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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Top guest favorite

A spacious master bedroom is shown, featuring a bed positioned near large windows that provide expansive views of the surrounding landscape. Soft carpeting covers the floor, and natural light fills the room. A small area is visible to the left, suggesting additional amenities.

Home in Warsaw

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!

LocationValueLaundry

4.94 out of 5 average rating, 389 reviews

Superhost

An open living area showcases high wooden ceilings and log cabin walls. A spacious sectional sofa is positioned on a patterned rug in front of a wooden coffee table. The kitchen, partially visible, features modern appliances and a central island with bar seating.

Home in Deepwater

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

FamilyLocationCleanliness

4.73 out of 5 average rating, 56 reviews

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

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.

FamilyLocationCondition

4.96 out of 5 average rating, 128 reviews

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

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.

FamilyLocationAmenities

4.92 out of 5 average rating, 168 reviews

Top guest favorite

Home in Stockton

*Fox Run Retreat - Cozy and Relaxing Close to Lake

Fox Run Retreat—your cozy escape from the busy. This is the kind of place where you can sip coffee on the porch, breathe a little deeper, and let the day unfold at your own pace. We designed it to feel easy, comfortable, and just a little bit special. Conveniently located near shopping, dining, and local venues. The beach and boat launch are around the corner (check out the maps in listing photos)., You’ll have the best of both worlds—close to everything, yet peaceful enough to truly relax.”

ValueLocationSleep quality

5.0 out of 5 average rating, 52 reviews

Top guest favorite

Home in El Dorado Springs

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.

FamilyValueLong stay

5.0 out of 5 average rating, 41 reviews

Superhost

The Fireside Cabin, painted in deep blue, is nestled among tall trees offering shade and privacy. A gravel path leads to the entrance, with a small porch visible. Lawn space surrounds the cabin, providing an area for outdoor activities.

Cabin in Deepwater

Fireside Cabin on Truman Lake

Fireside Cabin invites you to slow down and reconnect with the simple joys of life. Whether you're off for a peaceful day of boating, hunting, exploring hiking trails, or unwinding by the fire with a beverage in hand, this is where rustic comfort meets outdoors. -Less than 1 mile from two Corp of Engineers boat ramps -Large fire pit & brand new covered deck -Wood swing set with sandbox for the kids -Deck slide -10 miles from Bartle Boy Scout Camp & Iconium with the legendary peach float

FamilyLocationQuiet

4.71 out of 5 average rating, 17 reviews

Top guest favorite

Cabin in Stockton

Sac River Cabin *Walk-In Cooler for Hunters*

Welcome to the perfect mix of relaxation and outdoor activities along Sac River. This charming cabin has something to offer for everyone: peaceful secluded acres for those wishing to escape, amenities centered around family fun, and close proximity to countless hunting and fishing experiences. - 4 miles to Blackjack Access boat ramp - 7 miles to Caplinger Mills Kayak/Canoe Rental - 16 miles to Osage River - Truman Tributary - Walking distance to 415 ac of Public Hunting in Moresi Unit

LocationFamilyAmenities

5.0 out of 5 average rating, 16 reviews

Top guest favorite

A modern kitchen is visible, featuring stainless steel appliances and ample counter space. A dining area with four wooden chairs is positioned at a central island, while light wood flooring complements the light walls. Decorative plants add a touch of greenery to the space.

Home in Stockton

The Voyager at Lake Town Estates *HOT TUB*

Welcome to Lake Town Estates! Located only minutes away from the beloved lake town of Stockton, MO, this home offers everything you need for your lake vacation or quiet getaway! Nearby, you will find a local grocery store, a small-town coffee shop/cafe, and a variety of things to do, such as kayaking, hiking, boating, and more! Whether you're bringing the whole family or travelling alone, The Voyager at Lake Town Estates will be the perfect home away from home!

LocationValueNearby

4.98 out of 5 average rating, 98 reviews

Superhost

Cabin in Osceola

Secluded Cottage in the Woods - with hot tub

Escape to a cozy American Cottage tucked away in the woods, bordered by 900 acres of public Corps of Engineers land—perfect for hunters, fishermen, or anyone craving peace and quiet. Less than a mile away, access Weaubleau Creek, which feeds into the Osage River. Sip coffee on the patio, explore the wet-weather creek, or spend the evening relaxing in the hot tub beneath the stars. A secluded place to slow down, reconnect, and do absolutely nothing at all.

ValueViewGrill

5.0 out of 5 average rating, 4 reviews

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

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.

ValueLocationAir conditioning

4.98 out of 5 average rating, 449 reviews

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

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!

LocationValueComfort

4.9 out of 5 average rating, 168 reviews