
Vacation rentals with a pool in Waukesha
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Top-rated rentals with a pool in Waukesha
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Waukesha rentals with a pool
House rentals with a pool

Woodhaven, a Luxury Lake Geneva HotTub-Pool Estate
“We had a fantastic two-day stay at Ellen’s place place! The home was exactly as described—spotlessly clean, comfortable, and well-equipped with everything I needed. The location was perfect, close to lake Geneva downtown which made exploring the area so easy. Ellen was incredibly welcoming and responsive, offering helpful tips about the area and making sure I felt right at home. The thoughtful touches, like the warm fireplace on arrival, towels in each room made my stay even more enjoyable. The hot tub was very comfortable this time of the year. I would absolutely stay here again and highly recommend it to anyone looking for a cozy and hassle-free getaway!”

Elssys Ranch 80 Acre Lake Geneva Retreat
We had our family spring break at Elssys Ranch. Beautiful surroundings and nice location. Nick was a great host. Always available to help. House was immaculately clean for our arrival. On one of the nights - we had a camp fire in the fire pit with the kids (which was the highlight of their trip), and there was plenty of space for the boys to run around and explore. The house is huge, and has a lot of character. Bunk beds were a great addition for the boys to bunk together and far enough at the other end of the house for the parents to have privacy. Kitchen has everything you need and want, but there are also plenty of restaurants driving distance nearby (we explored both the Lake Geneva town center and a nearby lake front area which had a great coffee shop) Definitely would recommend to anyone!

Cute and cozy 2 bedroom house perfectly located!
Our first time in Delafield and loved it!! Adorable little lake town with so many cute restaurants, coffee shop and ice cream just a short walk away. Elizabeth's home was exactly what we needed for a month long mother/daughter stay while attending treatment in the area. Meticulously clean at check-in and decorated so cute with finest attention to detail! So warm and cozy providing a perfect sanctuary. Elizabeth was flexible and responsive in all communication prior to and during our stay, and quickly addressed an Internet hiccup, ensuring the issue was resolved for us. Can't wait to return and highly recommend Elizabeth and this adorable gem of a home!!

Cozy cabin getaway near Lake Como and Lake Geneva
This was my first time using Airbnb. We had a group and it seemed like a better idea to try and find something we could share for the GaryCon convention. None of us were familiar with the area so I used the app and geo bracket for within 10 miles of the convention and came up with this beautiful home that had enough beds to accommodate each of us. I looked through the pics and was happy with what I saw. Sasha was responding quickly to answer my questions and we made the reservations. When we got to the place we were all happy with what we found. The hone was spacious with large beds in each room. 3 baths made it easy for us to get out quickly each morning. The kitchen was really great. The deck was really great. Seriously couldn't not have been happier and more pleased. Thank you for opening up your home to us. I understand why people live the area. I strongly recommend this home and Sasha if you're in the area.

EnglishPrairieBnB | Large Group | w Kidquariam
We had a great time at Mikes place! It was all the little things and extras. From the provided waffle mix with toppings, the golf simulator and indoor pool to the ping pong table and infinity game table. It was also very cozy and we all felt close and connected. We were a large group that gets together once a year for skiing. It was the first time we visited Wisconsin and we would definitely come back! Mike was very responsive with any issues that came up.

Newly Updated Modern Lake Condo
Great location close to shops and restaurants. We enjoyed the pool/hot tub area and ended up having dinner at Crafted Italia in the same building the pool is located, it was nice and close to the rented unit.

Big BLUE Skyline VIEW
Stayed for a convention, it was great having space to come back to instead of a tiny hotel room, and everything was super convenient.

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD
Great experience at this location. Our host was super communicative and made sure we had everything we needed. The accommodations were wonderful. Was very clean and great space for our family. We loved the little coffee/tea bar and the beds were ultra comfortable. Would highly recommend for a long or short stay.
Condo rentals with a pool

Beautiful Condo Minutes from Downtown Lake Geneva
Great place and perfect location

Quaint, quiet condo minutes from Lake Geneva
We loved Mackenzie’s place! It was a short walk to the Ridge hotel where we were attending an event. The condo was super cozy and fit our needs perfectly. And you walk outside and can see the lake! Would definitely stay here again.

Elegant 4-Season Lake Geneva Condo w/ Fireplace!
Couldn’t have enjoyed this spot more! Already planning on going back soon because it was everything we wanted and more. Highly highly recommend, just don’t reserve it too often so we can go back! Haha

Lake Geneva relaxation!
Very quiet and tranquil location for our extended weekend trip! Close enough to explore Lake Geneva and many more area favorites. We were able to walk to The Ridge Hotel where they had restaurants and live music on the weekend.

Abbey Springs - Lake Geneva - 2 BR - Sleeps 6
This place was absolutely perfect for a wedding in the area. It’s close to the action and the breakfast at Abbey Springs was delicious. Beds are comfy, couches are even comfier, and the screened porch allowed for peaceful vibes on an early fall weekend. Nancy and Fred’s accommodations were perfect and I can’t thank them enough!

2 BR 2 BA Abbey Villa B
I would give 10 stars if I could. I have been using AirBnB for many years, and our experience with Vida’s Villa 33B is hands down probably the best we have ever experienced. She is very responsive and helped us get an extra hair dryer. The unit looks newly remodeled, and had many thoughtful amenities, from tea and K-cups to a clothes steamer and hair curling iron. We were there for a family wedding from a few states away, and I’m a little sad we probably won’t have a reason to visit again. I highly recommend Vida’s Villa B if you are visiting the Abbey Resort.

Best Location in Lake Geneva!
Excellent spot right in the heart of Lake Geneva. The location was very safe, easy to access, and had everything I needed and then some for a great stay. Highly recommended!

Cozy 2 Bedroom Condo - Lake Geneva
Nice comfortable space, and a good easy location. Walking distance from the lake. Space was even larger than it looked in the pictures, and clean and comfortable.
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- Milwaukee Public Museum
- Wilmot Mountain Ski Resort
- Racine North Beach
- Grand Geneva Resort & Spa
- Erin Hills Golf Course
- Six Flags Great America
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- Milwaukee Country Club
- Springs Water Park
- Illinois Beach State Park
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- Harrington Beach State Park
- Alpine Valley Resort
- West Bend Country Club
- Discovery World
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Heiliger Huegel Ski Club
- Richard Bong State Recreation Area
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- America's Action Territory
- Milwaukee County Zoo
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