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Holiday Homes in Waukesha

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    Don't let other travellers get your favourite Waukesha area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 25 Rentals in Waukesha
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    Charming 3BR Waukesha Farmhouse w/Gorgeous Scenery1 / 25
    (1)Excellent
    Waukesha
    3 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    The following rentals are within 30 kilometres of Waukesha.
    Lake Michigan Tudor1 / 25
    (6)Excellent
    Milwaukee
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Beautiful Restored 1903 Victorian (close to Lake MI, UWM, Dntwn)1 / 31
    (4)Excellent
    Milwaukee
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Milwaukee
    2 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unbeatable location in the absolute heart of Brady Street, fine dining, nightlife, shopping, sports bars, etc. Come and stay at our charming house / You'll be within walking distance to the whole City! You’ll love our place because of the coziness, comfy hotel quality beds and clean bathroom. Our...
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    53202, Milwaukee, Wisconsin
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 10
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    Milwaukee
    2 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Brady Street home is the best option for corporate travel, bachelor/bachelorette, and family vacations to Milwaukee. The best part about our home is the location - you're 30 seconds from the hustle and bustle of Brady Street but our quiet neighborhood provides much needed peace and quiet when...
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    53202, Milwaukee, Wisconsin
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 10
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    Milwaukee
    3 Bedrooms, 2 Bathrooms, Sleeps 15 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A + Location! Literally the whole city is within walking distance and Brady St, where everything happens, is only a 4 min walk. There are tons of restaurants, bars, pubs, convenience stores and all that you can think of! If you're a beer lover our City has some of the America's largest breweries....
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    53202, Milwaukee, Wisconsin
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 15
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    West Allis
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Secure Parking
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Centrally located and minutes for all major attractions our home is a beautifully decorated 3 bedroom 1 bath lower unit of a Milwaukee style bungalow duplex. Home is equipped with 3 TVs fully stocked kitchen , modern bath with plenty of towels and linens, Great location and convenient to...
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    53214, West Allis, Wisconsin
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    Grandma's Cottage Bed and Breakfast1 / 10
    (3)Excellent
    Muskego
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Outdoor Dining Area
    • Hot Tub
    • Patio
    • Housekeeping Included
    • Air Conditioning
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2016
    We spent a week here for both of our birthdays & for our anniversary. Deb & Mike were very welcoming & wonderful. The breakfasts/brunches were wonderful. They gave us...
    Reviewed 1 July 2015
    We loved our stay at Grandma's Cottage. The cottage was beautiful and very comfortable. Deb & Mike are excellent host and hostess. They allow you your privacy but are...
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    About this property
    Set back from the road and main residence, the Cottage adjoins a 300 acre DNR conservancy, and is nestled amongst other buildings of our quiet hobby farm. It is the perfect setting for tranquility, romance and privacy. Located just a half hour from all the city of Milwaukee has to offer, yet on...
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    53150, Muskego, Wisconsin
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Oak Creek
    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • DVD Player
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Check the hustle and aggravation at the door. Our home features the warm, spacious, and comfortable feel of a family-friendly home, yet affords you the privacy of a hotel room. Come experience warm Wisconsin charm at its finest. Conveniently located right off the freeway~ less than 5 minutes from...
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    53154, Oak Creek, Wisconsin
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 13
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    Saint Francis
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in the trendy neighborhood of Bay View and enjoy the comforts of home in this lower duplex. Walking distance to restaurants and corner of South Shore Park/Beer Garden & 1 block from Lake Michigan beach. Enjoy beautiful walks/runs along the lakefront during the day and cocktails at night in the...
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    53207, Saint Francis, Wisconsin
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Olympia Vacation Owners Association1 / 6
    (2)Excellent
    Oconomowoc
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Indoor Pool
    • Washer
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Patio
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 November 2016
    So happy to find this great vacation rental. Friendly staff and clean comfortable condos with all the amenities of home. We will be booking our next stay soon!
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    About this property
    A great place to vacation in Oconomowoc Wisconsin. If you like to do things this is the place. Oconomowc is 30 minutes from Milwaukee and Madison and under an hour from Wisconsin Dells. If you can imagine it, you can do it. Golfing and Lakefront 10 minutes from the resort. Dining and shopping...
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    53066, Oconomowoc, Wisconsin
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Milwaukee
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our professionally cleaned and centrally located Brady Street home is yours to enjoy! Our home features hotel quality beds, a plush leather sectional sofa, and a large dining area for great times with friends and family. The home is less than 5 minutes walking to Bradford Beach, Brady Street, and...
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    53202, Milwaukee, Wisconsin
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Delafield
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly remodeled home with many great features, and only a short walking distance to Nagawicka lake, stores in town, outdoor restaurants, bars and other amenities. Family room with a fireplace, sunroom with patios doors to the deck with grill & wooded back yard. Featuring 4 bedrooms, & 3.5...
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    53018, Delafield, Wisconsin
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    The Country Retreat1 / 8
    (5)Excellent
    Richfield
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Housekeeping Included
    • DVD Player
    • Private Garden
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Matt and Laura's place is absolutely incredible. It is calm, scenic, accessible, and beyond cozy. I always bring my pups and some friends, and I leave in a better headspace than...
