Vacation Rentals By Owner In Sheboygan, WI

$83.43

Lakeview Loft - Just opened up for July!

Sheboygan, Wisconsin, United States

Looking for extended stays We offer monthly rates. Inquire within, or check out StayWithNSDbrbrBright and cozy 2-bedroom, 1-bath upper apartment just 2 blocks from Lake Michigan. Fully equipped kitchen, comfortable living room with smart TV, and flexible sleeping arrangements including a twin-to-trundle king bed. Perfect for families, couples, or business travelers seeking a convenient lakeside stay.brbrDiscover comfort and charm in this beautifully appointed 2-bedroom, 1-bath upper apartment, perfectly located just two blocks from the sparkling shores of Lake Michigan. Whether you’re whipping up a meal in the fully equipped kitchen or unwinding in the cozy living room with a smart TV, this home offers everything you need for a relaxing getaway.brbrThe flexible sleeping area cleverly converts from a twin bed to a trundle-style king bed, doubling as a convenient workspace — perfect for both rest and productivity. The master bedroom boasts a luxurious king-size bed for peaceful nights and sweet dreams. Gather around the dining area set for four and enjoy meals, games, or conversation in a warm, inviting space.brbr ’ :br✔ Prime location just 2 blocks from Lake Michigan’s beach and trailsbr✔ Fully equipped kitchen with modern appliances for all your cooking needsbr✔ Cozy living room with smart TV for entertainment and relaxationbr✔ Flexible sleeping arrangement: twin-to-trundle king bed and dedicated workspacebr✔ Spacious master bedroom with a comfortable king-size bedbr✔ Dining area for 4, ideal for meals and quality timebr✔ Free high-speed WiFi to stay connectedbr✔ Convenient upper-level apartment with plenty of natural lightbrbr :br* Sheboygan Breakwater Lighthouse (0.5 miles): Historic lighthouse with scenic shoreline walks and stunning photo opsbr* John Michael Kohler Arts Center (1 mile): Contemporary art exhibits, live performances, and interactive displaysbr* Deland Park (1 mile): Lakefront park with playgrounds, picnic areas, and volleyball courtsbr* Sheboygan County Historical Museum (1 mile): Explore local history and culture through engaging exhibitsbr* Road America (20 miles): World-famous race track hosting major NASCAR and IndyCar eventsbrbr & :br* The Duke of Devon (1 mile): Cozy British pub with traditional fare and craft beersbr* Lino Ristorante Italiano (1.5 miles): Upscale Italian dining with classic pasta and seafoodbr* The Black Pig (1 mile): Farm-to-table American dishes and craft cocktailsbr* Sly’s Midtown Saloon (1 mile): Casual tavern serving comfort food and drinksbr* Meatball Joe’s (1.5 miles): Family-friendly spot famous for meatball sandwichesbrbr & :br* Sheboygan Brat Days (August): Annual festival celebrating local heritage with food, music, and fireworksbr* Holiday Parade (November): Festive floats and marching bands to kick off the holiday seasonbr* Lakefront Music Festival (Summer): Free concerts at Deland Park featuring local and regional artistsbr* Farmer’s Market (May–October, Saturdays): Fresh produce, artisan goods, and seasonal treats nearbybr* Witches Gulch Fall Festival (October): Family fun with pumpkin decorating and seasonal tours

2

Bed

1

Bath

4

Sleeps

$465.38

/ Nightly

Condo

Modern South Pier Condo on Sheboygan River!

Sheboygan, Wisconsin, United States

Stay in luxury at this 2-bedroom, 2-bathroom vacation rental in Sheboygan, WI. Enjoy the convenience of a fully equipped kitchen, a modern interior, and a prime location. Situated in the South Pier District and just steps away from Lake Michigan, this condo provides easy access to local attractions like the delightful downtown area and nearby beaches. Experience the best of Sheboygan while having all the comforts of this gorgeous riverfront retreat!brbr-- THE PROPERTY --brbrModern Interior | Furnished Balcony | Lake Michigan View | Walk to Lake Michigan & Downtown | 1/8 Mi Walk to the BeachbrbrBedroom 1: King Bed | Bedroom 2: Queen Bed, Twin/Full Bunk BedbrbrINDOOR LIVING: 2 Smart TVs, electric fireplace, board games, dining tablebrKITCHEN: Fridge, Keurig/drip coffee maker, stove, dishwasher, microwave, cooking basics, toaster oven, trash bags/paper towels, air fryerbrGENERAL: Free WiFi, central heating & A/C, washer, dryer, complimentary toiletries, linens/towels, ceiling fans, hair dryerbrACCESSIBILITY: Single-story condo, step-free entry via elevatorbrPARKING: Community parking lot (2 vehicles), no boat/trailer parkingbrbr-- THE LOCATION --brbrSOUTH PIER DISTRICT: Southside Municipal Beach (0.2 miles), Harry's Prohibition Bistro (0.2 miles), Driftwood (0.4 miles), South Pier Parlor (0.4 miles), Lino Ristorante Italiano (0.4 miles), Breaker Bay Water Park (0.4 miles), Harbor Pointe Miniature Golf (0.5 miles)brDOWNTOWN SHEBOYGAN (0.7 miles): Local restaurants, boutiques, bike tours, Riverwalk, John Michael Kohler Arts CenterbrOPT OUTSIDE: Lake Michigan (walking distance), Bookworm Gardens (2 miles), James Tellen Concrete Park (4 miles), Kohler-Andrae State Park (6 miles)brAIRPORT: Milwaukee Mitchell International Airport (63 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- Hanging towels or clothing over the balcony railing is prohibitedbr- Photo ID may be required upon check-inbr- NOTE: This single-story condo offers step-free entry via the elevatorbr- NOTE: This is a residential building. Please be mindful of neighbors and maintain a quiet volume during mornings and eveningsbr- NOTE: Boat/trailer parking is not allowed on site. Violators will be towed at their own expense. Boat trailers hooked to a vehicle can be parked for 24 hours in the city of Sheboygan for 24 hours, or you can call the Harbour Center Marina for parking and slip reservations

