Apartment vacation rentals in Sheboygan

Modern Lower Apt - One block to the Lake

Part 1 of 2 Amazing AirBnB apartments in this ideally located duplex. *Disclaimer - this apartment offers a true lower level living experience. You may notice some noise, including foot traffic, from your amazing upstairs Airbnb neighbors. But.. with all the great restaurants, golf, fishing, and the beach nearby you won’t even have the time to hear it! Located only 1 block from the beach on Lake Michigan - you’ll find relaxation and a great time here at the heart of Sheboygan’s Shoreline.

The Beach | Sheboygan 2Br/1 Ba

Welcome to the Beach, a lakeside retreat in the heart of Sheboygan. Located just 3 blocks from Lake Michigan and a stones throw to down town Sheboygan, The Beach is the perfect place to center your visit to Eastern Wisconsin. The Beach is the main floor unit of a duplex featuring 2 bedrooms, 1 bathroom, a well stocked kitchen, a cozy living room, fast wifi and convenient amenities. We have an easy check out with no to-do lists. Just pack and go! *New cleaning staff hired January 2023!*

Overlook Oasis | Lakeside Stay in Ellis District

Welcome to Overlook Oasis by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026. Nestled in Sheboygan’s historic Ellis District, this newly remodeled upper-level retreat blends modern comfort with coastal charm. With 2 queen beds and a versatile king trundle, it’s perfect for families, couples, or groups. Step outside to the scenic lake walk, grab ice cream at Blast, or sip cocktails at Harbor Lights Bar—all just minutes away.

Cozy 2BR Upper Apt • Quiet Area • 1 Mile to Beach

Looking for a clean, comfortable, and budget-friendly place in Sheboygan? You’ve found it. This 2-bedroom, 1-bath upper-level apartment is perfect for travelers who want a quiet place to relax — just 1 mile from the beach and close to everything, without the noise (or the price tag) 📶 Fast, free Wi-Fi – Work, stream, or scroll with ease 🅿️ Plenty of street parking – Always free ✅ No pets, no parties — just peace and quiet ✅ Perfect for couples, solo travelers, small families,

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

Clean, Comfy Stay Near Parks, Downtown & Lake!

Enjoy a peaceful stay near Sheboygan’s lakefront, family parks, and downtown eats. This clean, cozy 2BR unit offers everything you need—walkable location, garage parking, full kitchen, and thoughtful touches like old-school Nintendo and local recommendations. ⭐ “Clean, comfy, quiet—close to everything. We’ll definitely stay again!” – Roger ✓ Minutes to downtown & Lake Michigan ✓ Family park across the street ✓ Garage + easy onsite parking

One Bdrm Apt - The Erie House near lake & downtown

This house was built in 1888 as a single family home and retains its nineteenth century charm along with today's modern conveniences. The location is just walking distance from both majestic Lake Michigan to the east and Sheboygan's charming downtown to the west. The lodging, which sits in an attractive, tree lined neighborhood, has been divided into several living units in which you will be staying on the first floor facing Erie Avenue.

The Blue Cobb House

My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.

Terrace View a Charming 1 Bedroom Apt

Relax in a mid-century modern inspired apartment with private access. This simple but inviting space has all the essentials you will need for your adventures. Whether you're golfing at Whistling Straights, going to a race at Road America, enjoying the beach or in town to work; stop here to wind down and rest well. Situated between the north side and downtown you are never more than 10 minutes away.