Search for vacation rentals in Sheboygan.

Whether it's vacation home rentals, apartments, condos, or cabins/cottages, we have you covered -- search for rental properties in the entire Sheboygan area to find the perfect spot for your vacay.

5631 Driftwood Ln
	5631 Driftwood Ln Sheboygan, WI $5,200 Vacation Rentals, Unknown Monthly rentals October through May. Looking for a serene winter-time retreat with walks on the beach? To work from home or be a digital nomad with Lake Michigan views? For the perfect short- or......

1118 Saint Clair Ave
	1118 Saint Clair Ave Sheboygan, WI $1,075 Vacation Rentals, Unknown *This property is currently on our waitlist. If you submit your information to schedule a showing, you will be notified when this unit has been removed from the waitlist and can schedule a viewing.......

1306 N 28th St
	1306 N 28th St Sheboygan, WI $1,800 Vacation Rentals, Unknown This single-family ranch style home will be available for rent soon. This home comes with stove, fridge, dishwasher, central air, rec room, large yard, and attached garage. The tenants will take......

3311 Main Ave #101
	3311 Main Ave #101 Sheboygan, WI $825 Vacation Rentals, Unknown This lower 2-bedroom apartment will be available for rent soon. This apartment comes with stove, fridge, off-street parking, a storage unit with laundry hook-ups in it. The tenants will take care......

3811 S 17th Pl
	3811 S 17th Pl Sheboygan, WI $1,700 Vacation Rentals, Unknown This great single-family home will be available for rent soon. This home comes with stove, fridge, dishwasher, microwave, laundry hook-ups, central air, garage, and a partially finished basement.......

1119 High Ave
	1119 High Ave Sheboygan, WI $1,150 Vacation Rentals, Unknown 3 bedroom, 1 bath single family home on Sheboygan's south side. Situated in a great neighborhood, this property includes off-street parking, large yard, stove, fridge, basement with washer/dryer......

1635 Alabama Ave
	1635 Alabama Ave Sheboygan, WI $1,449 Vacation Rentals, Unknown Structure Type: Single Family Home Number of Bedrooms: 2 Number of Bathrooms: 1 Utilities included with rent: None. Utilities paid by tenant: All Utilities Electric, Gas & Water. Lawn care and Snow......

914 N 4th St
	914 N 4th St Sheboygan, WI $1,600 Vacation Rentals, Unknown Light, sunny upper unit. Fully furnished, two bedrooms with big closets. Living and dining area. Freshly painted with hard wood floors. New windows. Updated bathroom. Small second story deck with......

2407 N 10th St
	2407 N 10th St Sheboygan, WI $1,700 Vacation Rentals, Unknown Beautifully updated 3-bedroom/2bath house for rent. This home comes with stove, refrigerator, dishwasher, central air, 1+ car garage, and basement space. The tenant pays for all utilities and takes......

2714 S 11th Pl
	2714 S 11th Pl Sheboygan, WI $1,400 Vacation Rentals, Unknown This great 3-bedroom single family home is now available for rent. This home comes with stove, fridge, dishwasher, microwave, and a garage. The tenants will take care of all utilities, lawn care......

913 N 5th St
	913 N 5th St Sheboygan, WI $900 Vacation Rentals, Unknown Wonderful northside Sheboygan lower unit available on April 1. This home was freshly painted, has new flooring and the duct work was cleaned in December 2023. Oven/Range, Refrigerator, Washer and......

1537 Martin Ave
	1537 Martin Ave Sheboygan, WI $1,650 Vacation Rentals, Unknown This great single-family home has recently been updated and comes with off-street parking, main floor laundry hook-ups, central air, stove, fridge, dishwasher, and a great yard! Tenant is......

2115 Milz Ct
	2115 Milz Ct Sheboygan, WI $1,450 Vacation Rentals, Unknown Single family house 4BR/1BA. This home comes with stove, refrigerator, central air, 1 car detached garage, laundry hookups, and partially fenced backyard/ Tenant pays all utilities Tenant does snow......