Bed

Bath

Sleeps

$157.11

/ Nightly

Private Vacation Home

Dog-Friendly Sheboygan Home - 1 Mi to Town!

Sheboygan, Wisconsin, United States

Experience the best of Sheboygan with your loved one from this 1-bed, 1-bath vacation rental! This newly renovated home offers 2 Smart TVs, a fully stocked kitchen, and access to the area’s top sites. Take a peaceful morning stroll through Kiwanis Park or Bookworm Gardens, then head to South Shore Beach and make a splash in Lake Michigan! For the golfers, tee off at Whistling Straits Golf Course. After your outdoor leisure, grab a bite at the homeowner’s Scenic Bar & Restaurant. It’s up to you!brbr-- THE PROPERTY --brbrConvenient Location | WFH Friendly | Fully Renovated | Patio w/ Furniture & Gas GrillbrbrBedroom: Queen Bed | Additional Sleeping: Extendable Sofa w/ Bedding, Pack 'n PlaybrbrINDOOR LIVING: 2 Smart TVs, dining table, laptop workspace w/ printer, Amazon Echos, high chairbrKITCHEN: Refrigerator, stove/oven, dishwasher, dishware/flatware, cooking basics, Ninja drip coffee maker, electric coffee grinder, microwave, toasterbrGENERAL: Free WiFi, window A/C unit, central heating, linens/towels, trash bags, paper towels, complimentary toiletriesbrFAQ: Pet fee (paid pre-trip)brACCESSIBILITY: Single-story home, 2 steps to enterbrPARKING: Reserved area (2 vehicles)brbr-- THE LOCATION --brbrOUTDOOR ADVENTURE: Kiwanis Park (0.8 miles), Bookworm Gardens (2 miles), Maywood (4 miles), Kohler-Andrae State Park (6 miles), Whistling Straits Golf Course (8 miles)brON THE WATER: Blue Harbor Resort (1 mile), South Shore Beach (1 mile), Deland Park (2 miles), Harbor Centre Marina (2 miles)brTHINGS TO DO & SEE: Scenic Bar & Restaurant (236 feet), John Michael Kohler Arts Center (1 mile), Above & Beyond Children's Museum (2 miles), Kohler Design Center (3 miles), Odyssey Fun Center (6 miles), Elkhart Lake's Road America (18 miles)brAIRPORT: General Mitchell International Airport (61 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 with a $75 fee (+ fees & taxes; dogs only, 2 max)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This single-story home requires 2 steps to enter

