Home Vacation Rentals By Owner In Sheboygan, WI

Showing 80 Of 119 Vacation Rentals
Slider Thumb
Exceptional(1)

$165.21

/ Nightly
Apartment

2 Mi to Dtwn: Studio Suite in Sheboygan

Sheboygan, Wisconsin, United States

Pet Friendly w/ Fee | Walk to Diner & Brewery | Private BalconybrbrSet sail for a getaway near the shore of Lake Michigan at this studio, 1-bath vacation rental in Sheboygan. The apartment is situated just 2 miles from local favorites like Deland Park for freshwater fishing and boating, plus the unique shopping and dining experiences found in historic downtown. Ready to relax This unit has all the at-home comforts you need, including a full kitchen and a comfy living space.brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Studio: 1 queen bedbrbrHOME HIGHLIGHTSbr- TV, dining tablebr- Small balconybrbrKITCHENbr- Refrigerator, stove/oven, microwavebr- Drip coffee maker, blender, toasterbr- Cooking basics, dishware & flatware, trash bags & paper towelsbrbrGENERALbr- Central heating, window A/C unitbr- Towels & linens, complimentary toiletries, hair dryerbr- Free WiFibr- Keyless entrybrbrFAQbr- Pet fee (paid pre-trip)br- Long-term tenant on-sitebrbrACCESSIBILITYbr- Single-story guest suite, 2nd floor, stairs requiredbrbrPARKINGbr- Driveway (2 vehicles)brbr-- THE LOCATION --brbr- 2 miles to downtown: coffee shops, restaurants, entertainmentbr- 2 miles to Deland Park: beaches, boat ramps, fishing, sailingbr- 2 miles to Vollrath Park: disc golf, sledding hillbr- 4 miles to Bookworm Gardensbr- 63 miles to Lambeau Fieldbr- 66 miles to Milwaukee 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- Pet friendly w/ $50 fee (+ fees & taxes, 2 pets max)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story guest suite is located on the 2nd floor and requires stairs to accessbr- A long-term tenant lives on-site in the downstairs unit and may be present during your stay
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

Slider Thumb
Exceptional(10)

$300.78

/ Nightly
Condo

NEW Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!

Sheboygan, Wisconsin, United States

brThis riverfront loft truly offers the best combination of views and location in Sheboygan. Situated right on the boardwalk over the river where the river meets the lake. Boutique shops, highly rated restaurants, spas, and Charter fishing are all right there to enjoy.brbr- Peaceful & private: located above a business so after hours you will have peace & privacy with no other residential properties on this side of the river.brbrInterior details:brbrAccess via indoor carpeted & well-light staircase. *Loft is not handicap accessible. brbrKitchen:br- fully equipped w/dinnerware, glassware, wine glasses, pots & pans, utensils, blender, can openers, measuring cups & bows, crock pot, etc. You won't want to cook with all the great restaurants in the area, but if you choose to, we have everything you need!br- dual brew Keurig (takes K-cups or 12 cup pot). We provide assorted K-cups, 12-cup filters, sugar, creamer, coffee syrups, assorted teasbr- island with seating for 3 brbrLiving room:br- queen sleeper sofa, leather swivel chairs & ottomans, electric fireplace w/heat option, 65 in flat screen TVbr- credenza/sideboard storage with games, puzzles, cards, coloring books & crayons as well as extra pillows & linens for the pull-out sofabr- kids nook behind the kitchen has a queen floor bed, nightstand, and 32 in TVbr- additional living space w/12 ft shuffleboard & queen bed for additional sleeping accommodationsbrbrGame areas; There is a 12 ft shuffleboard in the living area. We also have many board games, poker set, cards, puzzles, coloring books, and crayons. brbrDining area:br- seating for 6brbrBedroom:br- Huge bedroom w/king bed, sofa w/ottoman, electric fireplace, 75 in TVbrbrBathroom:br- 36 in shower stall with stationary & wand shower headsbr- towels, toilet paper, and toiletries providedbr- shampoo, conditioner, body wash providedbr- washer & dryer included w/laundry detergent, bleach, and dryer sheets providedbrbrAdditional Details:br- We provide all basic essentials - all linens, towels, toilet paper, paper towel, kitchenware, laundry detergent, shampoo, conditioner, body wash. We also have other complimentary toiletries (toothbrushes, mouthwash, hair spray, face wash, etc). br- Leave the cleaning to us! All that we ask is that the dishwasher is loaded and started and trash is bagged up. This is your vacation time and we understand that you want to make the most of it without having to feel like the hired help. brbrbrNEARBY AMENITIES/ATTRACTIONS:br- TLC Casuals boutique clothing store (right below) br- Anthony Flores Fitness - right next doorbr- Olivada - right next doorbr- Salon Sase - right next door br- Parker Johns - 2 doors down br- Weather Center Cafe - 7 doors downbr- The Wharf (hunting & fishing supplies) br- and so much more within just a few blocks or less!
Bed 1

