Vacation Rentals By Owner In Waterloo, IL

Welcome to a home where comfort meets calm.brbrThis thoughtfully designed 5-bedroom, 4.5-bath retreat offers two master bedrooms featuring King sized beds and attached private bathrooms. This home offers generous space for families and groups who value privacy, quality time, and a serene setting while still being close to stores and restaurants. Just an 8-minute drive to downtown Waterloo or a 38-minute drive to downtown St. Louis, this home can be your sanctuary after long days of exploring. Whether you're planning a holiday gathering, multi-generational trip, or long weekend escape, the layout allows everyone to spread out while still coming together with ease.brbrThe expansive living areas invite movie nights, card games, and unhurried conversations. The fully equipped kitchen makes preparing meals simple and enjoyable—perfect for guests who prefer dining in together.brbrStep outside and unwind in the hot tub, surrounded by peaceful private wooded views and fresh air. Guests often share how “at home” they feel here—comfortable, relaxed, and cared for.brbrTwo bedrooms share a bath, while the remaining bedrooms offer their own bathroom, creating a balanced blend of privacy and connection.brbrPets are welcome, because we know they’re part of the family.brbrLocated in a quiet, friendly neighborhood, you’ll enjoy the calm of a retreat while remaining conveniently close to restaurants, shopping, and local attractions.brbrMain Living Areas:brThe open-plan main floor is the heart of the home, featuring a cozy living room. A second living room in the basement with an electric fireplace provides even more space to spread out. For those mixing work with pleasure, a dedicated office brprovides a quiet space to focus.brbrEntertainment & Work:br High-Speed WiFibr 4 Smart TVsbr Dedicated office/work areabr Collection of books and board gamesbr PianobrbrKitchen & Dining:brYour inner chef will love the modern, fully equipped kitchen. The dining table seats 8-10, with additional seating for 6 at the large kitchen island.br Stainless steel appliancesbr Air fryer, crockpot, and waffle ironbr Ninja coffee maker (drip and Keurig compatible)brbrBedrooms & Bathrooms:brWith five uniquely decorated bedrooms and a pull-out couch, everyone can find their private corner. The home includes four and a half bathrooms, all fully stocked with essentials.br Bedroom 1: Queen Bed and Twin Bedbr Bedroom 2 (Primary Suite): King Bedbr Bedroom 3: Queen Bedbr Bedroom 4: Queen Bedbr Bedroom 5 (Second Suite): King Bedbr Additional: Comfortable pull-out couch in a living areabrbrOutdoor Living:brStep outside to enjoy your private wooded backyard.br Brand new 5-person hot tubbr Deck with a grillbr Covered patio with a sectional sofabr Three-season room for enjoying the outdoors in comfortbrGas fire pit for evening gatheringsbrbrAdditional Amenities:br Full-size washer and dryerbr Walk-in closets with hangers

Serene 5BR Retreat w/ Hot Tub & Privacy

Waterloo, Illinois, United States

Bed

Bath

Sleeps

$338.05

Just steps from downtown nightlife, restaurants, and shops! We’re right next door to the brand-new Coffee Girl, owned by local star Alexandra Kay, who once lived right here in The Loft on South Main. You’ll even be making coffee in the same kitchens she did!brbr*Rooftop deck with cabana & fire pitbr*Bridal suite with makeup stations, LED mirror, and full-length mirrors.br*Shuffleboard, foosball, and board games.br*Spacious 2 bedrooms, 2 bathrooms, plus a pull-out bed in the bridal suite.brbrArriving early in the day or leaving late Ask about our half-day add-on, if our calendar allows it.brbrSleeping Arrangements:brbr-BEDROOM #1: 1 King Bedbr-BEDROOM #2: 2 Queen Bedsbr-BRIDAL SUITE: 1 Pull-Out Bedbr-Cot Available: For additional comfortable sleepingbrbrTraveling with a group We’ve got options! We have two cottages right next door to each other, one pink and the other a speakeasy. Perfect to book together while still giving everyone their own space, just a block away. Check out Rosé Off Main and The Barrel under my profile.brbrKey Amenities:brbrROOFTOP DECK – For maximum seating and comfort, our rooftop deck features a cozy sectional and a stylish cabana. To keep everything clean and dry for our next guest, all cushions are stored indoors when not in use. To enhance your experience, we supply propane for the firepit and ensure at least half a tank is available for each guest's stay.brbrKITCHEN – Stainless steel appliances, dishes, cookware, air fryer, crockpots, toaster, blender, waffle iron, coffee maker (ninja), chemex, and so much morebrbrDINNINGROOM – Seats up to 8 guests comfortably. We have another table in the kitchen that will fit 4 guest as well.brbrTWO BATHROOMS – Both fully stocked with essentials.brbrBRIDAL SUITE – A dedicated space for getting ready, complete with a large makeup vanity, led mirror, full length mirror, and pull-out bed for extra sleeping accommodations.brbrGAMES– Enjoy shuffleboard, foosball, and a variety of board games.brbr-2,280 sqftbr-High-Speed WiFi br-3 Smart TV's – Stream your favorite shows and movies.brbrLocation Highlights:br-Waterloo has been named one of the safest towns in Illinois, and we're located just half a block from the police station for added peace of mind.brbr-Walking distance to local restaurants, nightlife, and shops on South Main Street.brbr-Close to Stubborn German Brewing Company, Hopskeller Brewing Company, Vintage Wine Bar, and RRR Bar.brbr-Easy access to parks, trails, and Waterloo’s best attractions.brbr-4 miles from Annbriar and many other golf coursesbrbr-36 miles from Scott Air Force Basebrbr-27 miles to downtown St. Louis We encourage all guests to purchase travel insurance to guard against unforeseen circumstances. *No refunds for weather/natural disasters/power outages/other things that are beyond our control.

