Vacation Rentals By Owner In Sheboygan, WI

Located just one lot in from the beautiful shores or Lake Michigan. This amazing location provides year round stunning views . This is a lower 2 bedroom 1 bath condo in a 4 unit building. You can listen to the waves or walk just a few feet and have the sand on your feet. This condo features granite countertops, stainless steel appliances, maple cabinetry and front and rear balconies. Makes for a great place to enjoy a weekend get away or a place to relax at night while on a business trip.brAll the adjacent beaches are public so you have easy access. Located less than a mile from downtown Sheboygan and in close proximity to all the golf courses around town. There is one television in the living room with Roku and basic cable. Each bedroom has a TV as well. There is Wi-Fi. There is a queen size mattress in each bedroom. There are ceiling fans in the bedrooms and the living room. One bedroom has a wall mounted air conditioning unit and the other has a portable air conditioning unit. There is a one car detached garage just off the balcony and street parking as well. Opposite side parking rules exist during the winter months only. There is a one car garage. There is also a parking space on the west side of the building, that if open, you are allowed to use.

BEACHSIDE GETAWAY IN SHEBOYGAN

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$531.02

This newly renovated home offers the ultimate blend of comfort, fun, and convenience. Located in the heart of the city, you’ll be just steps away from the area’s best restaurants, bars, coffee shops, and nightlife. brbrInside, enjoy a spacious area ideal for relaxing or entertaining. Each bedroom has its own smart TV. Challenge your friends or family in the fully equipped game room, featuring a pool table, air hockey, and more. After a day exploring the city, unwind in your private 2 person sauna.brbrbrStep outdoor to enjoy a spacious 20 foot gazebo with dinning room seating and a sectional couch, a charcoal grill for outdoor cooking and a brand new fire pit with cozy seating- perfect for summer nights. But that’s not all: the backyard offers direct access to a park with a basketball court, giving kids even more to love.

4- Bedroom Retreat with Sauna, Game Room, Patio & Walk to Bars & Restaurants

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$435.08

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

Villa

Luxury Villa on Lake Michigan!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$265.17

Amazing location just off of Lake Michigan. A quick walk to the public beach across the street or downtown as well. Previous owner was an architect and owned the home for 60 years before he decided to downsize. Over 2200 square feet of living space. All FIVE bedrooms and a full bath are upstairs. There is a half bath on the main floor. The full bath upstairs has a stand-alone shower and a new whirlpool tub. Three bedrooms have queen size beds and TV's. Two smaller bedrooms each have a twin size bed. A queen size air mattress can be set up in on the first floor when needed with prior notice. There is a laundry room just off of the kitchen. There is a half bath on the main floor.brPlenty of room for the whole family. Perfect for a golfing weekend., family trip or girls' weekend. There is a gas grill out back. 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 put in. There is a 65 TV in the living room. WIFI access and cable TV present. Plenty of street parking along with a large two car garage at the back of the property. Check in time is 4pm or later and check out time is by 10am. There is a keypad on the front door for easy check in. I will provide the code two days before your arrival.

