Holiday rentals with outdoor seating in Milwaukee

Townhouse in Walker's Point

An open concept kitchen and living area features a blue sofa adorned with colorful cushions, providing a comfortable seating space. The kitchen displays modern stainless steel appliances. A distinctive accent wall covered in black and white art adds character to the cozy environment.

4.98 out of 5 average rating, 183 reviews

NEW 2Br Downtown Home w/ Garage, Yard, Walkable

Nestled in the vibrant Walker's Point neighborhood, this charming home offers the perfect urban retreat. The stylish 4-bedroom abode combines modern amenities with cozy ambiance; whether you're exploring the bustling streets or enjoying a night in, this home provides a quiet and convenient base for your Milwaukee adventures. With easy access to eclectic dining, unique shops, and lively entertainment, you'll find plenty to see and do. 5 Min to Historic Third Ward 10 Min to Milwaukee Art Museum

An open concept kitchen features a large white island with seating, accompanied by modern cabinetry. The living space extends into a bright dining area, enhanced by natural light from a window. Decorative artwork and a wall clock add character to the surroundings.

4.95 out of 5 average rating, 183 reviews

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

4.94 out of 5 average rating, 423 reviews

A bright living area showcases a comfortable seating arrangement with decorative cushions. Potted plants add greenery, and light streams in through the large windows. Artwork adorns the walls, while a mix of textures is provided by the rugs and furnishings.

Apartment in Bay View

Bay View MKE Hideaway - with Parking!

Cozy, inviting, one bedroom apartment in the heart of Bayview, literally steps away from some of Milwaukee's best restaurants, bars and shops! One of two Airbnb guest spaces in our house, this downstairs apartment is our home base when we're in Milwaukee, and we love sharing it with guests when we’re on the road! We are within five minutes of Summerfest grounds and East Side & Historic Third Ward districts, and within 10 minutes of the airport, downtown, Marquette University, and Miller Park.

4.99 out of 5 average rating, 135 reviews

A cozy living area features a distinctive two-tone sofa facing a television. Large windows are adorned with flowing curtains, allowing natural light to brighten the space. A wooden bookshelf and a mid-century style chair complement the warm wooden flooring and charming wall decor.

Apartment in Riverwest

WeilHaus: A Cozy Urban Retreat

Welcome to our WeilHaus (we pronouce that "wheel" in Milwaukee). This cozy 2-bed apartment is centrally located on the southern end of Riverwest, close to the East Side, freeways, downtown, parks, bike trails and all the hip neighborhood goodness that Riverwest has to offer you. WeilHaus is one unit in a four-unit building with tons of old-fashioned charm. Enjoy a colorful, stylish retreat, with special books to read, art to enjoy, and thoughtful touches everywhere to help you feel at home.

4.98 out of 5 average rating, 173 reviews

A spacious living area features a light-colored sectional sofa adorned with decorative pillows, positioned around a wooden coffee table. Exposed wooden beams add character to the ceiling, while framed artwork lines the walls, contributing to the well-lit and inviting atmosphere.

Condo in Lower East Side

Private East Side Milwaukee flat with fenced yard

Enjoy the best that the East Side and downtown have to offer in this second floor standalone home on the Oak Leaf Trail with no shared walls, private fenced-in yard with spacious deck and patio, and private parking lot. This historic cream city brick building was constructed in 1897 and completely renovated in 2017 with custom features throughout. Gas fireplace, 70" TV in living room with custom hi-fi built-in stereo system, tons of natural light. Double guest suites with amenities galore.

Bungalow in West Milwaukee

A dining area features a round table surrounded by black chairs with plush white cushions. Sunlight filters through large windows, highlighting the vintage sideboard and plant. An inviting living space is visible through an archway, showcasing a blend of decor and natural light.

4.97 out of 5 average rating, 199 reviews

Adorn Abode

Charming upper level hygge bungalow (2 unit home total). Ten minutes from anywhere. Tucked away in the quiet village of West Milwaukee. Full of natural light and curated vintage decor. Walking distance to a few restaurants and bars, as well as the American Family Field. Enjoy a cocktail on the front balcony and watch the sunset while indulging in a classic vinyl collection. Small balcony off of the kitchen to watch the sunrise and enjoy a cup of coffee. Perfect for adventuring or relaxing.

4.99 out of 5 average rating, 134 reviews

The living room features a comfortable sectional sofa and a light-colored couch, accented with colorful pillows. A round wooden coffee table sits at the center, complemented by a decorative rug. Natural light filters through large windows with stained glass detailing.

Home in Shorewood

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.

4.88 out of 5 average rating, 113 reviews

Cozy East Side | Sauna |Parking | Near Downtown

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!

