Vacation Rentals By Owner In Sheboygan, WI

$313.26

3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

Sheboygan, Wisconsin, United States

brForget your worries in this spacious and serene Guest House Minutes from downtown Sheboygan/Kohler, a 5 star PGA championship golf courses. Kohler Water Spa, located on south side the Beaches /Dunes of Kohler Andrae State Parkbr Our home is just 3 blocks from Lake Michigan, driving distance is 2 min to Kings Park, & South beach,Welcome to our exclusive guest house, designed and furnished with you in mind.brWe are just 2 minute drive to lake and 4minutes drive to Downton, and South Pier areabr3blocks walking distance to the lake, yes! you can walk to South side beach

1

Bed

1

Bath

4

Sleeps

$955.63

/ Nightly

Private Vacation Home

Lake Michigan Home with gorgeous views, great spot for family or golf retreat

Sheboygan, Wisconsin, United States

Our beautiful lakefront home is perfect for a relaxing retreat! Minutes to downtown Sheboygan, downtown Kohler with 5 star PGA championship golf courses (Black Wolf Run, Whistling Straits, The Bull of Pinehurst), and sand dunes/beach of Kohler Andrae State Park. All linens, towels, toiletries are provided. Kitchen comes fully stocked with pots/pans, spices, etc. Coffee is provided to make sure you wake up early to enjoy the stunning sunrises! Pack light and make your travel plans hassle free with many amenities provided.brbrRecently updated gourmet kitchen with picture windows overlooking Lake Michigan. The huge open concept kitchen/family room provides the ideal space for hanging out. Enjoy the large backyard with oversized firepit and built in outdoor grill (we have a gas one as well!). Some noteworthy house details include marble kitchen backsplash, granite countertops, custom built cabinetry, gas-fired wall inserted fireplace, reclaimed tobacco barnwood flooring, and Kohler fixtures throughout.brbrNew in 2024 is our large hillside overlook deck! Newly renovated lower level recreational/movie room and 2 new lower level bedrooms! brbrRest easy with sleeping arrangements for 14+ (a queen sized air mattress is also available in the master walk-in closet)br

Bed

Bath

Sleeps

$305.73

/ Nightly

Apartment

Sheboygan Getaway w/ Deck + On-Site Lake Access!

Sheboygan, Wisconsin, United States

Plan for plenty of outdoor fun on your next Lake Michigan getaway when you stay at this Sheboygan vacation rental! With a private deck, stunning water views, and on-site lake access, this quiet 2-bedroom, 1-bath apartment is perfect for any nature enthusiasts looking for an opportunity to relax along Wisconsin’s coastline. Be sure to spend some time at nearby South Shore Beach, explore Kohler-Andrae State Park, or visit downtown’s Above and Beyond Children’s Museum during your stay!brbr-- THE PROPERTY --brbrLake Views | Central A/C | In-Unit Laundry | 2 Mi to Downtown SheboyganbrbrBedroom 1: Queen Bed, Twin Bed | Bedroom 2: Queen BedbrbrINDOOR LIVING: Smart TV, dining table, walk-in closet, walk-in shower, ceiling fans, board games, booksbrOUTDOOR LIVING: Private deck, balcony, lounge chairs, on-site lake accessbrKITCHEN: Refrigerator, coffee maker, stove/oven, microwave, dishwasher, toaster, Crockpot, dishware & flatware, cooking basicsbrGENERAL: Free WiFi, keyless entry, self check-in, cable, washer & dryer, iron/board, towels/linens, trash bags/paper towels, complimentary toiletries, hair dryerbrFAQ: Stairs required for access, homeowner on-site, 4 exterior security cameras (facing out)brPARKING: Free street parking (1 vehicle)brbr-- THE LOCATION --brbrOUTDOOR FUN: Lake Michigan Access (on-site), South Shore Beach (0.9 miles), Kohler-Andrae State Park (5 miles)brLOCAL PARKS: Lake View Park (0.3 miles), Deland Park (3 miles), Maywood Park (6 miles)brNEARBY ATTRACTIONS: John Michael Kohler Arts Center (2 miles), Above & Beyond Children’s Museum (2 miles), Bookworm Gardens (4 miles)brAIRPORTS: Milwaukee Mitchell International Airport (63 miles), Green Bay Austin Straubel International Airport (69 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property is located on the 2nd floor and requires stairs to accessbr- NOTE: The homeowner lives on-site, in a completely separate unit, and may be present during your staybr- NOTE: Your safety matters. This property features 4 exterior security cameras located on each exterior side of the building. The cameras face the main entrance, side yards, and back yards of the property. These cameras do not look into any interior spaces. The cameras record video and sound when activated by motion

