Vacation rentals in Monroe County

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Top-rated vacation rentals in Monroe County

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

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Top guest favorite

A well-organized bathroom features a modern vanity with a round mirror and stylish lighting. Soft towels are neatly arranged on a nearby shelf. The space is brightened by neutral wall tones and a soothing tile floor, creating a calm environment.

Home in Millstadt

4.95 out of 5 average rating, 314 reviews

Deluxe Barndominium | King bed + Pkg

Enjoy the unique historical setting of this recently remodeled Barndominium, just 5min away from DT Millstadt and 20min from DT St. Louis. Learn the old Illinois ways by relaxing in a contemporary decorated barn that was once an honor system farm stand. Blend of comfort, stylish décor & a rich amenity list are there to satisfy your every need. ✔ 2 Comfy Bedrooms (King Bed, Single over Double Bunk) ✔ Fully Equipped Kitchen ✔ Open Living Area ✔ 55’’ Flat-Screen TV ✔ Fast internet See more below

Top guest favorite

A comfortable sectional is arranged around a fire pit with decorative stones, set against a backdrop of a white brick wall featuring the property's name. The outdoor space is designed for relaxation and socializing.

Loft in Waterloo

5 out of 5 average rating, 22 reviews

Firepit, Rooftop, Glam room—Next to Coffee Girl

Just steps from downtown nightlife, restaurants & shops! We’re right next door to the brand‑new Coffee Girl, owned by local star Alexandra Kay—who once lived here at The Loft on South Main. *Rooftop deck with cabana & fire pit *Bridal suite with makeup stations, LED mirror, full‑length mirrors *Shuffleboard, foosball & board games *2,280 sq ft: 2 bedrooms, 2 baths, plus a pull‑out bed in the bridal suite. Arriving early or leaving late? Ask about our half‑day add‑on, calendar permitting. 

Top guest favorite

An open-concept living area showcases a modern kitchen with a large island and dark cabinetry, complemented by wood accents and warm lighting. The space includes a dining area with a light-colored table set for six, and a cozy seating arrangement near a stone fireplace.

Home in Columbia

4.93 out of 5 average rating, 58 reviews

Bluff View House

Beautiful, peaceful setting nestled between the bluff cliffs, looking over the river bottoms. Great outside deck and great place to watch the sunsets. 6 minutes out of Columbia, il. and just 20 minutes from Busch Stadium and within 40 minutes of St. Louis attractions. The house is set up just like home with all the amenities you need to relax. Full kitchen, outside grill, washer and dryer, two car garage, nice shaded driveway and parking area. Nice bathroom with soaker tub and shower.

Top guest favorite

Farm stay in Bloomsdale

4.95 out of 5 average rating, 151 reviews

FUNKS INN-no extra guest fees or cleaning fee

This house was built in 1870, it is a stone structure and was used as a family farm home. It has been remodeled for its use today. It is historically correct, which includes antiques of the time. Post Civil War era, furniture including the beds of this period. Another interesting aspect, is that the floors are all original. Mattresses, blankets pillows, bedding and towels are all new. The wine cellar that we have added, made on location. I always leave some out for guests. No fee.

Guest favorite

A wooden cabinet displays a textured cream-colored plant pot containing a vibrant green aloe vera plant. A terracotta pot with lush fern foliage and a small photo frame are positioned nearby, adding natural elements to the warm interior space.

Apartment in Columbia

4.97 out of 5 average rating, 122 reviews

Charming Apartment in Historical Small Town by STL

Hello and welcome! Nestled in the quaint small town of Columbia, you'll feel perfectly at ease in the quiet of this peaceful area. If it's the city attractions you're looking for, you will be a 15-20 minute drive from downtown. This area is also full of natural and historical attractions, such as Cahokia Mounds, Fort de Chartres, Illinois Caverns, nature preserves, hiking trails and more! The apartment itself is in a cozy historical building next door to a year round farmer's market.

Top guest favorite

A living area is depicted with a neutral-toned sofa and two armchairs, arranged around a black coffee table. The wall features three decorative mirrors that enhance the space, while a stylish area rug adds warmth. Black-framed double doors lead to another room, and greenery is present in the decor.

Home in Waterloo

4.98 out of 5 average rating, 131 reviews

The Ruby/Close to St. Louis and Waterloo Downtown

Welcome to The O'Bannon House in Waterloo, IL, where we offer the best of both worlds! The city limits of St Louis are only about 17 miles away, yet we are located within walking distance of all that the idyllic town of Waterloo offers: great restaurants, shops, and breweries. Enjoy our coffee bar, a fully-equipped kitchen, and a park-like backyard with a fire pit. If you have a larger group, consider booking this unit (The Ruby) and the soon-to-open upstairs unit (The Hugh)!

