Shorewood vacation rentals

4.94 out of 5 average rating, 254 reviews

Guesthouse in Richfield

Peaceful weekend or extended stay, full amenities

The Country Retreat at the historic Schmitz Family Farm is close to many attractions, ideal for couples, families, girls' weekends, extended stays, business travel, and is dog friendly. Enjoy a sunrise or sunset, get cozy at the fireplace, or indulge in the many activities our area has to offer. We feature two beautiful bedrooms, living room with two sleeper sofas (can also be used as a third bedroom, as door closes for privacy), laundry room, full kitchen, coffee nook, quiet deck and backyard.

4.97 out of 5 average rating, 143 reviews

Home in Thiensville

Quaint & Cozy Town Cottage Desirable N. Shore

Adorable small Town Cottage walkable to coffee shops, restaurants, parks & the riverwalk…bring the pup and experience something sweet. Everything you need to get away, business trip or extended stay. Well appointed kitchen, 2 small but cute baths with heated floors(1) and fast WiFi. Urban-like walk-ability w/ small town charm! Walk to (excellent) authentic Himalayan food at the Cheel or a glass of wine at Glaze and paint a new coffee mug! Go out or kick back with the fire/grill and s’mores!

4.88 out of 5 average rating, 258 reviews

Guest suite in Bay View

Vibrant 2BR Hillside Hideaway in charming Bay View

2nd floor of 1921 duplex in Milwaukee's lively Bay View neighborhood. Walk to restaurants or take a short bike ride or car ride to local well-loved taverns. Downtown is a 5 minute ride on the highway. 2 bedrooms, a cozy living room, and an eat-in kitchen. Beautiful Lake Michigan and multiple award-winning Milwaukee County Parks nearby offer year-round scenic walks, and seasonal farmers markets, ice skating and live music. Close enough to the action of the city with the comfort of a quiet street.

4.86 out of 5 average rating, 438 reviews

Home in Hubertus

Bark Lake, Entire Home, Private Lake Frontage 50ft

A 1,700 sqft home with 3 bedrooms, 2 baths, sofa bed and couch, large outdoor deck, hot tub, grill, 50 feet of lake access. Enjoy the morning sunrise from the East and relax by the waterfront and watch the sunset on the West. Bring the family and enjoy some lake life where the days linger on longer. During the Summer months we have a pier available to fish off of. There are two fire pits, one by the lake and another tucked away near the house. You will love it here, it is very calm and relaxing.

4.89 out of 5 average rating, 231 reviews

The exterior of the home features a stately design with prominent arched windows and a welcoming entrance. Lush greenery surrounds the property, while the evening sky casts a warm glow, enhancing the peaceful ambiance of the space.

Home in Walker's Point

Historic Home Sleeps 16 in MKEs Best Neighborhood

MAX of 16 guests! This luxury home has been designed especially for groups to gather and connect in-person. The huge second floor has ample space to gather everyone around a chef's kitchen and walk-out patio, while floors 1 & 3 are for sleeping Walk or bike everywhere! Minutes to Downtown, Third Ward, Bay View, Summerfest, and the best restaurants, breweries, trails, and music/sports venues. Just 5 blocks from easy freeway access and 12 minutes from airport! 2 driveway parking spots included

Apartment in Lower East Side

4.82 out of 5 average rating, 274 reviews

Best location in Milwaukee! Lower Duplex Unit

LONG TERM STAYS WELCOME. Unit is right off Brady Street, One of the best streets in Milwaukee. Over 70 places to eat or drink within walking distance, including bars with free shuttles to brewers games and Summerfest. There are many shops and grocery stores in the neighborhood and everything you could possibly want is a short Uber ride away. Best enjoyed by up to six people whether they be couples, friends, solo adventurers, business travelers, families (with kids), and furry friends (pets).

4.95 out of 5 average rating, 130 reviews

A softly illuminated waterfall cascades over a stone ledge, creating a serene scene at night. Surrounding the waterfall, patches of snow contrast with dark rocks and frosty vegetation. Buildings can be seen in the background, adding depth to the tranquil landscape.

Home in Menomonee Falls

Exhale, rest

Exhale. The perfect combination. This home is right in the village of Menomonee Falls with great shopping and restaurants within walking distance. Close to the highway, it’s also a mere half an hour to anything Milwaukee so games, museums, festivals are all also at your fingertips. At the end of dead end road with views of the river, access to trails, and a secluded deck and fire pit, there is definitely also a rural feel. This location has it all. Go out, live life, come back, exhale and rest.

