Vacation Home Rentals By Owner In Sheboygan, WI

$888.64

Boho Farmhouse - Fire Pit - Huge Backyard-Golfing - Family Friendly

Sheboygan, Wisconsin, United States

Experience the charm of our cozy home away from home!brbrComfortably situated halfway between Milwaukee & Green Bay, it is the perfect spot for families, golfers, race fans, anglers and all sports fans. brbrCharter Hill Retreat is tucked away in a quiet neighborhood, yet close to world class golf, 5 star Kohler restaurants & shopping, endless beaches (surfing anyone ), charter fishing and Road America. brbrUnwind and enjoy the huge private backyard, perfect for your morning coffee, bonfire with s'mores or dinner under the stars!brbrYour getaway awaits in Sheboygan at this brilliant house. With 4 bedrooms including 1 king, 2 queen, and 1 full bed, this amazing property offers plenty of space for guests to relax. With 2.5 bathrooms, getting ready for your weekend events will be a breeze!

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Bath

Sleeps

$313.26

/ Nightly

Private Vacation Home

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

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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.

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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.

4

Bed

2

Bath

9

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 :-)

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$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

$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

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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!

2

Bed

1

Bath

6

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.

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$454.0

/ Nightly

Private Vacation Home

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Sheboygan, Wisconsin, United States

Enjoy your Sheboygan getaway in this spacious 4-bedroom, 2-bath home just a 5-minute walk to the lake. Sleeps 11 and packed with fun for all groups.brbrThe Spacebr •. 4 bedrooms, 2 full bathroomsbr •. Pool table and arcade gamesbrbrPrime Locationbr • Walk to the lake and downtown br • Sheboygan’s best eats br • 15 minutes from Kohler golf courses including Whistling StraitsbrbrPet-FriendlybrFull privacy with local owner supportbrbrPerfect for lake days, golfing or tasting Sheboygan’s food scene

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$742.29

/ Nightly

Private Vacation Home

Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.

Sheboygan, Wisconsin, United States

Luxury Modern Farmhouse 4B-2Ba Lake & Beach House! brbrIs it time for a Cool Change Relax and rejuvenate at Sheboygan's newest whole-house luxury rental, just one block from the shores of Lake Michigan and in the heart of the action. Open the windows and hear the waves crashing...you are that close to the water! brbrAs for Cool Change itself, prepare to be swept off your feet! With 4 bedrooms and two full baths (including a main-level bedroom for added convenience), it comfortably sleeps 8. It's the ultimate retreat for families, friends, and anyone searching for a little slice of paradise. Relax in front of the cozy fireplace or play some Deluxe Scrabble at our game table. The home, with its open floor plan, was completely renovated down to the studs over the last year (2023). Every inch of our abode exudes comfort and style. And did we mention everything is NEW From the gourmet Chef's kitchen with a sleek island that seats 4 to the stunning high-end GE Cafe appliances, laundry on the main level, and central air conditioning throughout. Luxury beds and linens are used and we are committed to hospital-grade cleaning supplies too. Cool Change leaves no stone unturned in ensuring your stay is nothing short of perfection.brbrThis premium city location has direct access to Sheboygan's top Northside beaches, parks, and walking paths. On top of that, you can also walk in mere minutes to the marina, yacht club, art museums, the YMCA, and an array of tantalizing restaurants and shops along the river boardwalk....and Blast Soft Service ice cream, too...a Sheboygan favorite for all ages. If you love the theatre, you can walk there too. The Stefanie H. Weill Center for Performing Arts is just a few blocks away and surrounded by more amazing restaurants and amenities. brbrBut the fun doesn't stop there! Kayaking, surfing, biking - take your pick and let the adventures begin! And for the golf enthusiasts among us, rejoice! Five-star golf courses like Blackwolf Run and Whistling Straits are just a stone's throw away, promising days filled with swings, putts, and plenty of scenic views. Racing enthusiasts We are a 20-minute jaunt to the world-renowned Road America, and a mere 45-minute drive to the iconic Lambeau Field, the possibilities for adventure are endless.brbrCool Change isn't just a place to stay; it's a destination where memories are made, adventures unfold, and worries melt away. brbrDon't miss out - book your reservation now! brbrbrAGE REQUIREMENT: The primary guest booking the reservation must be at least 25 years of age to book this property and must physically occupy the Property overnight for the duration of the rental term. Large groups of unrelated tenants, guests, or invitees must receive prior written approval from the Host, which shall be determined at the Host's sole discretion. Failure to meet this requirement may result in cancellation without a refund.

