Beachfront holiday rentals in Sheboygan County

Beach House

This guesthouse is detached from the main house, comes with garage parking and has all the amenities you need including a wood-burning fire place! Towels, bath tissue, soaps & travel items. AC Window Unit. Kitchen includes pots/pans, dishes, mugs/glasses, coffee pot, toaster & microwave. Paper goods. New appliances/new water heater in 2020. Stairs to the apartment are on the northeast corner of the garage. The beach is steps away with a fire pit, boat house lounge, kayaks, beach toys & bicycles.

Lake Michigan Beach Home by Frank Lloyd Wright pro

Beautiful view and sand beach on Lake Michigan, completely private, surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room, and living room entertainment space, den with a see-through log-fired fireplace, screened-in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and a row boat are available for the boating enthusiast, with life jackets and other floating devices.

Tropical condo w/ beach access & fireplace

Warm lake breezes by day and cozy evenings indoors set the tone at this upper-level condo near Lake Michigan. Thoughtfully equipped and walkable to the waterfront, it’s an easygoing retreat for couples, families, or remote work stays. - Sleeps 5 | 2 bedrooms | 4 beds | 1 bath - Lake view from front & rear private balconies - Waterfront location w/ shared beach access - Electric fireplace & Roku TV - Kitchen, bathroom essentials & in-unit laundry - Beach essentials & dedicated workspace

Lakeview Beach Bungalow - With outdoor Hot Tub!

Enjoy Valentines Day or week at this Beautifully updated beach house just one block off of Lake Michigan. Enjoy the backyard with pergola & 6 person Hot Tub ALL WINTER! Watch the sunrise & sunset from the second floor master balcony. Walk to the lake across the street and walk the beach. Close to downtown and parks. This three bedroom home will impress. Tastefully decorated seasonally. Large bathroom w/deep soaking tub. For treasure hunters, a Metal detector for family fun at the beach.

Shamba on the Lake, Oostburg, WI

Large guest home , in a rustic setting, on a peaceful 2-acre wooded lot (only 5 homes on a very private road) on Lake Michigan with a large private beach a few feet from the deck. . Magnificent panoramic view, amazing sunrises, serene twilights ,and magical star-studded night skies. A slice of Paradise you must experience. Located a mile from I43, 40 minutes from downtown Milwaukee, 20 mins. from golf courses in Kohler, 30 mins. from Road America in Elkhart Lake...

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.

Beachfront getaway in Sheboygan

One of the few homes in Sheboygan that walks out onto the sands of Lake Michigan, this 3 bedroom/ 2 bath home is meant for total relaxation and fun. The open kitchen, dining and living room is full of light from the sliding glass doors on the back of the house, which access a deck and a large back yard. Upstairs is a spacious loft with a pull out couch. Fire pit in the back yard. Just steps from a playground at King Park. Amazing sunrises, worth waking up for.

Vibrant home w/ beach & lake access

Warm, welcoming, and thoughtfully designed, this entire home in Sheboygan’s Ellis Historic District puts you close to the lake, downtown, and everyday comforts while offering a relaxing place to unwind. - Sleeps 8 | 3 bedrooms | 4 beds | 2.5 baths - Bright open layout w/ chef’s kitchen & dining space - Electric fireplace & cozy living area - Private patio & backyard w/ BBQ - Beach essentials & bikes included - Walkable to beach, riverfront & downtown

Woodsy cabin w/ beach access & fireplace

Warm up to a cozy lakeside escape where woods meet water on Lake Michigan. This inviting cabin is made for relaxed group stays, fireside evenings, and nature-filled days year-round. - Sleeps 8 | 3 bedrooms + den | 5 beds | 2 baths - Private beach access & waterfront setting - Wood-burning indoor fireplace & outdoor fire pit - Huge grassy yard w/ games & playground - Fully equipped kitchen & dining area - Beach essentials & long-term stays allowed

Winter's a good time to stay in&cuddle at Surfdaze

We finally have stairs to the water! Plan your summer vacation today! Beautiful Cottage nestled on the WI shore of Lake Michigan. The high water has us stuck on top of the rocks but the deck is perfect for relaxing, enjoying a meal or morning coffee to the sound of the waves. Winter stay? No Problem! Cozy up next to the fire and enjoy the view out the enormous Living room windows. You will not be disappointed when you stay at SurfDaze!

Serene getaway w/ private beach & firepit

Welcome to a peaceful lakeside cottage where quiet mornings and wide-open water views set the tone for your stay. - Sleeps 7 | 2 bedrooms | 6 beds | 1 bath - 275 ft of private Lake Michigan shoreline w/ beach access - Two screened porches & deck w/ grill and outdoor dining - Indoor fireplace, fire pit & outdoor seating - Newly renovated cottage with lake views throughout - Quiet, wooded setting close to dining, golf & spa experiences

Wandering Waves | Beachfront Lake Michigan Stay!

Wandering Waves by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026. Wake up to sweeping Lake Michigan views in this stylish 2BR/2BA beachfront condo! Just steps from the sand, you’ll enjoy sunrise mornings, wave-filled nights, and unbeatable beach access. Inside, a modern open layout offers a fully equipped kitchen, cozy living area, and private patio with serene water views.