Holiday rentals with outdoor seating in Greenfield

4.91 out of 5 average rating, 264 reviews

A rustic interior showcases handcrafted stonework paired with warm wooden accents. Natural light highlights the cozy organization of the space, featuring a fireplace in the foreground and a ladder leading to an upper level, while a glimpse of the adjoining room is visible in the background.

Home in Racine

“Rustic Farmhouse Retreat” at a working farm

A charming little farmhouse filled with antiques & eclectic artwork from all over the world. It is situated in the middle of a working farm that raises a plethora of exotic fruits, vegetables, shiitake mushrooms, and flowers for local gourmet restaurants. The house interior has a unique design decorated with beautiful hand crafted stonework accented with exotic driftwood trim from old wooden shipwrecks. Try our outdoor Neapolitan wood fired oven for the best pizza ever. A truly unique getaway!

4.98 out of 5 average rating, 254 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.

4.94 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.

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.

4.78 out of 5 average rating, 179 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★

Welcome to this cozy beach themed home located in the heart of West Allis. Close to public transportation and a few minutes driving to State Fair Park, Milwaukee County Zoo, Potawatomi Hotel & Casino, bars, restaurants, and more! Peaceful and quiet residential spot with plenty of parking on premises (up to 3 cars.) Amenities include: Spacious Parking, Smart TV, WiFi, Self Check in, Fresh Sheets and Towels, Shampoo & Conditioner, Soap & Hand Sanitizer, Fully Stocked Kitchen, and much more!

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.

4.85 out of 5 average rating, 101 reviews

A cozy living space features a floral-patterned couch accompanied by a wooden coffee table. The walls are adorned with warm wood paneling, complemented by soft lighting from a wall sconce. Greenery is present with potted plants, adding a touch of nature to the space.

Home in Oak Creek

Spacious Ranch Home Oak Creek close to Airport

Chalet style ranch home is fully furnished and offers 2400 square feet of private usable space. The 3 bedrooms, living room, dining room, family room, 1 1/2 bathrooms, kitchen, and kitchen table area are all located on one floor. You will love waking up in the morning in this quiet suburban neighborhood and looking out the many windows at the park across the street. Close to the heart of Oak Creek Drexel Town Square, 4.6 miles from the airport, & 15 minutes from Downtown Milwaukee.

4.96 out of 5 average rating, 330 reviews

A historic stone home is presented, featuring multiple windows that enhance its classic appeal. A well-maintained garden with colorful flowers surrounds the exterior, creating a welcoming entrance to the Butler Place. A sign displaying the property's name is held by two guests in front of the house.

Guest suite in Sussex

The Loft @ The Butler Place. 1846 homestead.

The Loft at the Butler Place is a beautiful, quiet retreat set in the rural suburb of Sussex, just 30 minutes west of Milwaukee. The home is the 1846 homestead of the William Butler family, making the home older than the State of Wisconsin! The 2019 remodel of the Loft is in sophisticated farmhouse style and pays tribute to the history of the home in its furnishings, up cycled pieces, and beautiful setting. "Broken becomes blessed" both tells and compells as an invitation to all.

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

4.92 out of 5 average rating, 106 reviews

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.

Home in Wauwatosa

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, 371 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.

4.8 out of 5 average rating, 316 reviews

The studio features hardwood floors and exposed wooden beams adding character. A spacious bed is centrally positioned, accompanied by soft bedding. A small dining table and kitchenette with essential appliances are visible. A modern light fixture provides illumination near a cozy reading chair.

Apartment in West Allis

Kegel's Inn - Studio - Classic Apartment #3

Quaint little studio with lots of old-world character. This one-room studio has original hardwood floors, heavy wood ceiling beams and 1930's tile work in the bathroom. The apartment looks down on 59th street, which for the summer months between May and November, hosts the Kegels Beer Garden on the street! We're one of the last Authentic German restaurants and Inn's left in country and the studio apartment is right above it! We hope you love this place as much as we do!

4.93 out of 5 average rating, 188 reviews

Townhouse in Waukesha

Pet-Friendly | Large Yard | Fire pit | Sleeps 5

Wake up to the sunrise over a peaceful backyard and enjoy your favorite blend on your private balcony. Evenings are perfect by the fire pit under a starry sky. This renovated home has gas stove/oven, microwave, coffee maker, full-size fridge/freezer, in-unit washer & dryer, smart TV, and Wi-Fi - ideal for couples, small families, or traveling professionals. Only 1 mile from I-94 and 20 minutes from Milwaukee, blending quiet comfort with city convenience.

Popular amenities for Greenfield outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.9 out of 5 average rating, 109 reviews

A dining nook is highlighted, featuring two high-backed black bar stools surrounding a small round table. A wall-mounted sign lists several cities, and natural light filters in through nearby windows, illuminating the wood-like flooring and creating a bright atmosphere.

Home in Cudahy

Upgraded! 4BR in Milwaukee near Airport & Downtown

4.96 out of 5 average rating, 118 reviews

A log cabin sits perched on a grassy embankment, framed by trees. The exterior features large windows and a spacious deck with steps leading down to the water's edge. Two red chairs are placed near the shoreline, reflecting the cabin's warm colors on the water.

Home in Nashotah

Okauchee Lakefront Cabin Escape

4.99 out of 5 average rating, 125 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

4.98 out of 5 average rating, 143 reviews

A living area features a stone fireplace and large windows providing views of Lake Beulah. Comfortable seating surrounds a wooden coffee table. A dining table is visible, alongside decor elements that create a cozy ambiance. Natural light floods the space, enhancing the connection to the outdoors.

Home in East Troy

Lakeside Getaway

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

4.92 out of 5 average rating, 134 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

4.89 out of 5 average rating, 415 reviews

A modern kitchen showcases green cabinetry complemented by a wooden island and bar stools. Stainless steel appliances are integrated into the space, while a dining area with a wooden table is visible in the background. Natural light filters through the nearby windows.

Home in Walker's Point

The Pony Store in Vibrant Walker’s Point

4.97 out of 5 average rating, 221 reviews

A charming duplex stands with a triangular roof, featuring a colorful facade and multiple balconies. Stairs lead up to the front porch, where seating areas are present. Lush greenery and colorful flowers are visible in front of the stone boundary wall, complementing the vibrant exterior.

Home in Brewer's Hill

The Peacock Place w/ Shared Seasonal Outdoor Pool

Apartment rentals with outdoor seating

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.

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

4.89 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

4.94 out of 5 average rating, 145 reviews

The open-concept living area features a modern sofa with patterned pillows, a glass coffee table, and sleek cabinetry. Light-colored walls and recessed lighting enhance the spacious feel. A dining area with high chairs and a desk sits nearby, creating a functional and inviting space.

Apartment in Racine

The Hive 2BR Apt | Downtown w/Parking Spot

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

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

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.

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.

4.78 out of 5 average rating, 100 reviews

6BR Penthouse Loft Above Bakery | AC | Pool Table

Condo rentals with outdoor seating

4.98 out of 5 average rating, 163 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 Riverside Park

Private East Side Milwaukee flat with fenced yard

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

4.94 out of 5 average rating, 63 reviews

A charming two-story building is presented with white siding and a grey shingled roof. Large black awnings identify the Education & Conference Center and Virtual Office Suites. The entrance is framed by lush greenery, with outdoor seating areas featuring tables and chairs along the front.

Condo in Delafield

DElafield Rivers Gateway Luxurious Condo

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, 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.

Condo in Bay View

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

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.

4.93 out of 5 average rating, 201 reviews

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