Bed

Bath 1

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(12)

$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.
Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(14)

$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 4

Bed

Bath 1

Bath

Sleep 10

Sleeps

Slider Thumb
Exceptional(4)

$312.16

/ Nightly
Apartment

Overlook Oasis - Coastal Haven in Ellis District

Sheboygan, Wisconsin, United States

Welcome to Overlook Oasis — Presented by Great Lakes Getaways! brbrTake advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026.brbrNestled 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.brbrOverlook Oasis is perfect for a family getaway, relaxing lake escape, or productive business trip, this beautifully remodeled upper-level duplex combines modern updates with lakeside charm. Situated in the heart of Sheboygan’s historic Ellis District, you’ll be just steps from the waterfront, local dining, and vibrant downtown.brbr** , .brbr & brUnwind in a sunny, open living room designed for comfort and connection. Curl up on the cozy sectional, stream your favorite shows on the Smart TV, or enjoy board games and conversation after a day by the lake. Thoughtful touches and stylish modern finishes create a warm, welcoming atmosphere.brbr & brThe fully equipped kitchen makes mealtime effortless:br● Stainless steel appliancesbr● Ample counter spacebr● Stocked cookware, dishes & utensilsbr● Coffee maker with complimentary coffee & teabrbrWhether you’re whipping up a family breakfast before heading to the beach or bringing home takeout from Sheboygan’s local gems, this kitchen is ready for it all.brbr br● Bedroom 1: Queen bed, serene views, air purifier + white noise machinebr● Bedroom 2: Queen bed with private Smart TV for late-night streamingbr● Bedroom 3: Versatile king trundle bed (king on top with a twin pull-out trundle)brbrEach room features fresh linens, plush pillows, and calming decor, ensuring restful sleep after full days of adventure.brbr & brThe modern walk-in shower is stocked with fluffy towels, hairdryer, and starter toiletries so you can refresh and recharge with ease.brbr :br● High-speed Wi-Fi (perfect for remote work)br● Smart TV for streamingbr● Coffee station br● Heating & A/C for year-round comfortbr● In-unit laundry + essentialsbr● Free street parkingbr● Self check-in for flexible arrivalsbrbr – !brStay in the heart of the Ellis District and explore Sheboygan with ease:br● Blast Ice Cream – 2 min walkbr● Harbor Lights Bar – 2 min walkbr● DeLand Park & Beach (“Malibu of the Midwest”) – 8 min walkbr● Sheboygan Riverwalk – 10 min walkbr● Weill Center & downtown shops/galleries – 5 min drivebr● Kohler-Andrae State Park – 15 min drivebrbr brSip your morning coffee before a lakeside stroll, spend the afternoon surfing or paddleboarding, and end the day watching the sunset over the lighthouse. From bonfires on the beach to Sheboygan’s seasonal festivals, Overlook Oasis puts you at the center of it all.brbrBook your stay today and see why Sheboygan is one of Wisconsin’s best-kept secrets!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 3

Bed

Bath 1

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(8)

$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.
Bed 7

Bed

Bath 5

Bath

Sleep 16

Sleeps

Slider Thumb
Exceptional(165)

$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 3

Bed

Bath 1

Bath

Sleep 7

Sleeps

Slider Thumb
Exceptional(1)

$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!
Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps

Slider Thumb
Exceptional(6)

$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)
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(9)

$434.13

/ Nightly
Condo

Indigo Waters- Steps to the sand! Sleeps 7! Book today!

