Last Updated February 20, 2021 2/20/2021

26 Coolest Vrbo Rentals Wisconsin Has to Offer

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The northern Midwest state of Wisconsin has a little something for everyone – forests, lakes, delicious food, and plenty of family-friendly fun. As you travel across this beautiful state, you can learn a lot about local communities by staying in Vrbo properties in unique neighborhoods and wilderness areas. From rugged log cabins to luxurious vacation homes and even tiny houses for a dose of simplicity, here are the coolest Vrbo rentals Wisconsin has to offer.

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Retreat with Swimming & Fishing Near Wisconsin Dells – Mauston Dock at Spacious Retreat with Private Swimming and Fishing Pond
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Dock at Spacious Retreat with Private Swimming and Fishing Pond

Retreat with Swimming & Fishing Near Wisconsin Dells – Mauston

There are lots of great vacation rental properties around the Wisconsin Dells to help you check out the local attractions and spend time in nature. Here’s a highly rated Vrbo property for big groups that sleeps up to 16 people. It has four bedrooms, a loft, and three baths. You’ll be in the Glacier Point development on Castle Rock Lake and 20 minutes north of the Dells. This is a quiet getaway spot in the woods that has a deck, private pond, and three spacious acres to spend time on. You can catch and release fish in the pond, play volleyball and horseshoe in the yard, and feel right at home with your family because of all the kid-friendly amenities provided. Just a few miles away, you’ll find jet ski and pontoon boat rentals for some fun on the lake.

Lakefront Home, Minutes From Sister Bay – Rowleys Bay Lakefront Home, Minutes From Sister Bay
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Lakefront Home, Minutes From Sister Bay

Lakefront Home, Minutes From Sister Bay – Rowleys Bay

You’ll be just five minutes from Sister Bay when you stay at this home overlooking Lake Michigan. It sleeps up to 12 people and has four bedrooms and three baths. It also offers a washer and dryer, an updated kitchen, three decks with lake views, and Wi-Fi. It’s ideal for a family vacation home and has games, books, and movies to enjoy. Fun things to do here include kayaking, cross-country skiing, sand volleyball, and boating.

Eaglesnest-Log Home on Lake Chippewa – Hunter Exterior of Eaglesnest-Log home on Lake Chippewa
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Exterior of Eaglesnest-Log home on Lake Chippewa

Eaglesnest-Log Home on Lake Chippewa – Hunter

Enjoy 17,000-acre Lake Chippewa in this dog-friendly house that even has an invisible fence to keep pups protected. The hosts have a pontoon boat available for rent too. It has level frontage with no stairs to the lake and everything you’d want in a Northwoods home. The home is just 75 feet from the water’s edge. It has three bedrooms and two bathrooms to accommodate your family of up to six people. Fine dining and a casino are located nearby, and you can snowmobile right from out the back door.

Family-Friendly Log Cabin with Swimming Pond – Sparta Water View at Secluded Family-Friendly Log Cabin
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Water View at Secluded Family-Friendly Log Cabin

Family-Friendly Log Cabin with Swimming Pond – Sparta

Families also love this charming log cabin that’s 20 minutes from Black River Falls and Sparta, Wisconsin. It’s across the road from the county forest and situated on 40 acres. The home has two bedrooms, one bathroom, and sleeps up to seven people. Wi-Fi is not available because of the location, but there is a sandy beach and swimming pond to enjoy here. Rent a boat about 12 miles away from here at Fort McCoy, and also spend your days hiking, biking, fishing, golfing, and exploring the ATV trails when you book your stay.

Lake House, Steps from Lake Geneva – Fontana-on-Geneva Lake Exterior of Lake House Retreat Steps From Lake Geneva _ Abbey Springs Resort
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Exterior of Lake House Retreat Steps From Lake Geneva _ Abbey Springs Resort

Lake House, Steps from Lake Geneva – Fontana-on-Geneva Lake

For a pet-friendly lake house that sleeps up to 12 people, consider this 3,000-square-foot option that’s 1.5 miles from downtown Fontana and 8.5 miles from downtown Lake Geneva. It has four bedrooms, three baths, a den, and a location on the 18th fairway of the golf course. There’s a large deck here and also shared community amenities, such as two pools, three restaurants, a fitness center, sports courts, and private beach access. All the amenities are included with your stay except the golf course.

