Vacation rentals in Shorewood

4.84 out of 5 average rating, 138 reviews

A charming three-story flat with a welcoming front porch and multiple large windows. The light-colored facade is complemented by a neatly landscaped front yard. The balcony offers additional outdoor space, inviting relaxation and enjoyment of the surrounding neighborhood.

Townhouse in Shorewood

Gorgeous Shorewood stay by the Lake - Entire Flat

"This sunny 3bd lower flat is large enough to fit your whole family for your trip to Milwaukee. The bathroom is freshly renovated. We have been so lucky to meet the wonderful families and friends who have gathered here and called this space their home away from home. Walking distance to Village of Shorewood, UWM and Lake Michigan, and a short ride to the airport, Summerfest grounds, Harley Museum, the new Fiserv Forum, bars/restaurants/shopping, and much more. Baby friendly with Pack-and-play."

4.89 out of 5 average rating, 129 reviews

Home in Milwaukee

Good Land Home - Shorewood / Milwaukee, WI

From activities and attractions to fairs and festivals, Milwaukee, has something for everyone in your travel group! After each adventure-filled day, look forward to returning to this 3-bed, 1.5-bath upper duplex house featuring a fully equipped kitchen, bright living space, and comfortable accommodations for 6. There's a variety of things to do in Milw including award winning dining, pro Sports, Brewery tours, endless music festivals and more! Indoors or outdoors, the opportunities are endless!

4.95 out of 5 average rating, 329 reviews

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.

4.92 out of 5 average rating, 284 reviews

Condo 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.

A charming duplex upper features a well-maintained facade with dark wood siding and light-colored trim. A private balcony is visible on the second floor, and a landscaped front garden enhances the welcoming curb appeal. Steps lead up to the entrance, surrounded by greenery.

4.95 out of 5 average rating, 109 reviews

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, 106 reviews

Home in Milwaukee

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.

Townhouse in Upper East Side

The Milwaukee Public Market is illuminated at night, with its bold red neon sign prominently displayed. The market features a modern glass and steel structure, showcasing various shops and dining options, while surrounding streets are lightly lit, presenting a vibrant urban atmosphere.

4.99 out of 5 average rating, 121 reviews

Historic Gem|Steps to UWM|Lake Mich|Free Parking

🔹 5-Star Rated | Superhost Quality | Fast Wi-Fi | Free Parking 🔹 🏡 Experience a Slice of Milwaukee’s History in a 100-Year-Old Home! Step inside this charming first-floor retreat—a beautifully preserved prairie-style home blending historic elegance with modern convenience. Located right across from UWM, this top-rated Airbnb is perfect for visiting students, faculty, families, and travelers looking for a relaxing, walkable neighborhood.

4.83 out of 5 average rating, 150 reviews

The kitchen features a dining table with four gold-colored chairs and has beige walls. A black stove and microwave are present alongside a black refrigerator. Two doors are visible, leading to additional areas of the apartment.

Apartment in Riverwest

Mid-century Lower in Riverwest

This 2 BR duplex lower apartment is located in Milwaukee's Riverwest neighborhood, 2 miles directly north of downtown. It is furnished with many vintage mid-century furnishings, including a working HiFi. There is a garage space for your use during your stay, and ample street parking right in front making it easy to come and go. The kitchen has dishes, pots, pans, and all the utensils you will need during your time here.

4.91 out of 5 average rating, 651 reviews

Apartment in Milwaukee

Historic Lower East Side Apartment with Lake Views

This is one unit in a historical mansion with lake views! Layout is shotgun, open concept with a SMALL functional kitchen. Definitely gives off a pied-à-terre vibe. You have direct access to the back patio and a dedicated parking space around the corner. This unit is in the heart of the lower east side- close to the art museum, cathedral square, Brady st, 3rd ward, as well as the best restaurants and bars in MKE .

A welcoming front porch is visible, featuring two blue chairs positioned on a light grey surface. An entryway with a teal door is framed by arching details, and large windows allow for natural light. Decorative plants line the porch, enhancing the inviting aspect.

4.85 out of 5 average rating, 109 reviews

Modern, Comfortable and Updated in Shorewood!

Walking distance to bars, restaurants, coffee shops, parks and best of all... Lake Michigan! Extensive contemporary remodel with comfortable furniture and plush beds. If you'll need to get some work done we have a large desk and fast WIFI. Laundry is available for your use, located in the basement of home. Free & convenient street parking available in front of the home, always available!

4.99 out of 5 average rating, 239 reviews

A bottle of paraben-free lemon-scented hand soap is positioned beside a bathroom sink. The soap is contained in a clear pump bottle with a decorative label. Brown tiled walls create a retro backdrop, complementing the light-colored countertop.

Home in Milwaukee

Sunny Upper Flat in Shorewood Near UWM & Downtown

Beautiful two bedroom upper flat in Shorewood with great light. New carpet, pillow top mattresses, coffee brewer, and many more amenities. 5 minutes from UWM and close to lakefront, downtown, I43 and much more. A short ride to Summerfest grounds. Close to many restaurants of many different styles. You will feel at home in our cozy two bedroom flat.

