Holiday rentals with outdoor seating in Shorewood

4.9 out of 5 average rating, 107 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.

Flat 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.

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

Our home is perfect for a Milwaukee stay. Full of amenities and great location. This luxury home has two bedrooms, loft bed and two full baths. Large kitchen and dinning area and two living rooms areas. Two of the bedrooms are perfect couple retreats each with a plush king bed. This home has a lot of extra sleeping room if your family is large. Two large sectionals and a queen bed with the most comfortable cotton sheets and down comforters. Ask about parking and backyard patio for grilling.

4.81 out of 5 average rating, 193 reviews

Flat in Murray Hill

Eastside Upper 4BR w 2 Garage Spots

Welcome to Murray Hill in MKE. This 4BR, 1BA unit offers everything for a wonderful fun stay in MKE. Enjoy the L-shaped balcony facing in front + a smaller balcony in rear. Good sized rooms w high ceilings, main BR has desk. Use (at your own risk) grill/fire table. CHILDREN MUST BE SUPERVISED. Bike rental w/in 3 block walk, tour local parks, lakefront, and nightlife on nearby Brady St. A variety of nearby restaurants + coffee shops await your visit. We look forward to hosting your stay!

4.97 out of 5 average rating, 116 reviews

Home in Murray Hill

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

5 out of 5 average rating, 121 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.

Flat 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.

Apartment in Riverside Park

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.

4.98 out of 5 average rating, 163 reviews

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.

4.99 out of 5 average rating, 124 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.

4.92 out of 5 average rating, 306 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.

Apartment in Shorewood

English Tudor - Upper Flat blocks from the beach

Sophisticated 100 Yr Old English Tudor Upper Flat with hardwood floors, crown moldings, sunken living room, natural fireplace, built-in bookcases, and fully furnished. Spacious 2200 sq. foot 2nd-floor unit. Safe and QUIET neighborhood just blocks from Atwater beach. Cats are on the property and do not go any guest space. Make sure you have the correct number of guests on your reservation request. Bookings on a Friday or Saturday are required to include both nights.

4.9 out of 5 average rating, 307 reviews

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.

Home in Riverside Park

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.

4.92 out of 5 average rating, 143 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.

5 out of 5 average rating, 128 reviews

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.

Home in Riverside Park

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.

4.88 out of 5 average rating, 102 reviews

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.

Home in Lincoln Park

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.

Popular amenities for outdoor seating rentals in Shorewood

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.9 out of 5 average rating, 201 reviews

A cozy living area is captured, featuring two patterned armchairs and a blue sofa arranged around a light coffee table. A stone fireplace anchors the space, complemented by a colorful floral artwork on the wall. Natural light filters through the windows, enhancing the inviting ambiance.

Home in Johnson's Woods

Happy Days Home close to all MKE attractions

4.96 out of 5 average rating, 110 reviews

The kitchen area features modern appliances, including a retro-style refrigerator and a classic stove. Copper pans are hung on the wall above a stylish sink, while a cozy leather sofa invites relaxation nearby. Natural light streams through the window, highlighting the open layout.

Home in Lower East Side

Blair House 1890

4.95 out of 5 average rating, 243 reviews

A salt water hot tub is illuminated with soft blue lights, showcasing gentle water jets. Surrounding greenery and trees are visible in the background, providing a natural setting. A few metallic cups rest at the edge, enhancing the inviting atmosphere.

Home in Halyard Park

6BR house, yard, hot tub - 5 min drive downtown

4.99 out of 5 average rating, 224 reviews

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.

Home in Story Hill

Best stay for Brewers/AmFam private home w/parking

5 out of 5 average rating, 292 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

4.82 out of 5 average rating, 187 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 McCarty Park

Designer Cottage-Parking, Patio, & New Kitchen

4.82 out of 5 average rating, 102 reviews

The living area features large windows allowing natural light, with a mix of comfortable seating options, including a traditional sofa and an armchair. A coffee table holds decorative candles, while a dining area with a table and chairs is visible in the background.

Home in Concordia

Sadie’s Way House

4.86 out of 5 average rating, 145 reviews

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.

Home in Brewer's Hill

Brewers Hill cottage, newly renovated near FiServ!

Apartment rentals with outdoor seating

4.87 out of 5 average rating, 370 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.

Flat in Wauwatosa

Tosa Village Studio Apartment

4.94 out of 5 average rating, 127 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.

Flat in Bay View

Rare Bay View apt with 2 full baths & master suite

4.97 out of 5 average rating, 152 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.

Flat in Bay View

Spacious & Private 2 bdrm in the heart of Bayview

4.92 out of 5 average rating, 13 reviews

A bright studio space features large windows allowing natural light to fill the room. A queen bed is paired with a cozy throw and decorative pillows. A table with two chairs and a loveseat are positioned near a wall-mounted television, offering a comfortable area for relaxation or work.

Flat in Riverside Park

Updated East Side Studio- UWM-Parking-Pets OK

5 out of 5 average rating, 69 reviews

The spacious kitchen features wooden cabinetry with decorative items displayed above. A central island holds additional counter space and seating. Natural light filters through floral-patterned curtains, illuminating the gas stove and refrigerator. A ceiling fan adds comfort, and original flooring lends character to the room.

Flat in Riverwest

Sunny 3-bedroom Home Away from Home

4.96 out of 5 average rating, 72 reviews

The living area features a sleek leather sofa positioned near a wooden coffee table. A television is set against the wall, accompanied by a shelf holding decorative items. A floor lamp provides soft lighting, and a textured area rug adds warmth to the space.

Flat in Riverwest

Quiet 1BR Urban Retreat In Fun, Funky Riverwest

4.85 out of 5 average rating, 343 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.

Flat in St. Francis

Cozy Apartment Nestled Across from Lakefront!

4.94 out of 5 average rating, 402 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.

Flat in Bay View

Bay View MKE Hideaway - with Parking!

Apartment rentals with outdoor seating

Apartment in Brewer's Hill

4.88 out of 5 average rating, 77 reviews

Brewers Hill Belle, 2 bed + Loft & balcony

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.

Apartment 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.

4.98 out of 5 average rating, 63 reviews

A spacious deck surrounded by lush greenery offers views of the Milwaukee River. Comfortable seating is arranged around a bright yellow table, providing a welcoming space for relaxation. The deck features a patterned rug that enhances the outdoor setting.

Apartment in Riverwest

Riverwest 2BR • Outdoor Oasis • King Beds

4.98 out of 5 average rating, 251 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.

Apartment in Bay View

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

Apartment 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.

4.93 out of 5 average rating, 201 reviews

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

4.83 out of 5 average rating, 169 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.

Apartment in Milwaukee

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