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.

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Home in Mukwonago

5 out of 5 average rating, 5 reviews

Spacious and secluded farmhouse with pool and pond

Gathering Table Retreat is the perfect place to enjoy time with your family and friends. The 38-acre property gives you ample space and privacy with activities to keep everyone happy. The updated mid-century farmhouse features 6 bedrooms and 4.5 bathrooms. The updated kitchen is the heart of the home as it connects to the parlor for watching movies or March Madness on the 75” HDTV, the 14-foot farm table, and the sitting area that has 360-degree views of the garden, pool, woods, and pond. The primary bedroom has a queen bed, sitting area, walk-in closet, and en suite bathroom. Off the primary bedroom and second-floor loft, there is a bunk bedroom with three twin beds, an additional bedroom with a queen-sized bed, and a full bathroom with a walk-in shower. The spacious bedroom on the main floor has access to a full bathroom with a shower, claw foot tub that is off the library stocked with books, games, activities, and a queen-sized sofa sleeper. The lower level of the house has two bedrooms that share their own bathroom that is off the second 75” HDTV with an adjoining game room. Get the top score on arcade games, pop-a-shot, darts or foosball as you sit at the kitchenette bar or walk out the sliding doors to the massive backyard and fire pit. Once outdoors, you can adventure on defined walking trails across the property, have your s’mores and conversations at the multiple fire pits or relax by the heated pool as you look across the 3.5-acre pond and its spring-fed creek.

Serviced apartment in Brookfield

4.8 out of 5 average rating, 5 reviews

Family Fun at Monkey Joe's! Pool, Pets Allowed!

The property is conveniently situated on the outskirts of Brookfield, far from the hustle and bustle of the city. Put the Milwaukee Public Museum and Harley-Davidson Museum on your to-do list. With the New Berlin Hills Golf Course and Moorland Road Golf Center nearby, golf should also be on your itinerary. Skating is another option, as you can test your skills at the Pettit National Ice Center. Explore the beautiful parks and hiking and biking trails nearby for a reinvigorating experience.

Serviced apartment in Brookfield

Minutes from Endicott Park! 2 Spacious Units, Pool

Serviced apartment in Brookfield

4.4 out of 5 average rating, 10 reviews

Enjoy Wisconsin State Fair! Pets Allowed, Pool!

Serviced apartment in Brookfield

Rare Find! Indoor Swimming Pool, Pets Allowed!

Serviced apartment in Brookfield

Rare Gem! Pets Allowed, Indoor Swimming Pool!

Home in Hartland

5 out of 5 average rating, 4 reviews

2 Acre Pool Home, Central to Park, Beach & town

Meadow Hill Acres is awaiting your stay! Outdoor heated pool open May - Sept. Pontoon Rental available May - Sept! This 3 BR/3 BA home provides a beautiful retreat within a central location, stocked with the comforts of home. Seated on 2 acres, the property is fenced and dog friendly. Naga-Waukee Park borders the property, offering walking trails right outside your door. Nagawicka Lake and Beach are just a short walk. The Delafield shops, supreme restaurants and Hwy 94 are minutes away.

Serviced apartment in Brookfield

4.6 out of 5 average rating, 5 reviews

Stay Near Endicott Park! Pets Allowed, Indoor Pool

Rental unit in Brookfield

4.75 out of 5 average rating, 113 reviews

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

Rental unit in Brookfield

4.65 out of 5 average rating, 62 reviews

Family Adventure | Sightseeing . Free Parking

Superhost

Home in Sussex

4.87 out of 5 average rating, 99 reviews

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).

Condo in Oconomowoc

4.22 out of 5 average rating, 18 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.