Estia Villas - Vacation Rentals in Sheboygan
Villa
10.0
(
102 Reviews
)
4 Bedrooms
3 Bathrooms
12 Guests
-
Oceanfront -
Hot Tub -
Parking -
Ocean View
US $450
/Night
7 Nights - $3,150
Villa
10.0
(
4 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
925.7 ft²
-
Private Beach -
Parking
-
Ocean View
-
Balcony/Terrace
US $156
/Night
7 Nights - $1,090
Villa
10.0
(
15 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen -
Air Conditioner
US $194
/Night
7 Nights - $1,355
Villa
10.0
(
4 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
850 ft²
-
Parking
-
Pool -
Ocean View
-
Balcony/Terrace
US $790
/Night
7 Nights - $5,529
Villa
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
425 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $463
/Night
7 Nights - $3,238
Villa
10.0
(
1 Review
)
4 Bedrooms
4 Bathrooms
13 Guests
5328 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $549
/Night
7 Nights - $3,844
New
Villa
10.0
(
1 Review
)
1 Bedroom
3 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $474
/Night
7 Nights - $3,315
Villa
9.8
(
33 Reviews
)
2 Bedrooms
2 Bathrooms
8 Guests
1226 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $302
/Night
7 Nights - $2,113
See More Sheboygan Vacation Rentals
Luxury Places to Stay in Sheboygan
Over 862+
Luxury Places to Stay in or Near Sheboygan
House
6 Bedrooms
6 Bathrooms
12 Guests
-
Private Pool -
Hot Tub
-
Parking
-
Pool
US $4,761
/Night
7 Nights - $33,325
House
10.0
(
2 Reviews
)
5 Bedrooms
3 Bathrooms
11 Guests
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
US $3,047
/Night
7 Nights - $21,326
House
6 Bedrooms
3 Bathrooms
10 Guests
2400 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $2,117
/Night
7 Nights - $14,821
House
9.8
(
85 Reviews
)
10 Bedrooms
7 Bathrooms
24 Guests
10700 ft²
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,980
/Night
7 Nights - $13,862
House
10.0
(
8 Reviews
)
5 Bedrooms
3 Bathrooms
15 Guests
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $1,977
/Night
7 Nights - $13,840
House
10.0
(
9 Reviews
)
7 Bedrooms
5 Bathrooms
16 Guests
10495 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,753
/Night
7 Nights - $12,274
Cottage
1 Bedroom
1 Bathroom
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $1,748
/Night
7 Nights - $12,235
House
9.8
(
41 Reviews
)
4 Bedrooms
3 Bathrooms
9 Guests
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,737
/Night
7 Nights - $12,156
See More Sheboygan Luxury Vacation Rentals
Find More Sheboygan Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Sheboygan
Over 97+
Top-Rated Vacation Rentals with a Pool in or Near Sheboygan
Cabin
10.0
(
47 Reviews
)
3 Bedrooms
4 Bathrooms
34 Guests
3500 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $1,209
/Night
7 Nights - $8,460
House
10.0
(
41 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $859
/Night
7 Nights - $6,014
House
10.0
(
12 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $1,101
/Night
7 Nights - $7,704
House
10.0
(
12 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $327
/Night
7 Nights - $2,287
House
10.0
(
9 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
4000 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,686
/Night
7 Nights - $11,801
Hotel
10.0
(
7 Reviews
)
-
Private Pool
-
Pool
-
Child Friendly -
Wheelchair Accessible
US $131
/Night
7 Nights - $914
House
10.0
(
6 Reviews
)
5 Bedrooms
2 Bathrooms
14 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $1,184
/Night
7 Nights - $8,286
House
10.0
(
2 Reviews
)
5 Bedrooms
4 Bathrooms
13 Guests
3003.13 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,269
/Night
7 Nights - $8,883
Pet-Friendly Vacation Rentals in Sheboygan
Over 205+
Pet-Friendly Vacation Rentals in or Near Sheboygan
House
10.0
(
88 Reviews
)
4 Bedrooms
3 Bathrooms
12 Guests
2800 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $864
/Night
7 Nights - $6,046
Apartment
10 Bedrooms
12 Bathrooms
34 Guests
-
Private Pool
-
Hot Tub
-
Pool
-
Pet Friendly
US $64
/Night
7 Nights - $448
Apartment
1 Bedroom
1 Bathroom
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $1,126
/Night
7 Nights - $7,883
Cottage
10.0
(
52 Reviews
)
3 Bedrooms
1 Bathroom
7 Guests
740 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $328
/Night
7 Nights - $2,297
House
10.0
(
51 Reviews
)
5 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $363
/Night
7 Nights - $2,542
House
10.0
(
42 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $438