Bed

Bath

Sleeps

$356.39

/ Nightly

Condo

Breezy Beach - Villa 75 Steps from Lake Michigan

Sheboygan, Wisconsin, United States

Welcome to Breezy Beach — Presented by Great Lakes Getaways! brbrTake advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026.brbrJust 75 steps from the sandy shores of Lake Michigan, this charming villa is the perfect spot for your next getaway. Enjoy fishing, boating, hiking, and golf all nearby, or take a leisurely stroll to the pier for restaurants, bars, and mini golf.brbrFamily fun is right next door at the resort’s game arcade, while the luxurious Kohler Resort is only a short drive away. For motorsport fans, Road America is just 20 minutes out.brbrLakeside Escape | 2BR/2BA Condo in Sheboygan’s South Pier br Cozy Comfort • Prime Location • Lake Vibes GalorebrbrWelcome to your dream getaway just steps from the sparkling shores of Lake Michigan! Nestled in the vibrant South Pier neighborhood, this stylish 2-bedroom, 2-bathroom ground-level condo offers the perfect balance of comfort, convenience, and charm—ideal for families, couples, or small groups.brbr● Unwind by the cozy gas fireplace after a day of exploringbr● Dine al fresco on your private patio with peekaboo lake viewsbr● Wake up to your own complimentary coffee barbr● Walk to beaches, boutiques, cafes, and lakefront parksbrbrThoughtfully designed with both relaxation and adventure in mind, this fully furnished condo features:brbr✔ 2 spacious bedrooms (queen beds + bunk beds = sleeps 6 comfortably!)br✔ 2 full bathrooms for added privacy and easebr✔ Comfortable open-concept living area with fireplace & smart TVbr✔ Fully stocked kitchen with modern appliances, bar seating, & dining tablebr✔ Private patio with outdoor dining—enjoy the lake breeze anytimebr✔ Keyless entry for smooth check-in & peace of mindbr✔ Free WiFi, washer/dryer, and all the essentials you needbrbrWhether you’re curling up for movie night, sipping wine on the patio, or cooking breakfast before a beach day—you’ll feel right at home.brbr brWe’re a passionate local team dedicated to 5-star hospitality. You’re not just booking a stay—you’re booking an experience. Have a question or need a recommendation We’re here for you every step of the way.brbrNO waterpark access, but trust us—there’s so much more to love. From peaceful beach mornings to unforgettable local eats and vibrant summer festivals, Sheboygan has it all.brbr :br● Deland Park – Surfing, picnics, beach, shipwreck display (0.2 mi)br● Sheboygan Marina – Boat rentals, fishing, lake views (0.3 mi)br● North Point Park – Lakeside trails & epic sunsets (0.5 mi)br● John Michael Kohler Arts Center – Modern art & performances (1 mi)br● Above & Beyond Children’s Museum – Hands-on fun for kids (1 mi)brbr & :br● Lino Ristorante Italiano – Upscale Italian with lake views (0.4 mi)br● Weather Center Café – Chill spot for coffee & light bites (0.3 mi)br● Field to Fork – Local eats, bakery & coffee roastery (0.9 mi)brbr & :br● Deland Park Kite Festival – Colorful skies & family fun (0.2 mi)br● Sheboygan Farmers Market – Fresh produce & live music (0.9 mi)br● Midwest Powerboat Challenge – Adrenaline-pumping action (0.5 mi)brbr :brThis is a privately owned unit and does not include access to the Blue Harbor Resort water park. Day passes are not available as the Resort Amenity Fee has been waived by the owner.brbrRenters and guests of this condominium unit do not have access to or use of the Blue Harbor Resort water park and will not try to purchase a Day Pass, since the unit owner obtained a waiver of the Resort Amenity Fee.brbrRental Agreement Notice:brGuests are required to review and sign a rental agreement prior to check-in. The agreement includes important house rules and stay policies. Booking this property confirms that you agree to review and complete the rental agreement before your stay. Failure to complete the agreement may result in cancellation of the reservation.brbr brThe entire villa is all yours and it is all on one level. No steps to get in the villa and no steps in the villa.brbrYour Getaway Starts Here! From sunrise walks by the lake to cozy nights by the fire, this condo is more than a place to stay—it’s a place to create memories. Book now and start your next chapter in beautiful Sheboygan!