BEACHVIEW GETAWAY

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$325.3

Welcome to Wandering Waves — Presented by Great Lakes Getaways! brbrTake advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026.brbrWake up to sweeping Lake Michigan views in this stylish 2BR/2BA beachfront condo! Just steps from the sand, you’ll enjoy sunrise mornings, wave-filled nights, and unbeatable beach access. Inside, a modern open layout offers a fully equipped kitchen, cozy living area, and private patio with serene water views.brbrPerfect for couples, families, or friends, this condo is ideal for a weekend getaway or longer stay.brbrWelcome to your ultimate getaway! This beautifully renovated 2-bedroom, 2-bath beachfront condo offers a serene retreat just steps away from the pristine shores of Lake Michigan. With sweeping views, modern comforts, and a prime location, this is the perfect place for a relaxing and unforgettable vacation.brbr ’ :br✔ Master Suite with King Bed & Jetted TubbrEnjoy ultimate relaxation in the master suite, featuring a king-sized bed and a private en-suite bathroom with a jetted tub, ideal for unwinding after a day at the beach.br✔ Private Queen BedroombrThe second bedroom offers a cozy queen bed, designed for guests who want their own retreat while staying close to all the excitement. Thoughtful design with natural light ensures a peaceful rest.br✔ Fully Stocked Kitchen & Dining Area:brThe kitchen is fully equipped with everything you need to prepare meals, from cookware to utensils. Enjoy breakfast at the bar or share meals around the dining table with stunning lake views.br✔ Cozy Living Room with Gas FireplacebrThe living room is perfect for relaxation, with a gas fireplace to keep you warm. Watch TV, read a book, or simply gaze out the window at the waves crashing on the shore.br✔ Direct Beach AccessbrStep outside and you’re just a few feet from the beach! Spend your days lounging on the sand, collecting shells, or simply enjoying the stunning sunsets over Lake Michigan.br✔ Perfect Location & ComfortbrWith modern amenities and the natural beauty of Lake Michigan right at your doorstep, this condo provides the best of both worlds—luxury and serenity.brbrExplore the SurroundingsbrWhether you're looking to relax on the beach, enjoy scenic walks along the shore, or explore local attractions, this condo offers the perfect base for your Lake Michigan adventure.brbr :br* Deland Park – 0.3 milesbrBeach access, picnic areas, playgrounds, surfing, and the historic Lottie Cooper Shipwreck. Hosts 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 peaceful relaxation spots.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 kids.brbr & :br* Driftwood South Pier – 0.1 milesbrWaterfront bar & grill with American cuisine and river views.br* Lino Ristorante Italiano – 0.2 milesbrUpscale Italian dining with authentic dishes.br* Weather Center Café – 0.2 milesbrSpecialty coffee, teas, and light meals in a cozy setting.br* Field to Fork – 0.9 milesbrFresh, locally sourced breakfast and lunch with bakery and roastery.brbr & :br* Sheboygan Farmers Market – 0.9 milesbrWednesdays & Saturdays (June–October), fresh produce, crafts, and live entertainment.br* Deland Park Kite Festival – 0.3 milesbrAnnual vibrant kite displays and family fun.br* Sheboygan Midwest Challenge – 0.5 milesbrAugust powerboat races with high-speed excitement and festivities.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- This condo does not have any associated with Blue Harbor, and none of their amenities are included.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!

Villa

Wandering Waves - Beachfront Lake Michigan Stay!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$1589.0

Escape to your own private Lakeside Retreat. 4 BR, 2.5 bath Cape Cod overlooking Lake Michigan & Black River giving you the ultimate in privacy & serenity. Enjoy the view year-round from the 4-season sunroom. There are two 1st floor BRs. Upper primary suite offering a walk-in shower, fireplace, huge walk-in closet & patio doors to large upper deck with magnificent lake views! 2 car garage. Sunrises over Lake Michigan & sunsets over the Black River. Currently, there is no direct access to the water.

Pelican Point - Private Retreat - just 4 miles to downtown Sheboygann

Sheboygan, Wisconsin, United States

4

Bed

Bath

12

Sleeps

$376.82

Nestled in the heart of Sheboygan, our location is a true gem! We are just steps away from the shores of Lake Michigan and an easy stroll to all that the downtown has to offer. brbrWe have 3 bedrooms with plenty of room to spread out. We are a sucker for a good theme so in the two downstairs bedrooms you will find small nods to our love for golf and cheese. One bathroom and laundry located on the main floor. Upstairs you will find another bedroom/loft and private bathroom. There is also a desk and kids corner where we hope they will have hours of fun. brbrOther Features: br- Fully equipped kitchen with modern appliances for all your cooking needs. - - Staples like salt& pepper, oil and basic seasonings provided. br-Keurig and Regular coffee pot with fully stocked coffee bar. Even a small coffee pot in the upstairs bedroom perfect for those lazy morningsbr-Gas fireplace br-Bottomless popcorn for movie nights br- Wi-Fi and Smart TV's giving you access to all your favorite streaming channelsbr-Spacious private backyard. br-Board Games, puzzles and books sure to entertain for hours br- Pack & Play, High Chair, kids plates/bowls/cups, baby gate at the top of the stairs, Kids Toys br- Grill and Outdoor Seating br- Lawn Games & Foosball Table br- Beach Towels, Chair, Toys and Cooler provided br-15 minute drive to Whistling Straights and Black Wolf Run br-20 minute drive to Kohler-Andrae State Park br-Many parks within walking distance (including historic Deland Park)br-Farmers Market every Saturday in the warmer months. Within a 1 minute walk from the house br-Easy walk to downtown shops and restaurants

