Apartment holiday rentals in Shorewood

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Top-rated apartment rentals in Shorewood

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Superhost

Apartment in Brewer's Hill

4.91 out of 5 average rating, 34 reviews

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

Welcome to your perfect getaway in the heart of Milwaukee! This bright and airy 2nd-floor condo offers 1600 sq ft of stylish, open-concept living—ideal for a relaxing stay with family or friends. The spacious kitchen, cozy living room, and inviting dining area are perfect for unwinding after a day of exploring the city. Step outside onto the private balcony to enjoy the views of the peaceful Brewer’s Hill! Don’t miss the sunlit reading nook, a perfect spot for soaking in the neighborhood vibes.

Superhost

Apartment in Bay View

4.99 out of 5 average rating, 218 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.

Superhost

Apartment 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

Apartment in Lower East Side

4.97 out of 5 average rating, 117 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.

Superhost

Apartment in Milwaukee

4.82 out of 5 average rating, 111 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.

Superhost

Apartment in Walker's Point

4.98 out of 5 average rating, 199 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.

Superhost

Apartment in Riverwest

4.98 out of 5 average rating, 47 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

Apartment in Milwaukee

4.89 out of 5 average rating, 54 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.

Superhost

Apartment in Shorewood

4.92 out of 5 average rating, 281 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.

Superhost

Apartment in Milwaukee

4.82 out of 5 average rating, 310 reviews

2 Bedroom condo w/ king beds/Free parking/downtown

This luxury condo is in the heart of downtown Milwaukee close to theaters, Riverwalk, Summerfest grounds, and Theaters. It features an unmatched location with 2 kings size beds in each room, a pull out queen sofa, a fully furnished kitchen, an in unit washer and dryer, and includes a parking space. We can accommodate up to 8 guests for the night. This includes a parking pass for one car, addition cars can park in the garage at posted prices.

Superhost

Apartment in Milwaukee

4.95 out of 5 average rating, 132 reviews

Luxe 3rd St Condo • Fiserv + Perks & Add-Ons!

Escape to our cozy, spacious retreat in the heart of Downtown Milwaukee. Located on vibrant Old World Third Street, you’re steps from bars, restaurants, and historic charm. Enjoy plush bedding, a full kitchen, fast Wi-Fi, and stylish decor. We also offer exclusive add-ons—like curated food & drink packages or celebration setups—to make your stay extra special. Let us know how we can help create a 5-star experience!

Superhost

Apartment in Milwaukee

4.95 out of 5 average rating, 20 reviews

Hilltop House - Loft (2nd floor w/ balcony - 05)

Welcome to your home away from home! This charming two-bedroom rental is perfect for couples, families, or small groups looking for a comfortable and convenient stay. Each bedroom is thoughtfully furnished for a restful night’s sleep, and the shared spaces are designed to help you relax and recharge. Located in a prime spot, you'll be just a short distance from local restaurants, shops, and attractions.