2

Bed

2

Bath

8

Sleeps

$532.1

/ Nightly

Condo

Shoreline Sanctuary - Family Beach Villa with Deck and Sunsets

Sheboygan, Wisconsin, United States

Welcome to Shoreline Sanctuary — Presented by Great Lakes Getaways! brbrThis stunning 4-bedroom, 3-bathroom beachfront villa on Lake Michigan offers breathtaking views and direct access to the sand. With 4 queen beds, 1 king, and a twin bunk, it’s perfect for families or groups. Enjoy a fully stocked kitchen, spacious living areas, and an expansive deck for relaxing to the sound of waves. Unwind with unforgettable sunsets and peaceful lakeside mornings.brbrA beautifully updated two-story condo just steps from the sandy shores of Lake Michigan. This serene retreat offers the perfect blend of comfort, style, and convenience — ideal for families, couples, or groups of friends looking for a peaceful lakeside escape.brbr ’ br✔ Bright and airy interiors with an open layout and large windowsbr✔ Four spacious bedrooms spread across two levelsbr✔ A private master suite featuring a jetted soaking tub and attached bathroombr✔ Fully equipped kitchen, perfect for home-cooked meals or beach-day snacksbr✔ Private balcony with views of the lake and space to relaxbr✔ In-unit laundry for your conveniencebr✔ Just steps to the beach and lakefront pathbr✔ Walkable to dining, shops, live music, and family-friendly activitiesbr✔ Free on-site parkingbrbrMain Living Area (One flight of stairs to enter)br- As you enter this gorgeous villa, you’ll be immediately welcomed by its bright, airy atmosphere. The main floor features an inviting open-concept living and dining area, perfect for gathering with friends or family. Large windows flood the space with natural light, creating a warm and welcoming ambiance. The living room is thoughtfully appointed with cozy furnishings where you can unwind after a day at the beach or explore the local area. Step out onto your private balcony and take in the fresh lake air, as you enjoy the stunning views of the water or relax with your morning coffee.brbrAdjacent to the living area is the dining space, offering the perfect setting for family meals or intimate dinners. The modern kitchen is fully equipped, making it easy to prepare meals when you want to dine in.brbrTwo Spacious Bedroomsbr- The main floor also features two beautifully decorated bedrooms. Each room is designed to provide the utmost comfort, with soft linens and tasteful decor that will make you feel at home. These rooms are perfect for relaxing after a day of exploring all that Lake Michigan has to offer.brbrUpper-Level (One flight of stairs to enter)br- Head upstairs to discover a truly special retreat. The second floor houses an additional two spacious bedrooms, both with cozy, comfortable furnishings and calming tones that invite relaxation. Whether you're resting after a day of sun and sand or preparing for your next adventure, these rooms are perfect for getting a peaceful night’s sleep.brbrConvenience and Luxurybr- On the upper level, you’ll also find a convenient laundry area, making it easy to keep your clothes fresh during your stay.brbrFor a truly indulgent experience, step into the master suite – a private oasis that promises a restful night’s sleep. It’s the perfect place to unwind, featuring a jetted tub where you can soak and relax after a long day. The attached bathroom with a shower adds another level of luxury to this spacious and private area.brbrLake Michigan at Your DoorstepbrThis villa is a dream for beach lovers! With the sandy beachfront just steps away, you’ll enjoy the unique privilege of having Lake Michigan right at your doorstep. Spend your days lounging in the sun, swimming in the refreshing waters, or taking leisurely strolls along the shore.brbrIdeal LocationbrCentrally located, you’ll have easy access to everything you need during your stay, whether it’s local shops, restaurants, or exciting outdoor activities. Whether you’re looking to relax by the water, explore the area, or enjoy an afternoon on your balcony, this villa is the ideal home base for your getaway.brbr : br- This condo is privately owned and does not include access to the Blue Harbor Resort water park. Guests may not purchase day passes, as the unit owner has waived the Resort Amenity Fee.br- Renters and guests of this condominium unit do not have access to or use of the Blue Harbor Resort water park and will not try to purchase a Day Pass, since the unit owner obtained a waiver of the Resort Amenity Fee.brbrWe are excited to host you! Your satisfaction and comfort are our top priorities. Book now and experience lakeside living at its finest! Your Perfect Getaway Awaits!brbrRental Agreement Notice:brGuests are required to review and sign a rental agreement prior to check-in. The agreement includes important house rules and stay policies. Booking this property confirms that you agree to review and complete the rental agreement before your stay. Failure to complete the agreement may result in cancellation of the reservation.