Top guest favorite

A charming brick cottage is situated along a brick-lined street, adorned with vibrant greenery and flowering plants. The entrance features a light green door framed by lush plants, while large windows provide a glimpse of the inviting interior.

Cottage in Belleville

4.96 out of 5 average rating, 465 reviews

The Historic Garfield Inn

Welcome to the Garfield Inn. A cozy cottage off a brick-lined street in an historic Belleville neighborhood. Coffee, tea, hot cider and chocolate are provided. We are in walking distance to downtown Belleville, and free parking is available. The neighborhood is quiet and peaceful. There is a barbeque grill, covered back patio, gazebo and lovely gardens. Small well-behaved dogs are welcome. Enjoy your privacy The light is always on. We can't wait to see you.

Superhost

A simple entry door is positioned within a red brick wall. The door is light gray with a six-panel design and a lockbox to the right. A doormat rests in front of the door, and wooden steps lead up to the entrance.

Apartment in Belleville

4.75 out of 5 average rating, 128 reviews

Eskimo Inn Studio Apartment

"Come on without, come on within" welcome to Quinn Hospitality. Studio apartment with a Queen size bed and Queen pullout. Fully functional kitchen along with a bbq put outside for your use. Walking distance to downtown Belleville 15 min to SAFB 20 min diwntown STL Please be courteous to our permanent tenants in the building. This is not a party hosting spot. There are surveillance cameras, and we ask that quiet hours after 10 pm.

Superhost

A modern kitchen space is presented, featuring sleek cabinetry and stainless steel appliances. Pendant lights hang above a central island with seating. A round dining table is situated nearby, accompanied by four chairs. Soft, natural light filters in, highlighting the textured, neutral brick walls.

Home in Waterloo

4.85 out of 5 average rating, 68 reviews

Urban Loo Cottage

Welcome to the Urban Loo, part of the Off Main Gasthauses! Your family will be close to everything when you stay at this centrally-located place. Just feet away from all of the downtown attractions, you’re sure to enjoy your stay! This newly renovated home is little and cozy but sure to make you feel right at home. There is a front porch to enjoy your morning coffee and a back patio to wind down after your night around town.

Top guest favorite

A well-organized bathroom features a countertop with toiletries and a sink, complemented by two mirrors mounted above. White towels hang on a rack, and shelves hold additional necessities, all framed by light yellow walls and decorative accents.

Guesthouse in St. Louis

4.99 out of 5 average rating, 645 reviews

Cozy Barndominium Loft in Friendly Neighborhood

A modern, but cozy, 562-sq.-ft. loft apartment with full kitchen and bath, queen bed (with a Winkbeds Luxury Firm mattress)a twin Murphy Bed / desk, living room, walk-in closet, FireStick, Roku, DVD player, WiFi and more. Note that the barn is in our back yard and part of our home, so our rules are different than what you may find elsewhere. Please be sure to read everything to make sure you get the experience you seek.

Guest favorite

An outdoor seating area is presented with four wicker chairs, each featuring colorful cushions. A glass-top coffee table is placed in the center, surrounded by a brick patio. Greenery is visible in the background, adding a natural touch to the space.

Home in Waterloo

4.88 out of 5 average rating, 68 reviews

Haus on Main

We are 25 minutes away from downtown St. Louis. This house gives all the convenience of being close to the city, while still keeping that small town vibe. We are within walking distance of multiple restaurants, breweries, and a wonderful coffee shop. This house has three separate bedrooms that will all accommodate two people each. There are also two living areas, one has a pull out couch and the other has a futon.

Guest favorite

A rustic log cabin is nestled among lush green trees, showcasing a simple facade with a brown shingled roof. Outdoor seating is provided under a large umbrella, accompanied by a wooden dining table and chairs, set against a backdrop of a well-maintained yard.

Cabin in Waterloo

4.91 out of 5 average rating, 143 reviews

Cozy 1953 Countryside Log Cabin Minutes to STL

This one room log cabin was built in 1953 and is located in a safe, friendly Illinois town that is part of St. Louis metro area. You can walk to town (restaurants, craft breweries, concerts, plays) and you're still close to St.Louis attractions. Why fight traffic and worry about parking or safety? Guests love our clean and tranquil cabin and the welcoming town of Waterloo.