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.

Guest favorite

Cottage in Oostburg

4.97 out of 5 average rating, 229 reviews

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

Dec 10 – 17

$136 per night
Guest favorite

Cabin in Elkhart Lake

4.99 out of 5 average rating, 188 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.

Sep 12 – 19

$213 per night
Guest favorite

Cottage in Fond du Lac

4.97 out of 5 average rating, 230 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 16 – 23

$59 per night

Popular amenities for Osceola vacation rentals

Stay near Osceola's top sights

Long Lake Recreation Area7 locals recommend
Hamburger Haus6 locals recommend
Tiki Beach Resort on Kettle Moraine Lake6 locals recommend
3 Sweets Bakery & Cafe6 locals recommend
Armstrong Apples, Orchard & Winery4 locals recommend
Ice Age Visitor Center8 locals recommend

Other great vacation rentals in Osceola

Guest favorite

Townhouse in Port Washington

4.92 out of 5 average rating, 114 reviews

Steps Away From the Lakefront and Downtown

May 10 – 17

$81 per night
Guest favorite

Cabin in Campbellsport

4.96 out of 5 average rating, 24 reviews

Fraser Fir Rustic Cabin near Lake w/ Sunset Views

Sep 23 – 30

$237 per night
Guest favorite

Apartment in Campbellsport

4.96 out of 5 average rating, 67 reviews

GGG Spacious Log Cabin apartment on the IAT

Apr 5 – 12

$131 per night
Guest favorite

Cabin in Cascade

5.0 out of 5 average rating, 37 reviews

Rustic Chic Cabin in Kettle Moraine

Apr 29 – May 6

$350 per night
Guest favorite

Chalet in Campbellsport

4.96 out of 5 average rating, 83 reviews

Long Lake Chalet

Jun 5 – 12

$360 per night
Guest favorite

Cabin in Cascade

5.0 out of 5 average rating, 31 reviews

modern woodland paradise w/ sauna

Oct 22 – 29

$370 per night
Superhost

Cottage in Campbellsport

4.88 out of 5 average rating, 58 reviews

Picturesque Lakeside Oasis on Kettle Moraine Lake

Jul 23 – 30

$480 per night
Guest favorite

Apartment in Kewaskum

5.0 out of 5 average rating, 34 reviews

Cozy Country Farmhouse

Nov 24 – Dec 1

$107 per night
Guest favorite

Home in Waldo

4.98 out of 5 average rating, 57 reviews

Perfect Winter Getaway!

Sep 27 – Oct 4

$119 per night
Guest favorite

Guest suite in Waldo

4.92 out of 5 average rating, 37 reviews

Above Garage Apartment w/ Private Beach

Apr 23 – 30

$86 per night
Guest favorite

Home in Fond du Lac

4.89 out of 5 average rating, 19 reviews

Cute and Cozy Sleeps 6

Jul 2 – 9

$113 per night
Guest favorite

Home in Cascade

5.0 out of 5 average rating, 46 reviews

The Pines-Spacious Property, Private Home, Hot Tub

Sep 24 – Oct 1

$321 per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Fond du Lac County
  5. Osceola