Bed

Bath

Sleeps

$479.2

/ Nightly

Private Vacation Home

Art Collector's Dream - Remodeled w/ Gallery Vibes

Sheboygan, Wisconsin, United States

Newly renovated 1904 home in prime location. Remodeled kitchen and baths, gorgeous woodwork and floors, off-street parking. Full of original work (some for sale) from regional artists, cozy rugs, and a fun mix of mid-century and antique furniture. Stroll to downtown Sheboygan's Farmer's Market, stores, coffee shops and restaurants, the Kohler Art Center, and the beach. Or just relax on the front porch. We are also happy to share local tips including how to grill the area's famous brats.brbrYou will have plenty of space to hang out together or find your own private nook at the 515 Guesthouse and Gallery. An elegant Master Suite with a King bed features a large, lovely bathroom with custom cabinets, Kohler plumbing fixtures, and a heated tile floor. Two other bedrooms with Queen beds share a bathroom with custom-made tiles, a pedestal sink, and a shower-tub combo. Downstairs Den can be used as a cozy reading room or an extra bedroom with a high-end, comfortable (truly) single sofa sleeper and a pocket door for privacy. First floor also features a half bath, a gracious foyer, and a light and airy family room that connects to a new kitchen with an expandable table for games and family meals. The house combines the charm of another era with modern comforts like central air conditioning and ceiling fans to keep you cool, though usually the breezes from the lake just down the hill suffice. The wide front porch is a great place to sit in a rocker and watch the world go by. The neighborhood is amazingly quiet for being in the center of things. On one side is the owner, and on the other beyond the grassy lawn is a historic church with a belfry and stained glass windows that light up at night. This lovely property is unique in all the best ways - a perfect base for exploring Sheboygan and all that the area has to offer.brbrIt's 515 Somewhere also doubles as a showcase for artists so there is always new and interesting art on the walls, much of it for sale. We have spent the past years restoring this 1904 Foursquare, and ask that you help us preserve its wood floors for another 100 years by removing your shoes if they are wet or muddy or have high heels or cleats. We are excited to share 515 with you!brbrAfter booking your reservation, you will receive a notification and link to complete our Rental Agreement, confirming the terms and conditions of your stay at 515, as well as a refundable security deposit, which you will be able to execute and set up digitally.

Bed

Bath

Sleeps

$402.93

/ Nightly

Private Vacation Home

Beach and Golf House

Sheboygan, Wisconsin, United States

This home is in the perfect location to explore everything Sheboygan County has to offer. It is located in the historic Ellis district on the shores of beautiful Lake Michigan. The home is a 2 or 3 minute walk to Deland beach and the Sheboygan Marina and lighthouse. A short drive to world class golfing at Whistling Straights, black Wolf Run and the Bull. Road America is also a short 20 minute drive. Located half way between Green Bay and Milwaukee for those Packer and Brewer fans. brThe home has been beautifully renovated. The new kitchen and dining area is the heart of the home and has been stocked with dishes, pots and pans, utensils and high end stainless steel appliances. It is a great place to gather, cook and socialize. There is a master bedroom on the main floor and a master bedroom and two additional bedrooms on the upper level. The house has WiFi, cable tv, and a DVD player and movies. For extra entertainment the closet in the kitchen has games, cards and coloring books and the cute sun porch has a chess and checkers table for some competitive play. There is a laundry room with a washer and dryer for you convenience. The backyard has a deck, a grill, a basketball hoop and a fire pit and is a fun place to hang out. You are only minutes away from Deland beach playground, picnic area and sand volleyball courts. The beauty of Sheboygan is right out our front door as the walk along our beach and lakefront is stunning.

Bed

Bath

Sleeps

$1074.02

/ Nightly

Villa

Luxury Villa on Lake Michigan!

Sheboygan, Wisconsin, United States

Welcome to the ideal place on Lake Michigan for a family beach getaway, wind surfing, fishing, bachelorette weekend, golfing trips & more!brbrEnjoy access to Blue Harbor's indoor Waterpark and swimming pool. Just make sure to look at the Waterpark schedule and entry fees (waterpark is not open year-round and there is a daily entry cost for each guest.)brbrEnjoy direct access to Lake Michigan beach, a walk/drive to restaurants/cafes downtown, public beach, parks, etc.

Bed

Bath

Sleeps

$270.13

/ Nightly

Apartment

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

Sheboygan, Wisconsin, United States

Welcome to the Getaway!brbrGetaway: noun - an act or instance of getting away; a place suitable for a vacationbrbrYou will unwind in this peaceful 3 bedroom lower unit near Lake Michigan, Whistling Straits and Kohler/Andrae State Park. You can enjoy an evening around the fire pit, or if you don’t feel like staying in, head out to discover some of Sheboygan’s many hidden gems.brbrIf this unit is booked for your dates, send me a message to ask about our other available listings.brbrUnplug and relax in this 3 bedroom lower unit. brbrYou will find all the comforts of home in the fully equipped kitchen, with staples like sugar and basic spices provided. Enjoy the snack basket as you arrive and begin to settle in. In the morning, enjoy a complimentary cup of coffee.brbrEnjoy the fire-pit in the backyard, where there is plenty of room for your 4-legged family members to run around and stretch their legs. brIn addition to the dreamy master bedroom with a king-size bed, you will find a bedroom with queen-size bed, as well as a bedroom with a twin-size bed and kid-size reading nook, complete with books and toys for small children. We also provide a pack-n-play and highchair for your convenience.brbrIf the weather during your visit doesn’t allow for outdoor activities, no need to fret! In the living room, you’ll find a smart TV equipped with Roku. Login to Netflix, HULU, Amazon Prime, Disney+ or your favorite streaming service, and settle in to chill on the couch with a complimentary bag of popcorn provided in the snack basket. If board games are more your speed, you’ll find them along with puzzles in the closet in the smallest bedroom.brbrExtra towels are located on a shelf in the bathroom. You’ll also find shampoo, conditioner, body wash, dish soap, dishwasher tabs and other essentials. You'll also find a box fan in the master bedroom closet for extra air flow, or in case you prefer some ambient noise for sleeping.brbrThis unit has a private entrance, so you will have access to the whole place without sharing any indoor spaces with other guests. The entryway door is a keyless touchpad, so you can self check-in at your leisure. We will send a custom door code within 24 hours of your arrival. brbrThe backyard is a shared space, with two outdoor dining tables and a fire pit for all guests to enjoy.brbrMessage me if you have any questions!brbrI am available for any questions, concerns, or recommendations throughout your stay. I count it an honor that you choose to make this home a part of your visit to Sheboygan, and strive to provide an excellent experience for each and every guest.