Sheboygan, Wisconsin, United States

Welcome to Indigo Waters — Presented by Great Lakes Getaways! brbrTake advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026.brbrStep into this vibrant, updated condo where bold colors and unique touches make for an unforgettable stay. Featuring a custom mural of Sheboygan's South Pier, cozy luxury beds, a modern dining area, and a fully-equipped kitchen—ideal for cooking or hosting. Just steps from Lake Michigan’s beach, it’s the perfect place to relax, explore, and enjoy the best of the Midwest.brbrA stunning, newly renovated 2-bedroom, 2-bath condo just steps from the shores of Lake Michigan. Thoughtfully designed for style, comfort, and convenience, this lakeside retreat offers everything you need for a relaxing getaway — whether you're traveling with family, friends, or as a couple.brbr ’ :br✔ Steps from the BeachbrEnjoy the serene beauty of Lake Michigan right at your doorstep. Relax on the beach, take a stroll along the shore, or watch the waves from the comfort of your home.br✔ Modern Luxury Meets Cozy ComfortbrThis condo features chic, modern décor combined with all the comforts of home. It's the perfect retreat for relaxation or adventure.br✔ Spacious LivingbrKick back in the open-concept living room with a cozy fireplace and a large Roku TV—perfect for a movie night after a fun day at the beach. The queen-size sleeper sofa offers extra sleeping space for guests.br✔ Chef’s Dream KitchenbrWhether you're cooking a family meal or enjoying take-out, the modern kitchen with custom local art and ample counter space will make meal prep a breeze.br✔ Master Suite BlissbrA king-size bed, 40-inch Roku TV, and a luxurious en suite bathroom with a jacuzzi tub to unwind after a day of exploring Sheboygan.br✔ Comfort for AllbrThe second bedroom features a queen-size bed and a twin XL trundle pull-out, offering plenty of room for family or friends. Plus, an additional bathroom makes getting ready a breeze for everyone.br✔ Explore SheboyganbrFrom fishing and water sports on Lake Michigan to dining and shopping, there’s something for everyone right outside your door.brbr :br* Deland Park – 0.3 milesbrBeach access, picnic areas, playgrounds, historic Lottie Cooper Shipwreck, surfing, and annual kite festivals.br* Sheboygan Marina – 0.3 milesbrBoat rentals, fishing, and scenic waterfront views.br* North Point Park – 0.5 milesbrLake views, walking trails, and a peaceful environment for relaxation.br* John Michael Kohler Arts Center – 1 milebrContemporary art exhibitions and interactive installations.br* Above and Beyond Children's Museum – 1 milebrHands-on exhibits and educational programs for children.br* Harbor Centre Marina – 0.2 milesbrBoat rentals, fishing, and waterfront views.br* South Pier Parlor – 0.1 milesbrIce cream, mini-golf, and arcade games; popular for families.brbr & :br* Driftwood South Pier – 0.1 milesbrWaterfront bar & grill with American cuisine and river views.br* Lino Ristorante Italiano – 0.2 milesbrUpscale Italian restaurant with authentic dishes.br* Weather Center Cafe – 0.2 milesbrCozy café serving specialty coffees, teas, and light meals.br* Field to Fork – 0.9 milesbrFresh, locally sourced breakfast and lunch, bakery, and coffee roastery.brbr & :br* Sheboygan Farmers Market – 0.9 milesbrWednesdays & Saturdays (June–October), fresh produce, local crafts, and live entertainment.br* Deland Park Kite Festival – 0.3 milesbrAnnual kite displays and activities for all ages.br* Sheboygan Midwest Challenge – 0.5 milesbrAugust powerboat races with high-speed action and family fun.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.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.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!
Bed 2

