Vacation rentals in Osceola

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Top-rated vacation rentals in Osceola

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Guest favorite

Cabin in Elkhart Lake

4.99 out of 5 average rating, 192 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.

Dec 3 – 10

$178 per night

Guest favorite

Home in Howards Grove

4.95 out of 5 average rating, 151 reviews

Spacious lower level priv entrance no cleaning fee

Entire basement is for rent with a separate entrance. Kitchen area includes refrigerator, microwave, coffee pot, toaster, sink, dining table and chairs. NO STOVE OR OVEN IS AVAILABLE. Free Wifi and Cable TV. Air conditioning. Plenty of parking, keyless entry. 14 min to Road America, 13 min to Kohler, 9 min to Whistling Straits, 5 min to Lakeland University, 1 hr to Milwaukee, 1 hr to Green Bay. Lots of nice amenities, clean, spacious. No cleaning fee. Unit NOT set up for babies or toddlers.

Oct 19 – 26

$95 per night

Guest favorite

Cottage in Fond du Lac

4.97 out of 5 average rating, 235 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.

Sep 13 – 20

$59 per night

Guest favorite

Cabin in Fox Lake

4.95 out of 5 average rating, 122 reviews

Cabin on the Trail

Kick back and relax in this cozy space with up north, cabin vibes. In the summer months enjoy the excellent fishing, swimming and boating and in the winter have fun ice fishing by walking to the lake out your back door! *Please read the full description and look at all of the pictures of the property *Not suitable for parties or loud gatherings. Please note, there is a 4 person maximum, including children. *All dogs/pets must be pre-approved by the host. There is a $50 fee/stay.

Oct 12 – 19

$94 per night

Guest favorite

Home in Campbellsport

4.99 out of 5 average rating, 137 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!

Feb 6 – 13

$112 per night

Guest favorite

Apartment in Sheboygan

4.92 out of 5 average rating, 398 reviews

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

Nov 1 – 8

$78 per night

Guest favorite

Cabin in Wild Rose

4.91 out of 5 average rating, 319 reviews

Getaway Wild Rose - Milwaukee

An easy drive from the city, Getaway is a new way to experience the great outdoors. Nestled across dozens of acres of private woodlands, our modern, tiny cabins have everything you need (comfy bed, bathroom, fresh linens) and nothing you don’t. Featuring a private outdoor area (hello, fire pit), each cabin is designed to help you relax, unwind and disconnect from the everyday. Plus, as part of your stay, you'll receive firewood, a s'mores kit, coffee and bottled water*.

Sep 26 – Oct 3

$98 per night

Guest favorite

Home in Glenbeulah

4.98 out of 5 average rating, 111 reviews

Stay at Sunrise LLC, Like being at Grandma's

Welcome to Stay at Sunrise LLC. We offer a clean and comfortable home for your vacation enjoyment. We are in a rural farm area, the recreation trail head is 3 miles east of us as well as the Wade House, we are near the Kettle Moraine State Forest and the Ice Age Trail and 7 miles from Road America. Large yard, Fire pit, picnic table, child swing set. Garage parking on site if arranged in advance. Smoking is allowed outside of the home. No pets allowed.

Mar 14 – 21

$75 per night

Guest favorite

Cabin in Campbellsport

4.99 out of 5 average rating, 135 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!

Sep 28 – Oct 5

$248 per night

Guest favorite

Farm stay in US

4.98 out of 5 average rating, 181 reviews

Family friendly farmstay just outside Milwaukee

The Inn at Paradise Farm is an original 1847 log homestead in rural Wisconsin just a short drive from Milwaukee and close to many attractions, especially for nature lovers. Our very spacious private 4-room suite with private entrance is comfortable for couples, families, or business travelers who long to unwind in a pastoral setting. Visit with, and even help care for, our friendly animals! We are licensed and inspected. Paradise Farm welcomes all.

Sep 15 – 22

$97 per night

Guest favorite

Home in Campbellsport

4.98 out of 5 average rating, 133 reviews

The Lakehouse on Long Lake (plus Heated Boathouse)

Our family always dreamt of owning a Lakehouse. When we had the opportunity to finally make that dream come true, we crafted the ideal getaway and wanted to share it with others. The Lakehouse on Long Lake is the perfect getaway to relax on the water. The boathouse/game room is an ideal venue for family or friends to entertain, all while overlooking the beautiful lake. We are excited to share our vision of a family getaway with you.

Jan 20 – 27

$367 per night

Guest favorite

Apartment in Waldo

4.98 out of 5 average rating, 259 reviews

The Blue Cobb House

My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.

Mar 23 – 30

$94 per night