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Sheboygan, WI vacation rentals
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Best Vacation rentals and Airbnb offers in Sheboygan, WI

Best family friendly Sheboygan, WI vacation rentals

Among the 387 accommodations in Sheboygan, WI, here are the 4 best family friendly rentals

The Suncatcher- Steps To Lake Michigan. Pet Friendly & Fully Fenced - Sheboygan, WI
10 42 reviews

The Suncatcher- Steps To Lake Michigan. Pet Friendly & Fully Fenced

apartment, Sheboygan
This Sheboygan rental is centrally located, steps from Lake Michigan and a short walk to downtown Sheboygan's shops and restaurants, with easy access to Whistling Straits and Kohler-Andrae State Park.
This three-bedroom, two-bathroom apartment sleeps eight, offering a fully equipped kitchen, private backyard with grill and lawn games, plus beach essentials for Lake Michigan access and family-friendly amenities including a Pack & Play and high chair.
Overlook Oasis | Coastal Haven In Ellis District - Sheboygan, WI
9.9 24 reviews

Overlook Oasis | Coastal Haven In Ellis District

apartment, Sheboygan
This Sheboygan apartment rental, located in the Ellis District, is steps from the lakefront, DeLand Park, Blast Ice Cream, and Harbor Lights Bar, offering easy access to the Sheboygan Riverwalk and Kohler-Andrae State Park.
The three-bedroom, one-bathroom unit sleeps six guests comfortably and features a fully equipped kitchen with stainless steel appliances, air conditioning, and on-site parking, perfect for families exploring Sheboygan's attractions.
Beautiful 3br Home Near Lake Mi - Sheboygan, WI
9.8 47 reviews

Beautiful 3br Home Near Lake Mi

apartment, Sheboygan
This Sheboygan apartment is a family-friendly option with excellent user, location, and cleanliness ratings. It accommodates up to 7 guests and features a fully equipped kitchen, air conditioning, parking, and internet access.
The apartment is conveniently located in Sheboygan, offering easy access to local attractions and activities. It boasts a comfortable layout with one bathroom and a spacious living area, making it an ideal choice for families or groups seeking a memorable vacation rental.
Logan Ave Holiday House - Upper - Sheboygan, WI
9.8 12 reviews

Logan Ave Holiday House - Upper

apartment, Sheboygan
This Sheboygan apartment is located in a quiet end park setting with easy access to both the lake and downtown. The apartment has excellent user, location and cleanliness ratings. The layout is spacious with two queen bedrooms, a queen sleeper sofa in the living room and a fully equipped kitchen. Guests can enjoy amenities such as air conditioning, a garden, parking, a shared backyard, and pet-friendliness.

Best Sheboygan, WI vacation rentals with a pool

Among the 387 accommodations in Sheboygan, WI, here are the 4 best rentals with a pool

Luxury Pool Retreat-2 Acres-near Whistling Straits - Sheboygan, WI
10 10 reviews

Luxury Pool Retreat-2 Acres-near Whistling Straits

apartment, Sheboygan
This 4-bedroom, 4-bathroom house is situated on 2 private acres in Sheboygan, offering 12-guest capacity and convenient access to Whistling Straits Golf Course (8 miles), Road America (20 miles), and Lake Michigan.
This family-friendly rental features a heated in-ground pool (May-September), a large, fully equipped kitchen, multiple indoor living areas, and air conditioning, making it ideal for golf trips and family getaways.
Blue Harbor Resort And Conference Center - Sheboygan, WI
8.4 523 reviews

Blue Harbor Resort And Conference Center

resort, Sheboygan
Blue Harbor Resort and Conference Center sits right on the Sheboygan beach, just a short walk from the John Michael Kohler Arts Center, Stefanie H. Weill Center for the Performing Arts, and Above & Beyond Children's Museum. This resort consistently receives very good ratings from previous guests.
The resort offers a variety of accommodations for couples and families. Guests can enjoy a full-service spa, a complimentary waterpark, a fitness center, a restaurant, a bar, and a garden.
Baronwood Oasis | Pool + Arcade Mega Estate - Sheboygan, WI
10 9 reviews

Baronwood Oasis | Pool + Arcade Mega Estate

apartment, Sheboygan
This 10,500-square-foot luxury estate in Sheboygan, Wisconsin, is minutes from the Whistling Straits golf course, Kohler Co. amenities, and Lake Michigan.
This seven-bedroom, seven-bathroom home sleeps twenty guests and boasts an indoor pool and spa, a private arcade, a gourmet chef's kitchen, and concierge services including private chefs and massage therapists.
Your Own Private Resort For The Ryder Cup! - Sheboygan, WI
10 1 review

Your Own Private Resort For The Ryder Cup!

apartment, Sheboygan
This luxury resort-style apartment overlooks an environmental park with hiking trails and a river in Sheboygan, Wisconsin. It has excellent user, location, and cleanliness ratings.
The apartment has four bedrooms, three bathrooms, and can accommodate up to eight guests. It features a full Viking kitchen, three indoor fireplaces, a lower-level bar, a sunroom, custom bathrooms, and a laundry room. Guests can enjoy amenities such as an indoor lap pool and hot tub, a hand-hewn sauna, a large heated outdoor in-ground pool, multi-level decks with lush furnishings and fire tables, a 2-story heated gazebo with seating and a fire table, an outdoor bar, gas and charcoal grills, and a "band room" that can convert to a fourth bedroom.