Bed

Bath 2

Bath

Sleep 7

Sleeps

Slider Thumb
Exceptional(6)

$1165.78

/ Nightly
Private Vacation Home

Lakeview Farm | Beach · Hot Tub · Theater · Views

Sheboygan, Wisconsin, United States

Lakeview Farm · 6BR · Sleeps 14brbr Private Lake Michigan beach—your private oasisbr Theater w/ laser projector, surround sound & reclinersbr Arcade: Golden Tee, bumper pool, foosball, PS5 + morebr Hot tub, fireplaces, screened porch, & wet barbr 6 bedrooms + nursery · 5 baths · perfect for familiesbr Chef’s kitchen, wildflower meadow, and epic lake viewsbrbrBook your lakefront escape with Wisconsin Getaways! brbrWelcome to Lakeview Farm brbrPrivate Beach • Movie Theater • Hot Tub • 5,500 sq ft Luxury Lakefront EscapebrbrbrJust 2 miles from iconic Whistling Straits and perched directly on Lake Michigan, Lakeview Farm is a brand-new luxury home that redefines the lakeside getaway. This one-of-a-kind 5,500 sq ft masterpiece offers private beach access, a private movie theater, stunning water views from nearly every room, and high-end finishes throughout. Whether you`re planning a golf weekend, a family vacation, or a peaceful escape into nature—Lakeview Farm delivers a five-star experience like no other.brbr ️ Bedrooms & Sleeping Arrangements (Sleeps 14)brbrThis home is perfect for large families or groups, with 6 total bedrooms across the main home and a private mother-in-law suite.brbrMain House BedroomsbrbrBedroom 1 (Main Floor): King bed, ensuite bathroom with soaking tub & walk-in showerbrbrNursery Room: Crib for little ones brbrBedroom 2 (Upper Level): Queen bed with ensuite bathroom (shower/tub combo)brbrBedroom 3 (Upper Level): Queen bed with Jack-and-Jill bathroom (shared)brbrBedroom 4 (Upper Level): Two twin beds, shares bathroom with Bedroom 3brbrBedroom 5 (Lower Level): Two twin bunk beds (4 beds total), near full bathroom with tub/showerbrbrbrDetached Mother-in-Law Suite (accessed through the garage)brbrBedroom 6: Queen bed, private ensuite, kitchenette, and deck with lake views brbrFresh linens, plush bedding, and quality mattresses ensure everyone sleeps in comfort.brbrbr ️ Living, Kitchen & Dining SpacesbrbrWalk in and be greeted by panoramic Lake Michigan views across the open living room, dining area, and chef’s kitchen:brbrFully equipped kitchen with high-end appliances and massive islandbrbrDining space with seating for the whole groupbrbrLiving room with large windows and cozy furnishingsbrbrSunroom with a huge gas fireplace and views over the wildflower meadow and lakebrbrScreened-in porch for morning coffee or evening winebrbrbr Entertainment GalorebrbrThe lower level is a full entertainment zone designed for fun:brbrWet bar for mixing your favorite drinks brbrPrivate movie theater with professional laser projector, surround sound, and theater seating brbrGame room featuring:brbrTornado Foosball tablebrbrClassic bumper poolbrbrCommercial Golden TeebrbrStand-up arcade with 1,000+ gamesbrbrPlayStation 5 gaming setupbrbrbr Outdoor ExperiencebrbrA major investment in excavation work means you get your own private beach, with no homes in sight. Spend the day listening to the waves, walking the shoreline, or dipping your toes into Lake Michigan.brbrPrivate trail down to the beachbrbrWeber Genesis propane grill for cookoutsbrbrBrand new hot tub with a lake view brbrDecks with seating, screened porch, and outdoor dining spacebrbrWildflower meadow in the front for seasonal color brbrbr Prime Locationbrbr2 miles to Whistling Straits Golf Course ⛳brbr11 miles to the Village of Kohler for dining, spa, and shopsbrbr17 miles to Road America brbrOn scenic Lakeshore Drive, offering beautiful drives year-roundbrbrbr A Note on LandscapingbrbrAs this is a brand new construction, landscaping was completed in June 2025. The lawn has been freshly seeded and will be fully green by September. All amenities, including the beach, hot tub, and decks, are fully accessible and ready for your stay.brbrLakeview Farm is not just a place to stay—it’s a place to make memories. With space, style, and solitude, this one-of-a-kind home is your basecamp for everything Sheboygan County has to offer. brbr 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 limitsbr Maintain respectful noise levelsbr No external speakers or outdoor music of any kindbr 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.brbrIn alignment with our ongoing commitment to guest safety and comfort, this property has been inspected and approved as a lodging establishment by the Wisconsin Department of Agriculture, Trade and Consumer Protection. brbrFollow @WisconsinGetaways for updates, specials, and new property launches.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.
Bed 6

