Holiday 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.

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Home in Oconomowoc

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Home in Oconomowoc!

Your family will be close to everything when you stay at this centrally-located home. This beautifully maintained home was built within the last four years. The neighborhood is ideally situated near shopping, restaurants, and convenient highway access. The home is perfectly positioned in the desirable Oconomowoc–Delafield area. You'll benefit from excellent neighborhood amenities, including a community pool, walking trails, and a pickleball court—offering something for everyone to enjoy.

Top guest favourite

Home in Hartland

5 out of 5 average rating, 12 reviews

2-acre retreat steps from Nagawicka Lake

Private Lake Country Retreat on 2 Acres | Pool, Park & Prime Location Relax at this private Lake Country retreat on 2 secluded acres surrounded by mature trees. Enjoy a private outdoor pool, spacious yard, and peaceful setting just steps from a county park with trails and a public beach. A nearby boat launch makes lake days easy, while shopping, restaurants, and coffee spots are only minutes away. Perfect for families, couples, or extended stays seeking privacy with convenience.

Superhost

A spacious bedroom features a calming green accent wall, complemented by neutral-toned bedding. Framed artwork decorates the wall, and a bedside lamp adds a warm glow. The window is dressed with dark curtains, allowing light to filter softly into the room.

Apartment in Oconomowoc

4.3 out of 5 average rating, 20 reviews

Olympia VOA Oconomowoc WI Great getaway for fun

1, 2, and 3 bedroom condos availability at Olympia Vacation Owners Association with some dogs under 40 lb friendly units. Close to Madison and Milwaukee with Golfing and beaches in the area. The Olympia Hotel has been torn down and replaced with housing and store fronts so no pool access is available. Area has theatre, dining, shopping, water parks. Only an hour from Wisconsin Dells.

Top guest favourite

A single-story house is presented with a light exterior and a welcoming porch. A shaded area is provided by the overhanging roof, and a bench is positioned on the porch. A well-maintained lawn stretches in front, framed by lush green trees.

Home in Delafield

4.94 out of 5 average rating, 47 reviews

Cute and cozy 2 bedroom house perfectly located!

You’ll have everything you need within miles of you. Located conveniently right in between Milwaukee and Madison, you won’t have to travel far for anything. Delafield also offers a ton of great restaurants, coffee shops and cute boutiques within walking distance! Unfortunately during the winter months the pool is not able to be used and outside furniture is tucked away.