Apartment

Firepit, Rooftop deck, Games & Bridal Suite and right next to The Coffee Girl

Waterloo, Illinois, United States

Bed

Bath

Sleeps

$249.78

Step into The Barrel, a dark, moody, speakeasy-inspired retreat just one block off South Main. Walk to Waterloo’s best shops, dining, and local favorites. Perfect for couples, guys’ trips, weekend getaways, or anyone who loves unique, boutique-style stays.brbrNew listing, same five-star hospitality! Check out reviews from our other property to see why guests love booking with us.brbrWant a little extra time to unwind Ask about early arrival or late checkout options.brThe spacebrThis two-bedroom, one-bath hideaway features rich green tones, curated décor, warm lighting, and vintage-inspired details that create an intimate, atmospheric escape. Thoughtfully designed to feel like a hidden gem just off South Main.brbrGuest access-brGuests will enjoy full access to the entire property and will receive a personalized door code prior to check-in for seamless entry.brbrOther things to note-brSleeping Arrangementsbrbr• Bedroom 1: King bedbr• Bedroom 2: Queen bedbrbrKey Amenitiesbrbr• Fully equipped kitchen with stainless appliances, cookware, Keurig, toaster, blender, and waffle ironbr• Cozy living area with speakeasy-style ambiancebr• Seating for 3 at the kitchen bar + 3 at the custom barrel tablebr• Bathroom with plush towels, towel warmer, and essentialsbr• Outdoor patio with dining table and chairsbr• High-speed private WiFibr• 3 Smart TVsbr• Private off-street parkingbrbrTraveling with a group We’ve got options! Our pink cottage is right next door perfect to book together while still giving everyone their own space. We also have a larger property just one block away that sleeps 8. Check out Rosé Off Main and The Loft on South Main under my profile.brbrLocation HighlightsbrWaterloo is known as one of the safest towns in Illinois—with The Barrel located just one block from the police station for added peace of mind.brbrWalk to Waterloo favorites:br• Stubborn German Brewing Companybr• Hopskeller Brewing Companybr• Vintage Wine Barbr• RRR BarbrbrClose to parks, trails, boutique shops, and top attractions:br• 4 miles to Annbriar Golf Coursebr• 36 miles to Scott Air Force Basebr• 27 miles to downtown St. Louis

Speakeasy Cottage in downtown Waterloo

Waterloo, Illinois, United States

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Bath

Sleeps

$134.48

Nestled in the heart of a safe community in Waterloo, this quiet and cozy setting will be a great place to unwind after a hard day`s work, a long day of shopping, or a night out on the town. Your private suite, one of sixteen, features a sitting area, kitchenette with a mini fridge, microwave and a private bathroom with shower. Common areas are shared with others.brThis is a smoke free campus.

Bed & Breakfast

Waterloo Suites King

Waterloo, Illinois, United States

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Bath

Sleeps

$131.18

Nestled in the heart of a safe community in Waterloo, this quiet and cozy setting will be a great place to unwind after a hard day`s work, a long day of shopping, or a night out on the town. Your private suite, one of sixteen, features a sitting area, kitchenette with a mini fridge, microwave and a private bathroom with shower.

