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.

Spotless, Walkable- Downtown, Fiserv Forum

Conveniently located in Historic Brewers Hill neighborhood. This UPPER UNIT 2 bed/2 bath unit is centrally located to Fiserv Forum, MSOE. Walkable to Lake Front Brewery and restaurants such as Uncle Wolfies and Avli. Fresh Thyme grocery is just down the hill. 6 min. walk. We also own a 3 bedroom option. The space hosts up to 7 please visit the link to the lower unit. https://www.airbnb.com/rooms/1609061719132973138guests=1&adults=1&s=67&unique_share_id=f8095770-326a-4972-8fa9-5f8c54574f6b

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.

Downtown Oasis: Hot Tub, Garage, 2 King Huge yard!

Bring the whole family to this great place with lots of room for fun. A rock throw away to Milwaukee central featuring the city's best restaurants, bars, shops, and attractions. This exclusive 1800sqft Ranch 3 bedrooms, 9 beds, 2 full and 1 half bathrooms to sleep up to 14 guests. It features everything your family & friends need: Large Kitchen, Wash/Dry, Outdoor Patio, large back yard and a 8 person Hot Tub! Walking to the Fiserv Forum and downtown. Attached Garage w/ Driveway. 1 Gig Internet

Belleview House: Hot Tub, Fire Table, Fenced Yard

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

West Allis Oasis

Come stay with us at West Allis Oasis in West Allis, WI, bring your pets too! Your cozy 2-bedroom, 1-bathroom home on a quiet street in a fantastic neighborhood. Dog-friendly and perfect for families or solo travelers, enjoy easy access to I-94 and the State Fair Park just a few blocks away. Our home offers a peaceful retreat with comfortable furnishings, a fully equipped kitchen, cozy bedrooms, and large fenced in yard. Book your stay today for the perfect blend of comfort and convenience!

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!

Spacious+Mod Booth St Apt w Yard | 5 min to Fiserv

This 1890 apartment is a unit in our first home and we have loved getting to know the neighborhood and hope you do too! This unit was recently updated and kitchen remodeled by a Magnolia Network designer. It is just a block away from one of the best views of downtown and the Kadish Park and is a great place to be close to all the action but without the traffic and noise of downtown. We are happy to provide recommendations for things to do and/or restaurants/bars to hit up.

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!

Brewers Hill Gem w/hot tub & seasonal shared pool

Your family will be close to everything when you stay at this centrally-located place. Walking distance to Brady Street, the Milwaukee River Walk, shops, restaurants and coffee houses. Less than a mile from Fiserv Forum, downtown Milwaukee and just minutes from Bradford Beach. This pet friendly unit has a private fenced in yard, BBQ grill, off street parking for your vehicles and motorcycles, and a hot tub for your use.

Cream City Victorian | Parking | AC | Patio | Walk

Stay in our historic Cream City Victorian in Walker’s Point! Newly updated, sleeps 10 (option for 11th guest with pullout lounger). Features Central Air, 2 off-street parking spots, and a fenced-in backyard with seating and a gas firepit. Dogs welcome! Walkable to restaurants, bars, and breweries. Just a 3-5 minute Uber ride to downtown Milwaukee. Perfect for a getaway or special celebration!