Pet-friendly holiday rentals in Whitefish Bay

Charming home w/ fire pit, walk to Lake Michigan

Welcome to our home in a quiet neighborhood, a short walk to gorgeous views over Lake Michigan and two blocks to restaurants, shopping, and nightlife. Gather around the fire pit and grill dinner in the back patio. Listen to our vinyl collection or stream your own music while playing board games next to the smart TV. Super-fast internet, a fully equipped kitchen with coffee & tea, and in-unit laundry. Two comfy queen beds + a sleeper sofa. Here with kids? We have toys, a Pack n' Play, & more.

Spacious & Private 2 bdrm in the heart of Bayview

Beautiful 2 bedroom first floor buglalow in trendy Bayview with original details, updated kitchen & updated bathroom. Spacious open floor plans. Perfect to host families, groups of friends or a couple. Access to a private fenced backyard with fire pit, Infrared Sauna and grill. Add'l front seating on the cozy front porch. Perfect for relaxing with morning coffee or quiet dinners staying in. Easy street parking. Laundry in unit. Steps away from public transportation. Walkable restaurants/bars.

The LuLu Nest: Bay View Studio, 5 min to downtown!

Cozy and convenient studio apartment in the center of one of Milwaukee's hottest neighborhoods! Bay View, situated right betw downtown Milwaukee and the airport/Amtrak hub, is the perfect neighborhood to enjoy all the best Milwaukee has to offer. This studio apartment is only one of five in our building and is situated right above a popular neighborhood restaurant yet still quiet and tranquil enough for a good night's sleep. Book 5+ nights and receive a gift certificate to our restaurant!

Belleview House: Hot Tub, Backyard, Fire Table

Welcome to Belleview House, a delightful pet-friendly 3-bedroom home nestled in the heart of the vibrant Murray Hill/East Side neighborhood. We have renovated and redecorated the entire home and backyard (November 2025)! ✔ Hot Tub - closed during quiet hours ✔ Fast Wi-Fi ✔ Workspace ✔ Smart TVs ✔ Comfy king, queen, and twin beds ✔ Fenced Backyard with outdoor fire table ✔ Lawn bowling, horseshoe & cornhole ✔ Outdoor dining table ✔ 0.9 mi to Bradford Beach on Lake Michigan ✔ Stocked kitchen

Entire Wauwatosa Home!

Private, Renovated Home in Wauwatosa w/ Master Bedroom Suite, Workspace, Free Parking, Full Kitchen & Fitness Area 6 guests, 4 beds, 3 bedrooms, 2 full baths In walking distance of local restaurants & bars Near Hospitals 3.6 mi to State Fair Park 4.6 mi to Fiserv Forum 6.3 mi to Miller High Life Theater 6.9 mi to Summerfest Grounds -Washer & Dryer -WIFI -Smart TV -Fitness bike & equipment -Coffee bar -Towels -Toiletries -Dishes, Dishwasher -Games -Security System -Fenced Yard

East Side MKE |3BR | Walkable | Sauna | Parking

Welcome to your cozy Milwaukee getaway! Stay in a charming East Side maple hardwood floors, modern amenities, and a private sauna. Relax on the patio, then walk to dining, nightlife, and coffee shops on North Ave and Brady St. The lakefront with walking & biking paths is minutes away. Includes one off-street parking spot plus street parking. Close to UWM, St. Mary’s Hospital, and free shuttle pickup to American Family Field. Quick rides to Summerfest, Fiserv Forum, the Art Museum & more!

Cozy, Clean, and Pet Friendly Riverwest Apartment

The space is a pet friendly, lower level unit with a private entrance. 1 bedroom, 1 bath apartment with full kitchen including a coffee maker and air fryer. We are located close to a busy street in a vibrant neighborhood with bars and restaurants on our block because of this you will likely hear noise at night. If you are a light sleeper this may not be the right place for you. Close to the Lakefront, Deer District, Brady Street, & North Avenue. 4 minutes from the freeway

Bright 1.5BR in the Heart of Bay View - w/ Parking

Perfectly located in Milwaukee’s eclectic Bay View 4 blocks from the lake. Minutes from downtown, Summerfest, art museum, etc. You’ll have the entire second floor of this sunny duplex. The space is open concept - 1 bed with a King Casper mattresses, a bright kitchen with tons of space, a stylish living room with art throughout, and an office (with an air mattress). Fenced-in back yard that's great for pets and chill around the outdoor table for optimal hangs and BBQs.

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.

Barclay House in Walker's Point

Our Walker's Point house is recently renovated, nearly everything is new. Relax in this stylish space which includes a private backyard, w/rear & front decks. Located next to cafes and some of Milwaukee's best restaurants. It is also within walking distance to the Summerfest grounds. We are minutes from Downtown Milwaukee, bike trails and the pedal taverns are just a block away from the house. We just recently added a new hot tub!

The Dragonfly Loft

The second floor of this house is a spacious private lofted area that is very open and has high Located in the back of home, Private entrance and close to the city. Pets allowed! Near small bars, stores and short walk to buses that can take you into the city. I live on the lower unit, If you have any questions or request before check-in please message.

Brew City Hideaway - Historic Brewers Hill

Built of Cream City brick in 1858, this is truly one of the oldest standing houses in Milwaukee. It’s just one block north of the original Schlitz Brewery and about .8 miles from the Fiserv Forum! The home also has a fenced in yard with a stamped concrete patio which is shared with the other unit on the property. Also, one off-street parking spot.