Bed & Breakfast

Waterloo Suites Double

Waterloo, Illinois, United States

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Bath

Sleeps

$242.27

Newly renovated 3BR/1BA w/loft workspace/bridal-ready glam 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. Multiple full-length & lighted makeup mirrors. Relax in shaded backyard w/firepit, seating & grill. Quiet neighborhood w/ample free parking, near parks, trails, wineries, breweries, shops & dining. Walk ½ mile to The Coffee Girl & steps to Oh Sugar! Ice & Cream, close to festivals & nightlife, 30 mins to STL & Scott AFB.

The Yellow Haus, close to downtown Waterloo!

Waterloo, Illinois, United States

Bed

Bath

Sleeps

$250.08

Walk to Waterloo’s cutest shops, dining & local favorites from our charming pink cottage! Perfect for girls’ trips, weekends away, or just a fun stay in the heart of town.brbrNew listing, same five-star hospitality! Check out our other property’s reviews to see what guests love about staying with us.brbrLooking for a little extra time Ask about our early arrival/late checkout add-on!brbrbrRose Off Main is a charming two-bedroom, one-bath cottage with a cozy outdoor patio and private off-street parking. From pink doors to floral touches, every detail was designed with love, elegance, and a little inspiration from my grandmother.brbrSleeping ArrangementsbrbrBedroom 1: King BedbrbrBedroom 2: Queen BedbrbrLiving Room- CouchbrbrbrTraveling with a group We’ve got options! Our speakeasy-style cottage is right next door perfect to book together while still giving everyone their own space. We also have a larger property just one block away that sleeps 8. Check out The Barrel Off Main and The Loft on South Main under my profile.brbrKey AmenitiesbrbrPatio – Designed for comfort and relaxation, our patio includes a cozy couch, hammock, and dining table with an umbrella. To keep everything clean and fresh for our next guests, all cushions are stored indoors when not in use. brbrKitchen – Fully equipped with stainless steel appliances, dishes, cookware, toaster, blender, waffle iron, and a Keurig coffee maker. Plus plenty more for home-style cooking.brbrDining – Seats up to 4 guests at the kitchen bar and 4 more at the outdoor dining table.brbrBathroom – Stocked with all essentials for your convenience.brbrParking – Private off-street parking is available for your ease and convenience.brbrHigh-speed WiFibrbr3 Smart TVs – Stream all your favorite shows and moviesbrbrLocation HighlightsbrbrWaterloo has been named one of the safest towns in Illinois, and the home is located just over a block from the police station for added peace of mind.brbrWalking distance to local restaurants, nightlife, and shops.brbrClose to Stubborn German Brewing Company, Hopskeller Brewing Company, Vintage Wine Bar, and RRR Bar.brbrEasy access to parks, trails, and Waterloo’s top attractions.brbr4 miles from Annbriar Golf Course (plus several others nearby).brbr36 miles to Scott Air Force Base.brbr27 miles to downtown St. Louis.

Charming 2-bedroom cottage with Patio in Downtown Waterloo

Waterloo, Illinois, United States

Bed

Bath

Sleeps

$235.33

Doc’s Farmhouse is the perfect destination for those who want to enjoy the country and nature, yet still be close to the city, located 30 minutes from Downtown St. Louis, 5 mins from the historic town of Waterloo. Enjoy your time at our comfy 2,000 sq ft house with attached garage. Relax in the sunroom and be prepared to view wildlife such as deer, turkey and more! You have access to WIFI, Roku, fully equipped kitchen, coffee supplies, bed linens, towels, fire pit, BBQ grill, fishing poles and more. brbrEnjoy our Mid-19th Century Farmhouse architecture built in 1844, previously owned by Doctor Fleming & family. There is one bedroom with a queen bed on the main floor. Be prepared for a half flight of stairs as you enter the home, as well as a flight of stairs leading up to the additional 3 bedrooms on the second story. There are plenty of extra towels, washcloths and blankets available to make your stay comfortable. We are pet free on the inside of the house, but we have cats and a dog that may greet you when outside.brbrTake in some old photos and articles located throughout the house giving you a glimpse of what life was like in the late 1800’s and early 1900’s.brbr*Limit a max of 12 people on the property during the day. *Party and events are not allowed.brbr•Fast wifibr•Roku TV/Streaming servicesbr•Keurig Pot/Pods (Ground Coffee & K-Cups Available)brbrIf you're a hot sleeper there are extra fans throughout the house for your comfort.brbrPlease verify your guest count prior to booking, to prevent any additional fees assessed during your stay. Extra guest fees are applied after 4 guests.brbrIf you enjoy golf, we suggest you visit Annbriar Golf Course, a #1 ranked golf course in Illinois, less than a mile away. You may want to consider calling ahead for reservations, just in case.brbrVisit us on FB at Doc's Farmhouse Vacation Rental to find more things to do in Monroe County, IL and surrounding area.brbrAll illegal substances are strictly prohibited.brbr

