Holiday rentals with outdoor seating in Glendale

4.9 out of 5 average rating, 111 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

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.

ValueLocationAmenities

4.93 out of 5 average rating, 204 reviews

The exterior of a charming house is showcased, featuring a welcoming front porch adorned with string lights. Lush greenery surrounds the home, with a flower garden displaying purple blooms. A pathway leads to the entrance, enhancing the inviting atmosphere of the property.

Home in Menomonee Falls

Exhale, rest

Exhale. The perfect combination. This home is right in the village of Menomonee Falls with great shopping and restaurants within walking distance. Close to the highway, it’s also a mere half an hour to anything Milwaukee so games, museums, festivals are all also at your fingertips. At the end of dead end road with views of the river, access to trails, and a secluded deck and fire pit, there is definitely also a rural feel. This location has it all. Go out, live life, come back, exhale and rest.

Outdoor spacesValueHeating

4.94 out of 5 average rating, 425 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.

LocationOutdoor spacesBathroom

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, 201 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.

LocationOutdoor spacesBiking

4.99 out of 5 average rating, 137 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.

LocationOutdoor spacesSleep quality

4.99 out of 5 average rating, 154 reviews

Tall sunflowers bloom vibrantly in a garden, displaying bright yellow and orange petals. A wooden gazebo with hanging lights stands in the background, surrounded by lush greenery. Soft sunlight filters through the trees, enhancing the serene outdoor setting.

Guest suite in Sussex

Garden Retreat in law Suite

Welcome to our in-law suite apartment featuring a full eat-in kitchen, living room, queen bed in large bedroom, walk in closet and full bathroom with walk-in shower. Our beautiful two acre yard has many areas to relax in, including a hammock and fire pit for the evenings. Twenty mins. to Erin Hills and Holy Hill and a half hour to most downtown Milwaukee attractions, as well as the RNC activities taking place this summer. Lots of city tips and suggestions for our guests.

Outdoor spacesValueCheckout

4.92 out of 5 average rating, 153 reviews

A well-equipped kitchen features white cabinetry, stainless steel appliances, and green tile backsplash. The space is illuminated with recessed lighting and includes a dining area with a wood table. An open doorway leads to another room, enhancing the overall flow of the layout.

Home in Shorewood

Shorewood house - near shops w/ WiFi & parking

Just down the road from Lake Michigan, this charming duplex upper is the perfect space for a relaxing getaway. After a day of shopping, eating good food, and exploring Milwaukee, look forward to kicking back in the cozy living room, or on the patio. This duplex has 2 bedrooms; a King bed master, and one bedroom with two Twins. There is one charming bathroom with a bathtub. Well stocked kitchen, and plenty of backyard space. The lower tenant is respectful of guests.

ValueOutdoor spacesWalkability

An open living area features a modern style with a gray sofa and a wooden coffee table at the center. A dining space with a dark table and chairs is visible to the left, while a staircase leads to the upper level in the background.

4.89 out of 5 average rating, 106 reviews

Cozy 2-bedroom cottage close to everything!

This newly remodeled, cozy cottage has been called a hidden gem. It’s walking distance from Bayshore Mall. Five minute walk to biking/hiking trail, Milwaukee River for fishing and kayaking and Whitefish Bay. Twelve minutes from Lake Michigan, Downtown and the Historic Third Ward! Booking requirements: Full/Complete Air BnB profile. Government ID check for pre-approval and upon arrival. No parties or events. Active noise monitoring device. No pets allowed.

ValueOutdoor spacesLaundry

4.88 out of 5 average rating, 213 reviews

An open-concept living space features a modern kitchen with a large island and stainless steel sink, complemented by pendant lighting. A comfortable seating area with a light-colored sofa and large windows invites natural light, while a dining area with white chairs is visible in the background.

Home in Mequon

Mequon Ranch Experience

Escape to our stunning vacation home in Mequon, WI for a peaceful group getaway. Completely renovated and fully furnished, our home comfortably accommodates up to 8 guests. Enjoy complete privacy on our one-acre lot, and relax on the patio, grill up a delicious meal, or gather around the fire pit. Only blocks away from the Milwaukee River and minutes to downtown Mequon, our home offers easy access to nearby attractions. Book now for an unforgettable stay!.

