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Waukesha Holiday Homes

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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 24 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.
    Olympia Vacation Owners Association1 / 6
    (5)Very good
    Oconomowoc
    2 Bedrooms, 2 Bathrooms, Sleeps 6 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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    Grandma's Cottage Bed and Breakfast1 / 10
    (3)Excellent
    Muskego
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Grill
    • Outdoor Dining Area
    • Hot Tub
    • Patio
    • Housekeeping Included
    • Air Conditioning
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 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 2 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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    Muskego, Wisconsin 53150
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Milwaukee, Wisconsin 53202
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 10
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    Lake Michigan Tudor1 / 25
    (6)Excellent
    Milwaukee
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • DVD Player
    • Parking
    • Waterfront
    • Air Conditioning
    • Housekeeping Included
    • Patio
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 June 2017
    The whole weekend is a cherished family memory. We had such a great time! This location was absolutely, totally -- and I am not exaggerating -- awesome! This spacious home was...
    Reviewed 22 June 2016
    Such a wonderful place to stay. Just minutes from downtown. Beautiful views of the lake and we enjoyed evenings sitting on the back patio listening to the birds chirp and...
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    About this property
    This spacious and elegant 2300 SF, 3 BR, 1.5 bath lower level duplex overlooks Lake Michigan and is 8 minutes from downtown and 7 minutes from the airport. It is located in the trendy Bay View area of Milwaukee. Enjoy views of the downtown skyline or sunrise over the Lake from the deck or...
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    Location Information
    Milwaukee, Wisconsin 53207
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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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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    Location Information
    Milwaukee, Wisconsin 53202
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 15
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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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    Saint Francis, Wisconsin 53207
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Oak Creek
    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • 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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    Oak Creek, Wisconsin 53154
    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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    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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    Location Information
    Saint Francis, Wisconsin 53207
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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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 29 March 2018
    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 11 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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    Location Information
    Richfield, Wisconsin 53076
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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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
    Milwaukee, Wisconsin 53202
    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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    Amenities & Details
    • 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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    Location Information
    Milwaukee, Wisconsin 53202
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 10
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    Wauwatosa
    7 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • 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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    Location Information
    Wauwatosa, Wisconsin 53213
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 14
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    Milwaukee
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Location Information
    Milwaukee, Wisconsin 53212
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    Delafield, Wisconsin 53018
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Saint Francis
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Location Information
    Saint Francis, Wisconsin 53207
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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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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    West Allis, Wisconsin 53214
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    Milwaukee
    3 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Conveniently located near downtown Milwaukee, MKE airport, Amtrak stations and Lake Michigan Ferry. A clean and well maintained first floor home. Full kitchen and outdoor patio with grill for your use. This house offers wifi plus TV with Roku box and DVD player. Three bedrooms, 7 beds total...
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    Milwaukee, Wisconsin 53207
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 10
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    Milwaukee
    5 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    • Wi-Fi
    • Washer
    • Secure Parking
    • Private Garden
    • Grill
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The space Our home has 5 bedrooms (11 beds = 3 Queen, 8 Twin) & additional blow-up mattress (2) can be provided with notice. The house has 2 full bathrooms and one half bathroom. The master bathroom has two private showers. Fully equipped with all necessities while being away form home with a...
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    Location Information
    Milwaukee, Wisconsin 53211
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 18
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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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    Hartland, Wisconsin 53029
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Milwaukee
    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *NOTE: Contact Evolve for long term rental prices* Experience Milwaukee from this 1-bedroom, 1.5-bath vacation rental home! This cozy home sleeps 8 and is the perfect getaway for a group of friends or family. A quick 10-minute drive takes you to the trendy downtown area where you can treat...
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    Location Information
    Milwaukee, Wisconsin 53207
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    Mukwonago
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Terrace
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Washer
    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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    Mukwonago, Wisconsin 53149
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    Wauwatosa
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * Please note the homeowner lives on site, in the upstairs unit, and may be present during your stay* Get ready to fall in love with this elegant vacation rental apartment! The 2-bedroom, 1-bathroom home has room for 4 guests. The cozy space is decorated beautifully inside and out! Enjoy quiet...
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    Location Information
    Wauwatosa, Wisconsin 53216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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