House holiday rentals in Milwaukee

INSTA-worthy 2 Br Downtown Home Sleeps 8 Walkable!

Looking for a fun and vibrant place to stay in Milwaukee? The Pink Lady is the perfect rental for your next girl's weekend, bachelorette party, or birthday celebration. With an open-concept living space, pink kitchen, champagne bar, and private patio, you'll have everything you need for a fun-filled stay. With easy access to top restaurants, breweries, and cultural spots, come experience the best of Milwaukee with us. Book now and immerse yourself in the charm and excitement of Milwaukee!

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

Funky 2BR in Prime Bay View - w/ Parking

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

The Menlo Guesthouse

A vintage, lower flat in a 100-year-old duplex with modern comforts and conveniences. Perfect for short or long stays while visiting Milwaukee. Situated in the walkable/bikeable Milwaukee neighborhood of Shorewood. The flat is located just a few blocks north of UWM and a few blocks east of the Oak Leaf Trail. Three minutes from Atwater Beach. Ten minutes or less to Bradford Beach, museums, and Summer Fest. Fifteen minutes or less to Fiserv Forum, Panther Arena, and American Family Field.

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!

KING BED/Amazing Location/Free parking/Wi-Fi

Enjoy a fun and relaxing stay with family or friends in this stylish, cozy, and comfortable lower unit, which features: 2 bedrooms (1 king, 1 queen ) 1 bathroom Fully equipped kitchen with dining table and designated coffee bar Living room with a 65” smart TV (Netflix included) Home office space Free parking spot Located just a short drive (4 min) from I94, this home offers easy access to all the city's major attractions * the ideal base for exploring the best of Milwaukee

Bright Eastside MKE cottage w/ FREE Parking

Welcome to our peaceful little cottage in the heart of Milwaukee. This adorable 2 bedroom, 1 bathroom home will meet all of your needs with 1 king bed, 1 queen bed, a fully stocked kitchen, wifi, driveway for off street parking, and bikes to use on the nearby Oak Leaf Trail. This is the perfect place to enjoy the friendly city of Milwaukee with a comfortable place to sleep at the end of the day. Enjoy all of the restaurants and shops on the Eastside of Milwaukee.

Historic on The Avenue

Entire Home- 3 bedrooms This beautiful historic home is centrally located in the heart of Wauwatosa! Steps from the quaint village with restaurants, bars, coffee shops and boutiques! This property marries old world charm with modern amenities. Less than 15 minutes via freeway to downtown Milwaukee, the lakefront, Marquette University, less than 10 minutes to American Family Field, 5 minutes to the Milwaukee Zoo and Froedtert/Children's hospital.

Swan City Cozy Boho in Bay View

Welcome to Swan City located in the heart of Bay View. With beautiful hardwood floors and a cozy boho-inspired decor, our space is designed to make you feel right at home from the moment you arrive. Centrally located, we are within walking distance of several restaurants, bars, and co-ops. This community is known for its lively atmosphere and friendly locals, and there's always something exciting to see, or an event to attend in the neighborhood.

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.

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!

Luxe Brady St home, 5 min to Bucks/Marquette!

Walk to restaurants, bars, coffee & the lake! Free shuttle to Brewers & Bucks 1 block away. Fully renovated property w/backyard oasis. 2 parking spots provided Located in lively entertainment district Squeaky clean home with tons of amenities! 5 min to Fiserv Forum, Third Ward, Summer fest, Breweries, Art Museum, Children's Museum, Parks etc. Perfect for friends, families & colleagues!