ValueOutdoor spacesSkiing

4.96 out of 5 average rating, 156 reviews

A spacious dining area features a wooden table surrounded by six chairs, complemented by an archway leading to a cozy living room. Natural light filters through large windows, illuminating the elegant combination of exposed brick and light-toned walls.

Home in Wauwatosa

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.

ValueLocationCheck-in

5 out of 5 average rating, 303 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!

LocationValueComfort

4.98 out of 5 average rating, 173 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.

LocationOutdoor spacesTV

Popular amenities for Glendale 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

LocationValueAccuracy

A cozy living area is presented with two dark leather sofas, accompanied by bright red cushions. A glass coffee table occupies the center, while light enters through two large windows adorned with navy blue curtains. A stylish lamp and a decorative piece complete the room.

4.9 out of 5 average rating, 330 reviews

Historic East Side Duplex, 3BD. No Cleaning Fee!

ValueOutdoor spacesAir conditioning

4.79 out of 5 average rating, 186 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★

ValueLocationHospitality

4.98 out of 5 average rating, 127 reviews

Belleview House: Hot Tub, Backyard, Fire Table

Outdoor spacesLocationWalkability

4.84 out of 5 average rating, 112 reviews

A dining area features a large wooden table surrounded by eight brown leather chairs. Natural light fills the space through two windows, highlighting a decorative chandelier above the table. A wall adorned with greenery and a mirror adds elegance to the setting.

Home in Shorewood

Beautiful Luxury Suite A of Shorewood Home

LocationValueLaundry

4.89 out of 5 average rating, 100 reviews

A functional kitchen area is highlighted by modern appliances, including a stainless-steel refrigerator and microwave. White cabinetry contrasts with the tiled backsplash. A wooden work table is positioned beneath hanging pots, while a colorful rug adds a welcoming touch to the tiled floor.

Home in Wauwatosa

Family friendly, Private Patio, Walkable, Quiet

ValueLocationHospitality

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, 184 reviews

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

LocationValueGetting around

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, 152 reviews

Brewers Hill cottage, newly renovated near FiServ!

LocationOutdoor spacesAir conditioning

Apartment rentals with outdoor seating

4.87 out of 5 average rating, 380 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

LocationValueLong stay

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

LocationDecorAir conditioning

4.98 out of 5 average rating, 162 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

ValueLocationGetting around

4.97 out of 5 average rating, 395 reviews

A calming bedroom features a dark wooden headboard with a collection of textured pillows in various colors placed on a neatly made bed. A bedside table holds a lamp, with a small photo frame beside a potted plant, providing a touch of greenery.

Apartment in Cedarburg

Prime location in the heart of it all

Outdoor spacesLocationWalkability

4.98 out of 5 average rating, 388 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)

LocationOutdoor spacesFamily

4.97 out of 5 average rating, 324 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

LocationValueLong stay

4.84 out of 5 average rating, 356 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!

ValueLocationSkiing

4.99 out of 5 average rating, 137 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

LocationValueComfort

Condo rentals with outdoor seating

4.98 out of 5 average rating, 174 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

LocationOutdoor spacesGetting around

4.86 out of 5 average rating, 80 reviews

Condo in Milwaukee

Brewers Hill Belle, 2 bed + Loft & balcony

LocationAmenitiesCheck-in

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

ValueOutdoor spacesCheckout

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

LocationOutdoor spacesLaundry

4.98 out of 5 average rating, 258 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

LocationOutdoor spacesNearby

Condo in Historic Third Ward

An intimate living area features a comfortable sofa adorned with decorative pillows, paired with a wooden dining table. An open kitchen area with sleek cabinetry is visible in the background. Six tall windows allow natural light to brighten the space, with a patterned rug underfoot.

4.91 out of 5 average rating, 211 reviews

Third Ward - High End 1 Bedroom up to 6 + Parking

ValueLocationCleanliness

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!

LocationNearbyHospitality