Apartment vacation rentals in Sheboygan County

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Top-rated apartment rentals in Sheboygan County

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Guest favorite

Rental unit in Sheboygan

4.97 out of 5 average rating, 139 reviews

Modern Upstairs Apt - Steps from Lake Michigan

Have you ever wondered what Lake Life is like? Here is your chance! This is 1 of 2 AirBnB units in this cute duplex Come stay in this beautiful upper apartment located just one block from Lake Michigan. Take a quick walk to the lake in the morning to jump on your fishing boat or take the family to the beach in the afternoon! Located close to shopping and many local bars and restaurants within walking distance. You'll find relaxation and a great time here at the heart of Sheboygan's Shoreline!

Guest favorite

Rental unit in Sheboygan

4.98 out of 5 average rating, 49 reviews

North 7th Place - Spacious 2 Bedroom Lower Unit!

A quiet cozy 2 BR space just a few minutes walk to the beautiful Lake Michigan. Conveniently located less than a mile from downtown Sheboygan, where you can enjoy locally owned shops, charming restaurants, and a fun night out! Other amenities include; free use of the back yard, fire pit, outdoor grill, Wi-Fi, Netflix, work space, sunroom, spin bike, fully equipped kitchen, onsite laundry, and you can bring your pets! Please check us out, as our family would love the opportunity to host you!

Superhost

Rental unit in Plymouth

4.63 out of 5 average rating, 289 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.

Guest favorite

Rental unit in Sheboygan

4.97 out of 5 average rating, 66 reviews

Quaint Blast from the Past - walk to lake/8th st

Renovated 1930's home located in the historic downtown district within walking distance of breathtaking views of Lake Michigan, trails, parks, shopping, dining, Kohler Art Museum, Children's Museum and more! You will enjoy the 1200 square foot, two bedroom renovated upper unit of this historic home. Great care was taken to keep the old world charm. We know you will enjoy our "Blast from the Past" as you play records, tapes, and cd's. Send inquiry on big discounts on stays ore than 2 days!

Guest favorite

Rental unit in Sheboygan

4.87 out of 5 average rating, 86 reviews

The Beach | Sheboygan 2Br/1 Ba

Welcome to the Beach, a lakeside retreat in the heart of Sheboygan. Located just 3 blocks from Lake Michigan and a stones throw to down town Sheboygan, The Beach is the perfect place to center your visit to Eastern Wisconsin. The Beach is the main floor unit of a duplex featuring 2 bedrooms, 1 bathroom, a well stocked kitchen, a cozy living room, fast wifi and convenient amenities. We have an easy check out with no to-do lists. Just pack and go! *New cleaning staff hired January 2023!*

Guest favorite

Rental unit in Sheboygan

4.95 out of 5 average rating, 38 reviews

Peaceful apartment close to the lake

Beautiful, newly furnished & updated, 2 Queen bedroom upper apartment with large closets, 1 bath, desk with workspace, stocked kitchen, in unit laundry, private balcony, high speed internet, 2 Smart TVs, keyless private entrance Central downtown location walking distance to restaurants/bars, parks, the beach, festivals, Museums, Arts Centers, Stephanie H. Weill Center & more! 10-15 min. driving distance to Kohler golf courses, The Bull at Pinehurst Golf Course, Road America, Elkhart Lake

Guest favorite

Rental unit in Sheboygan

4.98 out of 5 average rating, 130 reviews

Lovely modern two bedroom home with fire pit

Newly renovated two bedroom home just a mile from the beach and five star restaurants. Enjoy a game of golf at world class Whistling Straight. Car enthusiasts will love Elkhart Lake Road America. Salmon fishing the Great Lake Michigan or just have a relaxing time around the fire pit. There is a laundry with washer/dryer, steamer and folding table. Dogs under 30 pounds. No cats sorry. No smoking in the house. Ample street parking at the front door. Fire pit in back yard.

Guest favorite

Rental unit in Sheboygan

4.92 out of 5 average rating, 456 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.

Guest favorite

Rental unit in Sheboygan

4.88 out of 5 average rating, 77 reviews

One Bdrm Apt - The Erie House near lake & downtown

This house was built in 1888 as a single family home and retains its nineteenth century charm along with today's modern conveniences. The location is just walking distance from both majestic Lake Michigan to the east and Sheboygan's charming downtown to the west. The lodging, which sits in an attractive, tree lined neighborhood, has been divided into several living units in which you will be staying on the first floor facing Erie Avenue.

Guest favorite

Rental unit in Waldo

4.98 out of 5 average rating, 269 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.

Guest favorite

Rental unit in Sheboygan

4.84 out of 5 average rating, 291 reviews

Sheboygan Surf House - The Elbow

Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our newly remodeled Urban living oasis is a studio and a half that is conveniently located in the heart of downtown, just steps from renown bars and restaurants and only blocks to Lake Michigan, The Sheboygan River, South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake or leisure time SSH is perfect for you.

Superhost

Rental unit in Sheboygan

4.89 out of 5 average rating, 293 reviews

Spiritual Vibes Downtown Walk-up

New art and hand crafted decor. Some are even available for purchase, others are for guests to enjoy during their stay. Cozy, inviting, private apartment close to restaurants, shops and entertainment. Wonderful morning and evening light. Large deck for relaxing outdoors or enjoying the sun. We have a storage shed for bikes, strollers and the like if needed. Just give us the heads up and we'll give you the key.