Bed

Bath 5

Bath

Sleep 14

Sleeps

Slider Thumb
Exceptional(7)

$241.24

/ Nightly
Apartment

Dtwn Sheboygan Apt Above Local Bar!

Sheboygan, Wisconsin, United States

Nestled in the heart of downtown, this 4-bedroom, 1-bathroom Sheboygan vacation rental is a walkable utopia for your next Wisconsin trip. Head over to the shore of Lake Michigan for some summer sun, catch a live concert right downstairs at Craft30, or go bar-hopping around the neighborhood — there's something for everyone to see and do! With a full kitchen, Smart TV, and a cozy living area, this apartment has all the necessities to come back to after a day of exploring.brbr-- THE PROPERTY --brbrWalk to Bars & Restaurants | Electric Fireplace | Pet Friendly w/ FeebrbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Queen Bed brbrAPARTMENT AMENITIES: Smart TVs, deck, outdoor seating areabrKITCHEN: Dishwasher, refrigerator, stove/oven, drip coffee maker, Crockpot, microwave, toaster, ice maker, water filter, dishware/flatware, spices, basic cooking essentialsbrGENERAL: Free WiFi, keyless entry, central A/C, washer/dryer, laundry detergent, iron/ironing board, towels/linens, hair dryers, complimentary toiletries, trash bags/paper towels brFAQ: Stairs required to access, 2 exterior security cameras (facing out), pet fee (paid pre-trip), located above beer bar (live music on weekends)brPARKING: Street parking availablebrADDT’L ACCOMMODATIONS: An additional 5-bedroom property for 12 guests is available on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbrFAMILY FUN: Above & Beyond Children’s Museum (0.4 miles), John Michael Kohler Arts Center (0.7 miles), Bookworm Gardens (3.3 miles), Kohler Design Center (4.7 miles), Road America (17.2 miles), Sheboygan Marsh Tower (19.5 miles), Lambeau Field (64.1 miles)brOUTDOOR REC: Deland Park (1.0 miles), Vollrath Park (1.1 miles), Sheboygan Breakwater Lighthouse (1.1 miles), Breaker Bay Water Park (1.6 miles), Quarry Beach Adventure Park and Water Sports (2.5 miles), Kohler Park Dunes State Natural Area (6.9 miles), Kohler-Andrae State Park (7.0 miles) brGOLF COURSES: Blackwolf Run Golf Course (5.1 miles), Whistling Straits Golf Course (6.9 miles), The Bull at Pinehurst Farms Golf Course (8.4 miles)brEVENTS: Ryder Cup - Whistling Straits Golf Course (September), Democratic National Convention - Milwaukee (August)brDINING & SHOPPING: Craft30 (on-site), Downtown Sheboygan (on-site), 3 Sheeps Brewing Company (1.9 miles), Downtown Kohler (5.0 miles), Downtown Milwaukee (58.4 miles)brAIRPORT: General Mitchell International Airport (66.2 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/ $50 fee (+ fees & taxes, max 2 pets)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs to accessbr- NOTE: Your safety matters. This property features 2 exterior security cameras: one camera is located on the front entrance to the building facing out, and another camera is behind the building facing the dumpsters. The cameras are outward facing and do not look into interior spaces. While both cameras record video, only the camera in the back of the building is activated by motionbr- NOTE: This property is located above a craft beer bar. The venue typically has live music playing on the weekends and there may be noise in the apartment. Please check the venue's schedule for more detailed information
Bed 4

Bed

Bath 1

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(16)

$408.58

/ Nightly
Private Vacation Home

Spacious Sheboygan Home w/ Grill & Fire Pit!

