Vacation rentals with a pool in Waukesha County

Find and book unique homes with a pool on Airbnb

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

5.0 out of 5 average rating, 4 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.

Nov 27 – Dec 4

R18,051 ZAR per night

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.

Nov 14 – 21

R6,130 ZAR per night

Guest favorite

Home in Milwaukee

4.97 out of 5 average rating, 60 reviews

Unique House with Indoor Heated Pool & Sauna

Amazing 4 Bedroom 3.5 bath 4,000 Square foot Split level with an Indoor Pool! Gorgeous sunken living room with stone gas fireplace. Newly updated kitchen with coffee/wet bar area. 3 Large bedrooms upstairs including Master with private bath. Amazing lower level with 4th bedroom, pool table, wet bar, Indoor Sauna and Indoor full size Pool! Park like backyard with Fountain, brick patio, Playset. This is our private residence so we do limited bookings but love to make your experience special.

Feb 7 – 14

R19,093 ZAR per night

Apartment in Brookfield

4.67 out of 5 average rating, 6 reviews

Endicott Park Vacay Starts Here! 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.

Sep 30 – Oct 7

R2,350 ZAR per night

Apartment in Brookfield

Rare Find! Indoor Swimming Pool, Pets Allowed!

Nov 10 – 17

R2,520 ZAR per night

Apartment in Brookfield

Experience Mitchell Park! Indoor Swimming Pool!

Sep 7 – 14

R2,520 ZAR per night

Apartment in Brookfield

Prime Location! 3 Relaxing Units, Indoor Pool!

Jan 1 – 8

R11,005 ZAR per night

Apartment in Brookfield

4.76 out of 5 average rating, 58 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

Jul 21 – 28

R3,255 ZAR per night

Apartment in Brookfield

4.53 out of 5 average rating, 32 reviews

Family Adventure | Sightseeing . Free Parking

Jul 25 – Aug 1

R2,992 ZAR per night

Home in Waukesha

4.94 out of 5 average rating, 16 reviews

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.

Apr 6 – 13

R18,391 ZAR per night

Superhost

Home in Sussex

4.85 out of 5 average rating, 82 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).

Mar 28 – Apr 4

R18,334 ZAR per night

Superhost

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.

May 20 – 27

R3,274 ZAR per night