Bed

Bath

Sleeps

$247.06

/ Nightly

Apartment

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Sheboygan, Wisconsin, United States

Welcome to the Coastal Comfort!brbrComfort: noun - a state of physical ease and freedom from pain or constraintbrbrCome in and unwind at our coastal 3 bedroom home near Downtown Sheboygan, Lake Michigan, Whistling Straits and Kohler/Andrae State Park. You can enjoy an evening at home with all your favorite streaming services, or head out to discover some of Sheboygan’s many hidden gems.brbrbrIf this unit is booked for your dates, send me a message to ask about our other available listings.brbrUnplug and relax in this roomy lower unit with a Coastal vibe. brbrYou will find all the comforts of home in the fully equipped kitchen, with staples like sugar and basic spices provided. Help yourself to the snack basket as you arrive and begin to settle in. In the morning, enjoy a complimentary cup of coffee on the enclosed front porch.brbrYou'll find two bedrooms furnished with queen-size beds, as well as a bedroom with twin-size bunk beds. In the living room under the TV, you'll find books and toys for small children. We also provide a pack-n-play and highchair for your convenience.brbrIf the weather during your visit doesn’t allow for outdoor activities, no need to fret! Just turn on the smart TV equipped with Roku. Login to Netflix, HULU, Amazon Prime, Disney+ or your favorite streaming service, and settle in to chill on the couch with a complimentary bag of popcorn provided in the snack basket. If board games are more your speed, you’ll find them along with puzzles in the closet.brbrExtra towels are located in the laundry room, and you’ll find shampoo, conditioner, body wash, dish soap, dishwasher tabs and other essentials are also provided. You can also find a box fan in the master bedroom closet for extra air flow, or in case you prefer some ambient noise for sleeping.brbrThis unit has a private entrance, so you will have access to the whole place without sharing any indoor spaces with other guests. The entryway door is a keyless touchpad, so you can self check-in at your leisure. We will send a custom door code within 24 hours of your arrival. brbrMessage me if you have any questions!brbrI am available for any questions, concerns, or recommendations throughout your stay. I count it an honor that you choose to make this home a part of your visit to Sheboygan, and strive to provide an excellent experience for each and every guest.

Bed

Bath

Sleeps

$287.09

/ Nightly

Condo

Charming, Modern Riverfront 2-bedroom South Pier, Sheboygan Condo

Sheboygan, Wisconsin, United States

Stay comfortably in Sheboygan at this 2-bedroom condo. The space features 2 lovely queen beds, 2 bathrooms with showers, and essential amenities like WiFi, full kitchen, smart TVs and a washing machine. Enjoy the beautiful surroundings and make the most of your stay in this amazing property. We hope you enjoy what our place and Sheboygan has to offer.

2

Bed

2

Bath

4

Sleeps

$539.13

/ Nightly

Villa

Beach front luxury spacious villa !

Sheboygan, Wisconsin, United States

Beach front luxury spacious condo! Beautiful remodeled four bedroom villa/condo overlooking Lake Michigan, well equipped to welcome Your family and friends. The main level has 2 bedrooms and 1 full bathroom. The second level has two additional bedrooms each with their own bathroom!brLocated just few minutes drive from World class golf course and walking distance from mini golf , kayaks rentals and excellent nearby restaurants combined with what Malibu of the Midwest got best to offer, surfing , sailing and fishing will make Your vacation unforgettable. Beach chairs , beach towels are provided. This condo is not associated with Blue Harbor Resort and not include water park passes !. Please be aware this condo include two flight of stairs , one to excess the unit and another to get to the second floor.