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Bath

Sleeps

$359.26

/ Nightly

Private Vacation Home

Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan

Sheboygan, Wisconsin, United States

Whether you’re on the hunt for some good cheese, a delicious fried brat, or just a simple lake retreat, this vacation rental is the perfect starting point! This 4-bed, 1.5-bath home offers endless comforts, including a fully equipped kitchen with a wine bar and technology like the Amazon Echo Dot to make your vacation even more relaxing. Practice your swing at one of the nearby golf courses or cheer on the vehicles at Road America before calling it a day as you curl up inside this spacious home.brbr-- THE PROPERTY --brbrWasher/Dryer | Wine Bar | 3,000 Sq FtbrbrYou, your family and your furry friends are in for a treat at this newly remodeled home, less than 1 mile from Lake Michigan and downtown Sheboygan!brbrBedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: Queen Bed | Bedroom 4: Queen Bed | Additional Sleeping: Futon, Pack-N-PlaybrbrINDOOR LIVING: Library, games, top-rated mattresses with 600+ thread count linens in bedroomsbrTECHNOLOGY: 60-inch flat-screen TV with video streaming, Amazon Echo Dot & Echo Show providing Alexa-enabled video, music, news & entertainmentbrKITCHEN: Fully equipped, stainless steel appliances, drip coffee maker, Keurig coffee maker, center island w/ eat-in counter & barstools brGENERAL: Free WiFi, iron/board, hair dryer, complimentary toiletries, linens/towelsbrPARKING: Driveway (4 vehicles)brbr-- THE LOCATION --brbrOUTDOOR RECREATION: Vollrath Park (1.3 miles), Deland Park (1.4 miles), Quarry Beach Adventure Park and Water Sports (2.1 miles), Kohler Park Dunes State Natural Area (11.2 miles), Kohler-Andrae Lake Michigan State Park (11.2 miles)brFAMILY ATTRACTIONS: Above & Beyond Children’s Museum (0.8 miles), Bookworm Gardens (3.2 miles), Road America (16.4 miles), Sheboygan Marsh Tower (22.3 miles)brGOLF COURSES: Black Wolf Run (5.0 miles), Whistling Straits (6.4 miles), The Bull at Pinehurst Farms (8.8 miles)brOTHER HOT SPOTS: John Michael Kohler Arts Center (1.0 miles), Kohler Design Center (4.6 miles), Lambeau Field (62.2 miles)brEATS+DRINKS+SHOPS: Downtown Sheboygan (0.9 miles), Downtown Kohler (4.9 miles)brAIRPORT: General Mitchell International Airport (63.9 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- Pet friendly w/ $100 fee (+ fees & taxes) and prior homeowner approvalbr- No events, parties or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-in