4.95 out of 5 average rating, 128 reviews

Home in Milwaukee

Downtown Oasis: Hot Tub, Garage, 2 King Huge yard!

Bring the whole family to this great place with lots of room for fun. A rock throw away to Milwaukee central featuring the city's best restaurants, bars, shops, and attractions. This exclusive 1800sqft Ranch 3 bedrooms, 9 beds, 2 full and 1 half bathrooms to sleep up to 14 guests. It features everything your family & friends need: Large Kitchen, Wash/Dry, Outdoor Patio, large back yard and a 8 person Hot Tub! Walking to the Fiserv Forum and downtown. Attached Garage w/ Driveway. 1 Gig Internet

4.97 out of 5 average rating, 118 reviews

Condo in Lower East Side

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.

4.85 out of 5 average rating, 256 reviews

A well-maintained backyard features a stone fire pit surrounded by seating. Beyond, a scenic view of Lake Michigan is visible, dotted with various boats. The grassy area is framed by lush greenery, creating a serene outdoor space for relaxation.

Apartment in Bay View

Lakeside Beauty

Stunning lower duplex on Lake Michigan in beautiful Bay View WI. Exceptionally large 2 bedroom unit boasts back yard overlooking Lake Michigan with fire pit for cozy evening fires. Unit is a mix of new and classic vintage. Walking distance to South Shore Yacht Club, South Shore Terrace Beer Garden, Award Winning restaurants, a unique European grocery store, and the second largest Farmer's Market in the state. Seven minutes to downtown Milwaukee. Owner lives upstairs. Two bikes available.

4.98 out of 5 average rating, 346 reviews

Apartment in Wauwatosa

Great Location, Wauwatosa (upper unit)

This bright & super clean upper (19 stairs) 2 bedroom duplex is in the heart of East Tosa. ( bel air cantina, cranky al's, rocket baby, rosebud theater, il mito, north ave. grill, camp bar and micro brewery within 1/2 a block to 4 blocks of this house) Centrally located for quick access to Medical College/Froedert, Miller park, Milwaukee County Zoo, Downtown, Harley Museum, Milwaukee Art Museum & Summerfest/lakefront festival grounds. 1 space off street parking. Bublr & bus stop nearby.

4.78 out of 5 average rating, 157 reviews

A long horizontal painting hangs on a beige wall, depicting gentle waves and three sailboats on a serene blue sea. The sky is bright with soft clouds, and the shoreline features scattered birds, creating a calming coastal scene.

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 spot with plenty of parking on premises (up to 3 cars!) Amenities include: - Parking - TV - WiFi - Self Check in - Fresh Sheets and Towels - Additional Pillows - Shampoo & Conditioner - Soap & Hand Sanitizer - Fully Stocked Kitchen

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Popular amenities for Shorewood vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Shorewood's top sights

Café Corazón10 locals recommend

Colectivo Coffee - Humboldt8 locals recommend

Estabrook Beer Garden5 locals recommend

Art Bar4 locals recommend

Sprecher Brewing Co., Inc.9 locals recommend

University of Wisconsin-Milwaukee4 locals recommend

Shorewood villa rentals

The exterior of the resort showcases a modern building set against a colorful sunset. Tall grass and shrubs line the foreground, while the lush green golf course stretches out in front. Warm lights glow from the windows, enhancing the serene atmosphere of the surroundings.

4.77 out of 5 average rating, 22 reviews

Villa Near Lake Geneva | Close to the Airport

The living area features a gas fireplace, a white sofa with decorative pillows, and a wooden entertainment unit. A flat-screen TV is mounted above the fireplace. The open kitchen area is visible in the background, equipped with white cabinets and essential appliances.

4.9 out of 5 average rating, 58 reviews

Interlaken Villa w/ Patio, Steps to Ridge Resort!

A stone entrance gate with a tower stands at the beginning of a well-maintained road. Lush green trees line both sides of the driveway, providing a natural frame for the welcoming entryway to the resort.

4.89 out of 5 average rating, 76 reviews

2 Bedroom Villa at Lake Geneva's GRAND Resort

A lush green lawn extends toward the lake, bordered by vibrant shrubs and trees. Two outdoor chairs are positioned to face the water, inviting relaxation while enjoying the serene lake views. The expansive sky above reflects a calm atmosphere, enhancing the outdoor space.

Villa in Racine

4.76 out of 5 average rating, 80 reviews

Wisconsin Lake Escape - A Mid Century Gem

An outdoor patio space is illuminated by string lights against a twilight backdrop. A fire pit occupies the center, surrounded by four chairs. The wooden railing features horizontal slats, adding texture to the setting, while large windows of the house reflect the warm glow.