4.9 out of 5 average rating, 150 reviews

The exterior of Black Husky Brewery is displayed, featuring large windows that invite natural light. Patio seating with red chairs surrounds a stone fire pit. Umbrellas provide shade over some tables, while greenery and decorative planters accentuate the space.

Apartment in Riverwest

Cozy Garden Apartment in Eclectic Riverwest

Stay in this cozy studio garden apartment located in the eclectic Riverwest neighborhood! Located within a block of neighborhood staples like Art Bar and Café Corazon and a quick 10 minute drive to downtown, this is the perfect spot for any visit to the Good Land! Ample street parking is available.

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Popular amenities for Shorewood vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Shorewood

4.98 out of 5 average rating, 46 reviews

The exterior of a two-story building features a brick façade with arched windows and a balcony. A flag is displayed on the left side, while colorful flamingo decorations are positioned in a landscaped area with greenery and flowers, enhancing the welcoming entrance.

Apartment in Shorewood

Cozy 3BD in Shorewood!

KeenaRating, 5 stars3 weeks ago

I was in town w my family for a reunion and we were all very happy to be together in this home. It was very spacious and the neighborhood was pleasant to stay in.

4.98 out of 5 average rating, 63 reviews

A kitchenette is equipped with a microwave and a coffee maker on a countertop. Above the appliances, open shelving displays brown plates, while a tray holds various snack items, creating a functional and easily accessible space for meal preparation.

Bungalow in Shorewood

Cozy Shorewood loft - quiet and near downtown!

KellyRating, 5 stars2 weeks ago

Robert's place is cute and charming and very welcoming. We appreciated the comfy beds! The neighborhood is quiet and close to everything we needed. We will stay here again on our next trip to Shorewood!

5 out of 5 average rating, 4 reviews

An outdoor seating area is arranged around a fire pit, featuring multiple chairs and a table. String lights hang overhead, illuminating the space. Lush greenery surrounds the area, creating a private and inviting atmosphere for outdoor gatherings.

Home in Whitefish Bay

Whitefish Bay Beauty!

TaylorRating, 5 stars11 months ago

This cute street is everything you are looking for a peaceful enjoyable getaway! This property is not just a rental property, but a home that is being shared by a wonderful host! The kitchen and backyard are fully equipped beyond expectations. This historical house has amazing charm and very comfortable beds. The backyard is a slice of heaven and a great retreat away. The host is very responsive and was able to tend to any request! I am a property manager with 19 properties in upstate NY and I only wish would be if this house was in my area so I could be part of this wonderful rental.

A coffee maker is positioned on the countertop beside a basket filled with assorted coffee pods. The coffee maker features a sleek design and a glass carafe, readily available for brewing a variety of beverages.

5 out of 5 average rating, 32 reviews

Lovely 3 bed near Lake Michigan

JennileeRating, 5 stars1 day ago

Amazing home! Very spacious, clean and had all the amenities we needed! Laurie was so kind to leave us some snacks, cheese, grapes, water, coffee and some beer from Wisconsin. Laurie’s place was perfect for the groomsmen getting ready for the wedding. We used the bakery that she recommended, delicious! Walking distance to coffee and restaurants. We will be staying at Laurie’s place again!

4.91 out of 5 average rating, 90 reviews

A cozy backyard patio is illuminated by twinkling string lights, creating an inviting atmosphere. Comfortable seating surrounds a fire pit, while a dining table is visible in the background. Lush greenery surrounds the space, adding a touch of nature.

Apartment in Shorewood

Charming home w/ fire pit, walk to Lake Michigan

KelliRating, 5 stars1 week ago

A return visit for us and it was great again - the location being walkable to so many restaurants, grocery and other stores as well as easy access to downtown Milwaukee cannot be beat. The design of the rental is comfortable and charming. We hope to return again.

The exterior of the vintage duplex features a striking dark blue facade, adorned with white trim and large windows. A covered front porch provides access, highlighted by a yellow and blue flag. Lush greenery surrounds the home, enhancing the inviting atmosphere.

4.99 out of 5 average rating, 100 reviews

The Menlo Guesthouse

EmilyRating, 5 stars1 day ago

Savannah’s home was PERFECT in every way! Absolutely no complaints. Not only was it so homey and decorated with such charm, but it was completely spotless - so clean! AND she had snacks waiting us, so sweet! We were walkable to things, had enough space for 5 of us, and just felt like we were in a cozy home for the weekend. If we return to Shorewood, this is exactly where I’ll be staying!

Large glass doors allow natural light to flood the room, framed by sheer curtains that gently sway in the breeze. A round coffee table is positioned in front, surrounded by a potted plant that adds a touch of greenery. The view outside displays a lush garden area.

4.79 out of 5 average rating, 43 reviews

Baby and Toddler friendly House by the Beach

BridgetRating, 5 stars9 months ago

We had a wonderful stay at Sitora’s house. The best house and location for ones with little kids. What a beautiful home. The distance to the beach was key for us. We enjoyed walking to both Atwood Park/beach and Shorewood nature preserve.