Vacation rentals in Waynesville

4.95 out of 5 average rating, 153 reviews

Cozy House On The HILL 10 Min from Ft. LeonardWood

We are located at the historical Rt 66 while only being 10 min from the main gate of Fort Leonard Wood. It is also walking distance to natural springs, trails, historic museums, gift shops, bars, restaurants, playgrounds, and so much more. We are a military family and know how much it means to be with your Soldier. Here you can relax, cook, play some games, sit outside and admire the remarkable view as well as the sunrises and sunsets. Don't feel like cooking, there are plenty options close by.

5 out of 5 average rating, 5 reviews

Charming Cottage-12 miles to FLW. Low Cleaning Fee

Welcome to The Nest. Perched on a scenic hillside, this charming and historic 1940's home with original wooden floors, offers a peaceful escape with stunning views of a sprawling field dotted with cows and a meandering river. Just a short stroll away is the heart of downtown, local dining and boutique shopping. Inside, slip into one of our soft, spa-quality robes and sink into bed with our luxurious linens. This is more than just a place to stay—it’s an experience. We can't wait to host you!

Tiny homes in Waynesville

4.98 out of 5 average rating, 234 reviews

Tiny Home with Hot Tub Near Ft. Leonard Wood!

Experience the best of the Ozarks with a stay at this charming vacation rental home. This warm retreat boasts a large outdoor rec area, a well-appointed interior, a fully equipped kitchen with complimentary coffee & tea, and is a short 10-12 minute drive to Ft. Leonard Wood. In the heart of Pulaski County, this lodge is minutes away from the Roubidoux park/riverside walking trails, Old Stagecoach Stop, Hoppers Pub and Frog Rock. Head back home for an evening soak in the hot tub under the stars.

4.97 out of 5 average rating, 220 reviews

Cottage in Rolla

Charming Victorian

The furnishings are Victorian-modern and beautifully accent the high ceilings, tall windows, and lovely wood trim throughout the home. After enjoying the beautiful outdoors, curl up in front of a toasty fire, and watch your 55" Roku Smart TV (be sure to bring your login information for your favorite streaming apps!). The Victorian is not suitable for children. For family-friendly stays, check out our other AirBNB listings: “Breathtaking Blacksmith Bungalow,” and the “Exquisite Log Cabin.”

4.83 out of 5 average rating, 109 reviews

Apartment in Waynesville

Affordable Apt w balcony near Ft Leonard Wood

Get you kicks on Route 66! Enjoy easy access to everything from this centrally located downtown apartment on Route 66. Shops, restaurants and bars are a short walk away. Enjoy fishing in the Roubidoux spring, a walk in the waynesville city park, visit museums or explore nearby trails. We are approx 5 miles from Fort Leonard Wood. The apartment is secured with no public access to the individual units. Guests must be buzzed in. Be our guest! The unit is smoke & pet free. NO smoking allowed

4.99 out of 5 average rating, 113 reviews

Cabin in Dixon

Cabin in the Sky

Take it easy at this unique and tranquil getaway overlooking the breathtaking Gasconade river valley. This cabin has many features and was specifically designed to accommodate the view. Large outdoor space with dining table, grill and extra seating. Close proximity to Fort Leonard Wood. Also minutes from public boat ramp and public hunting land. Interior features Wi-Fi-,full kitchen, laundry. Family friendly--kids are welcome. Several family-friendly activities nearby in St. Robert.

4.89 out of 5 average rating, 157 reviews

Cozy Home Near Ft. Leonard Wood

This house is perfect for creating memories as you attend that special Soldier's graduation. Enjoy our pool table, smart TVs (located in the living room and family den), Pacman Arcade, highspeed WIFI, etc. while being located only minutes away from Fort Leonard Wood. As military members ourselves we understand the rarity of family get togethers, and designed this place in hope that you would be able to fully enjoy those precious moments together.

4.97 out of 5 average rating, 139 reviews

Home in Lebanon

The Bungalow on Third

Nestled in a quiet urban oasis just a stone's throw from downtown, our practical, cozy, pet-friendly bungalow is the perfect spot. We've taken care to ensure your stay is as smooth as possible. Fresh linens, an abundance of towels, and a selection of toiletries are all provided for your convenience. The Bungalow is the place you've been seeking, conveniently close to downtown, with a full kitchen.

4.94 out of 5 average rating, 64 reviews

Ms Julie's on 66

Minutes to FLW, enjoy modern and stylish comfort on historic Rt 66 with easy access off I-44. This charming home offers a rare king bed sleeping option. Includes full kitchen with complimentary coffee, tea, and hot chocolate with 3 coffee making options. Comfortable work space for two, family games, large spacious yard with deck and park grill for visiting and enjoying good weather.

4.92 out of 5 average rating, 367 reviews

Cottage in Rolla

Historical Cottage with a shabby chic flair!

Historical cottage in neat country setting yet in town and close to everything you need. Quiet and secluded with covered front porch and lots of wildlife to enjoy. Open living area, spacious kitchen with work space, large full bathroom, main floor bedroom with a queen bed plus a small bed in the upstairs loft. Cute and clean! Near a park and the popular bike/walking trail.

Superhost

Cabin in Rolla

4.92 out of 5 average rating, 12 reviews

Chancen Way

Take it easy at this unique and tranquil getaway, nestled back into the forest. This cozy A-frame is the perfect place to reset and take in nature! Built in March 2025 boasting beautiful, rustic finishes, an abundance of natural light, a fire pit, trails, and we're just down the roadfrom Lane Springs and The Mark Twain National Forest. Book your stay today!