Bed

Bath

Sleeps

$375.03

/ Nightly

Condo

Beachside Condo Downtown with Lake Michigan Views

Sheboygan, Wisconsin, United States

You will see & hear the beauty of Lake Michigan during your stay at this main floor Waves of Happiness Condo hosted by Sheboygan Vacation Rentals.brbrA deck to the north allows views of the magnificent Blue Harbor Resort. The south deck gives more amazing views of the lake, plus a park just steps out the back door. You can stroll the beach, walk the River Boardwalk, or tour our historical downtown full of shops, art opportunities, & exquisite restaurants--all walkable from the condo.brbrThis main floor condo has 2 bedrooms (king/queen) and 1 bathroom (walk in shower). There is a fully stocked kitchen, decks to the front and rear of the condo- both with lake views and less than 200 feet to the beach.brbrIt is located in a quiet 4 plex on a dead end street which leads directly to the lake. To the rear is a large park with green space, public charcoal grills, playground, and public beach access. There are decks on the front and back, both with lake views. Great place for romantic getaway, ladies weekend, family vacation, or a place to relax on a business trip. brbrIncluded extras: washer/dryer in unit, toiletries, linens, drip coffee, toys/games, life jackets and beach toys, beach towels and beach chairs, high speed business wifi, roku TV, electric fireplace, portable crib.brbrNo smoking or pets allowed in condo or on premises, please.brbrThere is a common entrance to the building. From inside, you will be able to access your unit using keypad entry.brbrSmall amount of stairs to enter the building.brbrPARKING: This unit offers one off street parking spot to the rear of the building as well as public street parking in front. Garage space may be seasonally available as well.brbrCheck in: 4pmbrCheckout: 10ambrbrIf early check-in or late check-out is requested, please make request at time of booking. We will do our best to accommodate requests though may be limited during peak season.brbrWe will be available by phone call or text during your stay.brbrSheboygan is considered the surfing capital of the Midwest. Just across the street from the condo, guests are often treated to views of kite-surfers on the water.brbrThe adjacent park offers grills, picnic tables, play equipment, and green space to expand your outdoor living.brbr The entire county offers amazing experiences. It boasts charter fishing, sailing, kayaking, walking trails, inland lakes and beaches, a water park, world known golf courses, Road America Racing, Farmer markets, music in the park, children's museum, John Michael Kohler Art Center, and the charm of small-town atmosphere. During the cold-weather months, the area offers beautiful lake views, hiking, skiing, sledding hills, and more!brbrWalking or biking to most amenities is possible. Approximately one hour from the Milwaukee or Green Bay airport. Whistling Straights is approx. 15 minutes away, and Road America is approx. 25 minutes. Sheboygan Marina and boat landing just a few blocks away. Bike paths throughout city/county. Windsurfing, swimming, boating, sailing, and jet skiing on the lake. Paddle boarding and kayaking on the river is also very close by. Lots of parks and children's play equipment available. Public transportation available if needed.brbrThis condo is perfectly placed with a variety of shops, restaurants, music venues, museums, axe throwing, rage room, children's parks/attractions and more all within a 2 mile radius (many of which are easily walkable/bikeable). Sheboygan offers rentable scooters during the warm weather months that can be used as a fun way to explore the city.brbrPopular Area Attractions:br*Bookworm Gardensbr*John Michael Kohler Art Centerbr*Above & Beyond Children's Museumbr*Kohler Andrae State Parkbr*Stephanie Weill Centerbr*Whistling Straitsbr*Tallest Flagpole in USbr*3 Sheeps Brewingbr*Charter Fishingbr*Shaw Park (all abilities playground)br*Victorian Chocolate Shoppebr*Der Sheboygan Biergarten (summer months only)br*EOS Paddleboard and surfboard rentalsbr*Olivu 426 (as seen on the Golden Globes!)br*Downtown MuralsbrbrWe also have another condo available in this same building on the UPPER floor for those groups who have need both spaces OR who prefer the views of the higher level. Message me for this listing link.brbrSheboygan is conveniently located one hour north of Milwaukee and one hour south of Green Bay. Additionally, it's just 1.5-2 hours from Door County and Chicago making it the perfect hub for your Wisconsin/Midwest trip!brbrThe area offers stunning recreation all year round- surfing, snowshoeing, kiteboarding, world famous golf courses, fishing, hiking, cross country skiing, and more!brbrAfter requesting your reservation, you will receive a notification and link to complete our Rental Agreement, confirming the terms and conditions of your stay at Waves of Happiness, as well as the refundable security deposit, which you will be able to execute and set up digitally.

