Family-friendly vacation rentals in Sheboygan County

Modern Upstairs Apt - Steps from Lake Michigan

Have you ever wondered what Lake Life is like? Here is your chance! This is 1 of 2 AirBnB units in this cute duplex Come stay in this beautiful upper apartment located just one block from Lake Michigan. Take a quick walk to the lake in the morning to jump on your fishing boat or take the family to the beach in the afternoon! Located close to shopping and many local bars and restaurants within walking distance. You'll find relaxation and a great time here at the heart of Sheboygan's Shoreline!

Indoor spaces · Family · Beach

The Garden | Sheboygan 2 Br/1Ba, Pet Friendly

Welcome to the Garden, a floral retreat in the heart of Sheboygan. Located just 3 blocks from Lake Michigan and a stones throw to down town Sheboygan, The Garden is the perfect place to center your visit to Eastern Wisconsin. The Garden is a pet friendly apartment on the second floor of a duplex with 2 bedrooms, 1 bathroom, a well stocked kitchen, a cozy living room, fast wifi and convenient amenities. Easy check out with no to-do lists. Just pack and go! *new cleaning staff hired Jan’23*

Kitchen · Family · Condition

Beach House

This guesthouse is detached from the main house, comes with garage parking and has all the amenities you need including a wood-burning fire place! Towels, bath tissue, soaps & travel items. AC Window Unit. Kitchen includes pots/pans, dishes, mugs/glasses, coffee pot, toaster & microwave. Paper goods. New appliances/new water heater in 2020. Stairs to the apartment are on the northeast corner of the garage. The beach is steps away with a fire pit, boat house lounge, kayaks, beach toys & bicycles.

Family · Indoor spaces · Hiking

House Near the Lake

Get out and enjoy nature, then return to a quiet mix of modern and retro in this family home only a block away from Lake Michigan. There are three parks and two beaches within a mile, as well as Terry Andrae State Park about 10 minutes away. If the outdoors aren't your thing, downtown Sheboygan hosts the Kohler Art Center, The Weil Center, Blue Harbor, and the Children's Museum, with Road America only 30 minutes away. Located between Milwaukee and Green Bay, this home has all the conveniences.

Indoor spaces · Kitchen · Location

Couple's or Family fun- With outdoor Hot Tub!

Enjoy a Day or week for couples or families at this Beautifully updated beach house just one block from the Lake. Enjoy the backyard with pergola & 2-6 person Hot Tub ALL WINTER! Watch the sunrise & sunset from the second floor master balcony. Walk to the lake & beech just across the street. Close to downtown and parks. This three bedroom home will impress. Tastefully decorated seasonally. Large bathroom w/deep soaking tub. For treasure hunters, a Metal detector for family fun at the beach.

Kitchen · Family · Nearby

Woodland Creek Retreat: explore & relax!

Lovely home nestled in 9 acres of peaceful woodland. 1.5 miles off I-43. Enjoy a walk in the woods or enjoy the dunes and wonderful views of Lake Michigan from Terry Andrae State Park only .2 miles away! Enjoy relaxing on the front porch or taking in the view of the woods from the spacious back deck. Be on the lookout for turkeys,deer and giant woodpeckers. Great wood burning fireplace and epic game collection(500+) for staying in! We love the cozy and open cabin feel and hope you will too!

Family · Kitchen · Quiet

Lake Michigan Beach Home by Frank Lloyd Wright pro

Beautiful view and sand beach on Lake Michigan, completely private, surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room, and living room entertainment space, den with a see-through log-fired fireplace, screened-in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and a row boat are available for the boating enthusiast, with life jackets and other floating devices.

Family · Kitchen · Getting around

LUXE Manor With Modern, Elegant Vibes - 4,500 Sq

Modern chic blends with classic sophistication in this late 1800s Historic Manor, The Herman Hayssen House. Enjoy 4,500 sq ft of elegance and character that adorns this well-appointed home. Complete with 4 bedrooms, 3 full baths, and 1 half bath, many different areas for entertaining, both inside and out. The neighborhood is of the most elite in Sheboygan, situated between the lakefront and downtown and is a short drive to Whistling Straights and within an hour of Milwaukee and Green Bay.

Kitchen · Family · View

Spacious/stylish, 2br loft

Beautiful, spacious loft in active downtown. Laundry, kitchen, 1.5 baths, 2 Qu, 2 Tw beds. Bakery & fitness studio on 1st floor (some a.m. noise). Stocked w/home essentials. Smart TVs, free WIFI. Pay-as-you-go parking in rear but free nights/weekends. Wonderful walkable neighborhood near shops, restaurants, art & children’s museum, river walk & lake front near-by. Short drive to Kohler, Whistling Straits golf course, Shops at Woodlake & Kohler Design Center. Marcus cinema near by.

Kitchen · Family · Parks

Logan's Guest Nest

Logan's Guest Nest is located in a nice small town feel area. With a small look on the outside your Nest has a big feel on the inside. Spacious rooms and quiet area to rest after a day at the many beaches lining Lake Michigan. Or coming back from the races at Road America. Not to mention a day of golf at the many area courses, Whistling Straits maybe. All these wonderful outings are just minutes from the Nest. Plenty of local dinning or delivery for a nice ending of the day.

Kitchen · Family · Value

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

Kitchen · Family · Check-in

Beachside Lake View - 2br - First Floor - Garage

Located just one lot in from the beautiful shores or Lake Michigan. Amazing location provides year round stunning views . This is a lower 2 bedroom 1 bath condo in a 4unit building were all the units have the same basic layout. You can listen to the waves or walk just a few feet and have the sand on your feet. This condo features 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.

Kitchen · Indoor spaces · Backyard