4

Bed

3

Bath

12

Sleeps

$317.52

/ Nightly

Private Vacation Home

Black River Retreat Eclectic-Unique-Intriguing

Sheboygan, Wisconsin, United States

brWow. An amazing home in an amazing location. Minutes from downtown Sheboygan, beaches at Kohler Andre & Lakeview parks, local golf courses & Road America. This beautiful Cape Cod has three bedrooms and a magnificent bath on the 1st floor & a giant suite upstairs w/ a private bath. Throughout the house are curiosities and unique pieces of art to keep you wondering around and always noticing new things. Wood-burning fireplace in the main living room and an eclectic study/second living room furnished in vintage furniture, and a rare pinball machine. Stay in to relax, ponder, and read. Or make it your base camp for exploring the area.brbrBeautiful brick house in the coveted Black River neighborhood. Public land right across the street for hiking. The unique Indian Mounds park is just blocks away with over a dozen archaeological significant Native American burial mounds. The amazing Kohler Andre State Park with its sand dunes and endless beach is just minutes away. The historic beach at Lakeview Park is just a mile away. Downtown Sheboygan, downtown Kohler, and all of the wonderful spots are within a short drive.brbrThis house has an indoor wood-burning fireplace for cozy nights in. It has a record player and collection as well as a awesome DVD collection where you’re sure to find things you’ve never seen :-) On the main level there’s a back room we call the study that’s decked out in vintage furniture to give you cool vibes and memories “Alright Alright Alright”. Upstairs is a huge studio with its own bathroom, up there is where you’re going to find the kids zone with plenty of toys and things to keep them busy and out of your hair! Up there there are 3 separate lounging areas, one of which is equipped with an indoor hammock.brThe yard is huge. It’s over an acre plenty of room for outdoor fun. brbrPerfect spot for NFL Draft, Lambeau Field, Road America Races, PGA golf events and Wisconsin Fun!brbrCome, check out this spot to make your memories :-)

Bed

Bath

Sleeps

$417.63

/ Nightly

Private Vacation Home

NEW! Charming 3BR/2BA Lake House in the Woods of the desirable Black River area

Sheboygan, Wisconsin, United States

Your much-needed retreat begins at this large 3-bedroom house 300-feet from Lake Michigan. This wonderful property features 3 queen beds, a twin bed loft, and a pullout queen sofa sleeper (sleeps 9 in total) - perfect for a family or group getaway. With amenities like WiFi, AC, radiant heat, and on-site laundry, guests can relax and unwind in this quiet forest home. The 2 bathrooms in the home enable your option of a quick post-beach rinse in the shower or a relaxing soak in the tub. A large living room provides extra space for lounging, catching up on your streaming TV, or playing board games with the family. The large dining room table is perfect for hosting family meals or competitive card games. The quiet yard on this low traffic street enables lots of great playtime, hunting for frogs, or just waiting for the many deer visitors that regularly pass through. And don't forget the ping pong table and the foosball table in the basement awaiting it's daily challengers to see who takes home bragging rights. 300-feet in one direction is the sandy beach of Lake Michigan where rock skipping is a must. 300-feet in the opposite direction of the lake is a locals favorite supper club where you can enjoy an old fashioned and a fish fry. Newly offered in Spring 2025 as a vacation rental following a recent renovation, this is a great place to call homebase while you're away. We are sure you will enjoy your stay. (NOTE: Large new gas grill recently added.)

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Bath

Sleeps

$244.97

/ Nightly

Condo

Scenic Lake Views in Sheboygan

Sheboygan, Wisconsin, United States

Watch the sun/moon come up over Lake Michigan across from the Sheboygan Marina and scenic lighthouse in this beautifully furnished condo. Public beach, tennis courts and YMCA a few blocks north of condo.brbrThis condo is in the perfect location being walking distance to the Sheboygan Harbor Center/Marina, Blue Harbor Resort / Water Park, historic Riverfront Boardwalk with shops and restaurants, John Michael Kohler Arts Center, Stephanie Weill Performing Arts Center, historic downtown Sheboygan with many renowned restaurants. Minutes away from The American Club, Kohler golf courses, Elkhart Lake, Road America, Kohler Andre State Park, Kettle Moraine State Forest-Northern Unit, Old Plank Bike/walking Trail, The Wade House, Children's Bookworm Gardens. Beaches, playgrounds, water park, shopping, restaurants including Trattoria Stefanos renowned Tuscan Restaurant, Il Ritrovo, Harrys Prohibition Bistro, Lino's Italian Ristorante and many more. Wine/ liquor stores , Schwartz fish market, charter fishing , Pier fishing, 3 Sheep's Brewing Company, Hops Brew Haus, and much more just steps away!brbrKeywords: Condominium

2

Bed

1

Bath

4

Sleeps

$263.0

/ Nightly

Apartment

The Beach town bungalow

Sheboygan, Wisconsin, United States

Cozy second-floor Airbnb in Sheboygan, WI, the “Malibu of the Midwest.” 2-bed, 1-bath with queen master, bunk room, full kitchen, living/dining area, workspace, and parking for two. Short distance from Lake Michigan, enjoy surfing, kayaking, or hiking at Kohler-Andrae State Park. Visit Bookworm Gardens, golf at Whistling Straits, or dine at Big Mikes bar and grill! Sheboygan’s festivals, Kohler Arts Center, and vibrant community offer year-round fun for all.brbr2 off street parking stalls to the left of three car garage.brbrFeel free to message me on the air bnb app or call me if needed.