House on 7.5 Acres – Caledonia House on 7.5 Acres
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House on 7.5 Acres

House on 7.5 Acres – Caledonia

This is a vacation home that’s perfect for large groups and can sleep up to around 20 people. It has three bedrooms and three bathrooms in 2,500 square feet of space. Children under 12 can stay here for no charge, and pets are allowed for an extra fee. It’s a fun spot for bachelor and bachelorette parties, weddings, family reunions, and corporate retreats. The home is on 7 ½ acres of land and allows campers in tents for extra space beyond the 16 people that the home can accommodate. Fun things to do in this part of Wisconsin include sledding, snowshoeing, boating, and paddleboarding. There’s an in-ground pool that’s open between May and October and a hot tub at the home as well.

Historic Log Cabin by the Bay – Gills Rock Exterior of Historic Log Cabin by the Bay
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Exterior of Historic Log Cabin by the Bay

Historic Log Cabin by the Bay – Gills Rock

You’ll enjoy this pet-friendly and historic cabin at the tip of the Door County peninsula in Gills Rock because of the picturesque bluffs, bay, and woods here. It is a charming Vrbo rental that sleeps up to six people and has one bedroom, a loft, a full bath, and a large kitchen. Guests also use the private waterfront patio and have lake access a minute’s walk away and across the street. Between November and early May, weekly and monthly off-season rates may be available. It’s a lovely place to enjoy the changing colors in the fall season too.

Lakeshore Home with Pier – Lake Geneva Lakeshore Home with Pier
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Lakeshore Home with Pier

Lakeshore Home with Pier – Lake Geneva

Here’s a nice Vrbo option for four to 10 people in a home with four bedrooms and five bathrooms. It’s less than seven miles from downtown Lake Geneva and an ideal place to boat, fish, and relax. The home has lovely views of the lake and is about 3,500 square feet in size. Pets are allowed here for a fee of $20 per pet, per night.

Luxury Home with Pool & BBQ – Burke, Sun Prairie, Madison Bedroom at Luxurious Destination Home
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Bedroom at Luxurious Destination Home

Luxury Home with Pool & BBQ – Burke, Sun Prairie, Madison

Here’s a vacation home that has three bedrooms and 2.5 baths when you want to explore Madison. The home is 15 minutes from Capital Square and 2,000+ square feet in size. It can sleep 10 people and has a fully stocked kitchen, large living room, dining room with natural light, and newly renovated master bedroom. There’s a washer and dryer for guests to use as well.

Tiny Home with Shared In-Ground Pool & Hot Tub – Bay City Outside View - One-of-a-Kind Tiny Home
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Outside View - One-of-a-Kind Tiny Home

Tiny Home with Shared In-Ground Pool & Hot Tub – Bay City

While many Vrbo rentals in Wisconsin are large homes, tiny homes like this one are popular too. This house sleeps four people and has a hot tub and pool. It’s an adorable tiny house that’s in a private place in the woods and offers a full kitchen and bath. The loft has a queen-size bed, there are fire pits for socializing, and the use of the kayak, canoe, and SUP is included with your rental. When you stay here, you’ll be 20 miles from Welch Village and seven miles from downtown Red Wing.

All-Seasons Home Away from Home – Wisconsin Dells All-Seasons Home Away from Home
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All-Seasons Home Away from Home

All-Seasons Home Away from Home – Wisconsin Dells

With this Vrbo rental, you’ll get a 3,400-square-foot house in the Wisconsin Dells that’s surrounded by all the local attractions. It has five bedrooms, five bathrooms, and can sleep up to 14 people. It’s a fun spot for families because there is a Pac-Man arcade game, darts, games, books, and puzzles here. There’s a shared pool that guests can have access to when staying here.

5-Star Sprawling Rock River Lakefront Home – Edgerton Interior of Five-Star Acre+ Sprawling Rock River Lakefront Home
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Interior of Five-Star Acre+ Sprawling Rock River Lakefront Home

5-Star Sprawling Rock River Lakefront Home – Edgerton

Groups up to 18 people can stay in this seven-bedroom, three-bathroom River Rock home that offers a rustic cabin experience. You can take a 15-minute boat ride to Rock River from here, which flows into the 10,500-acre Lake Koshkonong. Dogs are allowed here for a $100 fee. Stay here to get your own personal access to 220 feet of Wisconsin shoreline that looks out to the nature preserve.

House For Your Favorite Activities – Clinton House For Your Favorite Activities
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House For Your Favorite Activities

House For Your Favorite Activities – Clinton

Escape from your daily routine at this three-bedroom, two-bathroom house for six people. Dogs are welcome here too for $15 per dog, per night. Pontoon boat, kayak, canoe, and paddleboat rentals are available here to help you make the most of the lake location. The home is along Poskin Lake in Northwest Wisconsin and a great place for fishing and relaxing.

