Condo vacation rentals in Shorewood

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Top-rated condo rentals in Shorewood

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Top guest favorite

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

4.98 out of 5 average rating, 227 reviews

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

Our 3 bedroom parkside condo in a beautiful historic renovated home is unique, peaceful, and near everything Bay View has to offer. Enjoy views of Lake Michigan from the front porch and dining room. Secret Vintage Lounge downstairs with antiques from all over the world is the perfect unique space - there is nothing else like this in Milwaukee! This 1st floor condo has perfect proximity to South Shore Park on Lake Michigan - Just a minute walk away from South Shore Beach and a lakefront trail.

Guest favorite

A spacious living area is highlighted by a plush brown tufted sofa facing a glass coffee table. Natural light filters in through large windows draped with sheer curtains, while houseplants add a touch of greenery. A ceiling fan and exposed brick wall enhance the room's character.

Condo in Walker's Point

5 out of 5 average rating, 24 reviews

Dakota Gal Digs | King Sally

Welcome to The Bentley on 6th in beautiful and historic Walker's Point, Milwaukee. You will find yourself in a newly renovated building (Est. 1892) that has 4 separate condos. This listing is our stacked upper and lower condos. Both offer 2 large bedrooms (w/ 2 rollaway twins), 1 bath, a full kitchen, a garage, and a lovely fenced in backyard to enjoy. There are live plants, great vintage pieces, and cozy touches throughout. You will get the city feel while also having peace, quiet and privacy.

Superhost

An expansive living area features high ceilings and large windows, allowing natural light to fill the space. A sectional sofa is arranged around a central coffee table, complemented by a patterned area rug. The kitchen with wooden cabinetry and barstool seating overlooks the gathering area.

Condo in Brewer's Hill

4.84 out of 5 average rating, 57 reviews

Brewers Hill Belle, 2 bed + Loft & balcony

Discover the perfect blend of style and comfort in this expansive top-floor unit! Featuring a sleek open layout, upscale appliances, and a bonus loft—ideal for extra guests or peaceful relaxation. Enjoy the convenience of a private garage and a spacious yard, perfect for gatherings and outdoor fun. Unwind on the balcony while soaking in the charm of historic Brewer’s Hill. Whether you’re walking, biking, riding The Hop, or driving, you’re just minutes away from Milwaukee’s premier attractions!

Guest favorite

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

4.98 out of 5 average rating, 130 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.

Guest favorite

A well-maintained brick condominium is featured, with a welcoming entrance comprised of steps leading to a front porch. A manicured lawn surrounds the home, adorned with leafy trees and shrubs. Soft sunlight filters through the foliage, creating a serene outdoor atmosphere.

Condo in Milwaukee

4.84 out of 5 average rating, 123 reviews

Full Condo&Garage in Trendy Bay View Milwaukee

This practical and cozy condominium is located in the heart of Bay View right on historic KK Avenue. It is next to the quaint Morgan Park and a bus stop, across the street from Sprocket Cafe, minutes from the lake and walking distance from the greatest trendy shops, bars, restaurants, and other Bay View classics. Whether you are totally new to the Milwaukee scene or just visiting "home", we are glad to welcome you to this charming condo, perfectly placed to meet all your traveling needs.

Top guest favorite

A light-filled sitting area features a gray sofa adorned with two blue throw pillows, complemented by a yellow armchair. A wooden chair offers additional seating, while a flag in warm colors hangs on the wall. Natural light filters through two windows with wooden blinds.

Condo in Walker's Point

4.98 out of 5 average rating, 213 reviews

"Perfect" | Spotless Private Studio Walker's Point

5-star reviews and SuperHost! Immaculately clean and newly renovated studio on an exciting street. Easy self check-in process. INDOOR PARKING INCLUDED A few blocks from the Harley Davidson Museum, Great Lakes Distillery and dozens of MKE's hottest restaurants breweries and night spots. Fast Uber/Lift pick-up. Walk to 3rd Ward and downtown. Bike share just outside the door. Walker's Point is an original settlement that became MKE, cool mix of industry, residential and entertainment.

