Vacation rentals in Osceola

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Top-rated vacation rentals in Osceola

Guests agree: these stays are highly rated for location, cleanliness, and more.

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A spacious porch features wooden swing seating and two comfortable chairs, providing a relaxing area to enjoy views of the surrounding landscape. The porch is enclosed with large windows that invite natural light, and a grill is positioned for outdoor cooking.
Home in Deepwater
4.82 out of 5 average rating, 50 reviews

Secluded Lake Cabin w/ Hiking Trails & Firepit

Cedar Ridge is a beautiful three bedroom and two bath house on Truman Lake, and is the perfect place to enjoy the lake. The cabin is two minutes from a boat ramp and has a two car garage to keep your boating and fishing equipment secure. The cabin is sparkling clean and has a fully equipped kitchen, living room, master bedroom and an attached bathroom downstair. Upstairs you'll find two more bedrooms and an additional bathroom. You'll love the porches with their beautiful views and the hikin

Guest favorite
Home in Warsaw
4.94 out of 5 average rating, 368 reviews

The Overlook

Adventure awaits! Enjoy the best sunsets and night skies from high above the shores of Truman Lake. An unforgettable way to unwind! Perfect for romantic getaways, thrill seekers, and tourists alike. Protected forests surround the neighborhood and the historic "Hallmark town" of Warsaw is minutes away. A modern marina is just down the road. Great opportunities for relaxation and recreation abound with memorable times sure to be had! Ask about our romance/birthday packages and pet friendly stays!

Top 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, 153 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
Home in Deepwater
4.96 out of 5 average rating, 121 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.

Top guest favorite
Cabin in Edwards
4.99 out of 5 average rating, 146 reviews

Hot tub, golf cart, kayaks/SUP with lake access!

✨Hot Tub+Golf Cart+Kayaks |Quiet Lake Escape Cairn Cottage is a cozy, vintage, one room stone cottage tucked into nature above the Osage Arm (69MM). Come slow down and enjoy the quiet side of the lake. Hot tub year-round, golf cart to the dock, and kayaks in season. A complimentary breakfast casserole, plus coffee and snacks, make mornings simple and relaxed. Not coming in summer? Check out our amenities slide that shares which amenities are available when. Reconnection is a reservation away!

Guest favorite
Home in Climax Springs
4.94 out of 5 average rating, 109 reviews

Family fun! Secluded cove and private slip!

Come stay at the Hawks Nest! Great location with MANY different outdoor areas to enjoy. Our house is set up wonderfully for families. Quiet secluded cove with buoyed off swim area and an abundance of wild life. Boat slip, Lily pad, kayaks and a paddle boat included for use with rental. Life jackets for all sizes. Great fishing, poles provided. Open main floor and plenty of comfortable sleeping. Located at the 48.5 MM. Close to Red Fox, Big Dicks and just a boat ride from many others!

Top guest favorite
A cozy living area features warm wooden walls and an inviting sectional sofa. Natural light enters through a large window, illuminating a rustic coffee table. A stone fireplace is centered against the wall, complemented by a serene landscape painting above. Access to the kitchen is visible in the background.
Cabin in Warsaw
5 out of 5 average rating, 18 reviews

Honey Hole Cabin at Truman Lake

Tucked away on 3 peaceful acres, this cozy cabin offers the perfect escape for those looking to relax, recharge, and reconnect with nature. Sleeps 6 with 2 Bedrooms and 1 Full Bathroom Enjoy a fully equipped kitchen, open living area, with a few rustic touches to complete the cabin vibe. Enjoy the hot tub, large back deck, and firepit near Berry Bend and Truman Lake. Located just minutes from public lake access, boat ramps, trails, and outdoor fun—your perfect Honey Hole getaway awaits.

Top guest favorite
Home in El Dorado Springs
5 out of 5 average rating, 26 reviews

Country Paradise

Surrounded by farmland, grazing cattle, blue skies & green grass, enjoy this little piece of country paradise. Looking for a clean place to stay while in the area or while you hunt, this is it. DIRECTLY across the road you can enter over 2400 acres of Missouri Conservation Land, known as Linscomb Wildlife Area! Also nearby are the Sac and Osage Rivers, that are great for fishing with the latter being known for snagging Spoonbill/Paddlefish. Located between El Dorado Springs and Osceola.

Top guest favorite
The exterior of the Grain Bin Cabin is showcased beside a tranquil pond, reflecting the cabin's metallic structure. Adirondack chairs surround a firepit on the grass, with picnic tables positioned nearby, creating an inviting outdoor space.
Cabin in Versailles
4.99 out of 5 average rating, 177 reviews

The Highland GrainBin, Highland Cows, Firepit

Welcome to our charming boho-inspired Grain Bin Cabin, the Highland is ideal for 2-3 adults or 2 adults and 2 smaller children. Upstairs, you'll find a comfortable king bed in the loft, while downstairs features a cozy futon in the main living space. The full kitchen is equipped with everything you need. Full Bath with a walk-in shower downstairs. Experience a serene countryside getaway with breathtaking sunsets and peaceful surroundings, just moments away from Versailles.

Top guest favorite
Cottage in Wheatland
4.97 out of 5 average rating, 435 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.

Top guest favorite
A cabin exterior features a covered porch with two blue chairs and a swing. Potted plants add greenery, and a sign indicating 'Parkhouse' is displayed on the wall. The setting includes gravel landscaping and surrounding trees, providing a natural and serene atmosphere.
Cabin in Warsaw
4.97 out of 5 average rating, 104 reviews

Countryside Cabin by the Lake

This spacious cabin has 1 bedroom with a comfortable, king sized bed, a queen sized hide a bed couch in living room, and a well equipped kitchen. The outside sitting area is a peaceful oasis with the view of the cattle and horse farm. An outside outlet is available for charging your boat. Bike, walking trails, and a marina are all within 1. 4 miles. Downtown shopping area is 5 minutes away. Roku and wifi are available.

Guest favorite
A spacious covered dock is situated on a calm lake, surrounded by trees reflecting autumn colors. Kayaks and a paddle boat are visible on the dock, alongside a ladder leading into the water. A wooden walkway connects the dock to the shore.
Cabin in Blairstown
4.82 out of 5 average rating, 274 reviews

Honey Creek Hideaway at Back Country Camp

Escape to this quiet, seemingly remote country getaway nestled down a peaceful, tree-canopied lane. Relax and unwind amid big woods, creeks, woodland trails, complete with a very large strip pit lake, and smaller lake just mere feet from your private cabin. Use our large covered dock, kayaks, paddle boat, canoe and explore all this huge waterscape and land have to offer. All manner of Missouri wildlife reside here.

Popular amenities for Osceola vacation rentals

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