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Vacation rentals with a pool in Waukesha County

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Top-rated rentals with a pool in Waukesha County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Superhost
Home in Hartland
3Bd/3Ba, dog friendly, near Nag Park, Beach & town
Meadow Hill Acres is awaiting your stay! This 3 BR/3 BA home provides a beautiful retreat within a central location, stocked with the comforts of home. Seated on a rolling 2 acres of land, the property is fenced and dog friendly. Outdoor heated pool open May - Sept. Naga-Waukee Park borders the property, offering natural serenity and walking trails right outside your door. Nagawicka Lake and Beach are just a short walk. The Delafield shops, supreme restaurants and Hwy 94 are 3 minutes away.
Sep 28 – Oct 5
$324 per night
Apartment in Brookfield
Family Retreat | Museums . Free Shuttle
Discover an elevated experience with design, programming and service unlike any other at Sheraton Milwaukee Brookfield Hotel. Attractions are just nearby: ✔ Take a tour at a living plant museum at the Domes ✔ Admire more than 100-year history of Harley-Davidson motorcycles ✔ Scenic views at Boerner Botanical Gardens ✔ Visit over 2,100 animals at Milwaukee County Zoo ✔ Learn about local history, world's natural and cultural diversity and more at Milwaukee Public Museum
Jul 2 – 9
$108 per night
Home in Waukesha
Frank Lloyd Wright style home near Milwaukee
You will love this 4 bedroom home within walking distance to a grocery store and parks. 20 minutes to Milwaukee and Fiserv. Home is well cared for and will be thoroughly cleaned before your stay. Just a short hop takes you to Milwaukee and all it's delightful festivals. In the summer you can use our pool! You understand that you use our pool at your own risk. We are not responsible for any injuries. Children are not allowed in the backyard without an adult at their side.
Feb 1 – 8
$850 per night

Popular amenities for Waukesha County rentals with a pool

House rentals with a pool

Guest favorite
Home in Lake Geneva
Home away from Home
Jan 6 – 13
$488 per night
Superhost
Home in Cudahy
Make Yourself At Home! Close to Lake & Airport!
Jun 19 – 26
$76 per night
Guest favorite
Home in Lake Geneva
Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD
Apr 19 – 26
$176 per night
Guest favorite
Home in Whitewater
Nestled in the Southern Kettle Moraine Forest
Nov 7 – 14
$278 per night
Superhost
Home in Lake Geneva
Lodge Home - 2.8 Miles to Town - 3 Acres
May 4 – 11
$525 per night
Guest favorite
Home in Milwaukee
Central Location w/ Skyline View
Mar 3 – 10
$90 per night
Guest favorite
Home in Milwaukee
The Gem of Brewers Hill w/hot tub & heated pool
Jul 20 – 27
$576 per night
Guest favorite
Home in Lake Geneva
Cabin getaway near Winter Realms and Alpine Valley
Dec 15 – 22
$520 per night
Superhost
Home in Lake Geneva
Woodhaven, a Luxury Lake Geneva Pool Estate
Oct 14 – 21
$819 per night
Superhost
Home in Lake Geneva
Newly Updated Modern Lake Condo
May 29 – Jun 5
$348 per night
Guest favorite
Home in Delavan
Lake Days ~ Family friendly & dogs welcome
Jan 26 – Feb 2
$239 per night
Superhost
Home in Lake Geneva
Geneva Grove with Private Pool, 4bd/2ba Sleeps 8
Nov 22 – 29
$446 per night

Condo rentals with a pool

Guest favorite
Condo in Lake Geneva
Charming, Cozy & Quaint Condo in Lake Geneva!
Aug 3 – 10
$130 per night
Guest favorite
Condo in Lake Geneva
Relaxing Villa with Amazing Amenities!
Sep 21 – 28
$135 per night
Guest favorite
Condo in Lake Geneva
Lake Geneva Cloud 9
Nov 22 – 29
$139 per night
Guest favorite
Condo in Lake Geneva
New! Cozy Fireplace! Lake Geneva! Patio!
Apr 24 – May 1
$110 per night
Guest favorite
Condo in Lake Geneva
LakeView-SummerPool-FamilyFriendly-CloseToTown
Mar 25 – Apr 1
$87 per night
Superhost
Condo in Lake Geneva
Flexible rental In Lake Geneva Area
Jan 4 – 11
$100 per night
Guest favorite
Condo in Lake Geneva
Magnificient views in a Lakefront condo, Fireplace
Dec 22 – 29
$215 per night
Guest favorite
Condo in Geneva
Quaint, quiet condo minutes from Lake Geneva
Sep 10 – 17
$129 per night
Guest favorite
Condo in Lake Geneva
Updated 2BR Lake Geneva Condo
Mar 6 – 13
$147 per night
Guest favorite
Condo in Lake Geneva
Lakeside Haven with Cozy Fireplace & Nespresso
Jan 3 – 10
$126 per night
Guest favorite
Condo in Lake Geneva
Cozy Lake Geneva Retreat with Year-Round Views!
Jul 17 – 24
$436 per night
Superhost
Condo in Lake Geneva
2 Bedroom villa at Lake Geneva's GRAND Resort
Dec 12 – 19
$343 per night

Destinations to explore