A welcoming hallway is displayed, featuring light-colored walls and a combination of wooden and tile flooring. An ornate mirror hangs on one wall, while decorative hooks are mounted nearby. Natural light streams in through a window beside the front door, enhancing the inviting atmosphere.

5 out of 5 average rating, 133 reviews

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.

5 out of 5 average rating, 301 reviews

A secluded outdoor patio is highlighted by a well-equipped hot tub, surrounded by lush greenery and wooden fencing. Comfortable seating is arranged nearby, with a patterned rug beneath a shaded area. Decorative plants and a charming umbrella enhance the relaxing atmosphere.

Home in Wauwatosa

The Little Gray House

Summer time in the 414! We've got a few small openings left this summer, maybe they work for you? Time to start thinking about booking for fall and winter so you can get in on the best little Airbnb around! All the home upgrades are done, and we'l be posting photos within the next couple of weeks. The Little Gray House has attained rave reviews from travelers around the world for its comfort, cleanliness, and convenience. Happy to have you!

4.83 out of 5 average rating, 212 reviews

2 King Bed/Near Downtown Milwaukee/Free P/WiFi

Have fun yourself, the whole family or with friends at this stylish, cozy and comfortable UPPER place with: *2 king size bedrooms * 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

4.98 out of 5 average rating, 171 reviews

Townhouse in Milwaukee

Historic Gem|Steps to UWM|Lake Mich|Free Parking

🔹 5-Star Rated | Superhost Quality | Fast Wi-Fi | Free Parking 🔹 🏡 Experience a Slice of Milwaukee’s History in a 100-Year-Old Home! Step inside this charming first-floor retreat—a beautifully preserved prairie-style home blending historic elegance with modern convenience. Located right across from UWM, this top-rated Airbnb is perfect for visiting students, faculty, families, and travelers looking for a relaxing, walkable neighborhood.

Popular amenities for Milwaukee outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

A welcoming living area is furnished with a light-colored sofa adorned with decorative pillows. Two armchairs are positioned beside a round coffee table, with a TV mounted on the wall across from them. Soft lighting enhances the cozy ambiance, and large windows allow natural light to fill the space.

4.89 out of 5 average rating, 119 reviews

Cozy Modern Retreat, 5min to DT, Newly Refurbished

A stylish living room is furnished with a striped sofa and two cream-colored reclining chairs, complemented by a wooden coffee table. Soft lighting from side lamps creates a cozy ambience, while natural light filters through the window blinds. A large piece of abstract art adorns the wall.

4.99 out of 5 average rating, 229 reviews

Best stay for Brewers/AmFam private home w/parking

4.79 out of 5 average rating, 185 reviews

A cozy living room is highlighted by a light gray sofa adorned with decorative cushions. A small blue coffee table sits in front, complemented by a candle and a framed picture. Natural light enters through a window, brightening the neutral-colored walls.

Home in West Allis

★Cozy Beach Themed Home★2 Beds★Spacious Parking★

5 out of 5 average rating, 134 reviews

Modern Home Near Downtown | Rooftop Patio + Garage

4.83 out of 5 average rating, 193 reviews

A cozy living area features a spacious sofa against a vibrant, textured wall. A colorful area rug adds warmth to the hardwood floor, while framed artwork decorates the surrounding walls. Access to the kitchen and stairway is visible in the background.

Home in West Allis

Designer Cottage-Parking, Patio, & New Kitchen

4.98 out of 5 average rating, 127 reviews

Belleview House: Hot Tub, Backyard, Fire Table

A modern kitchen is presented with a blend of white upper cabinets and navy blue lower cabinets. Stainless steel appliances, including an oven and dishwasher, are visible. A light-colored countertop complements the space. Open shelves display minimal decor, and a woven rug adds texture.

4.86 out of 5 average rating, 151 reviews

Brewers Hill cottage, newly renovated near FiServ!

4.92 out of 5 average rating, 145 reviews

The living room features a stylish tan sofa accompanied by a textured throw and decorative pillows. A round mirror hangs on the wall, reflecting the room's layout. A light fixture hangs overhead, and colorful artwork is displayed. A modern coffee table is positioned on a striped rug.

Home in Bay View

Funky 2BR in Prime Bay View - w/ Parking

Apartment rentals with outdoor seating

4.87 out of 5 average rating, 379 reviews

A spacious bed is dressed in neutral linens, complemented by a decorative striped blanket and a pillow with 'relax' text. A wooden bedside table with a lamp rests nearby, and wall art is mounted above the bed, enhancing the room's inviting ambiance.