/Night
7 Nights - $3,063
House
10.0
(
31 Reviews
)
3 Bedrooms
1 Bathroom
5 Guests
1370 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $276
/Night
7 Nights - $1,935
Apartment
10.0
(
29 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $373
/Night
7 Nights - $2,613
See More Pet-Friendly Vacation Rentals in Sheboygan on PetFriendly.io
Large Vacation Homes & Villas in Sheboygan
Over 209+
Large Vacation Homes & Villas in or Near Sheboygan
House
9.8
(
72 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
2600 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $556
/Night
7 Nights - $3,890
House
10.0
(
3 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
3003.13 ft²
-
Parking
-
Spa -
Balcony/Terrace
-
Internet
US $567
/Night
7 Nights - $3,971
House
10.0
(
85 Reviews
)
4 Bedrooms
2 Bathrooms
12 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $486
/Night
7 Nights - $3,402
House
10.0
(
62 Reviews
)
3 Bedrooms
3 Bathrooms
11 Guests
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $482
/Night
7 Nights - $3,375
House
10.0
(
34 Reviews
)
6 Bedrooms
2 Bathrooms
11 Guests
2000 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $479
/Night
7 Nights - $3,353
House
10.0
(
32 Reviews
)
5 Bedrooms
3 Bathrooms
14 Guests
-
Parking
-
Spa
-
Balcony/Terrace
-
Kitchen
US $678
/Night
7 Nights - $4,743
House
10.0
(
30 Reviews
)
4 Bedrooms
4 Bathrooms
12 Guests
2800 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $842
/Night
7 Nights - $5,897
House
10.0
(
26 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
3900 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,108
/Night
7 Nights - $7,757
See More Family Vacation Rentals in Sheboygan on FVR
Wheelchair Accessible Vacation Homes in Sheboygan
Over 50+
Wheelchair Accessible Vacation Homes in or Near Sheboygan
Condo
10.0
(
122 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1800 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
US $344
/Night
7 Nights - $2,407
Bed & Breakfast
9.2
(
37 Reviews
)
8 Bedrooms
7 Bathrooms
29 Guests
826.67 ft²
-
Oceanfront
-
Breakfast -
Parking
-
Ocean View
US $203
/Night
7 Nights - $1,418
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $396
/Night
7 Nights - $2,773
Condo
10.0
(
80 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1400 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $367
/Night
7 Nights - $2,571
New
Condo
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
6 Guests
1700 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $368
/Night
7 Nights - $2,573
Condo
9.4
(
43 Reviews
)
2 Bedrooms
2 Bathrooms
7 Guests
1400 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $499
/Night
7 Nights - $3,496
Condo
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
12 Guests
1756 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
US $355
/Night
7 Nights - $2,487
Condo
10.0
(
60 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1480 ft²
-
Oceanfront
-
Ocean View
-
Balcony/Terrace
-
View
US $150
/Night
7 Nights - $1,050
Sheboygan Vacation Rentals and Airbnb Places to Stay Under $200
Over 226+
Sheboygan Vacation Rentals and Airbnb Places to Stay Under $200
House
10.0
(
46 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $192
/Night
7 Nights - $1,344
Apartment
1 Bedroom
1 Bathroom
2 Guests
699.65 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $69
/Night
7 Nights - $483
RV Rental
7.8
(
37 Reviews
)
1 Bedroom
1 Bathroom
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $149
/Night
7 Nights - $1,043
House
10.0
(
38 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
1000 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $187
/Night
7 Nights - $1,307
Apartment
10.0
(
30 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
900 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $142
/Night
7 Nights - $997
House
10.0
(
26 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
860 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $191
/Night
7 Nights - $1,339
House
10.0
(
24 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
1200 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $162
/Night
7 Nights - $1,136
Condo
10.0
(
13 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $145
/Night
7 Nights - $1,013
See More Sheboygan Vacation Rental Deals
Instantly Bookable Vacation Homes in Sheboygan
Over 487+
Instantly Bookable Vacation Homes in or Near Sheboygan
House
9.8
(
169 Reviews
)
3 Bedrooms
1 Bathroom
7 Guests
1457 ft²