Bed

Bath

Sleeps

$383.43

/ Nightly

Private Vacation Home

Family Home, 1 Block to Lake Michigan Beach!

Sheboygan, Wisconsin, United States

- Game Roombr- Central Locationbr- Recently RemodeledbrbrFrom Lake Michigan to downtown, there's something for everyone at this 3-bed, 2-bath Sheboygan vacation rental. Recently remodeled, this home offers top-notch amenities, a full kitchen, and new flooring! Walk to the lake for a beach day, visit John Michael Kohler Arts Center, watch stories come alive in Bookworm Gardens, or hit the links.brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTS: br- Bedroom 1: Queen Bed br- Bedroom 2: Full Bed br- Bedroom 3: 2 Twin Beds br- TV Room: Sleeper Sofa br- Game Room: Futon brbrINDOOR LIVING: br- Smart TV w/ cable, cable TV br- Dining table br- 3 living spaces br- Laptop-friendly workspacebr- Renovated interior brbrOUTDOOR LIVING: br- Patio w/ outdoor dining table br- Gas grill br- Fire pit br- Basketball hoop brbrKITCHEN: br- All major appliances including dishwasher br- Coffee maker br- Blender, knife set, dishware & flatware brbrGENERAL: br- Free WiFi br- Complimentary toiletries br- Linens & towels br- Central heating & A/C br- In-unit washer & dryer, laundry detergent br- Memory foam mattress brbrPARKING: br- Driveway (2 vehicles) br- Free street parkingbrbr-- THE LOCATION --brbr- 0.9 miles to Harbor Centre Marina br- 65 miles to Lambeau Field br- 65 miles to General Mitchell International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Quiet Hours are at 10:00pm on weekdays and 11:00pm on weekendsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-in

Bed

Bath

Sleeps

$340.0

/ Nightly

Private Vacation Home

Sheboygan Riverside Condo

Sheboygan, Wisconsin, United States

Experience the Malibu of the Midwest in this stunning 2-bedroom retreat! The king suite offers a private balcony with a cozy fireplace overlooking the serene Sheboygan River. The second bedroom features two queen beds, perfect for families or friends. Enjoy an open-concept living space, modern kitchen, and easy access to Sheboygan's best attractions. With a 2-car garage and nearby conveniences, this is your ideal getaway spot!

Bed

Bath

Sleeps

$217.32

/ Nightly

Apartment

Storybook 2-bedroom apartment 1mi from Lake Michigan

Sheboygan, Wisconsin, United States

Welcome to The Fox & Folly Inn —a unique whimsical retreat. Perfect for families and those who are kids at heart!brbr• Creative and cozy home with art and murals.br• Themed with original characters. Audio stories & endless charm!br• Master Bedroom - King Bedbr• 2nd Bedroom - Bunk Bed = Full Lower, Twin Upperbr• Sleeps 5br• 1 Full Bathroom - Towels, Hair Dryer+br• Fully Stocked Kitchenbr• Off-Street Parkingbr• Minutes from the beach & Bookworm GardensbrbrYour storybook adventure awaits!brbrTHE SPACEbrbrPEACEFUL NEIGHBORHOODbr• Quiet hours 10:00PM -7:00AMbr• Respectful and kind neighborsbrbrLucinda O - Neighborhood was quiet and peaceful. The backyard is fenced in and perfect for children to get some energy out! A delightful place to stay!brbrThe Fox and Folly Inn is a great place for a relaxing getaway. **If you are group looking to party outside, please note Sheboygan has a nuisance code that we are required to follow. Please bring your group indoors after 10:00pm (see more in House Rules).**brbrTHE HOUSEbr• 2-bedroom, 1-bath apartmentbr• Lower level of a cozy homebr• Private apartment, not sharedbr• Approx. 1,000 sq ft + 150 sq ft game roombr• Smart keypad locks for easy entry/exitbrbrMASTER BEDROOM (The Rabbit Hole)br• King size bedbr• Suitcases fit under bedbr• Direct access to bathroombr• Headboard with phone charging stationsbr• Wall-mounted fanbr• Built-in dresser + closet for hanging clothesbrbrSECOND BEDROOM (The Owl's Roost)br• Bunk bed (full mattress below, single mattress above)br• Desk/workstationbr• Ceiling fanbr• Built-in dresser + closet for hanging clothesbrbrBATHROOMbr• Connects to master bedroombr• Full bath with tub/shower combobr• Shampoo/conditioner/body washbr• Hair dryerbr• Bath towelsbr• First aid kitbrbrKITCHENbr• Reverse osmosis filtered drinking waterbr• Fully stocked - pots, pans, dishes, utensils+br• Dishwasherbr• Fridge and Freezerbr• Toasterbr• Microwavebr• Electric skilletbr• Electric kettlebr• Blenderbr• Fire extinguisher & fire blanketbrbrDINING ROOMbr• Keurig coffee bar (regular & decaf coffee k-cups, tea, sugar, creamer)br• Table set for 4 - can seat 6 (extra chairs in closet)br• Cabinet stocked with board gamesbrbrLIVING ROOMbr• 70 smart TVbr• Lots of pillowsbr• Full couch & comfy, oversized armchairbrbrFRONT PORCHbr• Sitting area with 4 chairsbr• Street parking availablebr• String lights for evening relaxingbrbrBACK YARDbr• Patio with table & 2 chairsbr• Fire pit with 4 chairsbr• Fully fenced in, waist heightbr• String lights for yard games at nightbr• (In garage) Corn hole & ring tossbr• (In garage) 4 boogie boards + 2 beach chairsbr• On-site parking, Fox & Folly Parking sign reserves your spacebrbrEXTRASbr• Wi-Fibr• Washer & dryerbr• Bonus TV room in basement, accessed through laundry room. The laundry room is a shared space with upstairs tenant who helps manage the property.brGuest accessbrThe property consists of 2 apartments, an upper and lower. You will be staying in the lower apartment - 1000 sq ft with 2 bedrooms and 1 bathroom. There is also a shared basement where laundry is located, as well as a bonus room with a futon and television (the bonus room is exclusive to Fox & Folly Inn guests).brbrOther things to notebrProximitybr1 mile to South Beach on Lake Michiganbr1 mile to the Sheboygan Pierbr1.7 miles to HSHS St Nicholas Hospitalbr1.8 miles to Deland Park (Lighthouse)br2 miles to North Beach on Lake Michiganbr2 miles to Aurora Medical Centerbr3.6 miles to Black Wolf Run Golf Coursebr6.2 miles to Kohler-Andrae State Parkbr8 miles to Whistling Straits Golf Coursebr17.5 miles (20mins) to Road Americabr64.5 miles (1hr) to Lambeau Field