Guest favorite

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.

Condo in Riverwest

4.98 out of 5 average rating, 52 reviews

Riverfront 2BR • Outdoor Oasis • King Beds

Welcome to Riverwest Vienna, a 2-bedroom WATERFRONT condo (UPPER) located in the Riverwest neighborhood 4 outdoor spaces (shared) • Large deck overlooking the Milwaukee river ☀️ • Patio with picnic table ☕ 🍺 • Front porch • Back lawn Space is newly rehabbed inc. A/C + Tempur-Pedic KING beds + Free Parking + all of the essentials you need Breweries, coffee shops, restaurants all within walking distance. Central to Fiserv Forum, Summerfest, Downtown, Lake Michigan, 3rd Ward, UWM

Superhost

The exterior of a classic Lannon-stone home is showcased, featuring a distinct gabled roof and an inviting entryway. Flowerbeds with colorful blooms line the front, complemented by an American flag displayed by the door. Shade is provided by large trees on the property.

Condo in Milwaukee

4.88 out of 5 average rating, 60 reviews

Relaxing 2-bedroom upper unit close to everything

Quiet, pet-friendly upper unit in a classic Milwaukee Lannon-stone home. Across from a country club and a couple blocks from beautiful Brown Deer Park, this comfy apartment is a wonderful jumping off spot for any Milwaukee visit. We are 15 minutes from the Deer District and downtown Milwaukee, 15 minutes to Miller Park, and 20 minutes to Summerfest grounds. Take a drive to surrounding areas-- 20 minutes to Cedarburg, 25 minutes to Port Washington, and 35 minutes to scenic Holy Hill.

Guest favorite

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

4.92 out of 5 average rating, 286 reviews

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.

Guest favorite

A cozy living area features a comfortable gray sofa adorned with a welcoming cushion. A coffee table sits in the center, accompanied by decorative plants. An elegant dining space is visible in the background, highlighted by a stylish light fixture and a large mirror reflecting natural light.

Condo in Milwaukee

4.89 out of 5 average rating, 19 reviews

Hilltop House - Escape

Your cozy and convenient getaway—just minutes from the heart of the city! This comfortable, thoughtfully designed space is perfect for small groups or families. With a pull-out couch, it sleeps up to 4 guests. This is one of four private units — like a boutique hotel, but way homier and with more amenities. You’ll enjoy a stocked Keurig coffee maker, free WiFi, in-unit laundry, and a full kitchen. Whether you're here for work or play, you'll feel right at home.

Top guest favorite

A wooden shelving unit features various decorative items, including a gold-colored radio and a small stack of books. A woven planter with lush green leaves rests on the shelf, accompanied by a pair of decorative bird figurines perched on a branch.

Condo in Milwaukee

4.98 out of 5 average rating, 252 reviews

Penthouse • Fiserv, Bars, Perks & Big City Views

Spacious, cozy penthouse in the heart of Downtown Milwaukee! Located on vibrant Old World Third Street, you’re steps from historic charm, bars, and dining (including one right in the building). Enjoy a chef’s kitchen, plush bedding, and fast Wi-Fi. We also offer exclusive add-ons—like celebration setups, food & drink packages, and local experiences—to make your stay truly unforgettable. Let us know what you need for a 5-star stay!

Superhost

A modern kitchen features sleek black cabinetry and open shelving, showcasing white dishware. A spacious island with wooden countertop is accompanied by four wire bar stools. The dining area includes a sturdy, dark wooden table, complemented by a potted plant for a touch of greenery.

Condo in Historic Third Ward

4.87 out of 5 average rating, 451 reviews

Luxury 3rd Ward Condo - w/ parking / exec/ family

This is a top of the line one bedroom 1000+ sq foot condo in the heart of the Artistic and Posh Third Ward. There are only 31 units in the Atelier building. The space is immaculate and decorated with high end furnishings. This place is perfect for solo business executive in town for a short few weeks (or months) or up to a family of 4 to 6 that wants to experience all of what downtown offers