Peaceful Country Atmosphere – Cumberland Gather together with family & friends in peaceful country atmosphere - exterior view
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Gather together with family & friends in peaceful country atmosphere - exterior view

Peaceful Country Atmosphere – Cumberland

This budget-friendly Vrbo house rental sleeps eight people and has four bedrooms and two baths. It’s a farmhouse in a quiet dairy farming community that’s five miles from Cumberland and 10 miles from Rice Lake. You’ll have a spacious kitchen for preparing meals and comfy queen beds in the large bedrooms here. Snowshoeing and cross-country skiing in the woods here is nice in the winter, while boating, fishing, and swimming are popular summer activities. Within a few miles, you can also get to the St. Croix Casino in Turtle Lake and the tourist spots in Hayward.

Large Home with Lake Views – Markesan Large Home with Lake Views
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Large Home with Lake Views

Large Home with Lake Views – Markesan

When you book this Vrbo vacation home, you can also rent a 16-passenger Hummer limo or 28-passenger bus at a discounted rate for your group. The home sleeps up to 15 people and has five bedrooms and 2.5 baths. It’s 4,800 square feet in size and has a lovely wraparound deck for enjoying some time outdoors. It’s a family-friendly place with a high chair, outdoor games, and other child amenities. Other perks here are the pool table, large yard, and great kitchen with an island for cooking meals. Green Lake center is about eight miles away.

Family Home Near Castle Rock Lake & Wisconsin Dells – Mauston Family Home Near Castle Rock Lake & Wisconsin Dells
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Family Home Near Castle Rock Lake & Wisconsin Dells

Family Home Near Castle Rock Lake & Wisconsin Dells – Mauston

Located at the southern end of Castle Rock Lake and on seven wooded acres, this Wisconsin vacation home sleeps up to 18 people. It has four bedrooms, a convertible bed, and 3.5 baths in 3,000 square feet of space. You’ll be about 20 minutes from the Dells and three blocks from the lake when you stay here. Guests who book this Vrbo property enjoy the natural light through the large windows and kid-friendly amenities, such as a pack-and-play. The home has a full kitchen with appliances, knotty pine vaulted ceilings, and a great room with a wood-burning fireplace.

Perfect for Large Groups and Families – Madison Perfect for Large Groups and Families
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Perfect for Large Groups and Families

Perfect for Large Groups and Families – Madison

Another great house for large groups is this one that has five bedrooms and three baths for up to 16 people. It offers an in-ground pool, year-round hot tub, and large deck with lots of seating and a grill. Guests can use the 72-inch TV, three-car garage, full kitchen, and man cave when they stay here. Wi-Fi is available as well. When you’re here, you’ll be just five minutes from the University Ridge Golf Course and seven minutes from the Hawks Landing Golf Course.

Lakefront Home – Pelican Lake Exterior of Lakefront, quiet, spacious home for family reunions and special events
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Exterior of Lakefront, quiet, spacious home for family reunions and special events

Lakefront Home – Pelican Lake

Huge groups looking for a place to spend a reunion or celebrate a big group can use this 19-bedroom, 4.5-bathroom house that is 9,500 square feet in size. It can sleep up to 39 people and accommodate up to 60 people during the day. You’ll be along a 3,585-acre lake in a 1928 hotel that has been renovated for rentals and be able to use the entire building. The sunsets are lovely when you spend time at the 330 feet of lakefront and look out to Pelican Lake from here. The lake is a great place for boating, fishing, kayaking, and water skiing.

Exceptional Log Home Living Retreat – Eagle River Exterior of Exceptional Log Home Living Retreat
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Exterior of Exceptional Log Home Living Retreat

Exceptional Log Home Living Retreat – Eagle River

There’s nothing quite like renting a log home for your Wisconsin vacation. This log home sleeps up to 10 people and has five bedrooms and 3.5 baths on the Eagle River Chain of 28 lakes. It’s 5,500 square feet in size and offers a private pier for fishing. There are kayaks, a canoe, and a paddleboat available for you to use here, and boats and wave runners can be rented nearby. You’ll enjoy the recreation room and great room here, as well as the lawn games along the 187 feet of shoreline on the lawn.

Camper with Shared Pool & Hot Tub – Bay City Campsite for Camper Experience with shared in-ground pool & hot tub
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Campsite for Camper Experience with shared in-ground pool & hot tub

Camper with Shared Pool & Hot Tub – Bay City

There are also unique Vrbo rentals in Wisconsin, such as this camper that sleeps four people in Bay City. It has a seasonal pool and year-round hot tub that is shared with the rest of the property. You’ll be near Lake Pepin with simple lodging that includes a kitchen and full bath. It also offers Wi-Fi and the use of the kayak, canoe, and SUP. There are various animals that live on the property so approval is needed before you bring pets. This property is 20 miles from Welch Village.