1011 Clara Ave
	1011 Clara Ave Sheboygan, WI $949 Vacation Rentals, Unknown *This property is currently on our waitlist. If you submit your information to schedule a showing, you will be notified when this unit has been removed from the waitlist and can schedule a viewing.......

319 Niagara Ave #2
	319 Niagara Ave #2 Sheboygan, WI $850 Vacation Rentals, Unknown Due to high demand, we will not respond to generic tour requests/inquiries/applications sent through a 3rd party syndication such as Zillow or Apartments.com. *Applicants MUST meet the following......

N6209 N 61st St
	N6209 N 61st St Sheboygan, WI $2,900 Vacation Rentals, Unknown This stunning brick ranch home is up for rent and move-in ready. Located on almost 1 acre, it offers a two-car garage, a large living room in addition to a spacious family room featuring a natural......

1514 N 16th St
	1514 N 16th St Sheboygan, WI $1,500 Vacation Rentals, Unknown 3 Bedroom 1 Bath brand new lower unit in craftsman duplex. New windows, flooring, kitchen and baths, etc. Separate basement areas with laundry hookups and storage in basement. Tenant will be......

1238 Main Ave
	1238 Main Ave Sheboygan, WI $1,700 Vacation Rentals, Unknown ** Please read the entire ad, including "Lease Requirements" and "How to Schedule a Tour". Inquiries that don't contain the requested information may be ignored ** ** Some of these are older pics......

1726 N 9th St #1726
	1726 N 9th St #1726 Sheboygan, WI $1,250 Vacation Rentals, Unknown Structure Type: Duplex. Level: Lower Number of Bedrooms: 3 Number of Bathrooms: 1 Utilities included with rent: None Utilities paid by tenant: Electric and Heat. 50% of Water charged to Tenant Lawn......

1522 N 15th St
	1522 N 15th St Sheboygan, WI $1,580 Vacation Rentals, Unknown *We will not respond to generic tour requests/inquiries/applications sent through a 3rd party syndication such as Zillow or Apartments.com.**You must communicate to property mgr. that you meet all......

1414 N 17th St
	1414 N 17th St Sheboygan, WI $1,650 Vacation Rentals, Unknown Large and Spacious, 3+ bedroom, 1.5 bath single family house available for rent. The tenant pays for all utilities, handles lawncare and snow removal. Stove and refrigerator included. Pets welcome......

1313 N 15th St
	1313 N 15th St Sheboygan, WI $1,600 Vacation Rentals, Unknown Sharp! Spacious 3 bedroom, 1.5 bath single family home available for rent. The tenant pays for all utilities and handles lawn care and snow removal, Stove and refrigerator included. Main floor......

1621 Mehrtens Ave
	1621 Mehrtens Ave Sheboygan, WI $1,700 Vacation Rentals, Unknown Large, spacious 3 bedroom, 1 bath single family house available for rent. Tenants pay for all utilities, handle lawn care and snow removal. Great yard space, off street parking, 1 car garage. Pets......

1814 Cambridge Ave
	1814 Cambridge Ave Sheboygan, WI $1,700 Vacation Rentals, Unknown Sharp, 3 bedrooms, 1 bath single family home available for rent. The tenant pays for all utilities, handles lawn care and snow removal. Central air, Stove and refrigerator included. Laundry hook......

1435 Huron Avenue 1329 A N #15
	1435 Huron Avenue 1329 A N #15 Sheboygan, WI $850 Vacation Rentals, Unknown Structure Type: Duplex Level: Lower Number of Bedrooms: 2 Number of Bathrooms: 1 Utilities included with rent: None. Utilities paid by tenant: All Utilities - Electric, Heat, Water and Gas. Lawn......

409 Erie Ave
	409 Erie Ave Sheboygan, WI $1,700 Vacation Rentals, Unknown Nice 3 bedroom flat, lower unit, big backyard by Lake Michigan. Great place! Sit on the front porch and hear the waves! Walk one block east and you are on the beach and walking or biking path.......