Bed

Bath

Sleeps

$457.86

/ Nightly

Condo

Beachside Condo w/ Stunning Lake Views

Sheboygan, Wisconsin, United States

Blue water+White sand+Waves will surely make your stay in our second-floor Waves of Happiness Condo hosted by Sheboygan Vacation Rentals.brbrDecide whether to sit on the north or south deck to enjoy the sights and sounds of Lake Michigan. Less than 200 feet to the beach and a sprawling city park for our backyard. Plan to stroll the beach, walk the River Boardwalk, or tour our historical downtown full of shops, art opportunities, & exquisite restaurants--WALKABLE from the condo.brbrThis 2nd story condo has 2 bedrooms (king/bunk with trundle) and 1 bathroom (walk in shower). There is a fully stocked kitchen, decks to the front and rear of the condo- both with lake views and less than 200 feet to the beach.brbrIt is located in a quiet 4 plex on a dead end street. To the rear is a large park with green space, public charcoal grills, playground, and public beach access. There are decks on the front and back, both with lake views. Great place for romantic getaway, ladies weekend, family vacation, or a place to relax on a business trip. brbrIncluded extras: washer/dryer, toiletries, linens, drip coffee pot, toys/games, life jackets and beach toys, beach towels and beach chairs, high speed business wifi, roku TV, desk for remote working, electric fireplace, portable crib.brbrNo smoking or pets allowed in condo or on premises, please.brbrThere is a common entrance to the building. From inside, you will be able to access your unit using keypad entry.brbrSmall amount of stairs to enter the building as well as staircase to get to 2nd floor condo.brbrPARKING: This unit offers one off street parking spot to the rear of the building as well as public street parking in front. Garage space may be seasonally available as well.brbrIf early check-in or late checkout is requested, please make request at time of booking. We will do our best to accommodate requests though may be limited during peak season.brbrWe will be available by phone call or text during your stay. brbrLonger stays are allowed.brbrThe condo is located in a 4plex on a quiet dead end street which leads to the lakefront. To the south is a public park. brbrSheboygan is considered the surfing capital of the Midwest. Just across the street from the condo, you will have the distinct opportunity to watch surfers and kitesurfers as the launch from “kite beach”. The adjacent park offers grills, picnic tables, play equipment and green space to expand your outdoor living.brbrSheboygan is one hour from Milwaukee, one hour from Green Bay, 1.5 hours from Door County and Madison, and only two hours from Chicago, making it the perfect hub for your Wisconsin/midwest sightseeing adventures!brbrWalking or biking to most amenities is possible.Whistling Straights is approx. 15 minutes away, and Road America is approx. 25 minutes. Sheboygan Marina and boat landing are just a few blocks away. During the warmer months, the city offers electric scooters for your use. Bike paths are available. Windsurfing, swimming, boating, sailing, and jet skiing are possible on the lake. Paddle boards and kayaks can be rented downtown or from the Riverfront. Lots of parks and children's play equipment available. Public transportation available if needed. In the colder months, the area offers fantastic views, hiking, sledding hills, and more! Approximately one hour from the Milwaukee or Green Bay Airport.brbrSheboygan is conveniently located one hour north of Milwaukee and one hour south of Green Bay. Additionally, it's just 1.5-2 hours from Door County and Chicago making it the perfect hub for your Wisconsin getaway! brbrThe area offers stunning views and recreation all year round--brsurfing, snowshoeing, kiteboarding, world famous golf courses, fishing, hiking, cross country skiing, and more!brbrThis condo is perfectly placed with a variety of shops, restaurants, music venues, museums, axe throwing, rage room, children's parks/attractions and more all within a 3 mile radius (many of which are easily walkable/bikeable). Sheboygan offers rentable scooters during the warm weather months that can be used as a fun way to explore the city.brbrPopular Area Attractions:brbr*Bookworm Gardensbr*John Michael Kohler Art Centerbr*Above & Beyond Children's Museumbr*Kohler Andrae State Parkbr*Stephanie Weill Centerbr*Whistling Straitsbr*Tallest Flagpole in USbr*3 Sheeps Brewingbr*Charter Fishingbr*Shaw Park (all abilities playground)br*Victorian Chocolate Shoppebr*Der Sheboygan Biergarten (summer months only)br*EOS Paddleboard and surfboard rentalsbr*Olivu 426 (as seen on the Golden Globes!)br*Downtown MuralsbrbrWe also have another condo available in this same building on the MAIN floor for those who have a larger group and need both spaces OR who prefer the lower unit to avoid the full staircase. Message me for this listing link.brbrAfter requesting your reservation, you will receive a notification and link to complete our Rental Agreement, confirming the terms and conditions of your stay at Waves of Happiness, as well as the refundable security deposit, which you will be able to execute and set up digitally.

2

Bed

1

Bath

5

Sleeps

$322.91

/ Nightly

Private Vacation Home

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Sheboygan, Wisconsin, United States