Frequently Asked Questions about vacation rentals in Sheboygan, WI

  • What are the must-see sights in Sheboygan, Wisconsin?

    Sheboygan has a lot to offer! The Sheboygan Maritime Museum is a great place to learn about the city's rich history as a shipbuilding and fishing center. The John Michael Kohler Arts Center showcases contemporary art in a stunning setting. For a taste of local history and architecture, stroll along the historic Eighth Street business district. Finally, don't miss the beautiful Sheboygan Riverwalk, perfect for a relaxing walk.
  • What are the best Airbnb and vacation rentals in Sheboygan, WI?

  • Are there unique natural phenomena in Sheboygan, Wisconsin?

    While Sheboygan doesn't have dramatic geological features, its location on Lake Michigan provides beautiful natural scenery. The lake itself offers stunning sunsets and opportunities for swimming, boating, and fishing. The shoreline provides nice walking paths and views. Kohler-Andrae State Park, just south of Sheboygan, offers beaches, dunes, and diverse birdlife.
  • What are the most popular Airbnbs in Sheboygan, WI?

    Among the Airbnbs in Sheboygan, WI, Cozy Sheboygan Upper, Carriage House Sheboygan - Garage Parking Included and Downtown Walk-up are the most popular ones.

  • What essentials should you bring along for a trip to Sheboygan, Wisconsin?

    Pack comfortable walking shoes, as you'll likely be doing a lot of exploring on foot. Depending on the season, you'll want layers of clothing, including a light jacket or sweater even in summer. Sunscreen and a hat are essential, especially during the warmer months. Don't forget your swimsuit if you plan on enjoying Lake Michigan!
  • What are the best vacation rentals with a pool in Sheboygan, WI?

  • What famous events or festivals are happening in Sheboygan, Wisconsin?

    Sheboygan's biggest event is probably the Bratwurst Festival, a massive celebration of, you guessed it, bratwurst! It's a multi-day event with live music, food, and family-friendly activities. The city also hosts various smaller events throughout the year, so checking the local event calendar closer to your travel dates is a good idea.
  • What are the best rentals for families and kids in Sheboygan, WI?

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Sheboygan, Wisconsin?

    A daily budget of $150-$300 per person should cover a comfortable trip to Sheboygan. This is just an estimate, and costs can vary depending on your accommodation choices, dining preferences, and activities. Budget-friendly options are available, and you can easily adjust your spending to fit your needs.
  • What are the best rentals or Airbnbs with a jacuzzi in Sheboygan, WI?

  • Where can you find the best restaurants serving local dishes in Sheboygan, Wisconsin, and what are the must-try specialties?

    Sheboygan is known for its German heritage, so you'll find many restaurants serving traditional German fare. The local bratwurst is a must-try! Several restaurants along Eighth Street offer delicious meals. For a broader range of options, explore the city's diverse culinary scene; you'll find everything from seafood to Italian cuisine.
  • What are some less-famous attractions in Sheboygan, Wisconsin that are worth the visit?

    The Sheboygan County Historical Museum offers a deeper dive into the area's history. The Blue Harbor Resort and Spa, while known for its amenities, also has beautiful grounds worth exploring. Consider a visit to the local farmers' markets for a taste of the region's fresh produce and local goods.
  • What are the best activities for engaging with locals and understanding their culture in Sheboygan, Wisconsin?

    Attending the Bratwurst Festival is a great way to experience Sheboygan's community spirit. Visiting local shops and businesses in the historic Eighth Street district allows you to interact with residents. Consider attending a local event or farmers' market to get a feel for everyday life.
  • What unique natural landscapes and terrain features can travelers explore in Sheboygan, Wisconsin?

    Sheboygan's most striking natural feature is its Lake Michigan shoreline, with its sandy beaches and the impressive dunes of Kohler-Andrae State Park. The Sheboygan River also offers scenic views and opportunities for kayaking or paddleboarding.
  • How many days are ideal for visiting Sheboygan, Wisconsin, and what are some itinerary suggestions?

    Two to three days is a good amount of time to explore Sheboygan at a relaxed pace. A possible itinerary could include a day exploring the downtown area, including the Maritime Museum and Arts Center; a day at Kohler-Andrae State Park; and a day enjoying the Riverwalk and perhaps a local brewery.

