Vacation rentals in Osceola

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Top-rated vacation rentals in Osceola

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Top guest favorite

Cabin in Elkhart Lake

4.99 out of 5 average rating, 298 reviews

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

Top guest favorite

A person is seen holding a dark mug labeled 'The Coffee Corner Bistro Est. 1999' filled with a frothy beverage. The warm wooden interior of the café is visible in the background, enhancing the cozy atmosphere.

Apartment in Kewaskum

5 out of 5 average rating, 50 reviews

Local Landmark KL / Coffeehouse / Kettle Moraine

One-of-a-kind, newly renovated, turn-of-the-century Coffee Corner Suites, located at the "Gateway to the Kettle Moraine". Step out your door and into the iconic Coffee House. West Bend -- 5 minutes, Foundry 45 -- 3 minutes, Lomira -- 15 minutes. Rest easy knowing we have thought of everything to make your stay worry-free! King bed, full kitchen, keyless entry, heated towel bars, and on-site laundry. GOOGLE "Kewaskum is somewhere I just feel at home" and check out CBS 58 Story on Kewaskum.

Superhost

The interior living area features exposed wooden beams and large windows that allow natural light to illuminate the space. Comfortable seating arrangements include sofas and armchairs beside a wood-burning stove. A dining area with a large table is visible in the background, enhancing the open atmosphere.

Cabin in Campbellsport

4.75 out of 5 average rating, 24 reviews

Peaceful Lakeview Cabin Stay On Private Pennisula

Tucked on a private peninsula in Wisconsin’s Kettle Moraine, Birchwood Log Cabin is a quiet 4-bedroom, 2-bath retreat with stunning lake views and space for up to 14 guests. Enjoy a wraparound deck, wood-burning fireplace, and open-concept great room for cozy nights in. While our lake is view-only, you’re just a short walk to Kettle Moraine Lake’s public beach, boat launch, and vibrant Tiki Bar. Come for the stillness, stay for the trails, sunsets, and connection. Open year-round. Pets welcome!

Superhost

A simple entrance is highlighted by a white door adorned with a small window, framed by green siding. A festive decoration, resembling a snowman, composed of evergreen branches and a golden hat, is positioned beside the door, adding a cheerful touch.

Apartment in Plymouth

4.63 out of 5 average rating, 329 reviews

Pineyard Plymouth Apartment

Enjoy this older upper floor apt. with two single bedrooms with a twin bed in one and a full bed in the other, full bath, kitchen, living room, and off street parking. VCR/DVD player and internet is available. Kitchen is equipped with dishes, pots, pans, stove, and refrigerator. We are five minutes from Road America, fifteen minutes from Sheboygan, and thirty minutes from Fond du Lac. Only three blocks from downtown Plymouth enjoy many shops and eating establishments. Pets are NOT allowed.

Top guest favorite

A charming log cabin features rustic wooden architecture, complemented by red window frames. Surrounded by lush greenery, the structure offers a welcoming front porch. Natural light bathes the exterior, enhancing the serene setting among the trees, with a pathway leading to the entrance.

Cabin in Campbellsport

4.96 out of 5 average rating, 95 reviews

Fraser Fir Rustic Cabin near Lake w/ Sunset Views

Take time to slow down in this timeless cabin on Kettle Moraine Lake. In the summer, enjoy quiet moments watching the sun set from the front porch, then relax by the fire pit under a sky full of stars. Fish from the dock, kayak around the lake, or bring your boat to soak up the sun. In the winter, grab your ice-skates or ice-fishing gear and head out on the lake. With countless trails nearby, the hiking options are limitless and beautiful in every season. Your next adventure awaits.

Guest favorite

A historic lighthouse stands at the water's edge, illuminated by the vibrant colors of sunset. Smooth stones line the shoreline, reflecting the serene lake. Lush greenery is visible in the background, creating a peaceful coastal setting.

Home in Fond du Lac

4.92 out of 5 average rating, 89 reviews

Woltring Waters Waterfront Home

Wake up to a beautiful view of Lake Winnebago, and enjoy you cup of coffee with the sound of crashing waves off the back porch. You will have breathtaking sunsets with the historical light house backdrop that is in viewing distance from the property. From dining to convenient stores everything you need is in walking distance. Take a peaceful stroll around the marina or take the kids to Lakeside Park, offering a petting zoo, carousel, train, jungle gym & splash pad. Everyone will enjoy!

