Condo vacation rentals in Sheboygan County

A serene view from the second-story balcony overlooks the sandy beach and expansive lake. Soft waves lap at the shore under a cloudy sky, with a faint rainbow visible in the distance, creating a tranquil atmosphere for relaxation.

4.97 out of 5 average rating, 101 reviews

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

5.0 out of 5 average rating, 5 reviews

Seagulls Nest | Steps 2 Lake! Massage Chair!

Escape to this cozy 2-bedroom condo, comfortably sleeping up to 5 guests! Located just steps from the lake, it’s the perfect home base for relaxing, exploring, and making memories. Enjoy easy access to nearby restaurants, shopping, outdoor adventures, and plenty of activities for all ages. Whether you’re planning a weekend getaway, family vacation, or lakeside retreat, you’ll love coming home to this comfortable and inviting space. Relax, recharge, and enjoy everything the area has to offer!

Superhost

5.0 out of 5 average rating, 3 reviews

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!

A bridge is seen raised, allowing a sailboat to pass through the waterway. Clear blue skies provide a backdrop to the scene, while trees with autumn foliage line the riverbank. The calm water reflects the colors of the surroundings.

4.95 out of 5 average rating, 129 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!

Superhost

An aerial view captures the expansive waters of Elkhart Lake, with shimmering reflections of sunlight. The shoreline is lined with lush greenery and a sandy beach, complemented by a few boats gently floating on the surface. Nearby, various residential structures can be seen nestled among the trees.

4.96 out of 5 average rating, 25 reviews

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!

4.81 out of 5 average rating, 16 reviews

A Glorious Getaway Sheboygan - LUX Lake Condo

Unwind in this spacious 4-bedroom, 3-bath beachfront condo perfect for families or groups. Enjoy 7 beds, a luxurious master suite with a 2-person jacuzzi tub, cozy gas fireplace, and private balcony overlooking the courtyard and Lake Michigan. Stylish living spaces, a fully stocked kitchen with coffee bar, in-unit washer/dryer, fresh linens, towels, toiletries, and essentials included. Family-friendly, professionally cleaned, and offering over 2,500 sq ft of relaxing lakeside comfort.

A view from the open door showcases a spacious deck leading to a grassy area with trees. Beyond the greenery, the blue waters of Lake Michigan are visible, capturing a serene outdoor scene.

4.88 out of 5 average rating, 218 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.

The spacious living area features a comfortable light-colored sofa adorned with decorative pillows. A cozy rug covers the wooden floor, while a small coffee table sits in front. Soft lighting is provided by a lamp, and a coastal artwork is displayed on the wall.

4.92 out of 5 average rating, 36 reviews

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.

An open concept kitchen and living area features a large island with seating for four, complemented by modern bar stools. Dark cabinetry contrasts against a brick wall, and stainless-steel appliances are visible, enhancing the functional design of the space.

5.0 out of 5 average rating, 46 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.

5.0 out of 5 average rating, 12 reviews

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

A comfortable living area is furnished with a navy blue sofa and matching armchair, arranged around a coffee table. A flat-screen TV is mounted on the wall, while large glass doors provide access to a patio with outdoor seating, allowing natural light to fill the space.

4.73 out of 5 average rating, 15 reviews

Modern 2 Bedroom Condo with Lake Michigan View

New modern 2 bedroom condo on the banks of the Sheboygan River and shores of Lake Michigan. 1 Year Month Lease Available Only - Please message if needing a year lease. Full amentities and perfect location for Downtown's best views, restaurants and night life. Short walks to the beach, fishing charters, and Blue Harbor (Not part of the resort). Easy drives to Road America, Kohler's golf courses, and all of Sheboygan's attractions.

An outdoor balcony features a wooden table with colorful place settings and a small planter. Comfortable seating is provided by woven chairs and a red cushioned chair. A decorative privacy screen and clear blue skies create a warm and inviting outdoor space.