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 to 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 waterpark

VicVill | WaterViews | Vintage Charm Meets Comfort

☀︎Welcome to VicVill! Historic charm meets lakeside comfort in this 2BD/2BA Condo. Located in Elkhart Lake Beach Resort Enjoy stunning lake and pool views throughout Relax at the private resort beach+seasonal indoor/outdoor pool Plush King master+matching twin-over-full bunks Steps to TikiBar Walk to village shops, restaurants, and water sports rentals Perfect for track fans (5 mins to Road America), golfers (20 mins to Whistling Straits) Settle In+Check Out+Enjoy your time away!

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!

Lakefront Condo, Private Beach/Pool, Walk to Town

Elkhart Lake’s beauty awaits year-round! This 3BR/3BA condo boasts a 600 ft private beach, private outdoor pool, hot tub, water sports rentals, Tiki Bar and 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!

The Lakeside Duo | Side-By-Side Beachfront Condos

Perfect for large families or groups, this listing includes two side-by-side beachfront condos with full access to both units. While there is no direct interior connection, guests can comfortably use the condos together, offering a combined 6 bedrooms, 5 bathrooms, and over 5,000 sq ft of lakeside living. Enjoy multiple kitchens, living areas, private balconies, and stylish interiors just steps from Lake Michigan—ideal for gathering, relaxing, and making unforgettable memories.

The Lake Street Kickback in Elkhart Lake!

Welcome to The Lake Street Kickback! This privately owned studio condo is located at The Elkhart Lake Beach Resort (Formerly The Shore Club of Wisconsin) & has access to all resort amenities. During your stay enjoy the outdoor pool/hot tub, resort beach and Tiki bar. 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.

Private Beach, Pools & Full-Kitchen

🌊 Million-Dollar Views of Elkhart Lake from Covered Patio 🏊‍♂️ Outdoor Pools 🌿 Expansive Green Spaces 🚤 Private Beach & Lake Access 🍳 Full Kitchen w/High-End Gas Stove 🛁 Spacious Bathroom w/ Walk-In Tiled Shower 🛌 Charming Bedroom w/ Classic Touches & Historic Character 🏖️ Access to Private Shore Club Beach on Elkhart Lake 🕰️ Historic Touch: Part of the Old Schwartz Hotel + Prohibition-Era FBI Lookout Tower 📍 Unique, Standalone Condo

Welcome to our Cozy Lake Condo!

Welcome to your perfect getaway by Lake Michigan! Cozy 1-bedroom condo with stunning Sheboygan River views! Located across from Blue Harbor Resort, this 2nd-floor retreat sleeps 2 comfortably (4 with pull-out couch). Enjoy 600 sq. ft. of living space plus a large balcony—perfect for morning coffee or evening sunsets. Walk to shops, dining, and the beach. Book your stay and experience Sheboygan from the comfort of your own lakeside haven!

Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home

Escape to this spacious downtown riverfront retreat with easy access to nearby beaches, restaurants, and local shopping boutiques. Unbeatable location in the heart of Sheboygan right on the riverfront boardwalk and easy walking distance to Lake Michigan's sandy beach. Fantastic amenities include world-class golf at Kohler and charter fishing expeditions available right out the back door.