Apartment holiday rentals in Sheboygan

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!

'Beautiful Day Getaway' - Lake Michigan Views

Set your sights on the coastal community of Sheboygan, where you can find 2 miles of sandy beaches, epic sailing, and a quaint historic district. This 4-bedroom, 3-bathroom vacation rental condo, located in the Blue Harbor Resort community, is a splendid retreat. Enjoy quick access to Lake Michigan and plenty more to do on-site with a spa, trails, shops, restaurants, and more. Top off your travels with a tee time at Blackwolf Run Golf Course or take a surf lesson with EOS Surf close by.

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

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

Beach condo for 12! 2,000+ s/f. Safely located on 2nd & 3rd floors. Walk easily to the beach, restaurants, shops, and seasonal entertainment. Never have to leave south pier during your stay, but you should to explore what Sheboygan has to offer! 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 with breakfast bar (4). Dining table (6). Treadmill. Absolutely no parties.

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!

Urban Townhouse

Enjoy Sheboygan in this beautifully renovated, 3 bedroom town house with a chic, mid-century vibe. Drink your morning coffee on a private outdoor deck or sleep in late on a plush queen sized bed. The homes lovely tile and wood floors, glass railing, and free Netflix are just some of the features you'll love. Free off street parking is included. Only a 10 minute drive to the American Club in Kohler and a 10-15 minute walk to downtown attractions and Lake Michigan beaches.

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! Discover the ultimate retreat at Sheboygan's Riverfront condo with stunning views of Sheboygan River and Lake Michigan. This top-floor, 3-bedroom, 2-bath unit features a jacuzzi tub in the master bath for relaxation and over 1600 sq ft of space. Enjoy riverside dining on the River Walk, charter boats for fishing, and explore nearby shops, restaurants, and championship golf at Kohler properties.