Vacation rentals in Osceola

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Top-rated vacation rentals in Osceola

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Guest favorite
A spacious living area is visible, featuring a cozy sofa and a patterned area rug. Natural light enters through several windows, illuminating the open layout, which includes a dining table and kitchen area in the background.
Home in Clinton
4.96 out of 5 average rating, 142 reviews

The Orchard House by Katy Trail

Dubbed the Orchard house since being on Orchard street. This newly renovated stand alone home on a quiet dead end road is just what the doctor ordered. Located just 2 miles to the start of the historic Katy Trail makes this a great spot. Also, we are only minutes away from Truman Lake which boasts some of the best crappie and spoonbill fishing around. A dedicated shed with lock is provided at the back of the home for bike storage. A short walk to the historic square with shopping + eateries!

Guest favorite
A screened-in porch features wooden walls and a rustic wooden ceiling, providing a cozy gathering space. Comfortable seating is arranged around a central table, while a standing heater adds warmth. Potted flowers and decorative cushions contribute to a welcoming environment amidst views of lush greenery.
Treehouse in Stockton
4.95 out of 5 average rating, 135 reviews

Rustic Elegance Treehouse Cabin Stockton Lake, MO

Rustic Elegance tops this Treehouse cabin just a mile from Stockton Lake Dam and 2.5 miles to Stockton Town Center. Enjoy total privacy in this wooded scene looking out over the neighbors cattle as well deer and turkey. Sitting on Bear Creek which is spring fed and a kayak is available to explore the creek for a small fee. Fire pit and Weber grill help round out your evenings pleasures. Grocery store, gas station, restaurants, and shopping are all within 10 minutes. Outside electric included.

Top guest favorite
The entrance to the home features a wooden deck with steps leading up to the front door, framed by two windows with green shutters. A metal sculpture of a child fishing stands beside the steps, with a decorative rocky landscape and lush plants below.
Home in Deepwater
4.96 out of 5 average rating, 114 reviews

A Cozy Getaway

Minutes away from Harry S. Truman Dam & Reservoir & the upper end of the Lake of the Ozarks. The lake is a popular fishing destination for crappie, largemouth bass, hybrid stripers, catfish, as well as some of the Nation's finest snagging for spoonbill paddlefish. The surrounding area (110,000 acres) provides plentiful & diverse opportunities, including hiking, horseback riding, golfing, biking, bonfires, bird watching, off-road vehicle adventures, & some of the best hunting in the country.

Guest favorite
A lively outdoor scene showcases a group of people enjoying a sunny day by the river. A picnic table and several blue chairs are arranged around a fire pit, surrounded by lush green trees. A child plays nearby, while smoke from the fire gently rises into the air.
Cottage in Stockton
4.89 out of 5 average rating, 9 reviews

Water’s Edge Cabin: King & Queen Beds (Cabin 4)

Cabin Four is super cozy, featuring a private sleeping loft and a picnic table & fire pit on the waters edge. Learn more about Cabin 4: Our cabins, are fully furnished, outfitted with full kitchens, bathrooms, heat and AC. You will have an amazing view of the Sac River from your bed, sofa, patio, and fire pit. Fishing, rafting, swimming & beautiful exploring opportunities abound all within walking distance. Explore our listing more to learn more about Cabin Four and Hideaway River Farm!!

Superhost
A hot tub is situated under a wooden gazebo, surrounded by a lattice design that allows for natural light. Dark steps provide easy access, and the interior of the tub is filled with clear water, creating an inviting space for relaxation.
Cabin in Pittsburg
4.84 out of 5 average rating, 172 reviews

Wolf Cub Cabin with Private Hot Tub!

The Wolf Cub is one of three cabins located near Pomme de Terre Lake. Reserve this one bedroom cabin for romantic getaway or all three for a group or family gathering. This Cabin has a beautiful fireplace inside and hot tub located in the gazebo off the back deck. Enjoy the hammock and fire pit in the back as well. This cabin is located with in walking distance to the lake where you can put your boat in, swim or fish. Sleeps up to four, full kitchen towels and gas/charcoal grill.

Top guest favorite
The cottage is nestled among dense trees, featuring a welcoming front porch with white railings. Large windows allow natural light to enter, while a set of stairs leads up to the entrance. The surrounding greenery creates a serene, secluded atmosphere.
Cottage in Wheatland
4.97 out of 5 average rating, 417 reviews

Cozy Woodland Cottage

This cozy cottage in the woods (completed in June 2017) is perfect for a couple seeking a romantic getaway, enjoying a honeymoon, or celebrating an anniversary. (The sofa is a full convertible bed, if others plan to share the 400+ sq. ft. space.) Located in the Lake Hill (formerly Shadow Lake) Golf Course neighborhood (course is currently closed) about a mile from the NW shores of beautiful Pomme de Terre Lake, and about 6 miles south of Lucas Oil Speedway.

