Shorewood vacation rentals

4.94 out of 5 average rating, 254 reviews

A charming red farmhouse is set against a colorful sky at sunset, surrounded by a picturesque yard filled with wildflowers. The property features a wooden fence and mature trees, contributing to a serene rural atmosphere.

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, 140 reviews

An outdoor patio area features a circular fire pit surrounded by four chairs on a stone surface. The lawn is well-maintained, bordered by wooden fencing with greenery in the background, enhancing the outdoor space's charm.

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, 255 reviews

The exterior of a two-story duplex is presented, featuring a welcoming porch with white railings. A driveway with a parked vehicle leads to the side of the house. The well-maintained yard displays greenery, and the structure is flanked by neighboring homes.

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, 433 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

An open-concept living space is highlighted by vaulted ceilings and a spiral staircase leading to an upper level. Natural light floods in through multiple arched windows. Elegant furnishings are arranged for communal gatherings, while a dining area offers ample seating alongside a cozy lounge.

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

A compact bathroom features a bathtub with an overhead shower. Natural light filters through a glass block window. A small sink and cabinet provide storage, while a towel hangs from a rack. Neutral tones and a bath mat add to the functional design.

4.83 out of 5 average rating, 272 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, 128 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.

4.96 out of 5 average rating, 125 reviews

An outdoor space features a large hot tub surrounded by lush green grass. Several lounge chairs are positioned nearby, while a picnic table and dining setup can be seen farther in the yard. A large patio area adjoins the house, creating an inviting environment.

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, 116 reviews

A comfortable living room features a spacious sectional sofa, a flat-screen TV mounted above a white gas fireplace, and large windows allowing ample natural light. Indoor plants and decorative items add a touch of greenery and warmth to the space.

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, 254 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.

4.99 out of 5 average rating, 342 reviews

The exterior of a two-story duplex is presented, featuring a green facade with multiple windows. A welcoming porch with railings is visible, adorned with potted plants. The yard is grassy and bordered by a sidewalk, with a driveway leading to a detached garage in the background.

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.

4.77 out of 5 average rating, 153 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

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Popular amenities for Shorewood vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Shorewood's top sights

Café Corazón100 locals recommend

Colectivo Coffee - Humboldt47 locals recommend

Estabrook Beer Garden35 locals recommend

Art Bar34 locals recommend

Sprecher Brewing Co., Inc.31 locals recommend

University of Wisconsin-Milwaukee28 locals recommend

Shorewood condominium rentals

4.98 out of 5 average rating, 199 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

4.98 out of 5 average rating, 47 reviews

Condo in Riverwest

2BR • 10 mins Downtown, Lakefront • King Beds

4.91 out of 5 average rating, 33 reviews

A spacious living room is featured with a modern sectional sofa and coffee table. Natural light enters through two windows and glass doors that open to a patio. A decorative rug complements the hardwood flooring, while wall art adds a subtle touch of elegance.

Condo in Brewer's Hill

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

4.92 out of 5 average rating, 280 reviews

Condo in Shorewood

English Tudor - Upper Flat blocks from the beach

4.95 out of 5 average rating, 132 reviews

A modern arena is prominently displayed with a sleek glass facade and a distinct curved roof. Surrounding landscaping includes trees and paved areas, creating an inviting environment for visitors. The building's name is clearly visible, signifying its importance as a local entertainment venue.

Condo in Milwaukee

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

4.99 out of 5 average rating, 217 reviews

Condo in Bay View

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

4.86 out of 5 average rating, 65 reviews

A modern kitchen features a spacious white countertop with two upholstered stools. Red pendant lights hang above, illuminating the area. New stainless steel appliances are visible, alongside cabinets with a sleek black backsplash. A doorway leads to another room in the background.

Condo in Bay View

Spacious Bay View Historic Storefront Apartment

4.89 out of 5 average rating, 54 reviews

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

Relaxing 2-bedroom upper unit close to everything

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Other great vacation rentals in Shorewood

4.89 out of 5 average rating, 114 reviews

A spacious patio area features multiple turquoise chairs arranged around a fire pit, complemented by a grill nearby. The setting is surrounded by lush greenery and tall trees, creating a serene outdoor space for relaxation.

Home in Muskego

Muskego Hideaway on 2 Acre Lot

4.94 out of 5 average rating, 16 reviews

An outdoor patio area is featured, equipped with a round table and six black metal chairs. A multi-colored striped umbrella provides shade. Lush greenery and flowering plants are visible in the background, with a stone retaining wall and steps leading to a raised garden area.

Home in Whitefish Bay

Whitefish Bay Getaway; next to Starbucks!

4.92 out of 5 average rating, 60 reviews

The entryway features a wooden staircase with a decorative chandelier above. A small table and lamp are positioned to one side, while light-colored hardwood floors complement the cream walls. Views of a living area and a dining space are visible through open doorways.

Home in Mequon

Mequon Wedding Retreat

4.89 out of 5 average rating, 19 reviews

Home in Milwaukee

Milwaukee's Heights retreat

4.91 out of 5 average rating, 57 reviews

A stylish living room features a grey sectional sofa and an orange accent chair. A round mirror is mounted on a bold, patterned blue wall, while a light fixture stands beside the seating area. A geometric area rug and small coffee table complete the space.

Home in Lower East Side

Walk to Brady St-Family Friendly-ModernVictorian

5 out of 5 average rating, 23 reviews

A carefully landscaped exterior showcases a charming craftsman home, featuring a stone façade and a welcoming entryway. Lush greenery surrounds the property, including large hostas and colorful plants. A spacious deck sits above the garage, offering outdoor seating and a view of the vibrant landscaping.

Home in Wauwatosa

The Mayfair Midcentury

4.69 out of 5 average rating, 29 reviews

The image captures a serene lakefront view with a wooden dock extending into the calm water. Beside the dock, two chairs are positioned for relaxation. Sunlight filters through the trees, creating a warm atmosphere over the grassy yard, with a winding path leading down to the lake.

Cabin in Wind Lake

A Place in the Sun 2 on Wind Lake