Bed

Bath

Sleeps

$2512.92

/ Nightly

Private Vacation Home

Baronwood Oasis | Pool + Arcade Mega Estate

Sheboygan, Wisconsin, United States

Private mega estate with an indoor pool, 14-person hot tub, massive arcade, and 10,500 sq ft designed for unforgettable group stays.brbr✔ Year-round indoor pool + oversized hot tubbr✔ Private arcade w/ simulators, PS5 + classicsbr✔ 7 bedrooms + 16 beds for multi-gen groupsbr✔ Jumbotron lounge, bar + 7 fireplacesbr✔ Minutes to Whistling Straits, Kohler + Lake MichiganbrbrThe spacebrTHE EXPERIENCEbrbrA 10,500 sq ft private mega estate with an indoor pool, 14-person hot tub, and a full-scale arcade—designed for unforgettable group stays.brbrStart your mornings in a sunlit estate surrounded by six acres of privacy. Spend your day rotating between the indoor pool, arcade, and outdoor courts. End the night with drinks by the fire, a movie with the kids, or late-night competition in the game lounge.brbrGuests consistently call it:br“Better than expected”br“Perfect for large families”br“A place where no one ever gets bored”brbrWHY GUESTS BOOK THIS HOMEbrbr✔ Indoor pool + 14-person hot tub (rare, year-round experience)br✔ Private arcade + Jumbotron lounge (commercial-level entertainment)br✔ 10,500 sq ft estate built for large groupsbr✔ 6-acre private setting (space you won’t find elsewhere)br✔ True multi-gen layout (separate zones for kids + adults)brbrTHE SPACEbrbrMain Level — Elevated GatheringbrGrand living room with soaring ceilings + stone fireplacebrChef’s kitchen with commercial-grade appliances + oversized islandbrFormal dining for 12+ guestsbrBilliards room + multiple fireplaces throughoutbrDedicated fitness + office suitebrbrPrimary Suites (Main Level)brBedroom 1: King suite with spa bathroom (soaking tub + walk-in shower)brBedroom 2: King + trundle, fireplace, connected accessbrbrENTERTAINMENT & AMENITIES brbrLower Level — The Ultimate Hangout ZonebrJumbotron lounge with 4-TV sports setupbrAir hockey, shuffleboard, and group gaming spacebrFull bar + lounge + massage chairbrbrPrivate Arcade (Standout Feature)brDriving simulators + motorcycle racingbrGolden Tee 2025 + basketball gamesbrPlayStation 5 + classic arcade machinesbrDesigned to rival commercial game spacesbrbrIndoor Pool & SpabrHeated indoor pool with basketball hoopbr14-person hot tubbrPrivate cove hideout for kidsbrYear-round use regardless of weatherbrbrThis is the kind of home where your group never runs out of things to do—no matter the weather or time of year.brbrSLEEP & LAYOUT ️brbrSecond Level — Rest + FlexibilitybrBedroom 4: Two twins + ensuitebrBedroom 5: King + shared Jack & JillbrBedroom 6: King + trundlebrbrBedroom 7 (Kids Suite)brPrivate movie theaterbrSkeeball + dedicated play spacebr4 twin beds + hidden reading nookbrbrLower LevelbrBedroom 3: King + two twinsbrbrDesigned for:br✔ Multiple familiesbr✔ Large groupsbr✔ Kids + adults needing separate zonesbrbrOUTDOOR EXPERIENCE brbrPrivate 6-acre setting built for both activity and relaxation:brbrPickleball + basketball courtsbrBackyard fire pit for evenings under the starsbrChildren’s playhouse + pondbrExpansive lawn for games + explorationbrbrThis becomes the central gathering space between activities.brbrLOCATION ADVANTAGEbrbr8 minutes to Whistling Straits (world-class golf)brClose to Kohler spas, dining, and shoppingbrEasy access to Lake Michigan + Kohler-Andrae State ParkbrbrPrivate 6-acre setting just minutes from top destinationsbrbrTHE WISCONSIN GETAWAYS STANDARDbrbrProfessionally cleaned and inspectedbrFast, responsive communicationbrFully stocked, guest-ready homebrSeamless arrival experiencebrbrBacked by one of Wisconsin’s highest-performing luxury rental brandsbrbrIMPORTANT DETAILSbrbrGuest Verification Required (Post-Booking)brValid ID requiredbrSigned rental agreementbrbrHouse Rules (Strictly Enforced)brMax occupancy enforcedbrNo parties or eventsbrNo outdoor music or speakersbrQuiet hours requiredbrMax 6 vehicles | No street parkingbrbrBOOK YOUR STAYbrbrLarge estates with this level of amenities and indoor pool access are extremely rare—and book quickly.brbrIf you’re looking for:br✔ A true all-season group destinationbr✔ High-end entertainment + spacebr✔ A home that keeps everyone engagedbrbr Book now to secure your dates before peak weekends fill.br Important — Guest Verification Required After BookingbrbrTo ensure a smooth and secure stay, all reservations complete a quick post-booking verification directly with Wisconsin Getaways. This secure step is completed outside of the platform and includes:brbr Providing a valid driver’s license or government-issued ID for the primary guestbr✍️ Signing our standard rental agreement directly with the HostbrbrThese items simply reaffirm the house rules shown here and do not override Airbnb or Vrbo’s Terms. Once completed, you’ll receive your arrival instructions—property address, parking details, and door codes—typically two weeks before check-in.brbr Quiet Community SettingbrbrMany of our homes are located in peaceful lakefront and residential neighborhoods. Guests love the tranquility, and we ask everyone to be mindful of neighbors and keep outdoor noise low, especially in the evenings. This helps maintain the relaxing atmosphere our properties are known for.brbr House Standards (Must Be Followed)brbrTo keep our homes and communities in excellent condition, the following expectations are firmly enforced:brbr Stay within posted occupancy limits (including visitors)br Maintain respectful noise levels (neighbors should not hear yelling or cursing at any time)br No outdoor speakers or amplified music (leave your speakers at home)br No unauthorized gatherings or eventsbr No indoor smoking ($600 violation)br Guests may bring a total of up to 6 vehicles. When a garage is available, it must be used to help limit the number of cars in the driveway. Absolutely no street parking is allowed at any time.brbrThese guidelines ensure every guest enjoys the high-quality, peaceful experience Wisconsin Getaways is known for.

