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Whitefish Bay vacation rentals

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Top-rated vacation rentals in Whitefish Bay

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Home in Shorewood

4.91 out of 5 average rating, 131 reviews

The Prospect House - 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 lower duplex house featuring a fully equipped kitchen, bright living space, classic creaky wood floors, comfy accommodations for 6. There's a variety of things to do in MKE including award winning dining, pro Sports, Brewery tours, music festivals and more! Indoors or outdoors, the fun is endless!

Guest suite in Brookfield

5 out of 5 average rating, 210 reviews

In the Canopy (beautiful Brookfield/Milwaukee)

Relax “in the Canopy” of beautiful maples! If you’re looking for party central…this isn’t it. But if you want a comfortable place in a tree-filled neighborhood, just a few minutes from all the best Milwaukee has to offer, you’re in luck! Perfect location for quick access to the city—or to Lake Country to the west. Quiet, comfortable, safe, surrounded by beautiful gardens. We’re in a perfect launching spot to visit Summerfest, Brewers/Bucks games, or Milwaukee's western suburbs. Bring the kids!

Guest suite in Upper East Side

4.97 out of 5 average rating, 184 reviews

THE JUNGALOW- a Milwaukee Craftsman Treasure!

Welcome to our 1924 Craftsman Bungalow! Marrying Prairie House style with the innovations of the Chicago Craftsman, our brick bungalow is awaiting your stay. You'll enjoy the upper suite, with private entrance, two bedrooms, kitchen, and full bath. Newly redone porcelain marbled floors inspire luxury with each step, along with the new 'Article' sectional, 50" TV with streaming, 100% Cotton bedding and towels, a kitchen full of perks and appliances, and lush greenery to keep the air clean.

Home in Wauwatosa

4.98 out of 5 average rating, 203 reviews

Wauwatosa/Milwaukee “Inglewood Place”Best Location

Great location near all Milwaukee attractions. Cozy upper two bedroom duplex with keyless entry in quiet Tosa. Extras such as ironed sheets, snacks and personal items are included. Walk to popular bars and restaurants in the village and along North Ave. Full kitchen and new beds make this a home away from home. 10 min to Froedtert & The Medical College of WI & Children’s Hospital of WI. Near Am Fam Field (Brewers stadium) and the lakefront. 4 miles to downtown Milwaukee. COME STAY WITH U

Rental unit in Wauwatosa

4.98 out of 5 average rating, 325 reviews

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.

Condo in Shorewood

4.92 out of 5 average rating, 277 reviews

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.

Rental unit in Germantown

4.93 out of 5 average rating, 124 reviews

1853 Farmhouse Apartment

Welcome to a two-bedroom apartment. The space includes a private bathroom, kitchen and living area. There is no kitchen/dining table. The apartment is on the second floor of the house and has an outside staircase leading up to it. The entrance/staircase is not shared by the hosts and there are no shared spaces in the home. The staircase may be steep for persons who have difficulty navigating stairs. Guests are welcome to use the patio area on the property.

Rental unit in Upper East Side

4.96 out of 5 average rating, 293 reviews

East Side Home

Upper flat located on Milwaukee's Historic East Side! We hope your stay with us feels like home. Spacious layout for most any kind of group. Stones throw to UWM, Lake Park, and Historic Downer Avenue shopping. Ten minute drive to downtown Milwaukee. We have been so lucky to have great guests, and we are constantly looking to improve your time here. If there is anything you might want for your trip please ask and we will do our best to accommodate.

Rental unit in Walker's Point

4.98 out of 5 average rating, 148 reviews

Cozy Dig w/ a view in the heart of Walker's Point

Cream City historical brick building with incredible views of signature landmarks of Walkers Point. Cozily designed space by interior designer to make a romantic getaway or personal solo retreat to concentrate on your higher purpose. Very safe building and walking distance from foodie restaurants, breweries, jazz clubs, and the famed Iron Horse hotel. A perfect getaway for you and yours.

Rental unit in Milwaukee

4.93 out of 5 average rating, 229 reviews

Flexhome Brewery District M4 - Fiserv+Gym+Parking

This Flexhome is situated in one of Milwaukee's most historic buildings, the old Pabst malt house. Architectural features include original Cream City brick, exposed beams, arched windows, and city skyline views. The building is fully loaded with amenities including a fitness center, theater, work/study booths, and a game lounge with darts, pool, and bags (otherwise known as cornhole).

Home in Milwaukee

4.99 out of 5 average rating, 215 reviews

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.

Home in Whitefish Bay

4.98 out of 5 average rating, 115 reviews

3 BDR Home with places to see, things to do!

3 bedroom, sleeps 6, 1.5 bath, full kitchen, newly added laundry washer/dryer, dining room, family living area with gas fireplace. You are minutes away from downtown Milwaukee. Walking distance to the scenic shores of Lake Michigan, Whitefish Bay or Shorewood business district. It is fully furnished to enjoy your home away from home.

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Popular amenities for Whitefish Bay vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Whitefish Bay's top sights

Bayshore76 locals recommend

Atwater Park58 locals recommend

Kopp's Frozen Custard51 locals recommend

Estabrook Beer Garden35 locals recommend

Sprecher Brewing Co., Inc.31 locals recommend

Outpost Natural Foods - Milwaukee26 locals recommend

Other great vacation rentals in Whitefish Bay

Rental unit in Shorewood

5 out of 5 average rating, 30 reviews

Cozy 3BD in Shorewood!

Home in Shorewood

5 out of 5 average rating, 11 reviews

Lovely 3 bed near Lake Michigan

Home in Milwaukee

4.88 out of 5 average rating, 8 reviews

Cozy home on a quiet block

Rental unit in Shorewood

5 out of 5 average rating, 19 reviews

Trendy, new condo next to the Beach w/ 2 FREE Pkg

Home in Shorewood

5 out of 5 average rating, 13 reviews

Beautiful 4BR Home-Walk to Beach

Home in Milwaukee

4.99 out of 5 average rating, 70 reviews

East Side 2nd floor Gem

Home in Shorewood

5 out of 5 average rating, 24 reviews

Charming Mediterranean Lower Flat

Home in Wauwatosa

4.94 out of 5 average rating, 47 reviews

Brew City Boho - Wauwatosa

Quick stats about vacation rentals in Whitefish Bay

Total rentals
50 properties
Total number of reviews
790 reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Whitefish Bay?
Yes! Work meets play with ease at over 20 vacation rentals in Whitefish Bay featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Whitefish Bay?
Four-legged friends are welcome in Whitefish Bay. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there family-friendly house rentals in Whitefish Bay?
Whitefish Bay has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Whitefish Bay have wireless internet?
Absolutely! We offer over 40 house rentals with wireless internet in Whitefish Bay. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Whitefish Bay have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Whitefish Bay. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Whitefish Bay?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with wireless internet, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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