Apartment holiday rentals in Sheboygan

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Top-rated apartment rentals in Sheboygan

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Top guest favourite
A serene view from the second-story balcony overlooks the sandy beach and expansive lake. Soft waves lap at the shore under a cloudy sky, with a faint rainbow visible in the distance, creating a tranquil atmosphere for relaxation.
Apartment in South Pier
4.96 out of 5 average rating, 72 reviews

Amazing views beach condo for 12: 4 bdrm, 3 bath

Beach condo for 12 2,000+ s/f Safely located on the 2nd & 3rd floors of the building Walk out to the beach. Restaurants, shops, seasonal entertainment walkable on South Pier. 4 bedrooms. 2.75 baths. One bath with oversized jetted tub for 2. One bedroom great for kids: double bed + a bunk bed! Full kitchen. Breakfast bar seats 4. Dining table seats 6. Free in-unit washer/dryer 2 parking spots + free public overnight lot Guests do not have access to or use of Blue Harbor Resort water park

Guest favourite
An aerial view captures the expansive waters of Elkhart Lake, with shimmering reflections of sunlight. The shoreline is lined with lush greenery and a sandy beach, complemented by a few boats gently floating on the surface. Nearby, various residential structures can be seen nestled among the trees.
Apartment in Elkhart Lake
5 out of 5 average rating, 22 reviews

Lakefront Condo, Private Beach/Pools, Walk to Town

Elkhart Lake’s beauty awaits year-round! This 3BR/3BA condo boasts a 600 ft private beach, pools (indoor/outdoor), hot tub, water sports rentals, and easy access to nearby Osthoff Lake Deck, hiking, golfing, and town. Fall brings vibrant foliage, trail hiking, and golf on scenic courses. Winter offers cross-country skiing, snowshoeing, ice skating, sledding and trail hiking, while spring delights with blooming wildflowers, birdwatching, and farmers markets. Experience nature’s magic any season!

Guest favourite
A textured gray sectional sofa is positioned against a light-colored wall, adorned with several patterned throw pillows. Above the sofa, a vintage sign proclaims 'Welcome Race Fans' and promotes local dining and lodging, featuring a weathered red background.
Apartment in Kiel
4.91 out of 5 average rating, 23 reviews

Historic&Modern Kiel 4B near Elkhart Lake & Kohler

Your family, friends or race team will stay in the heart of Kiel, WI. Fine dining, Yard 65 Brewery and restaurants all within walking distance in beautiful & safe downtown Kiel. 10 minutes to the main gate of historic Road America in Elkhart Lake & under 1 hour to Milwaukee and Green Bay. Within minutes of Wisconsin supper clubs like the Fork & Dagger or Schwartz's. Perfect fit for families or larger groups coming from all over and want to stay together or 2 couples wanting some privacy!

Top guest favourite
Apartment in South Pier
4.95 out of 5 average rating, 115 reviews

Janelle's Dockside Condo

GREAT LOCATION!! Built in late 2020. Come visit our luxury, "Nautical Themed" 2 bedroom condo in Sheboygan, WI located on the confluence of Lake Michigan and the Sheboygan River in the charming South Pier District. Relax on the deck with a beverage and watch the sailboats pass by. Stroll the boardwalk for fine dining, charter fishing, quaint boutiques or an afternoon ice cream. World class golfing at Black Wolf Run or Whistling Straights. Equipped with everything you need and more!

Guest favourite
Apartment in Elkhart Lake
5 out of 5 average rating, 19 reviews

The Lake Street Kickback in Elkhart Lake!

Welcome to The Lake Street Kickback! This privately owned studio condo is located at The Shore Club of Wisconsin & has access to all resort amenities. During your stay enjoy the outdoor pool/hot tub, resort beach, Tiki bar, on site restaurant, indoor pool & game room. A unique blend of updates, convenience, comfort & relaxation. Just steps away from local favorites including village restaurants, bars, farmers market, shops & neighboring resorts like Osthoff and Siebkens Resorts.

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Apartment in Sheboygan
New place to stay

The Lakeside Duo | Side-By-Side Beachfront Condos

Perfect for large families or groups, this listing includes two side-by-side beachfront condos with full access to both units. While there is no direct interior connection, guests can comfortably use the condos together, offering a combined 6 bedrooms, 5 bathrooms, and over 5,000 sq ft of lakeside living. Enjoy multiple kitchens, living areas, private balconies, and stylish interiors just steps from Lake Michigan—ideal for gathering, relaxing, and making unforgettable memories.