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$359.58

Welcome to our Delightful Seaside Picnic, hosted by Rose and Fern and Sheboygan Vacation Rentals! brbrThis newly renovated home offers a serene retreat just steps from Sheboygan’s stunning shoreline (and biggest and best beach in the area) where you can enjoy a sunrise stroll along the sandy beach or a refreshing dip in the lake. brbrNestled in the charming Ellis Historic District, our home is also just a short walk from the vibrant riverfront and downtown area, where you can explore a delightful array of local restaurants, cafes, boutique shops, and entertainment. The road end also offers easy access to the lovely Sheboygan North Pier and lake walk.brbrOur spacious home has been thoughtfully designed for comfort and style, featuring a bright, open floor plan and a beautifully appointed kitchen equipped with modern appliances and ample counter space – perfect for cooking up a feast or hosting dinner with family and friends. Throughout the home, you’ll find unique handcrafted furniture (Beds are hand crafted by the owner, a renowned furniture designer and woodworker), ultra high-end MillerKnoll seating in the living room, and artwork created by local artisans, adding a touch of Sheboygan’s artistic spirit to your stay.brbrThe neighborhood is quiet, safe, and brimming with historical charm. You'll love the tree-lined streets and classic architecture, making it an ideal place for leisurely walks. For those who enjoy an active lifestyle, Sheboygan is known for being incredibly walkable and bike-friendly (we provide the bikes), with scenic trails along the lake and river. During the summer months, hop on the local trolley for a nostalgic ride through town, or rent one of the many available scooters to explore at your own pace. Public bus transportation is also conveniently accessible for easy travel around the area.brbrWhether you’re here for a relaxing beach getaway, a culinary adventure, or to immerse yourself in the local culture, Rose & Fern’s Delightful Seaside Picnic offers the perfect home base for your Sheboygan experience. brbrWe look forward to welcoming you!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 Rose & Fern's, as well as the refundable security deposit, which you will be able to execute and set up digitally. brbrPlease note that cancellation fee is 3% to cover the credit card transaction fees.

Beachside, Chefs Kitchen, High-End Everything

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$810.72

Everything you need on one level. complete modern Open concept living room, kitchen and dinning area. Hosts two large kitchen islands and bar/tv entertainment area and additional coffee bar. Step out to the Patio and relax with electric concrete fire table. Basement has full bath and additional recreation room. And extra large bedroom.

Central located. Seconds from the highway to get to kohler, and Elkhart lake

Sheboygan, Wisconsin, United States

4

Bed

Bath

14

Sleeps

$256.45

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 garage parking, 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.

Fresh Coast Craftsman - Monthly Rentals Available!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$338.1

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 and prior homeowner approvalbr- No events, parties or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-in

Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$275.72

Beautiful home in Sheboygan WI. Entire home has been completely remodeled and updated. brbrThree entire floors of space for your family or friends. Original hardwood floors throughout the first floor, newly carpeted master bedroom upstairs with adjacent bedroom loft. Newly remodeled family room with two TV's on lower level. Private office area and full laundry also located on lower level.brbrAmazing backyard with huge deck, perfect for summer entertaining. Close to golf, beach, parks and more.

Wonderful 3+ Bedroom Home Completely Renovated

Sheboygan, Wisconsin, United States

4

Bed

Bath

7

Sleeps

$155.0

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.

