Holiday rentals with outdoor seating in Wauwatosa

4.98 out of 5 average rating, 255 reviews

The exterior of a two-story brick duplex is shown, featuring a welcoming entrance. Lush green lawns are bordered by manicured flower beds. Steps lead to the front door, flanked by hanging flower baskets and illuminated by wall-mounted lanterns. A concrete pathway curves gently through the yard.

Bungalow in Wauwatosa

Wauwatosa/MKE “Inglewood Place” Historic Place

Great location! Near all Milwaukee attractions and village of Wauwatosa.Cozy, upper two-bedroom duplex with keyless entry in quiet east Tosa. Extras such as ironed sheets, snacks and personal items are included. Walk to popular restaurants and bars in the village and along North Ave. Full kitchen and new beds make this a home away from home. 10 min to Froedtert & The Medical College of WI & Children’s Hospital. Near AmFam Field (Brewers stadium) and the lakefront. 4 miles to downtown Milwaukee.

4.99 out of 5 average rating, 225 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

Private home- no shared spaces with owners or other groups. Ultra clean, stylish yet cozy 3 bedroom home with mid century modern retro decor. Sleeps up to 8 in 3 bedrooms- incl. rollaway beds. Brewers stadium/AmFam Field 2 mi. away (free shuttle 1 block away). Downtown - Fiserv Forum, Rave, Wis. Ctr, Lakefront, Summerfest, Zoo, Med College, Casino within 5 mi. Please no smoking indoors, no pets, no parties, no more than 8 ppl allowed onsite without permission. Free parking in long driveway.

4.98 out of 5 average rating, 149 reviews

A historic cottage is set amidst lush greenery, featuring a mix of stone and siding on the exterior. A gravel driveway leads to the entrance, surrounded by well-maintained landscaping and mature trees that provide a tranquil atmosphere.

Home in Mequon

Pet-Friendly 1850 Estate, 8 Min to Cedarburg

A shared 5-acre family estate in Mequon, part of the historic Jahn Farmstead, built in the mid-1800s and listed on the National Register of Historic Places. This restored cottage blends 19th century charm with modern comforts like a full kitchen and gas fireplace. The estate includes our family home, this 3-bed cottage, and a 1-bed guesthouse. 8 minutes from Historic Downtown Cedarburg, 30 minutes from Milwaukee, 90 minutes from Chicago. Close enough to everything, far enough to truly unwind.

4.94 out of 5 average rating, 404 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.

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, 195 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.

4.82 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

LOCATION, LOCATION! • Fast Fiber Internet TIME (MIN) 5-10 McCarty Park (Water Park, Trails, B-Ball Court) STATE FAIR TOSA 10-15 Brewers, Bucks Harley, 3rd Ward Breweries, Zoo ATTN MEDICAL Near All Hospitals PRIVATE PATIO & FENCED-BACKYARD • Seating for 4 w/ table • 🐶 can roam • Safe & secure kids play • Space for games & bags SAFE PARKING • Allows 2-4 vehicles inc. trucks & boats • 100FT off street • driveway widens LAUNDRY • W&D • Pods & D-Sheets • Util. Sink • Iron+Board

A single-story ranch-style home is presented, featuring a well-maintained exterior with a light-colored stone façade. Green grass surrounds the property, complemented by neatly trimmed bushes and a paved walkway leading to the front door. The roof is covered with gray shingles under a partly cloudy sky.

4.92 out of 5 average rating, 106 reviews

Relax close to everything in Milwaukee

Ranch Style home in a quiet Neighborhood. You will feel at home and comfortable! The home is well maintained and very clean. In the winters you could cozy up to a nice fire upstairs and relax with a glass of wine. Downstairs is a second fireplace you have going and play a game of pool. In The summer you can enjoy the three seasons room, with looking a cup of coffee and look at the planted flower garden. Close to the Wauwatosa village down town. Even closer to Elm Grove Village.

4.87 out of 5 average rating, 372 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

Tosa Village Studio. (Wauwatosa is the first suburb west of Milwaukee). Walk to the Village and explore the boutique shops, restaurants and bars. Enjoy summer concerts in Hart Park. Miller Park (Milwaukee County Stadium - Home of the Brewers) only 3.5 miles away. Close to the Medical Complex, Froedert and Children's Hospitals. 6.5 miles to the Fiserv Forum (Home of the Milwaukee Bucks). Six miles to downtown Milwaukee. Enjoy Summerfest at the Lake Michigan shore.

4.87 out of 5 average rating, 172 reviews

The kitchen features dark cabinetry and modern appliances, complemented by a central wooden island with seating for two. Pendant lights hang above, illuminating the area. A window offers natural light, and open access to a hallway is visible in the background.

Townhouse in Story Hill

Central, Game Room, Quiet Walkable Area

Beautiful luxurious 4 bedroom (bonus sunroom) home central to everything Milwaukee has to offer. Located in sought after quiet community due to its proximity to all main attractions while providing safety and peace for residents and visitors. Our property is less than 10mins from heart of Milwaukee, walking distance to main attractions such as Brewers stadium and state fair. We do our absolute best to be exceptional hosts so hope you decide to stay with us

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.