4.87 out of 5 average rating, 30 reviews

Secluded 3 br Villa Patio BBQ, EV-Charger! Sleeps9

A glass gazebo features a comfortable green sofa and two round, brightly patterned chairs, arranged around a small table. Natural light fills the space, highlighting views of the surrounding greenery and outdoor hot tub through the large glass panels.

Villa in Delavan

4.9 out of 5 average rating, 59 reviews

Luxury Lake Geneva retreat w/hot tub on 2-acres

A large outdoor pool is surrounded by lounge chairs and shaded areas. The clear blue water reflects the sky, and the pool area is complemented by well-maintained landscaping. Nearby buildings with a relaxed architectural style provide a welcoming backdrop.

4.64 out of 5 average rating, 53 reviews

Villa Near Lake Geneva, close to Lake

4.92 out of 5 average rating, 36 reviews

The exterior of a mid-century modern tri-level home is showcased amidst a spacious green yard. Surrounding trees provide shade, contributing to the peaceful ambiance of the property. A large driveway is visible, accommodating multiple vehicles.

Villa in Hales Corners

Beautiful 6 bedroom with Heated Pool & Jacuzzi

Show all

Shorewood condominium rentals

4.98 out of 5 average rating, 201 reviews

The exterior entrance is characterized by modern design elements, featuring a large window displaying the interior space. A muted color palette of yellow and grey accents the building, with a simple door leading inside. Surrounding greenery adds a touch of nature to the urban setting.

Condo in Walker's Point

"Perfect" | Spotless Private Studio Walker's Point

4.92 out of 5 average rating, 196 reviews

Condo in Milwaukee

Old Wrld 3rd St/MLK - Downtown Milw (Fiserv Forum)

4.98 out of 5 average rating, 48 reviews

An inviting outdoor deck is positioned among lush greenery, featuring two chairs and a round table. A patterned rug covers the floor, and wooden stairs lead to an upper level, enhancing the connection to nature.

Condo in Riverwest

Riverfront 2BR • Outdoor Oasis • King Beds

4.91 out of 5 average rating, 34 reviews

Condo in Brewer's Hill

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

4.92 out of 5 average rating, 281 reviews

Condo in Shorewood

English Tudor - Upper Flat blocks from the beach

4.96 out of 5 average rating, 134 reviews

Condo in Milwaukee

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

4.99 out of 5 average rating, 219 reviews

Condo in Bay View

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

4.89 out of 5 average rating, 54 reviews

Condo in Milwaukee

Relaxing 2-bedroom upper unit close to everything

Show all

Other great vacation rentals in Shorewood

4.89 out of 5 average rating, 117 reviews

A modern dining area is shown with a wooden table surrounded by six light-colored chairs. Natural light enters through a large sliding glass door, leading to a backyard. Decorative elements include a chandelier overhead and a small plant centerpiece on the table.

Home in Muskego

Muskego Hideaway on 2 Acre Lot

4.86 out of 5 average rating, 29 reviews

Apartment in Wauwatosa

10 Minutes from Downtown! The Highlands Hideaway

4.97 out of 5 average rating, 98 reviews

An open-concept living area is featured, displaying a wood-burning fireplace and a flat-screen television mounted on the wall. A cozy seating arrangement, including a patterned chair and a wooden coffee table, is illuminated by natural light. Above, a loft area can be seen, accessed by a ladder.

Farm stay in Germantown

Lace & Woods Farm "Hammer Hideaway"

4.69 out of 5 average rating, 16 reviews

An entryway is captured, featuring a dark wooden front door with glass panels that allow soft natural light to flow in. A modern chair is positioned beside the door, adorned with a patterned cushion. A textured mat lies on the wooden floor, adding warmth to the space.

Home in Milwaukee

Central and Charming MKE Retreat

4.89 out of 5 average rating, 19 reviews

Home in Whitefish Bay

Whitefish Bay Getaway; next to Starbucks!

4.53 out of 5 average rating, 15 reviews

The city skyline is highlighted by modern architectural buildings, including a striking museum with a distinctive sail-like structure. Night lights reflect off the water's surface, creating a vibrant scene against the backdrop of urban life.

Home in Milwaukee

The Ultimate Family Suite 2! (Right unit)

4.92 out of 5 average rating, 60 reviews

A modern kitchen is featured with white cabinetry and granite countertops, illuminated by recessed lighting. Stainless steel appliances, including a refrigerator and a double sink, are present. The open layout connects smoothly to the dining area, enhancing accessibility for gatherings.

Home in Mequon

Mequon Wedding Retreat