Guest favourite
The view from the balcony reveals a serene landscape featuring a green lawn that transitions to a sandy beach along Lake Michigan. Sunlight filters through the trees, illuminating the tranquil waters in the distance, while a clear sky enhances the inviting atmosphere.
Apartment in Sheboygan
4.88 out of 5 average rating, 213 reviews

Beachside Lake View - 2br - First Floor - Garage

Located just one lot in from the beautiful shores or Lake Michigan. Amazing location provides year round stunning views . This is a lower 2 bedroom 1 bath condo in a 4unit building were all the units have the same basic layout. You can listen to the waves or walk just a few feet and have the sand on your feet. This condo features front and rear balconies. Makes for a great place to enjoy a weekend get away or a place to relax at night while on a business trip.

Guest favourite
Apartment in Ellis Historic
4.9 out of 5 average rating, 21 reviews

Sheboygan Sunrise Beach Stay

*** STEPS AWAY FROM LAKE MICHIGAN*** Experience the vibrant energy from our stylish apartment with great views. Enjoy easy access to the beach, restaurants, bars and a cozy stylish getaway for unforgettable relaxation and adventure. The apartment features fully equipped kitchen, cozy living area, and comfortable bedrooms. You are in the center of it all, walking distance to Lake Michigan and the Beach, Bars, Restaurants, River Boardwalk, and Historical Downtown.

Top guest favourite
A balcony view overlooking the Sheboygan River features comfortable seating arrangements with dark wicker furniture. The railing offers an unobstructed glimpse of the water and surrounding greenery, while the serene sky adds to the tranquil atmosphere.
Apartment in South Pier
5 out of 5 average rating, 41 reviews

Riverwalk Retreat | 3BR Walk to Lake & Downtown

Riverwalk Retreat by Great lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026. Discover the ultimate retreat in this top-floor Riverfront condo with stunning Sheboygan River and Lake Michigan views. This 1,600 sq ft, 3BR/2BA unit features a master jacuzzi tub and easy access to River Walk dining. Dubbed "The Malibu of the Midwest," savor Lake Michigan sunrises, sandy beaches, and watch surfers ride the waves.

Top guest favourite
An aerial view captures the expansive sandy shoreline of Lake Michigan, bordered by lush green parkland. The shoreline is framed by a calm blue lake under a clear sky. Nearby, a modern white building is nestled among trees, providing access to the beach.
Apartment in Sheboygan
4.97 out of 5 average rating, 175 reviews

Cozy lakeside condo w/ fireplace

Welcome to your cozy lakeside retreat in Sheboygan - perfect for a peaceful Lake Michigan escape year-round. Relax by the fire, stroll to the shoreline, and enjoy easy access to downtown attractions. - Sleeps 4 | 2 bedrooms | 2 beds | 1 bath - Dual decks w/ lake views - Waterfront w/ shared beach access & lake access - Electric fireplace, 55 in HDTV w/ Roku - Kitchen, in-unit laundry, Wifi & workspace - Beach essentials & free garage parking (2 spaces)

Top guest favourite
An open concept kitchen and living area features a large island with seating for four, complemented by modern bar stools. Dark cabinetry contrasts against a brick wall, and stainless-steel appliances are visible, enhancing the functional design of the space.
Apartment in Elkhart Lake
5 out of 5 average rating, 36 reviews

Car Condo Rental in Elkhart Lake

New construction luxury condo in Elkhart Lake. Located in the Wolf Luxury Motor Courts complex. Spacious 2 bedroom 2 full bath condo with balcony. Open concept kitchen and living area with large island/eating space. Located 20 minutes from Whistling Straits golf course. Enjoy legendary Elkhart Lake, home to award winning restaurants, historic downtown, and gorgeous lake views from local night spots. Condo is 1/2 mile north of Road America race track.

Guest favourite
An open-concept living area features a cozy gray sofa and a round dining table with light-colored chairs. A modern electric fireplace is positioned beneath a large wall-mounted TV. Natural light floods in through expansive sliding glass doors, leading to a furnished balcony.
Apartment in South Pier
4.86 out of 5 average rating, 22 reviews

Modern South Pier Condo on Sheboygan River!

Stay in luxury at this 2-bedroom, 2-bathroom vacation rental in Sheboygan, WI. Enjoy the convenience of a fully equipped kitchen, a modern interior, and a prime location. Situated in the South Pier District and just steps away from Lake Michigan, this condo provides easy access to local attractions like the delightful downtown area and nearby beaches. Experience the best of Sheboygan while having all the comforts of this gorgeous riverfront retreat!

Popular amenities for Sheboygan apartment rentals

When is the best time to visit Sheboygan?

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Avg. price$221 SGD$220 SGD$224 SGD$241 SGD$227 SGD$330 SGD$337 SGD$304 SGD$242 SGD$225 SGD$275 SGD$262 SGD
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Quick stats about apartment rentals in Sheboygan

  • Total holiday rentals

    Explore 20 holiday rentals in Sheboygan

  • Nightly prices starting at

    Sheboygan holiday rentals start at $115 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,240 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Sheboygan holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Sheboygan rentals

  • 4.8 Average rating

    Sheboygan stays are highly rated by guests – averaging 4.8 out of 5!