Holiday houses in Osceola

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Top-rated holiday rentals in Osceola

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Top Guest favourite
Cabin in Edwards
4.99 out of 5 average rating, 136 reviews

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

Welcome to Cairn Cottage, a classic one-room, stone cottage sitting a stones throw from the Osage Arm of The Lake of the Ozarks (69MM). Relax in nature from the hot tub year around. From May to September (and sometimes later) you can enjoy the Kayaks and SUPs at the lake lot. Please note that the cottage and lake lot are a short golf cart ride from each other. A boat slip is available 5/31-9/7 upon request. We always recommend travel insurance but especially encourage it during winter months.

Top Guest favourite
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
4.94 out of 5 average rating, 145 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.

Guest favourite
A cabin with a light wooden exterior is positioned within a grove of cedar trees. It features a front porch with chairs and a small fire pit, complemented by a grassy area. The dwelling is framed by natural greenery, creating a serene outdoor setting.
Cabin in Wheatland
4.89 out of 5 average rating, 63 reviews

Little Cedar Lodge

Welcome to our charming cabin nestled in a grove of cedar trees. This cozy retreat offers an idyllic escape from the hustle and bustle of everyday life. Wake up to the soothing sounds of nature, and enjoy your morning coffee on the front porch. It is located just minutes from Pomme de Terre Lake, several swimming beaches, boat docks, a state park with fishing access, a walking path, playgrounds, tennis and basketball courts, and volleyball. You will also have walking distance to Dollar General.

Guest favourite
A spacious bed is positioned near large windows, offering a scenic view of serene woodlands blanketed in snow. Soft gray bedding contrasts with the vibrant greenery outside, which is visible through the clear glass panes, creating a tranquil atmosphere.
Home in Warsaw
4.94 out of 5 average rating, 360 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, the historic "Hallmark town" of Warsaw is minutes away, and a 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!

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, 178 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 favourite
Two blue mugs are placed on a glass-topped table overlooking the serene lake. The calm water reflects the surrounding tree-covered hills, creating a peaceful setting. Soft morning light illuminates the scene, enhancing the tranquil atmosphere of this lakeside retreat.
Home in Edwards
4.97 out of 5 average rating, 277 reviews

Rippling Point Lakefront House

Secluded at the end of a private drive on the quiet end of the Lake of the Ozarks, our lake home offers recreation, relaxation, and fishing opportunities. The house is on the water at the 67MM of the lake and features 300 feet of private shoreline. A deck that overhangs the water is just a few steps from a patio equipped with a propane/charcoal grill and outdoor cooking area. Two kayaks are included to explore the shoreline and its wildlife. An inviting hot tub beckons.

Superhost
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
4.9 out of 5 average rating, 157 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!

Top Guest favourite
The cottage's entrance features a covered porch supported by wooden pillars. Rocking chairs are positioned beside potted plants. The front door, framed in green, is flanked by large windows that provide natural light. Surrounding trees enhance the cottage's secluded feel.
Cottage in Wheatland
4.98 out of 5 average rating, 228 reviews

Rustic Hideaway Cottage

This nearly hidden cottage in the woods (completed in June 2019) is perfect for a small family, two or three couples enjoying a lake vacation together, or several friends connecting simply to hang out. 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 favourite
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, 247 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

Guest favourite
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, 66 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 favourite
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, 246 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.

Guest favourite
A single-story duplex is depicted, featuring a light-colored exterior and a private entrance with glass double doors. Flanking the doors are two planters with flowering plants. A gravel pathway leads to the entrance, with a grassy area on one side and a clear blue sky overhead.
Guest suite in Stockton
4.8 out of 5 average rating, 315 reviews

Nonnie & Poppies Hide-a-way

Nonnie & Poppies Hide-a-way is a duplex-style unit with a private entrance. It is only minutes from the lake and has easy access for vehicles with trailers. It is in a quiet area outside of town and it is next door to The Bait Shop where you can get cold drinks, ice and snacks.

Popular amenities for Osceola holiday rentals

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  2. United States
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  4. St. Clair County
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