Sheboygan, Wisconsin, United States

Escape the mundane and discover Lake Michigan bliss at this 5-bedroom, 3-bathroom Sheboygan vacation rental! Start your mornings off by sipping coffee and enjoying a meal made in the full kitchen, then venture out to explore downtown’s eateries, take in the scenic views from nearby lighthouses, or hit the links at Whistling Straits Golf Course. Come evening, return home to fire up the grill and recount the day’s memories beside the wood-burning stove. Adventure for all is just around the corner!brbr-- THE PROPERTY --brbrNear Whistling Straits Golf Course | Pet Friendly w/ Fee | Charcoal Grill | 3,800 Sq FtbrbrPerfect for golfers, Great Lakes lovers, and groups of friends, this Sheboygan home has everything you need for a blissful Wisconsin getaway!brbrBedroom 1: King Bed | Bedroom 2: Queen Bed, Full Sleeper Sofa | Bedroom 3: Queen Bed | Bedroom 4: Queen Bed | Bedroom 5: Queen Bed | Office: Twin/Full Bunk BedbrbrINDOOR LIVING: Smart TVs, DVD player, stereo, wood-burning stove, ceiling fans, board games, arcade game, gym equipment, high chair, breakfast bar brOUTDOOR LIVING: Screened-in porches, fire pit, outdoor seating areasbrKITCHEN: Fully equipped, stainless steel appliances, drip coffee maker, Crockpot, microwave, toaster, blender, ice maker, water filter, dishware/flatware, spices, basic cooking essentialsbrGENERAL: Free WiFi, central heating, window A/C units, washer/dryer, laundry detergent, iron/ironing board, towels/linens, hair dryers, complimentary toiletries, trash bags/paper towels brFAQ: Step-free access, pet fee (paid pre-trip)brPARKING: Driveway (7 vehicles), RV/trailer parking availablebrADDT’L ACCOMMODATIONS: An additional 4-bedroom property for 8 guests is available nearby with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbrFAMILY FUN: Above & Beyond Children’s Museum (5.4 miles), John Michael Kohler Arts Center (5.7 miles), Bookworm Gardens (7.4 miles), Kohler Design Center (7.5 miles), Road America (13.7 miles), Sheboygan Marsh Tower (16.4 miles), Lambeau Field (58.1 miles)brOUTDOOR REC: Quarry Beach Adventure Park and Water Sports (4.3 miles), Vollrath Park (5.1 miles), Deland Park (6.1 miles), Sheboygan Breakwater Lighthouse (6.1 miles), Breaker Bay Water Park (6.7 miles), Kohler Park Dunes State Natural Area (11.6 miles), Kohler-Andrae State Park (11.7 miles) brGOLF COURSES: Whistling Straits Golf Course (1.8 miles), Black Wolf Run Golf Course (8.6 miles), The Bull at Pinehurst Farms Golf Course (11.0 miles)brEVENTS: Ryder Cup - Whistling Straits Golf Course (September), Democratic National Convention - Milwaukee (August)brDINING & SHOPPING: Craft30 (5.0 miles), 3 Sheeps Brewing Company (3.9 miles), Downtown Sheboygan (5.5 miles), Downtown Kohler (7.8 miles), Downtown Milwaukee (61.6 miles)brAIRPORT: General Mitchell International Airport (69.4 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/ $50 fee (+ fees & taxes, 3 max)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-in
Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps

Home Most popular vacation rentals in Sheboygan