Holiday houses 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

A modern kitchen area features a contrasting blue cabinetry and wood paneling. A granite countertop adds a stylish touch, complemented by a small sink and utensils displayed in a white container. Natural light enters through a sliding glass door, enhancing the space.

Home in Saint Ann

4.89 out of 5 average rating, 74 reviews

Lower Level Layover

Keep it simple at this peaceful and centrally-located place. Located only 6 minutes to the airport. To accommodate our guests we are also happy to drive them to and from for short trips. Our home is walking distance to an AMAZING local cafe- the Sweet Spot! This is the lower level of our home. You will have full access to the lower level and it is completely separate. Entrance is around back through the walk out basement. Sometimes our small girl dogs will be out in the backyard which is shared

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, 117 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. See you soon!

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, 757 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!

Superhost

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 Saint Ann

4.78 out of 5 average rating, 117 reviews

Cozy Cottage in the City

This stylish place is perfect for your stay while in St. Louis. Whether here for family or business, this home is conveniently located just 15 minutes to Clayton, 20 min to downtown & the Central West End, or 15 minutes to St. Charles County. With only a 7 min drive (if you drive slow!!) to the airport, this 2 bedroom, 1 bath boasts a spacious kitchen, living room, & dining room for your stay-however long it may be! Please note that the piano in the photos is not available for guests to play.

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, 156 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.

Guest favourite

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.

Apartment in Maryland Heights

4.88 out of 5 average rating, 201 reviews

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!

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, 137 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!

Guest favourite

The living area features a neutral-toned sofa adorned with decorative pillows, complemented by a stylish armchair. A sleek desk is positioned next to the window, with natural light enhancing the space. A contemporary art piece and a small table with plants complete the inviting atmosphere.

Apartment in University City

4.82 out of 5 average rating, 135 reviews

A Modern Oasis in U. City/Clayton

Welcome to our apartment in the University City and Clayton area on Delmar Blvd near the Delmar Loop. We own this 4 unit apartment building with garage space and free off street parking. We have renovated this 3 bedroom, 1 bath spacious, airy and bright space for you. Enjoy the benefits and skip the hassle to stay in this cozy unit with modern furniture and clean accommodations in this safe neighborhood. Sleeps 6 but book with 2 other listings in this building for up to 18 guests total.

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 St. Louis

4.87 out of 5 average rating, 127 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 St. Louis

4.96 out of 5 average rating, 195 reviews

Great Fam Friendly Home w/ Lrg Deck & 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

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

4.91 out of 5 average rating, 32 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

Home in St. Louis

4.94 out of 5 average rating, 32 reviews

Modern St. Louis Retreat- LOW Cleaning Fee

Welcome to your cozy, centrally located escape in the heart of St. Louis! This beautifully designed space features an open layout, plush bedding, and a fully stocked kitchen, everything you need for a relaxing and convenient stay. Kick back on the comfy sofa with your favorite shows on the smart TV, or stay productive with fast, reliable Wi-Fi. Whether you’re visiting for work or fun, the space is thoughtfully set up for both.