Condo holiday rentals in Sheboygan

Heavenly Condo in the Malibu of the Midwest

7th Heaven Condo is in the popular South Pier district. Cute condo is on the 2nd floor with elevator access. Across the street is the sandy beach of Lake Michigan where wind surfers come from around the world to surf. Stroll down the riverwalk to many cafes, pubs and shops. Rent a boat or kayak. Fishing and tour boats also available. Day passes for water park & bike rentals are available at Blue Harbor Resort, just down the street. Kohler Golf & Road America are a short drive away. #Sheboygan

Beach condo for 12: 4 bdrms, 2+ baths, treadmill

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 nearby 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! Free in-unit washer/dryer Full kitchen. Breakfast bar seats 4. Dining table seats 6. Treadmill 2 parking spots and public lots Guests do not have access to or use of Blue Harbor Resort water park

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!

A Glorious Getaway Sheboygan - LUX Lake Condo

Located in "Sheboygan" Wisconsin's premier "Blue Harbor Resort" 20 Minutes from Whistling Straits, Black Wolf Run & The Bull at Pinehurst and much more... 4 Bedrooms with one King, four Qns and Bunk beds 3 Full Bathrooms Fully equiped kitchen with Coffee Bar Washer & Dryer On-sight Parking Over 2500 sq ft of living space Private west deck with Lake Michigan view Family Friendly with Pack & Play Fresh linens, towels, toiletries, & essentials provided Professionally cleaned every time

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, Tiki Bar, and easy access to 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!

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.

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!

Lighthouse Lookout - 3BR | Steps to Lake Michigan

Lighthouse Lookout by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026. Discover the ultimate retreat at Sheboygan's Riverfront condo with stunning river and Lake Michigan views. This top-floor 3BR/2BA unit features a master jacuzzi tub and over 1,600 sq ft of space. Enjoy riverside dining, fishing charters, nearby shops, restaurants, and championship golf at Kohler properties.