Vacation rentals in Shorewood

4.84 out of 5 average rating, 139 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, 130 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!

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

A vintage, lower flat in a 100-year-old duplex with modern comforts and conveniences. Perfect for short or long stays while visiting Milwaukee. Situated in the walkable/bikeable Milwaukee neighborhood of Shorewood. The flat is located just a few blocks north of UWM and a few blocks east of the Oak Leaf Trail. Three minutes from Atwater Beach. Ten minutes or less to Bradford Beach, museums, and Summer Fest. Fifteen minutes or less to Fiserv Forum, Panther Arena, and American Family Field.

4.92 out of 5 average rating, 285 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 exterior of a large, modern arena showcases a distinctive curved roof. The building features a combination of glass and metallic surfaces, with a prominent digital display on one side that features images of players. Landscaping with minimal shrubs is visible at the entrance.

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.

4.91 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, 110 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.

4.95 out of 5 average rating, 243 reviews

An open area connects the living room and dining space. A dining table with wooden chairs is positioned under unique lighting fixtures. The kitchen is visible in the background, featuring yellow cabinetry. Natural light filters through multiple windows, illuminating the wooden floors.

Apartment in Riverwest

Comfortable Riverwest apartment

Open, modern space in older home. Airbnb is located on the first floor, basic amenities are included. The family lives upstairs with very active kids that can be loud at times. Walking distance to coffee shops and neighborhood businesses, buses, downtown and the Milwaukee river. Street parking.

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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

4.96 out of 5 average rating, 47 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 stars4 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, 5 reviews

An outdoor dining area features a long table set with plates and glasses, surrounded by inviting seating options. A pergola overhead is adorned with string lights, casting a soft glow. Lush greenery lines the yard, and a fire pit is positioned nearby.

Home in Whitefish Bay

Whitefish Bay Beauty!

CharlesRating, 5 stars11 months ago

Beautiful home in a great area of town. Close to downtown but away from the hustle and bustle. The back patio area feels like an oasis and a great place to unwind after the day. The house has everything you need for a wonderful family trip and I would definitely recommend it to anyone visiting the area

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, 33 reviews

Lovely 3 bed near Lake Michigan

JennileeRating, 5 stars4 days 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 fire pit is surrounded by decorative stones, with flames dancing above. Two black chairs are positioned nearby, and string lights create a warm ambiance in the backyard. Soft greenery and a wooden table are visible in the background, enhancing the outdoor setting.

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.

4.94 out of 5 average rating, 79 reviews

A charming bungalow showcases a brick facade with arched windows and a welcoming front porch. Colorful bunting and small flags adorn the entrance, while well-maintained greenery and a manicured lawn enhance the exterior appeal. A large tree provides shade to the front yard.

Apartment in Riverwest

Charming Bungalow Unit Just North of Downtown Milw

EmilyRating, 5 stars1 week ago

Mary Anne's place was a perfect spot to relax on a weekend trip to Milwaukee. It was just as pictured, very tidy, and Mary Anne was friendly and helpful throughout the weekend. Would stay again!

5 out of 5 average rating, 33 reviews

Beautiful 4BR Home-Walk to Beach

NicoleRating, 5 stars3 days ago

the house was perfect! great neighborhood and a close walk to coffee shops, plus the beach is right nearby. A group of 9 of us stayed for the weekend and it didn't feel crowded at all. I would absolutely recommend this place to anyone and will be coming back next summer!

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.