Kohler Design Center Rentals, Kohler Andrae State Park Rentals, Whistling Straits Rentals Blue Harbor Rentals, Road America Rentals, Kohler Art Center Rentals, Black Wolf Run Rentals, Lake Michigan Fishing Charters Rentals, Green Bay Packer Rentals, Door County Rentals, Honeymoon Rentals, Women's Weekend Rentals, Lake Michigan Sunrise Rentals, Saugatuck, Michigan Rentals, New Buffalo, Michigan Rentals, Premier Host VRBO Sheboygan Wisconsin Rentals, Best VRBO Rentals, Dog friendly rentals, Handicapped Accessible RentalsbrbrOur check in time is 1 PM, check out time is 10 AM. brbrPlease note: We are dog friendly. Each dog is $25.00 per dog per night. The check out feature does not charge for a second dog. We can resolve this after booking. Thank-you!brbrThe mobile app incorrectly states 11 AM check out and 2 PM check in. Please be advised we operate under the 1 PM check in and 10 AM check out times.brbrLake Shore House is a fully equipped vacation rental on Lake Michigan. Beautiful unobstructed lake views on one of America’s Great Lakes, offers a relaxing mid-week, weekend, or week retreat. Since 2007 we have hosted hundreds of guests at Lake Shore House, providing them with ambience, cleanliness, and an easy reservation and access procedure. We are open 365 days a year. Guests come from Europe and all 50 states to enjoy the lake. In summer they enjoy the beach and tranquility, fall the autumnal colors and privacy, winter the frozen lake and winter activities and spring to cure cabin fever with a fresh getaway. The sunrise and moonrise shimmering across the lake have brought special memories to guests and families throughout the year and are reflected in the Lake Shore House visitor’s log.brbrNot your typical cookie-cutter destination, Lake Shore House offers privacy in a single-family home that features central air-conditioning, hardwood floors, laundry, wood-burning stove, one-car garage, expansive deck, updated kitchen and bathes. Sleeping accommodations for six, two second floor bedrooms with skylights and ceiling fans, one with a king size bed and a balcony overlooking the Lake, the other featuring a queen size bed, plus a queen sleeper sofa in the living room with abundant natural light from three directions. The main floor ceramic tile bath has a full-size tub with shower and pedestal sink. The lower level features a half-bath, laundry and a twin rollaway bed.brbrIf you are a couple, single, family, multi-generational, girl’s getaway or other guest, we have hosted just about every type and lifestyle of guest. We embrace diversity. We are dog friendly and have had just about every breed of dog. If you would like to bring yours, tell us something about them, we rarely turn well groomed and behaved dogs away.brbrAs your host, I am equipped to handle last-minute bookings.brbrExterior Maintenance: Like all accommodation providers, exterior maintenance (lawn mowing, weeding, pruning and snow shoveling) needs to be addressed occasionally during your stay at Lake Shore House. We attempt to limit these activities and arrange to accomplish them to 60 minutes prior to check out time (10 AM). Sometimes you might see me as the owner, or a person contracted to perform exterior routine maintenance on the property at other times as well.

Bed

Bath

Sleeps

$392.56

/ Nightly

Private Vacation Home

Huron Ave · Spacious & Peaceful Home in the heart of Sheboygan

Sheboygan, Wisconsin, United States

Come stay at a beautiful home close to Lake Michigan and downtown Sheboygan! Located in a quiet neighborhood, and two blocks away from downtown restaurants, coffee shops, and nightlife. Within minutes of world class Kohler golf courses, such as Whistling Straights, and the resort town of Elkhart Lake, WI, home of Road America! Additionally, Sheboygan and this property are positioned within an hour of both Milwaukee and Green Bay. We look forward to sharing this beautiful home with you!brbrThis rental is a three bedroom home with private parking in the back and a fenced-in back yard! A queen size and full size bed are located on the second floor, while a twin size bed is conveniently located on the first floor. Both bedrooms on the second floor are equipped with ample closet space, and dressers for your convenience. There are two fully stocked bathrooms located in the home; a half bath on the first level and a full bathroom located on the second floor. We also have a Washer and Dyer available for you to use as needed! Additionally, enjoy a comfy living room, beautiful dinning room, and spacious kitchen, stocked with all the cooking basics for you to use at your leisure.brbrWe primarily do self check-ins and check-outs for the convenience of our guests. However we are available for a personal check-in if requested. Feel free to contact us by phone, email, or through Air BnB throughout your stay with any additional questions you may have during your stay.brbrLocated within a block of Holy Name church, and within walking distance of many other churches located throughout downtown Sheboygan, our home is the perfect spot to stay during wedding weekends! Additionally, we are within walking distance of many cocktail bars, restaurants, and coffee shops. Take a 2-3 minute drive and enjoy beautiful North Beach, on the shores of stunning Lake Michigan!

3

Bed

1

Bath

5

Sleeps

$273.57

/ Nightly

Private Vacation Home

Large Backyard, Walk to Hospital: Sheboygan Abode!