    Reviewed 10 November 2017
    This is a modern, stylish and immaculate apartment, located on a beautiful, historic farm. Super family friendly, but would be great to relax there without kids too. We...
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    About this property
    The Country Retreat at the historic Schmitz Family Farm, is close to many attractions, ideal for couples, families, girls weekend or business travel. Enjoy a sunrise or sunset, get cozy at the fireplace, watch the pups and chickens, or indulge in the many activities our area has to offer. We...
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    53076, Richfield, Wisconsin
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Saint Francis
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in the trendy neighborhood of Bay View and enjoy the comforts of home in this upper duplex. Peekaboo view of the lake across the street, take long walks/runs along the lakefront and enjoy Southshore Park only 1.5 blocks away. Not to mention the brand new Beer Garden at the park, which over...
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    53207, Saint Francis, Wisconsin
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Charming Condo Wooded Views Near Lake Michigan - Attached Garage1 / 15
    (3)Excellent
    Cudahy
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Patio
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 December 2017
    I stayed here as an alternative to staying at a hotel. I was pleasantly surprised with the quality of my stay! This condo was very spacious as well. It is two stories, has an...
    Reviewed 29 November 2017
    We needed a place to stay for a week while in Milwaukee visiting family. Instead of waiting our money on a hotel, we decided to try staying here. Staying at this Condo in Cudahy...
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    About this property
    This 2 story town home style condo has it all! Remodeled kitchen with 2 person eat-at counter, dining room that seats 6, living room with large TV and gas fireplace. Half bath off kitchen. Upstairs has 2 bedrooms, each with it's own en-suite bathroom. The master bedroom is large with lots of room,...
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    53110, Cudahy, Wisconsin
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Milwaukee
    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Air Conditioning
    • Internet Access
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please contact Evolve for long term rental prices** Experience Milwaukee in this charming, 1-bedroom, 1.5-bathroom vacation rental home! This cozy home sleeps 8 travelers and is the perfect getaway for a group of friends or family exploring this Midwest metropolis. A quick 10-minute drive...
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    Location Information
    53207, Milwaukee, Wisconsin
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    Saint Francis
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in the trendy neighborhood of Bay View and enjoy the comforts of home in this lower duplex. Peekaboo view of the lake across the street, take long walks/runs along the lakefront and enjoy Southshore Park only 1.5 blocks away. As well as the new Beer Garden overlooking the lake! Beautiful and...
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    53207, Saint Francis, Wisconsin
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    The Massive Modern Milwaukee Manor - 8 Huge Beds!1 / 15
    (1)Terrible
    Milwaukee
    4 Bedrooms, 1 Bathroom, Sleeps 15 Quick View
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    • Central Heating
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern Updated Milwaukee Home right off Brady Street - walk to everything! 90 + Walk score - come fall in love with Milwaukee, 8 big beds - 6 kings, 2 fulls, enough space for the whole family! Big clean bathroom. Full dining room and living room! This is the absolute ideal location to visit and...
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    53202, Milwaukee, Wisconsin
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 15
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    Wauwatosa
    7 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It is multi-million dollar luxury historical mansion & registered Landmark, built by previous Governor of Wisconsin and millionaire, Harrison Ludington at 1881. One of 33 historical buildings since 1850 in Milwaukee Metropolitan. Original hardwood floor with hand-made pattern, craftsman woodwork,...
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    53213, Wauwatosa, Wisconsin
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 14
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    Milwaukee
    2 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is situated in a quiet neighborhood less than a 4 minute walk to Brady Street in Downtown Milwaukee. We chose this home primarily because of it's safe location and proximity to the best of the Milwaukee sights and sounds. You are a short ride to Bayview and a quick walk to the best bars...
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    Location Information
    53202, Milwaukee, Wisconsin
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 10
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    Milwaukee
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Parking
    • Washer
    • Wi-Fi
    • DVD Player
    • Balcony
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You would have your own private bedroom and large private bath within a two bedroom loft home. Your bedroom has a queen bed and full futon and you have full access and use of the kitchen, living room, laundry room, mini gym, party room, bbq area and riverwalk patio. BEST LOCATION & ROOMY - You...
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    53202, Milwaukee, Wisconsin
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Hartland
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Less than 10 minutes from Erin Hill! Private backyard with 100 yard driving range. Basement has a huge rec room with pool table, big screen tv and a bar that seats 8! Modern furniture and appliances. 3 bed room with finished rec room. Warm cozy and has a pull out couch and half bath. Only 10...
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    53029, Hartland, Wisconsin
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Milwaukee
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    • Grill
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My place is close to parks, restaurants and dining, and art and culture. You’ll love my place because of the coziness and the views. My place is good for couples, solo adventurers, and business travelers. a licensed massage therapist is available on request. a big garden for solitude ...big bay...
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    53212, Milwaukee, Wisconsin
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Mukwonago
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Waterfront
    • Internet Access
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Drift away on Phantom Lake while staying at this Mukwonago vacation rental house with 3 bedrooms, 2 full bathrooms, and 2 half bathrooms. You'll enjoy a peaceful getaway at this waterfront property with all the amenities of home, a jetted indoor tub, and numerous toys such as a paddle boat and 3...
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    53149, Mukwonago, Wisconsin
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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