2

Bed

1

Bath

5

Sleeps

$253.63

/ Nightly

Private Vacation Home

Fresh Coast Craftsman - Monthly Rentals Available!

Sheboygan, Wisconsin, United States

New Listing! Fresh Coast Craftsman by Great Lakes GetawaysbrbrWelcome to your private 2-bedroom, 1-bath entire home retreat! Featuring queen beds, a cozy living room with Smart TV, fully equipped kitchen, on-site washer/dryer, and private entrance. Enjoy the fully fenced backyard, 2-car garage, and pet-friendly accommodations. Perfect for up to 4 guests seeking comfort, privacy, and convenience in a charming craftsman home near Lake Michigan.brbrStay in comfort and style in this charming 2-bedroom, 1-bath entire home in Sheboygan. With a private entrance, fenced yard, and street parking and parking regulations , this home is perfect for families, professionals, or friends looking to enjoy the Lake Michigan lifestyle.brbrMain Floor LivingbrStep inside to a cozy living room featuring a Smart TV, comfy seating, and a desk + chair—great for remote work or catching up on emails. The adjacent dining area seats 4, making it the perfect spot for family meals or game night.brbrThe fully stocked kitchen has everything you need: pots, pans, dishes, utensils, and cooking essentials to prepare a home-cooked dinner after a day of exploring.brbrOn the main floor, you’ll also find a bright bathroom with a walk-in shower, sink, and toilet with bidet to keep you feeling fresh.brbrUpstairs RetreatsbrHead upstairs when it’s time to unwind. You’ll find two private bedrooms, each with a queen-size bed and plenty of storage for clothes and luggage. Cozy bedding and thoughtful touches create a restful night’s sleep so you can recharge for your adventures.brbrPet-Friendly FeaturesbrBringing your furry friends We welcome up to 2 well-behaved dogs. A comfy pet bed is included in the living room, and the fully fenced backyard means safe outdoor playtime and peace of mind.brbrExtra Conveniencesbr✔ On-site washer + dryer (downstairs) for longer staysbr✔ 2-car garage plus an off-street parking pad for 1 more vehiclebr✔ Fully fenced backyard for both privacy and petsbr✔ Smart TV for streaming + WiFi throughoutbrbrPerfect LocationbrThis home is close to it all:br✔ Downtown Sheboygan shops, cafes, and restaurantsbr✔ Local parks and walking trailsbr✔ Lake Michigan beaches & waterfront just minutes awaybrbrWhether you’re here for business, family time, or a relaxing getaway, Fresh Coast Craftsman has everything you need for a comfortable, private, and memorable stay.brbrRental Agreement Notice:brGuests are required to review and sign a rental agreement prior to check-in. The agreement includes important house rules and stay policies. Booking this property confirms that you agree to review and complete the rental agreement before your stay. Failure to complete the agreement may result in cancellation of the reservation.

2

Bed

1

Bath

4

Sleeps

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