Sheboygan, Wisconsin, United States

Mid-Term Stays & Travel Nurses Welcome | Near Fishing & Golf | WFH FriendlybrbrWhether you're here for work or play, you'll find a peaceful setting for your stay at this Sheboygan vacation rental! With easy access to Aurora Medical Center, Lake Michigan, and I-43, this 2-bedroom, 1-bath home is ideal for traveling healthcare workers, families, and nature lovers alike. After a long shift or fishing tournament, have dinner on the deck and roast marshmallows by the fire. Your next getaway awaits!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 3 twin bedsbr- Living Room: 1 queen sleeper sofabr- Additional Sleeping: 1 Pack 'n PlaybrbrOUTDOOR LIVINGbr- Private yardbr- Wood-burning fire pit, gas fire pitbr- Deck w/ dining area, electric grillbr- Outdoor lounge areabrbrINDOOR LIVINGbr- Smart TVsbr- Laptop-friendly workspacebr- Dining tablebr- Children’s wagon & strollerbrbrKITCHENbr- Refrigerator, stove/oven, dishwasherbr- Keurig coffee maker, toaster, rice cookerbr- Cooking basics, dishware & flatwarebr- Ice maker, trash bags/paper towelsbr- Air fryerbrbrGENERALbr- Central heating & A/Cbr- Washer/dryer, laundry detergent, iron/boardbr- Linens/towels, complimentary toiletries, hair dryerbr- Free WiFibrbrFAQbr- 1 exterior security camera (facing out)br- Basement not available for guest usebrbrACCESSIBILITYbr- Single-story home, exterior stairs to enterbrbrPARKINGbr- Garage (1 vehicle)br- Driveway (2 vehicles)br- Free street parking (first-come, first-served)brbr-- THE LOCATION --brbr- Quiet neighborhood near parks, shopping, dining & HSHS St. Nicholas Hospitalbr- 2 miles to downtown Sheboygan & Lake Michiganbr- 3 miles to UW-Green Bay Sheboygan Campus, Bookworm Gardens, & 8th Street Boat Launchbr- 5-8 miles to golf courses: Blackwolf Run, The Bull at Pinehurst Farms, Whistling Straitsbr- 56 miles to downtown Milwaukeebr- 65 miles to Milwaukee Mitchell Int'l 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- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story home requires exterior stairs to enterbr- The basement is not available for guest usebr- Your safety matters. This property features 1 exterior security camera located on the front door, facing the front outdoor entry. It does not look into any interior spaces. The camera actively records video and sound while guests are in residence

Bed

Bath

Sleeps

$401.64

/ Nightly

Private Vacation Home

Beach House on the shores of Lake Michigan Near downtown Sheboygan

Sheboygan, Wisconsin, United States

Amazing location on the shores of Lake Michigan. One of only a few homes in the city of Sheboygan that are right on the public beach. The home has just been remodeled and the bathrooms are completely redone. There are three bedrooms of which one is on the main floor. There is one full bathroom on the main floor with a shower/tub combo and one full bath upstairs with a corner shower. There is plenty of parking on the driveway. Please note the garage is currently not available for use.brbrINTERIOR PICTURES WILL BE POSTED WITHIN THE NEXT COUPLE OF DAYS. This is a 3-bedroom home. There are 2 bedrooms upstairs and one on the main floor. The primary bedroom upstairs has a king size bed and balcony and walk in closet. There is a 55 tv mounted on the wall. The second bedroom upstairs has a queen size bed and a bunk bed with 2 twin size beds. The max capacity of the upper bed is 250 lbs. The downstairs bedroom has a queen size bed and a 55 tv as well. The living room has a 65 tv.br

Bed

Bath

Sleeps

$603.76

/ Nightly

Private Vacation Home

The Links! - Luxury Golf Retreat with Golf Simulator

Sheboygan, Wisconsin, United States

Get ready to relax in this 4-bedroom house in Sheboygan. This superb property features 2 king beds and 2 queen beds, perfect for a soothing night's sleep. With 3 bathrooms equipped with hair dryers and showers, guests can freshen up with ease. Our place is equipped for both long or short stays to make your holiday one to remember.

Bed

Bath

Sleeps

$292.26

/ Nightly

Private Vacation Home

Sheboygan Retreat in Black River

Sheboygan, Wisconsin, United States

Only an hour drive north of Milwaukee and south of Green Bay. Experience all Sheboygan County has to offer. Kohler golf courses, biking and hiking, charter fishing, a variety of restaurants just to name a few of the many adventures available.brbrThis quaint 3 bedroom, 1.75 baths home is located on a quiet, partially wooded lot near a park for children to play. Enjoy a quick walk to beautiful Lake Michigan for an early morning sunrise on the beach. Cool summer breezes carry through open bedroom windows from the lake.brbrEnjoy stunning sunsets from the terraced back deck while sipping refreshing beverages with family and friends. There is plenty of room to lounge, inside and out. brbrA gas grill and a kitchen full of cookware provide all you need to prepare your own meals (some spices available). It is a short drive to town for a famous Wisconsin local Friday Fish Fry or a quick walk to the neighborhood restaurant. Chase the chill away evenings with a natural wood fireplace while watching a movie or just enjoy the peace and quiet with a good book. Gaze through the over-sized living room window and catch the deer and wildlife. brbrPerfect for a family vacation or just a relaxing weekend, this home is a welcoming comfortable retreat.brbrThe home is available for longer term rentals during the winter season and will be available again for weekend/weekly rentals beginning in May, 2017. brbrKeywords: House, Cabin, Cottage, Secluded, Quiet, Quaint, Family Friendly, Lake Michigan, Woods, Blackwolf Run, Whistling Straits, Kohler-Andrea State Park,

