Shorewood vacation rentals

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, 432 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.

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

The exterior of a charming house is framed by lush greenery and blooming flowers. A welcoming pathway leads to a set of steps that rise to a spacious porch, featuring a balcony above. Sunlight filters through the surrounding trees, creating a serene atmosphere.

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, 124 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

4.98 out of 5 average rating, 114 reviews

A spacious bedroom features a large bed with neutral linens and decorative pillows. Two bedside lamps are placed on either side. A dresser stands against one wall, while a wall-mounted television is positioned opposite the bed. Natural light enters through multiple windows, enhancing the room's brightness.

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, 341 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

4.9 out of 5 average rating, 147 reviews

A comfortable living area is highlighted by a soft sofa and armchair, accompanied by a stylish coffee table. A wall display features a cityscape artwork, while a lamp provides warm lighting. Natural light enters through large windows, enhancing the welcoming ambiance.

Home in West Allis

KING BED/Amazing Location/Free parking/Wi-Fi

Enjoy a fun and relaxing stay with family or friends in this stylish, cozy, and comfortable lower unit, which features: 2 bedrooms (1 king, 1 queen ) 1 bathroom Fully equipped kitchen with dining table and designated coffee bar Living room with a 65” smart TV (Netflix included) Home office space Free parking spot Located just a short drive (4 min) from I94, this home offers easy access to all the city's major attractions * the ideal base for exploring the best of Milwaukee

4.97 out of 5 average rating, 100 reviews

A wooden signpost points the way to Bradford Beach within the Milwaukee County Park System. The beach is visible in the background, with sand and visitors enjoying the sunny day. Lush greenery surrounds the sign, enhancing the natural setting.

Home in Lower East Side

Blair House 1890

Amazing location! Beautiful, newly renovated 2BR upper floor of a duplex built in 1890 is your cozy launch pad to explore Milwaukee. Only steps from the many breweries, restaurants and shops on historic Brady St, this house is tucked away on a safe and quiet street with easy street parking. Relax outside under the shaded pergola or enjoy city views from the front porch. The location, great natural light, comfy bedrooms, and stylish decor- sets this house apart!

Vacation rentals for every style

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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 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.

4.76 out of 5 average rating, 21 reviews

Villa Near Lake Geneva | Close to the Airport

An outdoor tennis court is shown, featuring a smooth surface and clearly marked lines. Surrounding trees are visible, with a small clubhouse in the distance. The sky is overcast, lending a serene atmosphere to the area.

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

An outdoor seating area is positioned on a lush green lawn, facing the vibrant blue waters of Lake Michigan. Two chairs with orange cushions surround a small table, providing a serene spot to enjoy the scenic lake view.

Villa in Racine

4.74 out of 5 average rating, 74 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

4.89 out of 5 average rating, 57 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

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Shorewood condominium rentals

4.98 out of 5 average rating, 199 reviews

A clean hallway features wooden flooring and a simple light fixture. A large door opens to a stairway with wooden steps leading upward. The walls are adorned with a mix of textured wood and smooth concrete, creating a modern yet rustic aesthetic.

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, 32 reviews

Double glass doors open to a private patio with outdoor seating. Natural light floods the space, showing warm wooden flooring and a cozy seating area. The green trees outside provide a refreshing view, enhancing the indoor-outdoor connection.

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, 216 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

4.75 out of 5 average rating, 16 reviews

A well-organized kitchen area features open shelving with various items including a microwave, bottles of water, and a fire extinguisher. A window allows natural light to brighten the space, enhancing the countertop made of wood.

Home in Milwaukee

2 Bedroom Home close to downtown

4.84 out of 5 average rating, 25 reviews

The exterior of a charming brick building is showcased, featuring distinct architectural elements such as arched windows and a prominent turret. Greenery is presented in planter boxes, contributing to a welcoming atmosphere, while the surrounding sidewalk provides access to nearby businesses.

Apartment in Wauwatosa

10 Minutes from Downtown! The Highlands Hideaway

5 out of 5 average rating, 112 reviews

The kitchen features an open layout with a large central island that includes storage baskets underneath. Stainless steel appliances are present, along with a stylish countertop. Natural light streams through the windows, highlighting the warm wood accents and providing a bright cooking environment.

Bungalow in Bay View

Bay View, Private, Sunny, Garden, Bungalow

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!

4.93 out of 5 average rating, 88 reviews

A balcony features two contemporary white chairs positioned on a patterned rug. A view of the neighborhood showcases nearby buildings and greenery, with blue skies overhead.

Home in Bay View

2BR Sunny Upper in Prime Bay View - w/ Parking

Apartment in Saint Francis

The exterior of a two-story apartment building is presented, featuring a combination of red and gray siding. A welcoming deck area with white furniture overlooks a snow-dusted parking lot, captured under soft evening light. Decorative string lights add a warm touch to the ambiance.

4.85 out of 5 average rating, 300 reviews

Cozy Apartment Nestled Across from Lakefront!