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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.
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
Superhost
Home in Sussex
Amazing Five Bedroom Milwaukee Vacation Home!!
Treat your friends and family to this five-bedroom vacation home just a half-hour from downtown Milwaukee on more than one acre of park-like, private surroundings. Guests of all ages will love the decked-out game room, the huge indoor pool and the comfy living space, with lots of room to spread out. Plus, you’re just 30 minutes from downtown. It’s all the peaceful feels of a country setting with the amenities of the city (think Uber, UberEats, and more).

Popular amenities for Waukesha County rentals with a pool

House rentals with a pool

Guest favourite
Home in Lake Geneva
Home away from Home
Superhost
Home in Cudahy
Make Yourself At Home! Close to Lake & Airport!
Guest favourite
Home in Milwaukee
The Peacock Place
Guest favourite
Home in Milwaukee
Central Location w/ Skyline View
Guest favourite
Home in Lake Geneva
Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD
Guest favourite
Home in Whitewater
Nestled in the Southern Kettle Moraine Forest
Superhost
Home in Lake Geneva
Newly Updated Modern Lake Condo
Superhost
Home in Lake Geneva
Woodhaven, a Luxury Lake Geneva Pool Estate
Guest favourite
Home in Delavan
Lake Days ~ Family friendly & dogs welcome
Guest favourite
Home in Lake Geneva
Cabin getaway near Winter Realms and Alpine Valley
Superhost
Home in Lake Geneva
Lodge Home - 2.8 Miles to Town - 3 Acres
Superhost
Home in Lake Geneva
Oasis on Oak -Lake Geneva House w/Pool

Condo rentals with a pool

Guest favourite
Condo in Lake Geneva
Charming, Cozy & Quaint Condo in Lake Geneva!
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Condo in Lake Geneva
Lake Geneva Cloud 9
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Condo in Lake Geneva
Relaxing Villa with Amazing Amenities!
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Condo in Lake Geneva
New! Cozy Fireplace! Lake Geneva! Patio!
Guest favourite
Condo in Lake Geneva
Magnificient views in a Lakefront condo, Fireplace
Guest favourite
Condo in Lake Geneva
Cozy Lake Geneva Retreat with Year-Round Views!
Superhost
Condo in Lake Geneva
Flexible rental In Lake Geneva Area
Guest favourite
Condo in Lake Geneva
Updated 2BR Lake Geneva Condo
Guest favourite
Condo in Lake Geneva
Lakeside Haven with Cozy Fireplace & Nespresso
Guest favourite
Condo in Lake Geneva
LakeView-SummerPool-FamilyFriendly-CloseToTown
Guest favourite
Condo in Geneva
Quaint, quiet condo minutes from Lake Geneva
Superhost
Condo in Lake Geneva
Lake Geneva relaxation!

Destinations to explore