Large Home with Privacy & Scenic Views – Hager City Seating at Larger Home with Privacy and Scenic Views
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Seating at Larger Home with Privacy and Scenic Views

Large Home with Privacy & Scenic Views – Hager City

This highly rated vacation home is massive and can sleep around 28 people if you have a large group. It has four bedrooms and 2.5 baths, and it’s just 45 miles southeast of the Twin Cities. You’ll be on 14 acres here and have lots of privacy along the river. The home spans 3,600 square feet in size and is an A-frame style house with lots of windows. It has a basement rec room with lots of fun games to play and an outdoor deck with water views. Guests also enjoy the swimming pool, ball courts, and being able to ski, canoe, hike, and bike nearby. There’s an infrared sauna available here as well with access on a case-by-case basis. Dogs are allowed for an additional fee.

4-Bedroom Home, Minutes to Skiing – Wausau 4-Bedroom Home, Minutes to Skiing
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4-Bedroom Home, Minutes to Skiing

4-Bedroom Home, Minutes to Skiing – Wausau

When you plan a Wisconsin ski trip, book this vacation rental home for up to 10 people. It has four bedrooms and two bathrooms, and it’s a family-friendly rental with baby amenities. You’ll be in the heart of Wausau in a historic neighborhood when you book this home on Vrbo. Long-term rentals are allowed here, and pets are welcome to stay and use the backyard with a fence.

Pirate Ship Adventure Cabin – Lyndon Station Pirate Ship Adventure Cabin
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Pirate Ship Adventure Cabin

Pirate Ship Adventure Cabin – Lyndon Station

How cool would it be to stay overnight in a pirate ship? You can do exactly that in Wisconsin when you book this Vrbo rental for up to six people. It’s a themed rental that’s fun for couples and families with kids. You’ll be 10 minutes from the Dells and close to Devil’s Lake here too. Therefore, it’s fun to book guided climbing and kayak tours when you stay here. There are two upper decks for relaxing outside but no Wi-Fi. The bathhouse is shared with other guests and about 150 yards away. The water is turned off in the winter, which means no showers between November and March. Pets are allowed here for a $40 fee for one pet or $55 for two pets.

Castle Rock Lake 3-Bedroom Penthouse Condo – Arkdale Aerial View of Beautiful Castle Rock Lake 3 Bedroom Penthouse Condo
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Aerial View of Beautiful Castle Rock Lake 3 Bedroom Penthouse Condo

Castle Rock Lake 3-Bedroom Penthouse Condo – Arkdale

This is a nice condo option that sleeps 10 people on scenic Castle Rock Lake. It’s north of the Dells and in the Northern Bay Resort in Arkdale. The year-round resort has a golf course, restaurant, tiki bar, pools, hot tub, playground for kids, and more amenities. Guests have three bedrooms and two baths here on the third-floor unit. Pets are not allowed in this condo.

Highly Rated Cottage with Perks – Fish Creek Interior Space at Prime Location & Highly Rated Cottage with 'Perks'
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Interior Space at Prime Location & Highly Rated Cottage with 'Perks'

Highly Rated Cottage with Perks – Fish Creek

Dogs are welcome to stay with you at this six-person cottage that has two bedrooms and two bathrooms. This Vrbo rental home is a popular option that’s comfortable and has an outdoor patio with Adirondack chairs, a fire, pit, hammock, and grill. The cottage is on main street and walkable from the Blue Horse Beach Café. There are other restaurants in town too and groceries from the Fish Creek Market. It’s fun to rent bikes, kayaks, and canoes to use nearby when you stay here. In the winter, you can go cross-country skiing at nearby Peninsula State Park. The fee for pets at this Door County destination is $75.

Beachfront Condo on Lake Delton – Wisconsin Dells View from Beachfront, Modern/Rustic Condo on Lake Delton
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View from Beachfront, Modern/Rustic Condo on Lake Delton

Beachfront Condo on Lake Delton – Wisconsin Dells

It’s also fun to stay in a condo when you’re in the Wisconsin Dells area, such as this 1,700-square-foot one with two bedrooms and two baths. It has a Northwoods vibe, is on the beach, and overlooks Lake Delton. There’s a private beach just 25 feet down the steps of the front door here. Up to six people can book this vacation rental and use the unlimited Noah’s Ark waterpark wristbands that are included with the stay. Amenities include access to indoor and outdoor pools, whirlpools, tennis courts, and a basketball court. There are lots of attractions within a few miles of the condo, such as golf courses, water parks, and mini-golf.

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