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$538.56

/ Nightly

Private Vacation Home

REMODELED HOME ON LAKE MICHIGAN

Sheboygan, Wisconsin, United States

3 Bedrooms and 1.5 Baths in this two-story brick home. Located about one mile south of downtown Sheboygan on a bluff overlooking the beautiful Lake Michigan. Just enter Sheboygan, WI 53081 in any search engine and you can easily figure out how far things are away. There is no direct access to the lake from the home, but it is located less than half a mile south of and north of two public parks with beaches with plenty of street parking. They are both an easy walk and drive to.brThe kitchen and both bathrooms have just been remodeled. It's like living in a new house that still has that old world charm. The kitchen features beautiful white cabinets with a quartz countertop and a glass mosaic backsplash and stainless-steel appliances. Each room has a queen size mattress. If extra room is needed, we can have a queen size air mattress out with prior notice. Will consider one-night stays but usually Friday and Saturday nights require a two-day booking. NO PETS, NO EXCEPTIONS.brNow with WIFI.brKeywords:brKohler, Plymouth, Elkhart Lake, Lake Michigan, Sheboygan, Sheboygan Falls, lake view, quiet, clean, special, rates, Michigan, lakefront, beach, sunrise, unique, updated, bluff, economy, neighborhood, park, condo, Super 8, holiday inn express, la Quinta, blue harbor resort, hotel, motel, lodging, tourism, tourist, summer, economy, vacation, rental home, Super 8, chamber of commerce, vacation, summer, PGA, fall, autumn, winter, spring, cozy, charters, economy, value, fishing, garage, last minute, American Club, golf, fishing, Green, Bay, Packers, Lambeau field

Bed

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Sleeps

$354.94

/ Nightly

Private Vacation Home

Updated Victorian in the Heart of Sheboygan. Beach, Downtown, Golf, Road America

Sheboygan, Wisconsin, United States

Lovingly restored 1890s Victorian home, updated to include the modern amenities you expect. Fully stocked kitchen, with gas & charcoal grills out back. 2,000 sqft with two rebuilt covered porches and a large, shaded backyard. 5 blocks to Sheboygan's beautiful sand beach and lakeshore path. 6 blocks to downtown shops, restaurants and nightlife. 10 minute drive to the village of Kohler and 12 minutes to Whistling Straits. Perfect residential location to enjoy Sheboygan County all year long.

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Sleeps

$512.65

/ Nightly

Private Vacation Home

Charming 4-bedroom house with WiFi and AC in lovely Sheboygan

Sheboygan, Wisconsin, United States

Unwind in this fabulous 1970's home with modern upgrades. This spacious 3700 SF retreat features 4 bedrooms (3 queen, 1 king ) , 4 bathrooms, 3 living areas, fully stocked kitchen, a breakfast area and the lower level also has a kitchenette with mini fridge, microwave oven and sink. Enjoy the convenience of a washer, dryer, blow dryer, iron and ironing board, WiFi and two ROKU TVs where guests can log into their own streaming accounts. There is a sleeper sofa and two futons for additional sleeping arrangements. Plenty of bedding and pillows available in the closets! Make your getaway memorable in this serene and inviting haven.

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Sleeps

$633.05

/ Nightly

Private Vacation Home

Beach Lake House walking disance to lake Close to Downtown & South Pier 4BR 2BA

Sheboygan, Wisconsin, United States

Amazing location just 3 blocks of Lake Michigan. a short walk to the public south beach, br2 min driving to the beach. 4 minutes driving from downtown. walk to south pier/Blue Harbor Resort 15min.brThe full bath upstairs has a stand alone shower. Three bedrooms have queen size beds Middle bedrooms with trundle bed with full mattress & twin size bed, An additional twin size mattress can be set up in on the first floor when needed with notice. furnished with dishes pots, pans cooking utensils etc......There is a full bath on the main floor.brPlenty of room for the whole family. Perfect for a golfing weekend and especially for the Ryder Cup.br Gas grill available. No smoking is allowed in the house. No parties or events are allowed on the property. Due to allergies, no pets are allowed. Minutes away from shopping and several golf courses around town. The interior of the home has just been repainted and new flooring, carpeting put in. 55 TV in the living room. WIFI access Plenty of street parking, Check in time is 3 pm or later and check out time is by 11am. There is a keypad on the front door for easy check in. I will provide the code before your arrival.

