Vacation rentals in Osceola

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Top-rated vacation rentals in Osceola

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Top guest favorite

A panoramic view of Stockton Lake is presented, showcasing calm waters framed by vibrant autumn foliage. Trees with green and yellow leaves blend into the lake's serene surface under a clear blue sky, reflecting the peaceful and natural beauty of the surrounding landscape.

Home in Stockton

4.99 out of 5 average rating, 105 reviews

Stunning Stockton Lake View

Stockton Lake is so pristine but staying on a beautifully remodeled lake view home will make it one-of-kind! It’s only 3 miles from town and just 1.5 miles from a quiet boat launch. Free parking on the premises with plenty of room on the driveway for your boat/trailer (driveway is 22’ wide x 47’ long). Lots of lake views throughout with more lake views and seating outdoors. It’s on a very quiet country setting, so come and unwind from the city hustle and bustle. It’s a truly spectacular getaway!

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, 123 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!

Superhost

The exterior of a two-story brick house is visible, featuring large windows that reflect the surrounding greenery. A wide driveway leads to the entrance, where a wooden bench sits. The yard includes manicured bushes and trees, providing a quiet, inviting atmosphere.

Townhouse in Stockton

4.89 out of 5 average rating, 220 reviews

Rest Near Stockton Lake

Why stay in a hotel when you can stay in a full house!!! Only a few miles from Stockton Lake. Fully furnished! Apple-TV in every room! Fully equipped kitchen. Very cozy and comfortable place! There are 4 beds. There is also a pack & play for an infant. BBQ grill right outside the front door. Washer & dryer for guest to use too! Also, property is equipped with ActivePure Air Purification unit that is proven to reduce up to 99.99% of allergens & pathogens including the virus that causes Covid-19!

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

4.94 out of 5 average rating, 125 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

A gravel driveway leads through a lush green field, bordered by grassy areas on either side. In the distance, a farmhouse is visible, surrounded by trees under a partly cloudy sky. The natural landscape conveys a sense of open space and tranquility.

Farm stay in Deepwater

4.94 out of 5 average rating, 53 reviews

"Private" House -30 acres {Bucksaw Marina-Truman}

Have a peaceful and relaxing stay in a Farm house ! 7 minutes away from Bucksaw Marina 18 minutes to Long Shoals ! Huge Deck to enjoy grilling and chilling!15 minutes from Clinton , Missouri to get groceries or to dine out. 1 bedroom with 2 king size beds and a bunk room with 2 full size beds and 2 twins on top. Plenty of parking . 1 bathroom with a shower. Laundry room with a washer and dryer. Pets are welcome also! Small pond to let kids fish! Trails on property to walk or enjoy wildlife!

Top guest favorite

A single-story home features a neutral exterior with green shutters and a metal roof. A front porch with steps leads to the entrance, surrounded by trees. The landscape is covered in autumn leaves, creating a quiet and natural setting.

Home in Deepwater

4.93 out of 5 average rating, 126 reviews

Truman Lake Family 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, bird watching, off-road vehicle adventures, & some of the best hunting in the country.

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

4.98 out of 5 average rating, 404 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

4.91 out of 5 average rating, 151 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, 227 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 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

4.98 out of 5 average rating, 53 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, 228 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 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, 78 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.