Doc's Farmhouse, Historic 1844 Home

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Sleeps

$126.12

This cozy one room log cabin was built in 1953 and is located in a friendly Illinois town that is part of St. Louis metro area. You can walk to town (restaurants, craft breweries, wine bar, shops, 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.brbrA log framed king bed plus double log framed futon will sleep 3 guests. (Mostly used by couples looking for a getaway or a business person seeking a quiet, comfortable retreat.) The newly rennovated bathroom has a shower. Kitchen features granite counter top with 4 bar stools. Stocked with kitchen appliances, cooking & dining items, bed linens and towels. Free WiFi & premium cable TV, dvd player. Parking for 2 cars and driveway through property from main street to back alley/side street. brbrAcross street from historic stage coach stop, Peterstown House. Summer Tuesday night band concerts and Sunday concert series at town square. Area public golf courses, parks, wineries. Grocery, & other stores and services nearby. Easy drive to downtown St. Louis and larger shopping centers. Close to 255, I-55, I-44, I-64 & I-70brbrDog-friendly (with homeowner approval) Children over age 12.br** Our property is protected by external security cameras. We also have a security / automation system that works with the door locks, smoke detectors, thermostat, and other devices.

Cabin

Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis

Waterloo, Illinois, United States

Bed

Bath

Sleeps

$362.43

Discover this newly renovated Modern 3-bedroom gem in Waterloo. This charming cottage offers a blend of comfort and luxury with 3 king beds, 2 Spa-style bathrooms, and plenty of space for outdoor entertaining. Each bedroom has its own vanity, large closets, and charging station. The kitchen is designed for both beauty and functionality. Featuring new appliances, ample cabinet space stocked for your convenience, this practical kitchen has everything you need for those who enjoy cooking. Our outdoor space provides additional amenities, including a sectional and firepit that are the perfect place to relax and enjoy the stars. Additionally, you will have an outdoor grill, griddle, and prep station fully stocked with more dinnerware for outdoor entertaining. Did we mention all the outdoor games and T.V.! Our location is one of our favorite parts about the home. At the Robin you are just steps from downtown Waterloo making it easy to walk to nearby restaurants, shops, and bars.

Luxury 3BR Cottage, King Beds, Spa-Style Baths and Outdoor Oasis

Waterloo, Illinois, United States

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Bath

Sleeps

$200.64

Welcome to Salt & Honey Cottage, a cozy and inviting home in the heart of Waterloo, Illinois—perfect for couples, families, or a relaxing weekend getaway.brbrOne of the best parts of staying here is the location. The cottage is just a short walk to Salt & Honey Bistro, a local favorite for coffee, breakfast, lunch, and events. Guests love being able to stroll over for a morning latte or a relaxing meal without needing to drive.brbrInside, the cottage offers comfortable living spaces designed for relaxing or getting a little work done if needed. The living room includes a Smart TV for streaming your favorite shows and a large table that works great for dining, games, or as a workspace for guests working remotely.brbrUpstairs you'll find a fun bunk room that’s perfect for kids or groups, featuring two sets of twin bunk beds (sleeping four) along with another Smart TV, making it a great space for movies, games, or winding down after a full day.brbrStep outside and enjoy the private fenced backyard, perfect for relaxing or spending time with family and pets. The outdoor space includes:br• Comfortable outdoor seatingbr• Gas grill for cooking outbr• Fire pit for evenings under the starsbr• Fully fenced yard for kids and dogs to play safelybrbrWe are also pet friendly, so your four-legged family members are welcome to join the trip.brbrStart your mornings the slow way with coffee on the front porch rocking chairs, enjoying the quiet neighborhood before heading out to explore Waterloo.brbrWhether you're visiting for a weekend getaway, family event, or just passing through, Salt & Honey Cottage offers a peaceful stay within walking distance of great food and local charm.

Salt & Honey Cottage Walk to Dining & Pet Friendly

Waterloo, Illinois, United States

Bed

Bath

Sleeps

$194.29