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

4.97 out of 5 average rating, 31 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 Sheboygan

5 out of 5 average rating, 8 reviews

'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.

Top guest favorite

Condo in Sheboygan

4.98 out of 5 average rating, 41 reviews

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

Top guest favorite

Condo in Sheboygan

4.97 out of 5 average rating, 118 reviews

Beautiful Beachside Condo w/ Stunning Lake Views

Blue water+White sand+Waves will surely make your stay in our second-floor Waves of Happiness Condo hosted by Sheboygan Vacation Rentals. You just decide whether to sit on the north or south deck to enjoy the sights and sounds of Lake Michigan. Less than 200 feet to the beach and a sprawling city park for our backyard. Plan to stroll the beach, walk the River Boardwalk, or tour our historical downtown full of shops, art opportunities, & exquisite restaurants--WALKABLE from the condo.

Top guest favorite

Condo in Sheboygan

4.97 out of 5 average rating, 36 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.

Top 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!

Top guest favorite

Condo in Sheboygan

4.97 out of 5 average rating, 65 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.

Top guest favorite

Condo in Sheboygan

4.88 out of 5 average rating, 206 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.

Top 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

4.79 out of 5 average rating, 14 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!

Top guest favorite

Condo in Sheboygan

5 out of 5 average rating, 31 reviews

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.