915A Georgia Ave
	915A Georgia Ave Sheboygan, WI $1,250 Vacation Rentals, Unknown OPEN HOUSE SUNDAY 1/14 @ 10:00am-11:30 Welcome to this newly updated Sheboygan upper unit READY TO RENT. Located just a few blocks from the heart of downtown Sheboygan and Lake Michigan. Outside......

831 N 28th St
	831 N 28th St Sheboygan, WI $1,900 Vacation Rentals, Unknown This stunning single-family home is up for rent. Boasting 4 bedrooms and 1 bathroom, it is perfect for families. The 1490 sqft property features modern amenities and is move-in ready. With a 1-year......

N 28th St
	N 28th St Sheboygan, WI $1,800 Vacation Rentals, Unknown This stunning single-family home is up for rent. Boasting 4 bedrooms and 1 bathroom, it is perfect for families. The 1490 sqft property features modern amenities and is move-in ready. With a 1-year......

1850 N 25th St
	1850 N 25th St Sheboygan, WI $1,600 Vacation Rentals, Unknown 2 bedroom, 1.5 bathroom. Attached garage. New flooring throughout and fresh paint. Updated first floor bathroom. Finished rec room with bar....

Elm Ave
	Elm Ave Sheboygan, WI $1,775 Vacation Rentals, Unknown 2 Bedroom 1 Bath home available for short term rental. FURNISHED: House has 2 queen sized beds. The bathroom has a full sized bathtub and shower. Custom built in storage in the bathroom. Laundry......

2529 Wedemeyer St
	2529 Wedemeyer St Sheboygan, WI $1,800 Vacation Rentals, Unknown Freshly painted house. Newer roof, central air, water heater, furnace. New floor in dining room and new carpet in bedroom #2. Major appliances included. Finished basement....

1129 S 12th St
	1129 S 12th St Sheboygan, WI $900 Vacation Rentals, Unknown This great 2-bedroom lower is available to rent on the south side of Sheboygan. This apartment comes with stove, fridge, dishwasher, laundry hook-ups in the basement, off-street parking for one......

515 Bluff Ave
	515 Bluff Ave Sheboygan, WI $3,000 Vacation Rentals, Unknown Bring the whole family to this great place with lots of room for fun. Welcome to a spacious haven perfect for your entire family. This inviting retreat offers plenty of room for everyone to enjoy......

617 N Franklin St
	617 N Franklin St Sheboygan, WI $875 Vacation Rentals, Unknown Check out this great 1-bedroom lower apartment! This apartment comes with stove, fridge, laundry hookups, off-street parking, with gas and water included. Pets considered with extra fee, no......

1012 Lincoln Ave #1012
	1012 Lincoln Ave #1012 Sheboygan, WI $650 Vacation Rentals, Unknown This lower store front is a unique find in the heart of Sheboygan, perfect for a small shop, office or even a recording studio! It features two offices, one with a fireplace, front store window......

1717A N 9th St
	1717A N 9th St Sheboygan, WI $845 Vacation Rentals, Unknown Check out this great freshly updated upper 1-bedroom/1 bath apartment available for rent now for $845/month. This apartment comes with a stove, fridge, laundry hookups, large yard, and heat/water......

2032 N 4th St
	2032 N 4th St Sheboygan, WI $1,500 Vacation Rentals, Unknown This well cared for home on Sheboygan's northside sits just 2 blocks from Lake Michigan, 1 block from Vollrath Bowl and 1 mile from the South Pier/ river walk. It has 2 bedrooms 1.5 baths, 4......

Alabama Ave
	Alabama Ave Sheboygan, WI $1,400 Vacation Rentals, Unknown Ground floor unit in a beautiful two story brick house . Large open space rooms (1350 sq.ft.), Covered porch, 4 mins drive to Lake Michigan and downtown harbor area. Hook-up available for washer......

2127 S 9th St
	2127 S 9th St Sheboygan, WI $1,800 Vacation Rentals, Unknown This beautifully updated southside charmer is located just blocks from the south side beach and Lake Michigan! You'll love the welcoming front porch, spacious living/dining room, with "built ins"......