Holiday rentals in Monroe County

The Farmhouse

Be our guests & keep it simple at a peaceful, centrally-located, completely remodeled 1920s Farmhouse. The home has been lovingly cared for by our family for OVER 100 years! Unique experience to stay on a farm in Grandma & Grandpa's house. 3 Bed, 1 Bath, 1.5 Story FARMHOUSE - 1/2 way between Columbia & Waterloo. 9 minutes to St. Louis, 17 min to the Arch, 5 min to Walmart, 17 miles to a Hospital. Downtown Waterloo & Columbia minutes away. Situated on our family farm in the PERFECT LOCATION!

Luxury Loft in The Loo

Experience the charm of Waterloo in this brand new luxurious loft nestled in the heart of downtown. With its prime location within walking distance of shops, entertainment & restaurants, you'll have everything you need for a memorable stay. Whether you're seeking a romantic getaway, girls or guys night out, weekend get away, family stay, extended stay, or you just want to immerse yourself in the vibrant atmosphere of Waterloo's street festivals, this loft (stairs) provides the perfect retreat.

The Brickhouse

Nestled right in the heart of downtown Waterloo, The Brickhouse is a cozy, eclectic getaway just blocks from all of the local restaurants, bars, and adorable shops ready to serve you. With two bedrooms, Brickhouse has one king size bed, four twin beds, and a pull out queen sized sofa to sleep up to 8 guests. Brickhouse has a kitchen stocked with all of the essentials you will need to cook meals. Other amenities include wifi, a 55' high definition TV, washer and dryer, and toiletries provided.

The Yellow Haus, close to downtown Waterloo!

Renovated 3BR/1BA w/workspace/bridal-ready makeup area. Sleeps 7 (2 queens, 3 twins). Ideal for groups & wedding stays. Features refinished wood floors, stocked kitchen, dining for 6, coffee bar, WiFi & 3 Smart TVs. Family-friendly w/pack n play, high chair & baby bath. Full-length & lighted makeup mirrors. Relax in shaded yard w/firepit, seating & grill. Quiet area w/ample parking, near parks, trails, wineries, breweries, shops & dining. Walk ½ mile to downtown. 30 mins to STL & Scott AFB.

Downtown Kimmswick~ Studio~ Newly Renovated

This condo has EVERYTHING you need for a fun getaway to Kimmswick! This studio condo is located right in the heart of Kimmswick, just steps away from festivals & the famous Mile High Pie at Blue Owl Bakery! •Walk Downtown •Fire Pit •BBQ •Cozy Studio Layout •Queen Bed •Kitchenette w/ Oven, Stove, Fridge/Freezer, Coffee Maker •Bathroom w/ Walk-In Shower •Parking for 2 Cars •Walking Distance to Apple Butter Festival & LaChance Winery •25 Min. to St. Louis •0.3 Miles from Port of Kimmswick

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.

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.

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. If you have a larger group, consider booking this unit (The Ruby) and the upstairs unit (The Hugh) so you can all stay in one place!

Lodge at Pine Lake - Hot tub, lake, pets welcome

Rooted by the water. Open to adventure. A place to slow down, reconnect, and make memories that last. Relax at Lodge at Pine Lake, a private two-bedroom retreat just 30 minutes from downtown St. Louis. Enjoy a full kitchen, Sleep Number bed, Smart TV, Wi-Fi, dedicated workspace, fire pit, gas grill, outdoor shower, and a private hot tub overlooking the lake. Pet-friendly, with catch-and-release fishing and watercraft plus nearby attractions. More than 2 guests and pets extra fee.

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.

Deluxe Barndominium | King bed + Pkg

Enjoy a family- and pet-friendly stay in this beautifully remodeled barndominium just 5 minutes from downtown Millstadt and 20 minutes from downtown St. Louis. This charming retreat blends modern comfort with history, set in a restored barn that once served as an honor-system farm stand. Perfect for families, it offers 2 bedrooms (King bed and single-over-double bunk), a fully equipped kitchen, open living area, 55” TV, and fast internet. See more below

The Loft

This unique and spacious upstairs Loft boasts 1900 sq. ft. of historical charm. Located a couple walking blocks from restaurants, brewery/bars, coffee shop, boutiques and beautiful downtown Red Bud. Conveniently located on Route 3. Free private parking on premises at the entrance to the Loft. Programmable keyless entry. Enjoy the fully-equipped kitchen and cozy seating areas. Comfortably sleeps four.