Nearby regions

Best Sheboygan, WI vacation rentals with a balcony

Beachside Condo W Stunning Lake Views - Sheboygan, WI
10 1 review

Beachside Condo W Stunning Lake Views

apartment, Sheboygan
This beachfront apartment in Sheboygan offers direct access to the shore with stunning lake views, situated steps from General King Park Beach and 1.3 miles from the Children's Museum.
This 800 square foot residence accommodates up to 9 guests with 2 bedrooms, 2 living rooms, a full kitchen, air conditioning, a patio, and an on-site playground and garden.
Beachside Beautifully Renovated Historic Home - Sheboygan, WI
No reviews

Beachside Beautifully Renovated Historic Home

apartment, Sheboygan
This newly renovated historic home in Sheboygan's Ellis Historical District offers an unparalleled waterfront location directly across from Deland Park and Lake Michigan, with downtown restaurants and shopping 4 blocks away.
This 3-bedroom, 2-bathroom rental accommodates up to 6 guests and features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, multiple porches, and is a 15-minute drive from Whistling Straits.
Beach House On The Shores Of Lake Michigan Near Downtown Sheboygan - Sheboygan, WI
9.2 7 reviews

Beach House On The Shores Of Lake Michigan Near Downtown Sheboygan

apartment, Sheboygan
This Sheboygan house is right on the public beach, offering direct access to Lake Michigan. The house is close to attractions like the Above & Beyond Children's Museum, Blackwolf Run, Blue Harbor Resort & Conference Center Water Park, and Bookworm Gardens. The house has three bedrooms, including one on the main floor, and comfortably accommodates up to eight guests. The house features a large balcony, multiple TVs, and a driveway with ample parking.
Sheboygan Riverside Condo - Sheboygan, WI
10 1 review

Sheboygan Riverside Condo

apartment, Sheboygan
This 2-bedroom, 1-bathroom condo in Sheboygan offers tranquil Sheboygan River views and is conveniently located near cultural venues such as the Stefanie H. Weill Center for the Performing Arts and the John Michael Kohler Arts Center.
This dwelling accommodates up to 6 guests and features a king suite balcony with a fireplace, a second bedroom with two queen beds, an open-concept living area, a fully-equipped modern kitchen, and a 2-car garage, providing easy access to family-friendly destinations like the Blue Harbor Resort & Conference Center Water Park.

Neighborhoods and points of interest in Sheboygan, WI

Best Sheboygan, WI vacation rentals with parking

Recombobulation Station-in The Heart Of Sheboygan! - Sheboygan, WI
10 98 reviews

Recombobulation Station-in The Heart Of Sheboygan!

apartment, Sheboygan
This upper unit apartment is located just a few blocks from Sheboygan's North Beach and downtown 8th Street district, placing you within walking distance of restaurants, shops, and the beach. This vacation rental has received excellent ratings for its location, cleanliness, and user experience.
The apartment has two bedrooms and one bathroom, accommodating up to five guests. Enjoy modern amenities like air conditioning, a fully equipped kitchen, a washer/dryer, and a garden, making your stay comfortable and convenient.
Sheboygan Lakefront - 2 Br Upper - Sheboygan, WI
9.5 23 reviews

Sheboygan Lakefront - 2 Br Upper

apartment, Sheboygan
This Sheboygan lakefront condo, directly across from the Sheboygan Yacht Club and a short walk from downtown shops and the beach, offers stunning lake views.
The two-bedroom unit sleeps four, features a kitchen with a fridge and microwave, air conditioning, and parking, providing convenient access to Sheboygan's attractions.
2 Min Walk To Food, 15 To Pier! 4 Bedrooms 2k/2q - Sheboygan, WI
10 157 reviews

2 Min Walk To Food, 15 To Pier! 4 Bedrooms 2k/2q

apartment, Sheboygan
This 1914 craftsman house is located in downtown Sheboygan, a block away from restaurants and bars, a 12-minute walk from the beach and pier, and a 10-minute drive from Kohler. The accommodation consistently receives excellent ratings for user experience, location, and cleanliness.
The house has four bedrooms and one bathroom, comfortably accommodating eight guests. Amenities include a well-equipped kitchen, a spacious porch, a charming pink bathroom, and a garden, providing a unique blend of historic charm and modern comfort.
Dog-friendly Sheboygan Home - 1 Mi To Town! - Sheboygan, WI
9.8 37 reviews

Dog-friendly Sheboygan Home - 1 Mi To Town!

apartment, Sheboygan
This Sheboygan vacation rental, conveniently located near Kiwanis Park, Bookworm Gardens, and South Shore Beach, offers easy access to Whistling Straits Golf Course.
The newly renovated single-story home features one bedroom, one bathroom, sleeps two, includes a fully equipped kitchen with modern appliances, a patio with a gas grill, two Smart TVs, and reserved parking for two vehicles.
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