Top guest favorite

Cabin in Cascade

5 out of 5 average rating, 172 reviews

hot tub and sauna on 5 private acres

Need a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your inspired getaway awaits!

Top guest favorite

A remodeled kitchen and living area feature neutral tones and modern appliances. Bar stools are positioned at a counter, while a washer and dryer are present nearby. A dark brown armchair and a square ottoman are set on the soft carpet beside a small coffee table.

Cottage in Fond du Lac

4.98 out of 5 average rating, 284 reviews

Cozy Guest House with Lake views.

Our remodeled two bedroom Guest House is adjacent to our Cottage and offers beautiful lake views. Access to Lake Winnebago available at near by boat launches. Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen bed and 2 twin beds, 1 full bathroom, and a fully stocked newly remodeled kitchen. Perfect getaway for some R&R with family or friends.

Top guest favorite

A historic stone building with arched windows is surrounded by well-maintained lawns and mature trees. A small shed is visible near the garden area, adding to the outdoor space's charm. Bright green grass and seasonal foliage contribute to the serene setting.

Home in Campbellsport

4.99 out of 5 average rating, 189 reviews

Gleason's Chouse

You'll love staying in our unique home, in a quiet neighborhood. This is a recently remodeled 1867 church converted to a "Chouse". Featuring 2 bedrooms, Full Kitchen, 1 Bathroom, Balcony, Parking, and a Gazebo.. all beautifully complimented by a range of antiques and decorations. 8 Miles East of Hwy 41, a 45 min drive to Oshkosh or an hour to Milwaukee. Just down the from Lake Bernice & Eisenbahn Bike Trail. Also close enough to the Kettle Moraine Forest to hike and sightsee!

Guest favorite

The cabin stands amidst lush greenery with a gently sloping lawn leading to a stone pathway. The modern exterior features large windows and a spacious upper deck surrounded by trees, providing a serene lakeside retreat.

Chalet in Campbellsport

4.97 out of 5 average rating, 106 reviews

Long Lake Chalet

This recently remodeled and tastefully furnished, PET FRIENDLY, cabin boasts a unique charm. Nestled along the shores of Long Lake in the heart of the Kettle Moraine Forest, this lakefront property offers 45’ of serene, peaceful beauty. This stunning home features a large yard, pier access and year round recreational activities. Disconnect, unwind and take in all that Kettle Moraine has to offer. Whether vacationing with family or friends this retreat is waiting for you.

Top guest favorite

The exterior of the cabin is illuminated during twilight, showcasing a blend of stone and siding. A fire pit surrounded by stones is situated in the foreground, with a bench nearby. The large windows provide a warm glow from inside, and a deck extends to the side.

Cabin in Campbellsport

4.98 out of 5 average rating, 45 reviews

Cozy Treehouse on the Lake

Treat yourself to a peaceful get-away in our cozy cabin on Lake Bernice! Enjoy the beautiful lake view from inside the cabin through the large picture windows or from the comfy reclining chairs on the lower patio or the dining area on the upper deck. Take a cup of coffee or your fishing pole down to the private pier to savor the quiet of the no-wake lake. Also, excellent ice fishing! Your canine companions are welcome as well (maximum 2 dogs), $60 total for your stay.

Top guest favorite

A warm living area features exposed log walls and a stone fireplace. Comfortable leather seating is arranged around a coffee table. A television sits on an entertainment unit, and framed photographs decorate the mantle. Natural light enters through windows near the ceiling.

Cabin in Campbellsport

4.98 out of 5 average rating, 149 reviews

Log Cabin Luxury on a Lake

Enjoy a 1,400 sq.ft. home in the Northern Unit of the Kettle Moraine Forest on 50' of shore. Enjoy the lake for swimming, kayaking, fishing, and floating! Lots of trails for hiking nearby and other fun summer activities! Updated home with a log cabin feel. Modern kitchen and great room—perfect for game night or sitting by the fireplace. Lake views from the master bedroom and sun room. Beautiful bathroom with big walk in shower. Come see for yourself!