Bed

Bath

Sleeps

$348.38

/ Nightly

Private Vacation Home

4 Bedroom Home on the River with Private River access

Sheboygan, Wisconsin, United States

Take in the coastal vibes as you enjoy your stay at this Riverfront home. With private access to the river, kayaks to use as you please, and a serene backyard oasis you are sure to enjoy your stay here. The eat-in kitchen is equipped with all necessities to whip up a delightful breakfast, satisfying lunch, and divine dinner. The family room has a variety of board games as well as a smart TV for entertainment. Complete with four very unique bedrooms to retreat to at the end of the day, each showing off their own unique flare.brbrWe have a smart TV that is connected to the home Wi-Fi network. You can cast audio from your device to the TV as long as your device is connected to the river home Wi-Fi network.brbrYou are welcome to use Hulu+, Hulu live, Disney+ and Netflix to watch your favorite TV shows, live television, and movies! When using the apps on the TV use the account River Home for your streaming needs. Hulu Plus has a variety of TV shows and gives you the opportunity to also watch live TV. Disney+ and Netflix have hundreds of movies to select from.brbrThere are complimentary coffee grounds, K cups, and teabags for you to use during your stay. Feel free to make use of any books and board games located in the living room bookcase during your stay. Two kayaks are available to use at your own risk. 3 Lifejackets are provided. Feel free to have a fire in the backyard fireplace.br

Bed

Bath

Sleeps

$149.98

/ Nightly

Apartment

BEST LOCATION IN SHEBOYGAN! Steps to beach & marina, walk to historic downtown!

Sheboygan, Wisconsin, United States

My husband and I love to stay in a reasonably priced condo or flat when we travel. We like to feel like we are at a home away from home, a place with all the amenities we have grown accustomed to, but especially we love having the space you get with a VRBO property over the cramped feeling of being in a hotel. brbrOur goal is to provide an affordable VRBO property where people like us want to stay. We wanted to keep it clean and simple. Located steps from Lake Michigan we are in the heart of the North Beach area, with bike/walking paths, the beach, sailing, restaurants and shopping just moments away. brbrOur guests tell us that our location truly sets us apart! Be sure to take in the sunrise from our small look out balcony or from the beach, just steps away.brbr2 bedroom upper flat with 1 full bed, 1 queen bed. In addition, to accommodate additional guests, the option is available to close off French doors to create a third private sleeping space with a click bed. Sleeps up to six.brbrPrivate entrance and a reserved parking space are provided. Additional street parking available.brbrContact us to inquire about early check-in, late departure, extended stays and monthly rentals.brbrWe are a 15 minute drive along the lake to Whistling Straits. Very convenient location and easy to navigate. brbr Feel free to reach out with any questions, we are happy to assist in any way we can!brbr

Bed

Bath

Sleeps

$316.5

/ Nightly

Condo

Riverwalk Retreat - Riverfront 3BR Condo w/ Jacuzzi & Lake Michigan Views

Sheboygan, Wisconsin, United States

Welcome to Riverwalk Retreat — Presented by Great Lakes Getaways! brbrTake advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026.brbrDiscover the ultimate retreat in this top-floor Riverfront condo with stunning views of the Sheboygan River and Lake Michigan. This spacious 1600 sq ft, 3-bedroom, 2-bath unit features a jacuzzi tub in the master bath for ultimate relaxation. Located on the River Walk, enjoy unique restaurants at your doorstep. Dubbed The Malibu of the Midwest, savor Lake Michigan sunrises, sandy beaches, and watch surfers ride the waves.brThe spacebrExperience laid-back lake life in this spacious 3-bedroom, 2-bath condo located on Sheboygan’s South Pier — a vibrant 42-acre peninsula nestled between Lake Michigan and the Sheboygan River. With nearly 1,700 square feet all on one floor (a rare find in this area), you’ll enjoy effortless comfort and plenty of room to relax, recharge, or entertain.brbr ’ :br✔ One-level living with panoramic river and lake views from the moment you walk inbr✔ Private balcony with seating for six and unbeatable views of the Riverwalk and Lake Michiganbr✔ Cozy living area with leather seating, a gas fireplace, 50 smart TV, and nostalgic full-size arcade consolebr✔ Designated workspace plus a buffet stocked with puzzles and board gamesbr✔ Fully equipped kitchen with granite countertops, breakfast bar for five, spices, oils, and a complimentary coffee/tea barbr✔ Dining table for six with additional buffet for serving or gamesbr✔ Master suite with king bed, soft seating, a walk-in closet, lake views, and ensuite with jacuzzi tub and walk-in showerbr✔ Second king bedroom with smart TV and plenty of storagebr✔ Third bedroom with two extra-long twin beds — perfect for kids or friends traveling togetherbr✔ Second full bath stocked with plush linens and toiletriesbr✔ Beach wagon, chairs, toys, and towels ready for your lake daysbrbrA Walkable VacationbrStart your mornings with a coffee stroll along the Riverwalk, spend sunny afternoons at the beach (just 5 minutes away), and enjoy evenings dining al fresco or catching live music nearby. From ice cream parlors and mini golf to Italian restaurants and waterfront BBQ, everything you need is steps away.brbr :br* Riverwalk promenade just outside your doorbr* Ice cream shops, local cafes, mini golf & boutique shoppingbr* Driftwood South Pier waterfront bar just steps awaybr* Deland Park and beach (0.3 miles)brSheboygan Marina & North Point Park (under 0.5 miles)br* Above & Beyond Children’s Museum (0.5 miles)brbr & :br* Lino Ristorante Italiano – fine Italian cuisine (0.2 mi)br* Weather Center Café – lakeside coffee & light bites (0.2 mi)br* Field to Fork – farm-to-table breakfast & lunch (0.9 mi)brbr & :br* Sheboygan Farmers Market at Fountain Parkbr* Kite Festivals at Deland Parkbr* Powerboat Races during the Sheboygan Midwest Challengebrbr : brFull access to the condo located on the second floor of the building. Keyless first floor access with stairs or elevator to take you to the second floor. Your codes for both doors will arrive via the app on check in day. You have the entire condo to yourself.brbr : brThe condo is located on the second floor of a mixed use building. The entrance to the four units on the second floor is private.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.

