Vacation rentals in Overland

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Top-rated vacation rentals in Overland

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Guest favourite

Home in Kirkwood

4.98 out of 5 average rating, 175 reviews

A Kirkwood Cottage, Quaint Suburb of St Louis

Quaint cozy cottage on a “No Thru Street”. The best place to stay in Kirkwood.This was my childhood home. Only 1/2 mile to downtown Historic Kirkwood with its many shops & restaurants,Farmers Market, Kirkwood Park & Pool & Train Depot. A couple of miles to Museum of Transport,Powder Valley Nature Center & Magic House Museum is a MUST if you have children.Home has steps to entry, railroad tracks up on the hill at the end of street. Close easy access to all major highways. Construction in area M-F

Nov. 7 – 14

$262 CAD per night

Guest favourite

Home in Saint Charles

4.98 out of 5 average rating, 496 reviews

301 Guesthouse SuperHost/Shop Discounts/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!

Sep. 29 – Oct. 6

$207 CAD per night

Guest favourite

Guest suite in Saint Charles

4.95 out of 5 average rating, 299 reviews

Creekside Suite - Peaceful, Spacious, and Comfy

Enjoy your stay in a spacious walkout basement-level suite that includes bedroom, bathroom, living/dining room & patio. Bedroom has queen bed, dresser, desk & TV. Living room has futon, books, games & TV. TVs have Netflix. Suite has minifridge, microwave, toaster & coffee-maker. Eat at the dining table or sit up to the window counter to look out on the creek & woodlands behind the house. Situated in a quiet, safe neighborhood with parks & ponds. Just 8 miles from historic downtown St Charles.

Jul. 19 – 26

$158 CAD per night

Guest favourite

Home in St. Louis

4.83 out of 5 average rating, 107 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!

Dec. 19 – 26

$99 CAD per night

Guest favourite

Tiny homes in Saint Ann

4.92 out of 5 average rating, 142 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.

May 19 – 24

$233 CAD per night

Guest favourite

Bungalow in Saint Charles

4.99 out of 5 average rating, 164 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

Feb. 17 – 24

$179 CAD per night

Guest favourite

Apartment in St. Louis

4.91 out of 5 average rating, 357 reviews

Private Upstairs Apartment minutes from Airport

Discover our historic home in a charming neighborhood with a small-town feel, minutes from the airport and close to St. Louis attractions and Creve Coeur Park Soccer Complex. Enjoy a private second-floor apartment with separate entrance, no shared spaces, and contact-free check-in via coded lock. Sleeps five comfortably with two queen bedrooms and two single beds in a common area/kitchenette. Perfect for those seeking a blend of convenience and serenity during their St. Louis visit

May 24 – 31

$168 CAD per night

Guest favourite

Home in Saint Charles

4.97 out of 5 average rating, 180 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 1930'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.

Nov. 16 – 23

$211 CAD per night

Guest favourite

Home in St. Louis

4.98 out of 5 average rating, 517 reviews

Garden Cottage-Safe Private Parking!

Thoughtfully renovated cozy bungalow offering a lush vibrant landscaped garden, meandering brick patio & deck overlooking waterfall pond w/ Koi fish. We lovingly restored our efficient space with a mix of old & new furnishings and updated appliances. A Romantic luxurious vibe ❤️ The perfect nest for two! Our quiet safe neighborhood is home to fabulous restaurants, bars, coffee shops and galleries. Close to everything including Hwys 40, 44, 55 . PLUS safe private parking!

Oct. 20 – 27

$217 CAD per night

Guest favourite

Place to stay in St. Louis

4.94 out of 5 average rating, 143 reviews

The Dogtown Loft -private loft and private parking

NO CLEANING FEES! The Dogtown Loft is situated in historic Dogtown in St. Louis, Missouri. The Loft offers privacy as well as private garage parking.The St. Louis Zoo at Forest Park, meals, drinks, coffee, and entertainment are a short walk away. The Loft is kid friendly and has quick access to the highways to enjoy Busch Stadium, Ballpark Village, museums, St. Louis Science Center, the Arch, and more! Keyless entry, washer/dryer, full kitchen, & free wifi.

Jun. 24 – Jul. 1

$193 CAD per night

Guest favourite

Home in Dittmer

4.95 out of 5 average rating, 358 reviews

Honeymoon Suite Camp Skullbone In The Woods

Romantic quiet cozy chalet for two! Vintage décor with all the modern amenities of home. Relax inside to unwind, kick back and watch a movie, surf the web via free wi-fi, curl up with a good book, open up a board game for a friendly challenge or share a drink with that special someone. Want some fresh country air? Lace-up those hiking boots and take like Camp Skullbones. . Enjoy the stars on the intimate deck with the glow from the gas fire pit.

Oct. 3 – 10

$218 CAD per night

Guest favourite

Home in University City

4.81 out of 5 average rating, 218 reviews

University City/STL Home, Centrally Location

A 3 bedroom/1 bath jewel in the center of everything STL. This safe, quaint home lays on a quiet tree lined cul de sec in University City, MO. This home is a 10 minute drive from Lambert Airport and central (10-15mins) to most popular attractions (zoo, forest park, aquarium, science center, arch), hospitals( barnes, SSM, SLU ) , and colleges ( Wash U, SLU, Fontbonne, Harris Stowe, Webster) in STL . Thanks for looking and safe travels

Sep. 7 – 14

$154 CAD per night