Guest favorite
A modern cabin is positioned on a gravel driveway, surrounded by lush green trees. The exterior features a combination of wood and stone elements, with a covered porch and four sturdy columns enhancing the entrance. Natural light illuminates the windows on both sides.
Cabin in Deepwater
4.92 out of 5 average rating, 155 reviews

Truman Lake Cabin Super Clean "Private" Getaway!

Quiet serene location! Our personal cabin is located just 400 yards from Truman Lake. Short walk to the cove for wildlife viewing or Higgins' Landing boat launch is just across the highway, and has plenty of parking for vehicle/s, boat trailer, and great bank fishing. Clinton and Warsaw are a 30 min drive, and Iconium is a 12 min drive. Don't forget to look around in the lake feeder creeks, lot's of arrowheads in the area. We now have super fast WI-FI!

Guest favorite
A cozy bedroom features a spacious bed with striped linens and decorative pillows. A comfortable armchair and bedside tables with lamps are visible, enhancing the room's functionality. Natural light enters through small windows, adding brightness to the neutral color palette.
Home in Appleton City
4.97 out of 5 average rating, 237 reviews

Tiny Cottage

Escape the big city hustle and bustle for a cozy tiny home with eclectic style in our safe small town of Appleton City. Enjoy the fresh air and open fields. Off street parking. Perfect for a couples get away. There's coffee, toaster, basic kitchen essentials, mini fridge with ice cube trays, lawn chairs for the front porch where you can enjoy your coffee in the morning shade in our quiet little escape. No pets

Top guest favorite
A secluded cabin is surrounded by autumn foliage, with leaves in shades of orange and yellow. The cabin features a wide deck with a wooden railing and large screened windows. A gravel path leads to the cabin, enhancing the tranquil setting among the trees.
Cabin in Osceola
4.97 out of 5 average rating, 59 reviews

secluded cabin in the Woods - Osceola, MO

This cozy cabin is located 1/2 mile from Weaubleau Creek where there is boat launch access that feeds the Osage River & Truman lake. This is the perfect place for any hunting/fishing trip, or to go do nothing that all! The cabin is secluded, completely unplugged from the outside world. A peaceful retreat for any outdoor or front porch coffee lover. A true gem in any season to recharge free of distractions.

Top guest favorite
A functional kitchen is equipped with white cabinetry and modern appliances, including a microwave and coffee maker. A black and white checkered mat is positioned in front of the sink, enhancing the space's practicality. Natural light fills the area, creating a welcoming cooking environment.
Cottage in Wheatland
4.97 out of 5 average rating, 239 reviews

Galmey Grove Cottage

* Wi-Fi Available! *Self Check-In (smart lock) Relax and unplug at our cozy little spot we call Galmey Grove Cottage. Located in Galmey, MO on County Road 273 just off 254 Hwy . We are close to several Pomme de Terre Lake swimming and boat access areas. Another attraction is 8 miles away at Lucas Oil Speedway host to Boat Racing, Off-Road Racing, and Dirt Track Races most weekends April-Oct.

Top guest favorite
The exterior of the tiny home is shown, featuring a red and gray color scheme with a metal roof. A spacious patio area with a table and chairs is visible, surrounded by small planters with vibrant flowers. A gravel pathway leads to the entrance, framed by trees.
Tiny home in Warsaw
5 out of 5 average rating, 29 reviews

King bed and pet friendly- 2 miles from Highway 65

This 12x30 tiny home has one bedroom, one bathroom, living area, kitchen area and lots of outdoor space. There is plenty of parking near the cabin in the front of the tiny home and plenty of boat trailer parking and turn around area. The backyard is spacious and has a great view. The tiny home was recently remodeled. Come let us host your next visit to Warsaw, Missouri.

Top guest favorite
The interior of the cabin features a high vaulted ceiling with rustic wooden paneling. A cozy seating area is arranged with a brown couch and a wooden rocking chair. A ladder leads to a loft area, while a flat-screen TV is mounted on the wall beside a small cabinet.
Cabin in Fair Play
5 out of 5 average rating, 91 reviews

OWL ridge cabin

Rustic housekeeping cabin. 10 minutes from lake Stockton for fishing and hiking. Close to Bolivar and SBU. This is a horse property and you will see horses, deer and other animals. It has separate heat in the bedroom and a central unit for the rest of the cabin. There is a nice shower/full bathroom and washer and dryer on the premises.

Popular amenities for Osceola vacation rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. St. Clair County
  5. Osceola