Apartment in Wauwatosa

Tosa Village Studio Apartment

4.93 out of 5 average rating, 134 reviews

A comfortable living area features a black sofa adorned with yellow throw pillows, positioned against light-colored walls. A mirror enhances the space, while a wooden coffee table rests on a decorative area rug. A dining area with a round table and chairs is visible in the background.

Apartment in Bay View

Rare Bay View apt with 2 full baths & master suite

4.9 out of 5 average rating, 109 reviews

A spacious living area features a large smart TV mounted on the wall, with modern furniture arranged for comfort. A sectional sofa and accent chair provide seating options. Natural light streams through the windows, and artistic touches enhance the welcoming atmosphere.

Apartment in Shorewood

Charming home w/ fire pit, walk to Lake Michigan

4.98 out of 5 average rating, 160 reviews

The living area features a stone fireplace and a flat-screen TV mounted above it. Two dark armchairs and a comfortable sofa create a cozy seating arrangement. Natural light enters through multiple windows, highlighting the original woodwork and a vibrant area rug on the hardwood floor.

Apartment in Bay View

Spacious & Private 2 bdrm in the heart of Bayview

4.98 out of 5 average rating, 386 reviews

A living area features large windows with natural light filtering through sheer curtains. Comfortable seating includes a plush sofa with red accent pillows, a matching armchair, and an ottoman. A textured area rug adds visual interest to the hardwood floor.

Apartment in Wauwatosa

Great Location, Wauwatosa (upper unit)

4.97 out of 5 average rating, 323 reviews

A spacious living area features a mix of seating options, including a leather couch and armchairs. Large windows allow natural light to brighten the room, highlighting the hardwood floors and area rug. A coffee table sits centrally, providing a functional gathering space.

Apartment in Milwaukee

East Side Home

4.84 out of 5 average rating, 355 reviews

The exterior of a two-story apartment building is presented, featuring a combination of red and gray siding. A welcoming deck area with white furniture overlooks a snow-dusted parking lot, captured under soft evening light. Decorative string lights add a warm touch to the ambiance.

Apartment in St. Francis

Cozy Apartment Nestled Across from Lakefront!

Apartment in Lower East Side

The exterior of the multi-story building is characterized by a traditional design, featuring brick and ornate detailing. The inviting entrance showcases large windows with a corner location, enhancing the urban atmosphere.

4.79 out of 5 average rating, 105 reviews

6BR Penthouse Loft Above Bakery | AC | Pool Table

Condo rentals with outdoor seating

A spacious deck is furnished with a dining table beneath a sun umbrella, alongside several lounge chairs. A hot tub is positioned on one side, with a view of the backyard and a garage in the distance under clear skies.

Condo in Wauwatosa

4.63 out of 5 average rating, 117 reviews

Stylistic Condo Hot Tub Tosa Village 2 blocks away

Private room in Milwaukee

3.75 out of 5 average rating, 4 reviews

Lovely 3 bedroom condo with cozy indoor fireplace.

4.93 out of 5 average rating, 311 reviews

The exterior of a brick building features a raised balcony adorned with a decorative banner. The structure displays a mix of rustic brick and stone arches, framed by green trim. Natural light illuminates the scene, creating a welcoming view of the entrance.

Condo in Shorewood

English Tudor - Upper Flat blocks from the beach

4.98 out of 5 average rating, 256 reviews

The well-appointed kitchen features wooden cabinetry, stainless steel appliances, and a sleek black countertop. A dining table with vibrant red chairs accommodates a gathering, while a striking light fixture adds a modern touch. Natural light fills the space through multiple windows.

Condo in Bay View

Bay View - Lake View on the Park w/Secret Lounge

4.83 out of 5 average rating, 172 reviews

The inviting living area features a large gray sectional sofa and a comfortable day bed. A neutral coffee table is centered on warm wood flooring. Exposed brick walls add character, while a decorative mural highlights the local culture. Natural light filters through the window, complementing the ceiling fan.

Condo in Milwaukee

New Big 2 King Bedroom Condo by FiservForum/3rd St

4.68 out of 5 average rating, 50 reviews

The view captures a modern neighborhood featuring a mix of contemporary buildings and greenery. Streetlights line the bustling street, and soft hues of sunset fill the sky, reflecting a serene ambiance in the urban landscape.

Condo in Lower East Side

Downtown Eastside gem near Fiserv Forum Bucks!

4.9 out of 5 average rating, 104 reviews

The spacious living area features large windows with light filtering through soft curtains. A comfortable seating arrangement includes a recliner, soft couch, and accent chair. A dining table with metal chairs is positioned beside a modern television mounted on the wall.

Condo in Bay View

Spacious Bay View Historic Storefront Apartment