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Holiday houses in Osceola

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Top-rated holiday rentals in Osceola

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

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Top Guest favourite
The exterior of a two-story house is depicted, featuring a gabled roof and a unique cupola. A spacious porch is visible at the front, with a bench and large triangular windows on either side. Surrounding greenery, including blooming trees, enhances the setting.
Home in Warsaw
4.98 out of 5 average rating, 210 reviews

The Citadel - Close to the Water and Warsaw

The Citadel is a pretty little place, modern with vintage cottage appeal right off Hwy 7 by the mile-long bridge leading into Warsaw. This 2 story, 2 bedroom, 2 full bath home (showers only) offers a well equipped kitchen, dining, living & sitting room w/Roku tv and tv w/dvd player, wifi, room to work, and outdoor seating. Large parking area. Close to swim beaches, the park at Drake Harbor for walking/boating/fishing, flea markets, antique shops, restaurants and the Overlook. No washer/dryer

Top Guest favourite
The spacious camper is illuminated in the evening light, showcasing its modern design. Steps lead up to the entrance, and outdoor seating is arranged nearby. A fire pit sits in the foreground, surrounded by landscaped gravel and soft lighting that enhances the tranquil setting.
Campervan/RV in Warsaw
4.96 out of 5 average rating, 206 reviews

Private Waterfront Relaxation at Peppermint Cove!

Our spacious camper is lake front with a gorgeous Cove view, sitting on our quiet, peaceful, private property on a private road. No sharing our space, and a 200 ft walk (across from camper) to the water, enjoy our dock with amenities, shady green space by the water, or the outdoor kitchen, patio and firepit at the camper. You’ll have access to our HOA boat ramp. We’re located on the Osage River Arm of Lake of the Ozarks on MM 84 (@ the power lines) and 15 minutes away from Truman Dam and Lake.

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, 357 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!

Top Guest favourite
A wooden cabin is positioned on a gentle hillside, surrounded by lush greenery. The wraparound porch offers a view of the expansive landscape, with rolling hills visible in the distance under a clear sky.
Cabin in Union Township
4.95 out of 5 average rating, 40 reviews

Deer Creek Cabin, on 26 acres in the Ozarks

Looking for a place to relax and recharge? Have a seat on our wrap around deck and take in the views of our 26 acres. Quietly nestled in the woods, but still within driving distance of Truman Lake and Lake of the Ozarks, this brand new cabin will provide the ultimate escape. Take a relaxing bath in our deep soaker tub, cuddle up by the fireplace with a good book, or watch for our many local deer from the porch. Perfect for a family vacation, romantic getaway, or a trip with friends.

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, 276 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.

Top Guest favourite
The exterior of the farmhouse is visible, showcasing a white structure with a dark green roof and large windows. A gravel driveway leads to the entrance, bordered by small shrubs and gathered stones. A wooden sign is positioned near the door, indicating the entrance.
Farm stay in Butler
5 out of 5 average rating, 111 reviews

The Lone Oak

Reconnect with nature at The Lone Oak, part of our working cattle ranch. Enjoy the quiet of the country while you go fishing in the pond, spotting the wildlife, and stargazing at night while enjoying the hot tub. Just five miles from town, right off the blacktop, and three miles from Interstate 49. The top level is a 1900 farmhouse that is being renovated to enlarge the bnb. The walk-out basement is all new and ready for you to have a relaxing, memorable get-away.

Guest favourite
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 favourite
Colorful flowers are arranged in a garden bed, featuring various blooms, including yellow and purple irises, surrounded by lush green grass. The background shows a cabin with wooden siding, framed by tall trees and a clear sky.
Home in Clinton
4.92 out of 5 average rating, 36 reviews

Cozy Cabin by Bucksaw Marina, Truman Lake

Your family will be comfortable and close to the lake when you stay at this 3 bedroom, 2 bathroom cabin. Ask us about our stocked private pond and we can get you access. It’s only a quarter mile away from the property! Also, there’s a small event center on the property that can be rented daily. Next to this house is also an RV hookup and water for extra guests. Enjoy the barbecue grill and two large walkout decks as you bask in the evening sunset.

Top Guest favourite
The modern cabin is nestled within a lush landscape, showcasing a sleek dark exterior under a clear blue sky. Surrounding trees provide a natural backdrop, while a manicured lawn extends in front of the structure.
Cabin in Lamar
5 out of 5 average rating, 44 reviews

Black Diamond Lodge

Newly Built, Modern Cabin w/stocked Private Pond and Yoga Deck. Just 3 miles outside the city limits. Live like Kings and Queens while immersed in nature and surrounded by luxury comforts at the Black Diamond Lodge. This space is designed to bring peace and calmness, relaxation, and truly a place to unplug & unwind. Every detail and item thoughtfully chosen to create the ultimate outdoor getaway for you and your family and friends to enjoy.

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, 229 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.

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, 63 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.

Guest favourite
A lakeside pavilion is visible, featuring a metal roof and wooden structure. Benches are placed underneath for seating. Lush green grass surrounds the area, and trees provide shade, with the calm water of the lake reflecting the surrounding greenery.
Home in Wheatland
4.95 out of 5 average rating, 22 reviews

Lake House- boat slips available for rent

We’re excited to share our family lake house that we are enjoying with our kids , with guests who love nature, relaxation, and quality time with loved ones. It’s family-friendly, with plenty of activities just steps away. There are nearby playgrounds, tennis/baskets courts, soccer/baseball. Bring your boat/Jet Ski or kayaks to enjoy the water. Race track about 10 min away . Boat slips $15/ day 7 min away .

Popular amenities for Osceola holiday rentals

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