3

Bed

2

Bath

6

Sleeps

$242.58

/ Nightly

Private Vacation Home

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

Sheboygan, Wisconsin, United States

This Sheboygan house boasts 4 inviting bedrooms with 3 queen beds and 1 crib. The pleasant and soothing atmosphere will make guests feel right at home. This property offers terrific comfort and convenience with 2 bathrooms and an additional office space with a futon. You're sure to make fantastic memories with a stay at our place.

3

Bed

1

Bath

7

Sleeps

$155.0

/ Nightly

Apartment

3 Bedroom lower unit -Brand New Remodel

Sheboygan, Wisconsin, United States

Complete Remodel just finished on this 3 BR 1 BA lower unit. New bathroom, kitchen, flooring, etc. in a central location in city of Sheboygan. Free laundry on separate side of basement and WIFI utilities and lawn/snow maintenance included. 2 car garage included with a 30+ day stay and driveway parking included for all stays.

3

Bed

1

Bath

5

Sleeps

$185.38

/ Nightly

Condo

3-bedroom condo in tranquil Sheboygan with AC comfort

Sheboygan, Wisconsin, United States

Your Sheboygan adventure begins at this 3-bedroom condo. Inside, guests find two queen beds and a cozy futon, perfect for relaxing after a day of exploring. The space feels peaceful and inviting, with heating and AC to keep you comfortable year-round. Whether you’re unwinding in the living area or getting ready in the well-equipped bathroom, this adorable condo offers a welcoming retreat. It’s an excellent choice for families or groups looking for a comfortable home base. We look forward to hosting you at our place.

3

Bed

1

Bath

5

Sleeps

$1282.88

/ Nightly

Private Vacation Home

Quiet and spacious home, close to downtown, the beach, and fantastic golfing.

Sheboygan, Wisconsin, United States

Nestled on a wooded acre in a quiet cul de sac. The cozy wood burning fireplace and wet bar in the family room is great for entertaining. And there is plenty of space with 3 bedrooms upstairs, and a full basement ready for game nights or a movie. A short walk out the patio will bring you to the large back yard with plenty of space around the fire pit to take in the evening stars. Enjoy your coffee on the deck of the master bedroom, and watch the wildlife wake up.

Bed

Bath

Sleeps

$546.7

/ Nightly

Condo

Luxurious artistic 2 bed - 2 bath Condo; feel like living by the Coast!

Sheboygan, Wisconsin, United States

This is a very well-taken care of condo in the most touristic part of Sheboygan. Be close to two beaches, a pier walk, and many restaurants and shops, all within walking. Check our charter fishing and the nearby waterpark. Enjoy a vacation in the Malibu of the Midwest. Enjoy the Farmer's market and art scenery, and listen to the waves of Lake Michigan while you relax in a beautifully decorated Condo owned by an artist. Enjoy the original artwork throughout the condo, which is also available to purchase. Full Kitchen equipped with everything you need, all selected and collected by the artist owner.

2

Bed

2

Bath

5

Sleeps

Vacation Rentals By Owner In Sheboygan, WI

$83.43

$465.38

$157.11

$375.03

$457.86

$322.91

$392.56

$273.57

$401.64

$603.76

$292.26

$348.38

$149.98

$316.5

$242.58

$155.0

$185.38

$1282.88

$546.7

Rent a place that suits your needs

Most popular vacation rentals in Sheboygan

$479.20

$603.76

$595.88

$546.70

$491.96

$457.86

$442.00

$457.05

$737.61

$474.40

Most Popular Cities in Wisconsin