Holiday rentals in Overland

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Top-rated holiday rentals in Overland

Guests agree: these stays are highly rated for location, cleanliness and more.

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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, 746 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!

Guest favourite
A cozy living area features a modern sofa adorned with decorative pillows, complemented by stylish armchairs. A stone fireplace serves as a focal point, with a TV mounted above it. Natural light filters through window shutters, illuminating the warm wooden floor.
Flat in Forest Park South East
4.92 out of 5 average rating, 238 reviews

The Boho-Grove Apartment

Enjoy a stylish experience at this centrally-located place. Warm colors and good vibes offer a retreat after a long day at work. Recharge your batteries on the ultra comfortable memory foam mattress, comfy couch with big screen, and loungy kitchen to entertain guests. If cooking is your zen, the cupboards are filled with all you need to design your next meal-creation. The Grove is in close proximity to Forest Park, BJC, Wash-U, SLU & The Central West End, Botanical Gardens & Tower Grove Park.

Guest favourite
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
4.92 out of 5 average rating, 153 reviews

Tranquil three-bedroom home in central St. Louis

Welcome to Spa 7748! Relax and enjoy the quiet, tranquil space we have to offer you. Three bedrooms, two full baths, laundry room, work out area, media/office area, fully equipped chef’s kitchen, two fireplaces, covered patio, outdoor fire pit, driveway parking, and street parking. Centrally located in University City, which is just minutes from the downtown Clayton business/entertainment district, Washington University, Fontbonne University Downtown STL, Central West End, The Grove, Dogtown.

Top guest favourite
A well-lit bedroom features a spacious bed adorned with soft linens and decorative pillows. A wooden nightstand holds a small vase with flowers. Natural light filters through two windows, framed by dark curtains, illuminating the warm tones of the wooden flooring.
Home in Dogtown
4.93 out of 5 average rating, 227 reviews

Cozy Cottage in a Quiet City Neighborhood!

Please inquire for longer stay rates. This 650sq.ft quaint cottage has EVERYTHING! Centrally located this sought after historical neighborhood, DOGTOWN!, is just minutes from Forest Park and a short drive to all of STL's BEST ATTRACTIONS! This charmer has all the amenities you could hope for @ your HOME away from home! 2 Bedrooms with a Queen Bed in each, 3 Smart TV's, a backyard patio, KEYLESS Self Entry, fully equppied kitchen with SS appliances, MAIN FLOOR LAUNDRY and fully UPDATED BATH!

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 St. Louis
4.79 out of 5 average rating, 259 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 brick bungalow is framed by a vibrant garden filled with colorful flowers and lush greenery. A stone pathway leads to the entrance, bordered by various plants. Natural light illuminates the area, showcasing the home's inviting exterior.
Home in Maplewood
4.92 out of 5 average rating, 460 reviews

Charming Cottage Near Forest Park in Quiet Area

Welcome to our home! It is a cozy brick bungalow from 1929. It is a quiet neighborhood. Partially fenced backyard. We're located close to historic Route 66, coffee shops, shops, restaurants. 15 minute drive from Gateway Arch National Park, Busch Stadium, Forest Park, Enterprise Center, Washington University, St. Louis University, Zoo, Art Museum, and Botanical Gardens. Smoking is not allowed inside or outside. Any smoke odor will result in a $150 fine. Noise monitoring device on property.

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
4.92 out of 5 average rating, 133 reviews

Near Airport • Fenced Yard • Hwy Access

9 minutes to STL Lambert Airport. With easy access to I-70, 170, 270 & 364. Comfortable home with fenced yard, fast WiFi, free parking, and self check-in. Quiet neighborhood ideal for work stays or travel. Fully equipped kitchen, washer/dryer, 2 smart TVs, and dedicated workspace. Close to dining and shopping, 20 minutes to downtown St. Louis. *Stays over 28 days require a signed lease, SD(refundable), $250 cleaning fee, & $200 per pet fee. Longer stays are welcome, inquire for more info!

Superhost
A spacious living area features a mounted television above a wooden media console. Light-colored walls and hardwood flooring create an airy ambiance. A comfortable sofa is accompanied by a coffee table, while a ceiling fan adds to the inviting atmosphere. The open layout leads to a well-equipped kitchen.
Home in Saint Ann
4.82 out of 5 average rating, 51 reviews

Charming quiet 2 bedroom duplex

Unwind in the peaceful 2-bedroom, 1-bathroom duplex, beautifully furnished for a comfortable stay. This charming home offers a warm and inviting living spaces ideal for families, friends, or business travelers seeking a relaxing getaway. Enjoy a thoughtful welcome package featuring complimentary coffee, toiletries, and snacks upon arrival. Just a short 5-minute drive from the highway, this neighborhood offers easy access to local dining and entertainment options, perfect for exploring.

Top guest favourite
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.
Home in Saint Charles
4.92 out of 5 average rating, 109 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 easy access to everything.

Guest favourite
Flat in Soulard
4.92 out of 5 average rating, 152 reviews

Rustic Lodge • Walk to Bars • Fiber WiFi • Laundry

Escape to Rustic Retreat in the heart of Soulard—St. Louis’ most walkable historic neighborhood. This cozy 1BR blends cabin-style charm with modern comfort: plush Queen bed, premium linens, fast fiber WiFi, Smart TV, full kitchen w/ Keurig, and in-unit washer/dryer. Step outside to Soulard Farmers Market, top bars, live music, and restaurants. Minutes to downtown, Busch Stadium, and the Arch. Perfect for couples, business travel, or weekend escapes. Walk Score 90. Book now!

Guest favourite
A spacious living area features a large flat-screen television mounted above a stone fireplace. Comfortable leather couches and an accent table are positioned for relaxation. Natural light floods the space through large windows, complemented by wooden flooring and neutral wall tones.
Home in Creve Coeur
4.93 out of 5 average rating, 124 reviews

St. Louis 4 bedroom house by Mercy and BJC

Bring the whole family to this great place with lots of room for fun. Centrally located in St. Louis and close to the highway so you and your family can get to the places St. Louis has to offer in 20 minutes or less. Close to BJC and Mercy hospitals, Edward Jones HQ, Worldwide technologies, Bayer, Danforth, and many others. Televisions in every bedroom for the kids. Netflix available. Strictly no parties and no smoking inside the house. EV Level 2 Car Charger J1772

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
4.86 out of 5 average rating, 230 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

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