a relaxing trip! Fully updated with stylish and comfortable furniture and decor. Fully equipped kitchen and an amazing backyard/deck. Quiet street by one of the best Mexican restaurants in St. Louis - Hacienda - (can walk 2 min there) Close to everything! 13 minutes to the St. Louis Zoo 10 minutes to The Magic House 15 minutes to Busch Stadium & Union Station

Top Guest favourite

The exterior of the house features a well-maintained lawn with shrubbery and a covered porch. A cozy seating area with a modern coffee table is shown, complemented by a sectional sofa. A well-equipped kitchen with appliances and a dining table set for six are also visible. A serene bedroom showcases a spacious bed with soft linens.

Home in Saint Charles

4.99 out of 5 average rating, 194 reviews

Little House By Main St -5 4K TV's- 1-75 Inch -1GB

Little House By Main St -5 4K TV's- 1-75 Inch -1GB Internet- No location has better access to so much. All the best amenities on both sides of Main Street St Charles! Walking distance from the Ameristar Casino, Texas Road House, Main Street (Honky Tonk, Big A's, Q, Thirstys), Starbucks, Taco Bell, Buffalo Wild Wings, McDonald's and the Bars / Restaurants on Main. An Awesome Location for all of the Festivals in St Charles! And secured parking in the 1 car garage!

Superhost

A bright kitchen featuring light green cabinetry and white countertops. An island with a circular design provides additional workspace. Natural light filters through the shutters above the sink, illuminating the dining area with a wooden table surrounded by four chairs.

Home in Creve Coeur

4.88 out of 5 average rating, 222 reviews

Home away from Home St. Louis Cnty Ladue Schools

15 min to Norwood Hills CC. Centrally located in Safe St. Louis County, Olivette/Creve Coeur area near many attractions, businesses, Universities, etc. Harkte Nursery is 2 houses away with farm fresh produce!! Lambert Intl Airport 13 min 7.7 miles Busch Stadium and St. Louis Ballpark Village, The Arch 20 min 13.8 miles Washington University 13 min 6.4 miles St Louis University 10 min St Louis Zoo, Forest Park, Science Center, Art Museum

Superhost

A spacious living area is highlighted by a dark fireplace and a large flat-screen television mounted on the wall. Soft blue furnishings, including a sectional sofa and armchairs, provide comfortable seating. A dining area is visible in the background, complemented by natural light filtering through the windows.

Home in University City

4.96 out of 5 average rating, 24 reviews

Spacious STL Retreat • Near Airport & Attractions

Explore St. Louis from this centrally located retreat! Only 10 min to STL Airport, Delmar Loop & Clayton. A short 15 min drive to The Hill’s Italian eats, Forest Park, Zoo, Science Center & leading hospitals like Barnes-Jewish, Children’s, Wash U and SLU. Enjoy a cozy firepit, plenty of parking and fast I-70/170/364 access. Downtown, Busch Stadium & the Arch are just 20 min away—perfect for families, medical staff, business travelers & group getaways!

Guest favourite

A vibrant living area features bright green sofas with pink accent pillows positioned around a colorful area rug. An archway leads to a dining space with orange chairs, while blue walls and purple curtains add modern charm.

Bungalow in St. Louis

4.93 out of 5 average rating, 127 reviews

Dog Friendly Home • Fenced Yard • Near Airport

Dog-friendly home near STL Airport with a private fenced yard, fast Wi-Fi, and free parking. Easy access to highways 70, 170, 270 & 364. Located in a quiet neighborhood ideal for families, weekend trips, and work stays. Fully equipped kitchen, washer/dryer, 2 smart TV’s, and workspace. Short drive to dining and shopping, about 20 minutes to downtown St. Louis. Every stay helps support local animal outreach — we donate 10% of net profits.