4.96 out of 5 average rating, 145 reviews

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.

4.81 out of 5 average rating, 116 reviews

A spacious dining area is furnished with a large wooden table surrounded by woven chairs. Natural light filters through multiple windows framed by cream-colored curtains. Decorated with a centerpiece of fruits, the room features warm wood paneling and a decorative chandelier overhead.

Home in West Allis

✺ La Casita ✺ 3 Bedrooms ✺ Spacious Parking ✺

La Casita is a 1930’s two-story bungalow home located in West Allis, WI. Short walking distance from Wisconsin State Fair Park, Pettit National Ice Center, and major highways. Enjoy the Mexican theme decor along with all the natural woodwork throughout! Plenty of free off street parking available. Amenities include: WiFi, Roku TV with Hulu & HBO Max, Washer & Dryer, Fully Stocked Kitchen, Hair Dryer, Fresh Sheets and Towels, and much more!

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.

5 out of 5 average rating, 292 reviews

The Little Gray House

Spring is here and it's time to share what we've been up to! Those of you staying with us after April will be treated to new kitchen counter tops, roof, windows and siding :) It'll still be the LGH, but with a little something more! We'll update the photos as soon as it's completed! The Little Gray House has attained rave reviews from travelers around the world for its comfort, cleanliness, and convenience. Happy to have you!

Popular amenities for Wauwatosa outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.89 out of 5 average rating, 114 reviews

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.

Home in Milwaukee

Cozy Modern Retreat, 5min to DT, Newly Refurbished

4.89 out of 5 average rating, 140 reviews

A paved driveway winds through a lush wooded area, bordered by greenery and tall trees. The home can be seen nestled in the distance, blending harmoniously with the natural surroundings.

Home in Muskego

Muskego Hideaway on 2 Acre Lot

4.95 out of 5 average rating, 238 reviews

A spacious bedroom features a white bed adorned with decorative pillows and a textured throw blanket. A striking lion portrait hangs above the bed. Natural light fills the room through a nearby window, with soft curtains partially drawn, complementing the warm brown walls.

Home in Milwaukee

Mid-Century Inspired Upper Duplex in Bay View

4.9 out of 5 average rating, 309 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!

4.94 out of 5 average rating, 178 reviews

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.

Home in Halyard Park

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

4.86 out of 5 average rating, 146 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!

4.97 out of 5 average rating, 273 reviews

A rustic kitchen area showcases exposed brick walls and wooden beams. A dark faucet and sink are paired with light countertop surfaces. A decorative sign reads 'Welcome to Brewers Hill', adding a welcoming touch to the space.

Home in Brewer's Hill

Brew City Hideaway - Historic Brewers Hill

A well-equipped kitchen features rich wooden cabinetry, complemented by polished granite countertops. Stainless steel appliances, including a range and sink, enhance functionality. Natural light filters through sheer curtains, creating a bright and inviting atmosphere, while a unique pendant light adds a modern touch.

5 out of 5 average rating, 32 reviews

The Mayfair Midcentury

Apartment rentals with outdoor seating

4.94 out of 5 average rating, 129 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, 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.

Apartment in Shorewood

Charming home w/ fire pit, walk to Lake Michigan

4.97 out of 5 average rating, 153 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

4.89 out of 5 average rating, 213 reviews

A dining area features a wooden table surrounded by six white chairs. Natural light pours through large bay windows, highlighting the warm wooden accents of the room. A cozy living space is visible in the background, adorned with potted plants and comfortable seating.

Apartment in Riverwest

Spacious 2 Bedroom Flat in Heart of Milwaukee

Apartment in Halyard Park

A round wooden dining table is surrounded by four upholstered chairs in a light color. A simple vase with dried flowers sits at the center of the table, while a subtle area rug complements the space. Soft natural light highlights the inviting dining area.

4.93 out of 5 average rating, 258 reviews

MKE-Spa Airbnb

Apartment in Upper East Side

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.

4.97 out of 5 average rating, 318 reviews

East Side Home

Apartment in Saint Francis

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.

4.85 out of 5 average rating, 345 reviews

Cozy Apartment Nestled Across from Lakefront!

5 out of 5 average rating, 122 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

Condo rentals with outdoor seating

4.98 out of 5 average rating, 165 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

4.88 out of 5 average rating, 77 reviews

Condo in Brewer's Hill

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.

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.

4.89 out of 5 average rating, 53 reviews

An open-concept living area showcases polished hardwood floors and ample natural light. A cozy sectional sofa is positioned around a decorative area rug. The dining space, featuring a wooden table and chairs, is visible beside a modern kitchen equipped with stainless steel appliances.

Condo in Brewer's Hill

Brewers Hill Belle • 2 bed, 2 bath, & balcony

4.93 out of 5 average rating, 307 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, 252 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