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$433.57

/ Nightly

Private Vacation Home

Serene Home One Block From Lake Michigan

Sheboygan, Wisconsin, United States

Welcome to our spacious, two-story 3-bedroom, 2-bathroom home just one block from Lake Michigan and beautiful Deland Park. Perfect for families, groups, or golf trips, this comfortable home offers a peaceful retreat within walking distance of North Beach, the YMCA, and downtown Sheboygan’s shops, restaurants, and nightlife. Enjoy the perfect mix of relaxation and adventure in a prime location.brbr Bedrooms & Bathroomsbr-Bedroom 1: Queen bedbrbr-Bedroom 2: Queen bedbrbr-Bedroom 3: Full-size bedbrbr-Bathrooms: Two full bathrooms, one on each floor, both fully stocked and pristinely cleanbrbr Kitchen & Living AreasbrThe fully equipped kitchen includes all basic cookware and utensils needed for meal preparation. Spacious dining and living areas provide plenty of room to relax, entertain, or gather after a day exploring the area.brbr Parking & TransportationbrPrivate driveway with space for multiple cars plus ample on-street parking available. Easy access to local bus routes. The home is within a short drive of major highways and less than an hour from Milwaukee and Green Bay.brbr Outdoor & NeighborhoodbrLocated in a quiet, friendly neighborhood just steps from Lake Michigan, Deland Park, and several other parks. Take a stroll to North Beach or enjoy the local YMCA nearby. Downtown Sheboygan’s vibrant dining and entertainment options are only minutes away.brbr✅ Amenities & Featuresbr-Fast Wi-Fi and smart TVbrbr-Washer and dryerbrbr-Heating and air conditioningbrbr-Self check-in and check-out for conveniencebrbr-Towels, linens, and essentials providedbrbr-Family-friendly, no smoking, no petsbrbr Nearby Attractionsbr-Lake Michigan (1 block)brbr-Deland Park & North Beach (steps away)brbr-Downtown Sheboygan (walking distance)brbr-Whistling Straits Golf Course (15 minutes)brbr-Kohler (15 minutes)brbr-Elkhart Lake & Road America raceway (25 minutes)brbr-Milwaukee & Green Bay (under 1 hour)

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Sleeps

$457.05

/ Nightly

Private Vacation Home

Beautiful 3BR Home Near Lake MI

Sheboygan, Wisconsin, United States

OverviewbrRelax and recharge in this charming 3-bedroom, 1.5-bath home just one block from Lake Michigan. Nestled in a quiet Sheboygan neighborhood, this cozy retreat is perfect for families, small groups, or golf and wedding weekends. Located near Deland Park, Vollrath Park, North Beach, and downtown shops and restaurants. With modern comforts, inviting spaces, and a prime location, this home offers everything you need for a memorable stay.brbr About the PropertybrThis home offers a bright and comfortable interior with space to relax and unwind after a day by the lake or exploring town.brbrBedrooms:brbrBedroom 1: Queen bed + crib, en suite half bathroombrbrBedroom 2: One full bed + one twin bedbrbrBedroom 3: Daybed with trundle + desk/workspacebrbrBathrooms:brbr1 full bath (shared)brbr1 half bath (attached to Bedroom 1)brbrInterior Features:brbrFully equipped kitchen with modern appliancesbrbrCozy living and dining areasbrbrFast Wi-FibrbrWorkspace for remote work or studybrbrFresh towels, linens, and basic toiletries providedbrbrParking:brbr1 private driveway spacebrbrAmple free street parkingbrbrAdditional Amenities:brbrCrib for families with infantsbrbrWasher and dryerbrbrSelf check-in with smart lockbrbrAir conditioning and heatingbrbr✅ SuitabilitybrFamily-Friendly: Crib, quiet neighborhood, nearby parksbrbrRemote Work: Dedicated workspace with Wi-FibrbrNot Pet-FriendlybrbrNo Smokingbrbr What’s NearbybrLake Michigan – 1 blockbrbrDeland Park & North Beach – 5-minute drivebrbrDowntown Sheboygan – 5-minute drivebrbrWhistling Straits Golf Course – 15 minutesbrbrKohler (The American Club, shopping, dining) – 15 minutesbrbrElkhart Lake & Road America – ~25 minutesbrbrMilwaukee & Green Bay – Less than 1 hourbrbrWhether you're here for lake views, golf, family fun, or local events, our home offers the ideal blend of comfort, charm, and convenience. We’d love to host you!

3

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2

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7

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