Condo holiday rentals in Sheboygan

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

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!

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!

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!

Tropical condo w/ beach access & fireplace

Warm lake breezes by day and cozy evenings indoors set the tone at this upper-level condo near Lake Michigan. Thoughtfully equipped and walkable to the waterfront, it’s an easygoing retreat for couples, families, or remote work stays. - Sleeps 5 | 2 bedrooms | 4 beds | 1 bath - Lake view from front & rear private balconies - Waterfront location w/ shared beach access - Electric fireplace & Roku TV - Kitchen, bathroom essentials & in-unit laundry - Beach essentials & dedicated workspace

A Glorious Getaway Sheboygan - LUX Lake Condo

Unwind in this spacious 4-bedroom, 3-bath beachfront condo perfect for families or groups. Enjoy 7 beds, a luxurious master suite with a 2-person jacuzzi tub, cozy gas fireplace, and private balcony overlooking the courtyard and Lake Michigan. Stylish living spaces, a fully stocked kitchen with coffee bar, in-unit washer/dryer, fresh linens, towels, toiletries, and essentials included. Family-friendly, professionally cleaned, and offering over 2,500 sq ft of relaxing lakeside comfort.

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.

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.

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.

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.

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.

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!