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $291
/Night
7 Nights - $2,038
House
9.6
(
11 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Air Conditioner
-
Internet
-
Laundry -
Bedding/Linens
US $131
/Night
7 Nights - $914
House
10.0
(
28 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $482
/Night
7 Nights - $3,375
Apartment
7.0
(
7 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
1200 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $302
/Night
7 Nights - $2,111
House
10.0
(
50 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
2000 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $556
/Night
7 Nights - $3,892
House
10.0
(
76 Reviews
)
4 Bedrooms
2 Bathrooms
9 Guests
1900 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $519
/Night
7 Nights - $3,631
Cottage
10.0
(
76 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
600 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $323
/Night
7 Nights - $2,264
House
10.0
(
66 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $275
/Night
7 Nights - $1,928
About Sheboygan Vacation Rentals
With more than 35 Sheboygan vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Sheboygan.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Sheboygan, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Sheboygan. Places to stay near Sheboygan are 950.34 ft² on average, with prices averaging US $541 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Sheboygan with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Use these Quick Filters to Find a Vacation Rental in Sheboygan
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Sheboygan.
Weather in Sheboygan
View the weather forecast for Sheboygan before booking your Sheboygan Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Sheboygan, WI
Estiavillas offers a large selection of top attractions around Sheboygan. Research things to do on your vacation before you visit Sheboygan.
Whistling Straits Golf Course
Blue Harbor Resort & Conference Center Water Park
Road America
Kettle Moraine State Forest
Wisconsin Maritime Museum
Kohler Design Center
Lincoln Park Zoo
Blackwolf Run
Skip Barber Driving School
Kohler-Andrae State Park
John Michael Kohler Arts Center
University of Wisconsin-Sheboygan
Chilton Speedway
St. Peter Claver Parish
Children's Museum
Wade House Historic Site
The Bull at Pinehurst Farms Golf Course
Hamilton Wood Type and Printing Museum
Stefanie H. Weill Center for the Performing Arts
Harrington Beach State Park
Other Places to Stay Near Sheboygan, WI
Sheboygan County
384 Properties
Ellis Historical District
237 Properties
Downtown
136 Properties
Rhine
104 Properties
Elkhart Lake
104 Properties
Sheboygan Falls
94 Properties
Plymouth
73 Properties
Chilton
71 Properties
Two Rivers
51 Properties
Manitowoc
38 Properties
Calumet County
34 Properties
Campbellsport
32 Properties
Complexes around Sheboygan, WI
Plymouth Rock Camping Resort
4 Properties
Resort
4 Properties
Downtown
3 Properties
Quality Inn Manitowoc
3 Properties
Quality Inn Sheboygan
3 Properties
Americinn
2 Properties
Baymont
2 Properties
Lakefront Manitowoc Mi Arrow Park
2 Properties
The Shore Club Wisconsin
2 Properties
Harbor Town Inn
1 Properties
Holiday Inn Manitowoc
1 Properties
Sheboygan Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Sheboygan?
There are a lot of options in Sheboygan. If you plan on staying in the Sheboygan area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Sheboygan:
- Beach front luxury spacious villa !
- Luxury Villa on Lake Michigan!
- Country Cheese Factory - King Bed!
- Waterfront and Pool View Condo!
- Riverfront Retreat! Water front and dog friendly!
- First Floor Pet Friendly Queen Suite with Single Pull-out
- Spacious Family Villa w/Decks in Chilton!
- Winner`s Circle | Luxury Stay Near Road America
- Lovely Lake Lookout - Cozy Condo Steps from Lake
- Country Guest House
How many vacation rentals have private pools in Sheboygan?
There are 29 vacation rentals with private pools near Sheboygan. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Sheboygan are best for families?
If you are looking for a family-friendly vacation home in Sheboygan, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Sheboygan:
How many vacation rentals are available in Sheboygan?
Currently, the total number of properties listed in 2026 is over 35 in the Sheboygan area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Sheboygan.
