Pet-friendly holiday rentals in Milwaukee County

Bay View Upper Parkside Gem

This 1920's era bungalow is in the heart of one of Milwaukee's most popular neighborhoods- Bay View. The area boasts a plethora of walk-able entertainment, fine restaurants, bars and our beautiful Lake Michigan. This well loved and maintained space will be the perfect retreat for your family and friends when visiting Milwaukee. Easy access, via car or public transit, to all parts of the city is nearby. Mitchell International airport is minutes away. Enjoy our fun city like the locals do!

Historic Walker’s Point Home, Garage & Yard

Welcome to The Bentley Hotel, a luxury selection of townhouses decorated with everyone in mind. We aim to provide a quality experience and memories that will last a lifetime. This townhome is finished with top of the line amenities including a 60” smart TV, board games, organic coffee and teas, a full kitchen with Caraway non-stick pans, workout mats, dumbbells and more. This is your new home away from home and the perfect place to gather whether you are in town for business or pleasure!

Wonderful Family Home Across from Park

Extended Stays Welcome! Everything you could want in a home away from home. Our place is a comfortable and beautifully updated mid-century brick ranch on a quiet tree-lined street overlooking 36-acre Greene Park. Super convenient location, just 10 min from both the airport and downtown. Walkable to Lake Michigan and just down the road from Bay View's great restaurants and nightlife. Pet-friendly and perfect for families, small groups, or business travel. You'll feel right at home here!

Historic East Side Duplex, 3BD. No Cleaning Fee!

Minutes from downtown Milwaukee by car or bus, the whole group will enjoy easy access to the city from this central location less than a mile from the UWM campus. A block from the Urban Ecology Center and Oak Leaf Trail access and easy walking distance to North Avenue's restaurants, bars, and the Oriental Theater, there's no shortage of activities, entertainment, and dining options around this historic and charming East Side abode. Or stay in with our grill and fire pit.

King Bed/Near Downtown Milwaukee/Free Parking/WiFi

Have fun yourself, the whole family or with friends at this stylish, cozy and comfortable UPPER place with: *2 bedroom, (king, queen and twin size bed) * 1 bathroom, *Full size kitchen/dining table *Outstanding Dining room/coffee bar/home bar, with coffee shop or restaurant style *living room with smart 55” tv including free Netflix * home office *private balcony where you can enjoy a cup of coffee ☕️ , beer 🍻 or a delicious cocktail 🍹 * Free parking spot

The Cheese House

Large well appointed two bedroom, living room, dining room, kitchen, and private balcony. Apartment is located on the second floor right above the award winning West Allis Cheese & Sausage Shoppe. Each stay includes 4 breakfast sandwiches and house coffee vouchers for the cheese store cafe. The rental is centrally located minutes from Pettit National Ice Center, Milwaukee County Zoo, Wisconsin State Fair, and Brewers Stadium not to mention local restaurants.

Charming Bayview House, steps from MKE Merriment!

You will be in the heart of the Bayview neighborhood, centrally-located, three blocks from the vibrant restaurant and bar scene on historic Kinnickinnic Avenue. Enjoy a walk through Humboldt Park. Easily explore the eclectic, independent, and creative hub that makes Bayview so special. You are a 10-minute ride from the airport, and a 10-minute ride to the MKE Public market. Our cozy home and all-embracing neighborhood are waiting for you.

Stay at Sobelman's!

This Milwaukee escape is nestled above the classic burger and bloody mary restaurant, Sobelman's! In the heart of the Menomonee Valley, you are a quick 5-minute drive to the city's most visited spots; the Harley Davidson Museum, Brewers Stadium, the Third Ward, Public Market, and more. Start your day off with one of the Best Bloody Marys in town before venturing out to explore all that our city has to offer. We can't wait to host you!

The Peacock Place w/ Shared Seasonal Outdoor Pool

This 3 bedroom, 1 bath, open concept lower unit of a duplex is located in Brewer's Hill. This unit has tons of natural light, original hard wood floors, pocket doors and claw foot soaking tub. This pet friendly unit has off street parking for 2 vehicles or motorcycles, and a private yard with patio and BBQ grill for your use. Walking distance to Brady Street, downtown and Fiserv Forum.