Pet-friendly holiday rentals in Waynesville

Charming 2 bedroom home - The Winchester.

Experience comfort and charm at The Winchester, a beautifully restored 1930s ranch bungalow nestled on a peaceful street in historic St. James. Just a short walk from St. James Park, it offers the perfect blend of relaxation and adventure. Explore the breathtaking Maramec Park and rivers, or enjoy nearby golf courses, pickleball, wineries, shopping, biking, and hiking trails. Whether you're here for a quiet retreat or an action-packed getaway, The Winchester is your ideal home away from home!

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.

Family-Friendly 4BR | 5 min to Fort Leonard Wood

Stay 5 minutes from Fort Leonard Wood’s main gate in this spacious 4-bedroom home designed for families, graduation visits, and military travel. Relax on the private deck, grill dinner in the fenced backyard, and start your morning with fresh coffee from the complimentary coffee bar. Why Guests Love This Home ✔ 5 minutes to Fort Leonard Wood main gate ✔ Spacious 4-bedroom layout for families & groups ✔ Fully fenced backyard ✔ Private deck with propane grill ✔ Coffee bar ✔ Quiet neighborhood

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.”

Charming Craftsman

Beautifully remodeled 40s home with lots of original character. This single family home is perfect for a small town stay, yet close to Lake of the Ozarks, Fort Leonard Wood, and Springfield. Or vacation here to enjoy our beautiful state parks like Bennett Springs or Ha Ha Tonka. The space Entire house 1000 sq ft 2 bed 1 bath with basement. Private driveway, Central heat and air, custom kitchen cabinets, brand new appliances and windows, everything has been freshly painted inside and out

White Pine Lodge

Nestled in the woods, just a quick 5 minute drive to Bennett Spring State Park, this brand new cabin features a full living room, bedroom, kitchen, laundry area, and outdoor fire pit and grilling space. White Pine Lodge is located close enough to several outdoor activities to keep you busy, but off the grid enough to provide some peace and relaxation. There is a full coffee bar, stocked with coffee, tea, and hot chocolate. Queen size bed, full size hideaway. Wi-Fi Internet & smart TVs!

Home away from Home

Reconnect with loved ones in this family-friendly place just minutes from Fort LeonardWood. Close to the Gasconade river, Mark Twain National Forest, and a short drive to Lake of the Ozarks and Bennet Springs state park. 3 cozy bedroom's, 1 king, 1 queen, 2 twin beds, and 2 full bathrooms. With a fenced in backyard for your furry family members. Outdoor fire pit with firewood included. Trampoline with enclosure, swings, and hammock for an outdoors retreat away.

Maggie's Modern MEGA YURT (30ft)

30 ft YURT with a loft and all the luxuries of a home (including HEAT and AIR)! This unique space is situated on our 50 acre farm with miles of trails and plenty of privacy. This is not your ordinary tent! This is glamping at its best with a full kitchen, regular plumbing, climate control and all the comforts of home. Keep in mind, we list this as 2 bedrooms but the 2nd bedroom is a open loft area and not private. You will love your stay in Maggie's MEGA Yurt!

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.

Cozy two bed cottage near park, S&T & Fort Wood

Step into this fully restored 1950s cottage for the perfect relaxing getaway. Located in Green Acres park with walking trails nearby. Just a short distance to downtown, Fugitive Beach, MS&T campus, Fort Leonard Wood, wineries, and much more! Enjoy this cozy home with your family or pets. Stylishly designed with old world elegance, this home features all of the luxury comforts you'd expect.

Julie's Place on Rt 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.

Route 66 Cottage Near Wineries•Firepit & Parking

Enjoy a clean, warm, cozy, comfortable stay in this renovated 2-bed, 1-bath home in historic Saint James, ideal for families, friends, and pets. Unwind around the outdoor fire pit or explore nearby shops, Leatherwood Cigar Lounge, and Sybill’s. Just minutes from Maramec Springs, Forest City Bike Trail, Rolla MS&T, and Fort Leonard Wood.