Pet-friendly holiday rentals in Milwaukee

2BR Sunny Upper in Prime Bay View - w/ Parking

Perfectly located on the main strip of KK in Milwaukee’s eclectic Bay View directly next to bars, restaurants, and shopping. Minutes from downtown, Summerfest, art museum. You’ll have the entire 2nd floor of this sunny duplex. Stylishly designed - 2 bedrooms with Casper mattresses, a bright kitchen with seating area, a work space in the master, and a comfy living room with a smart TV. The space has 2 patio spaces, a small backyard area, an in-unit washer & dryer as well as 1 free parking space.

Cream City Lounge | Parking| AC | Patio | Pets

Welcome to Milwaukee! This remodeled home offers a spacious and stylish retreat for up to 11 guests. With four bedrooms, two full bathrooms, and charming cream city brick accents, this home seamlessly blends modern comfort with historic charm. Enjoy the coffee bar with an outdoor patio, fireplace, and dining area. Private parking for up to 4. Lounge-style living. Close to Brady St. Restaurants, bars, salons, shops and convenient stores just outside the front door. Bring the family dog as well!

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.

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

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!

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!

Fabulous Walkers Point Mansion w/ Bar andFireplace

This stunning Walker's Point historic mansion is completely re-imagined with interior spaces that will delight you and your guests. Host a memorable get together with friends or family and relax by the bioethanol fireplace, enjoy everything the vibrant neighborhood has to offer. We have some beautiful spaces for your enjoyment, including a finished-attic hangout space, and a secret vintage-inspired lounge in the basement. Enjoy plenty of Milwaukee history in a spectacular new form!

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.

Our Cozy Bay View Bungalow Getaway

Our relaxing, clean, fully equipped Bay View bungalow delivers a perfect getaway. We are equipped with 1g wifi, 4K smart TV, dimmers, and a washer/dryer. Tastefully decorated, uncomplicated, and comfortable. There are cozy coffee shops, restaurants, and local bars just a few blocks from the house. The Bay View Dog Park is one block away. We have parking for two cars. We follow an Enhanced Cleaning Protocol, and are 100% smoke free without exception.

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!

*FREE PARKING*Brady Street Private Residence

Welcome to your Milwaukee home-away-from-home! Located just a short stroll from the iconic Brady Street, this spacious and thoughtfully designed unit puts you right in the heart of the city’s energy—boutiques, cafes, restaurants, nightlife, and local flavor are all just steps away Book now and experience Milwaukee like a local—with all the comfort and convenience you need to relax, recharge, and explore.

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.