Condo vacation rentals in Sheboygan County

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Top-rated condo rentals in Sheboygan County

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Guest favorite

Condo in Sheboygan

5 out of 5 average rating, 25 reviews

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

Guest favorite

Condo in Sheboygan

4.93 out of 5 average rating, 86 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!

Condo in Elkhart Lake

5 out of 5 average rating, 3 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 and has access to all resort amenities. During your stay enjoy the outdoor pool/hot tub, resort beach, Tiki bar, on site restaurant, indoor pool and game room. A unique blend of updates, convenience, comfort and relaxation. Just steps away from local favorites including village restaurants, bars, farmers market, shops and neighboring resorts like Osthoff and Siebkens Resorts.

Guest favorite

Condo in Sheboygan

4.96 out of 5 average rating, 27 reviews

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.

Guest favorite

Condo in Elkhart Lake

5 out of 5 average rating, 11 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, 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!

Guest favorite

Condo in Sheboygan

5 out of 5 average rating, 13 reviews

Riverwalk Retreat - Overlooking Sheboygan River!

Welcome to Riverwalk Retreat by by Great Lakes Getaways! Discover the ultimate retreat in this top-floor Riverfront condo with stunning views of the Sheboygan River and Lake Michigan. This spacious 1600 sq ft, 3-bedroom, 2-bath unit features a jacuzzi tub in the master bath for ultimate relaxation. Located on the River Walk, enjoy unique restaurants at your doorstep. Dubbed "The Malibu of the Midwest," savor Lake Michigan sunrises, sandy beaches, and watch surfers ride the waves.

Guest favorite

Condo in Sheboygan

4.97 out of 5 average rating, 59 reviews

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.

Guest favorite

Condo in Sheboygan

4.96 out of 5 average rating, 23 reviews

Perfect Paradise: Monthly Rates Available!

Starting 12/1/2024 Rent for an extended stay. Monthly rates until 4/1/2025 Explore your dream destination in this stunning 4-bedroom beachfront condo! With 7 beds and 3 full baths, it's perfect for relaxation. Luxurious master suite, 2-person jacuzzi tub, balcony boasting picturesque courtyard and lake views, a TV, and a gas fireplace. Convenience meets comfort with an in-unit washer/dryer and a fully stocked kitchen, providing everything you need for a seamless stay.

Guest favorite

Condo in Sheboygan

4.88 out of 5 average rating, 205 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 favorite

Condo in Sheboygan

4.97 out of 5 average rating, 35 reviews

A Glorious Getaway Sheboygan - LUX Lake Condo

Steps to Lake Michigan Located in "Sheboygan" Wisconsin's premier "Blue Harbor Resort" 20 Minutes from Whistling Straits, Black Wolf Run & The Bull at Pinehurst 4 Bedrooms with one King, four Qns and Bunk beds 3 Full Bathrooms Fully equiped kitchen with Coffee Bar 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

Guest favorite

Condo in Elkhart Lake

5 out of 5 average rating, 28 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.

Condo in Sheboygan

4.83 out of 5 average rating, 12 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!