Apartment

3 Bedroom lower unit -Brand New Remodel

Sheboygan, Wisconsin, United States

3

Bed

1

Bath

5

Sleeps

$481.24

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

Shoreline Sanctuary - Family Beach Villa with Deck and Sunsets

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$191.82

Welcome to the Beachy Bungalow!brbrCome in and unwind at our beachy 3 bedroom upper unit near Lake Michigan, Whistling Straits, Road America and Kohler/Andrae State Park. You can enjoy an evening at home with all your favorite streaming services, or head out to discover some of Sheboygan’s many hidden gems.brbrbrIf this unit is booked for your dates, send me a message to ask about our other available listings.brbrUnplug and relax in this 3 bedroom upper unit.brbrYou will find all the comforts of home in the fully equipped kitchen, with staples like sugar and basic spices provided. In the morning, enjoy a cup of complimentary coffee on the deck overlooking the spacious backyard, which is shared with other guests.brbrEnjoy the fire-pit in the backyard, where there is plenty of room for kiddos to run off steam.brbrIn addition to the relaxing master bedroom with a queen-size bed, there is a bedroom with twin-size bed, as well as a bedroom with two twin-size beds. You will also find a pack-n-play and highchair so the whole family can be comfortable.brbrIf the weather during your visit doesn’t allow for outdoor activities, no need to fret! In the living room, you’ll find a smart TV equipped with Roku. Login to Netflix, HULU, Amazon Prime, Disney+ or your favorite streaming service, and settle in to chill on the couch with a complimentary bag of popcorn provided in the snack basket. If board games are more your speed, you’ll find them along with puzzles in the closet.brbrExtra towels are located in the basket in the bathroom. You’ll also find shampoo, conditioner, blow dryer, body wash, dish soap, dishwasher tabs and other essentials. There is a box fan in the bedroom closet for extra air flow, or in case you prefer some ambient noise for sleeping.brbrThis unit has a private entrance, so you will have access to the whole place without sharing any indoor spaces with other guests. The entryway door is a keyless touchpad, so you can self check-in at your leisure. We will send a custom door code within 24 hours of your arrival. Feel free to call or text if you have any questions.brbrThe backyard is a shared space, with an outdoor dining table and fire pit for all guests to enjoy.brbrStreet parking is available for this house. Not to worry - most homes on this one-way street have driveways, and parking is never an issue!brbrWe are so glad you are staying with us!!brbrYou can park on the street in front of the house. It is a one-way street and parking is allowed on both sides of the street, except during winter months. brbrThe home is equipped with a Nest Thermostat. Instructions for use are included below:brbr- Tap the touch bar on the right side of the thermostat to open the menu.br- Swipe up or down to select an option, and tap again to confirm.br- Swipe up on the right side of the thermostat's touch bar to raise the temperature, and swipe down to lower it.br- Tap to confirm.

Apartment

Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$192.98

Find rest and relaxation where the Sheboygan River flows into Lake Michigan at this 2-bedroom, 1.5-bathroom townhome. This 2-story Sheboygan vacation rental is the perfect place to spend time on the water, with on-site river access and proximity to beaches lining the shores of the lake close by. Take the kayak and paddleboard out for a peaceful ride, stroll the boardwalk through the sand dunes and golden beach of Kohler-Andrae State Park, or walk downtown to explore the museums and nightlife.brbr-- THE PROPERTY --brbrFurnished Balcony | Gas Grill | Kayak & Paddle Board | 1,200 Sq FtbrbrBedroom 1: King Bed | Bedroom 2: King Bed, Queen Murphy Bed | Living Room: Sleeper Sofa | Additional Sleeping: Queen Air Mattress, Pack ‘n PlaybrbrINDOOR LIVING: Smart TVs w/ cable, Amazon Alexa, board games, breakfast bar w/ seatingbrOUTDOOR LIVING: Bicycles w/ helmets, beach chairs, beach towels & blanket, beach cart, cooler, outdoor gamesbrBABY SUPPLIES: High chair, bath seat, swing, sound machinesbrKITCHEN: Cooking basics, cooking spices, dishware/flatware, dishwasher, refrigerator, stove, microwave, cooler, coffee maker, K-cups, tea, blender, Instant Pot, air fryer, toaster, ice maker, garbage disposalbrGENERAL: Free WiFi (500 Mbps), keyless entry, central heating & air conditioning, ceiling fans, complimentary toiletries, linens/towels, washer/dryer, laundry detergent, clothes steamer, iron/board, hangers, hair dryer, hair straightener, sharps container, trash bags/paper towelsbrSUITABILITY: Stairs required for access, 2-story townhomebrPARKING: Street parking (first-come, first-served)brbr-- THE LOCATION --brbrOUTDOOR ADVENTURE: Kiwanis Park (0.7 miles), Bookworm Gardens (2.7 miles), Maywood (3.3 miles), Kohler-Andrae State Park (6.7 miles), Whistling Straits Golf Course (6.9 miles)brON THE WATER: River access (on-site), Deland Park (1.4 miles), Harbor Centre Marina (1.5 miles), Blue Harbor Resort & Water Park (1.5 miles), South Shore Beach (1.8 miles)brNEARBY FUN: Above & Beyond Children's Museum (0.9 miles), John Michael Kohler Arts Center (1.0 miles), Kohler Design Center (4.4 miles), Odyssey Fun Center (5.8 miles), Elkhart Lake's Road America (16.9 miles) brAIRPORT: General Mitchell International Airport (65.9 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- No pets allowedbr- 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 access

Riverfront Sheboygan Townhome w/ Grill!

Sheboygan, Wisconsin, United States

Bed

1

Bath

8

Sleeps

$166.94

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-bedroom condo in tranquil Sheboygan with AC comfort

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$314.4

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

Breezy Beach - Villa 75 Steps from Lake Michigan

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$305.73

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

Apartment

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

Sheboygan, Wisconsin, United States