
Vacation rentals with a pool in Waukesha County
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Top-rated rentals with a pool in Waukesha County
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Popular amenities for Waukesha County rentals with a pool
House rentals with a pool

Elssys Ranch 80 Acre Lake Geneva Retreat
We had an amazing time at this property! Nick was a fantastic host—super responsive and quick to answer any questions we had. The property itself is beautiful with plenty of space for kids to run around and play. The kitchen was well-equipped with lots of utensils and dishes, making it so convenient to cook and eat at the house. The fire pit and grill outside were a wonderful addition to our stay! The location is perfect too! It’s near a charming Boxed & Burlap coffee shop, and just a short 5-mile drive to downtown Lake Geneva. Downtown offers parks, a public library, great shopping, and stunning views of the lake with walking trails. We can’t wait to return and stay again! Highly recommend!

Family friendly & dogs welcome
Jane responded fast to text messages. very kind, offered to tell about restaurants and local entertainment. I had an issue with the door ( operator error ) called Jane and she called me back to see if i was able to fix the issue, which was a simple fix. I will definitely make sure I reserve there again when I go back into town if available.

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.

Vacation home: heated inground pool on 4+ acres
This is the perfect place to get away from it all! Clean and quiet. Surrounded by nature. A true place to relax, spend time with the family, and reset from a busy life. Thank you!!!

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
I absolutely love the location of this property. Steve's place is perfectly secluded for quiet mornings & peaceful evenings. I hope to return in the winter to take in the beautiful snowfall. I also appreciate the fact that it's not far from a small cozy town with a walking path along the lake. Thank you for sharing your wonderful property & I look forward to returning!

Nestled in the Southern Kettle Moraine Forest
It is always a welcome refresher to escape to The Den and spend time with the animals, on the trails, and relaxing in such a cozy, inviting home. You have everything you could possibly need to hunker down and enjoy the beautiful surroundings. Jarvis and Chris' hospitality is truly second to none. We are already thinking about our next visit :)
Condo rentals with a pool

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.

Magnificent waterfront views & cozy fireplace
my wife and I stayed here for her birthday weekend and we loved it. we would definitely stay again if we go back to the area.

LakeView-SummerPool-FamilyFriendly-CloseToTown
We loved our stay at this beautiful location. It was close by to everything we wanted to do and the condo was exactly what we were hoping for! Rachel gave great recommendations and was so responsive to our questions. We will definitely stay here again!

Relaxing Villa with Amazing Amenities!
Lovely space! Very clean, Comfy bed, beautiful views of the lake, even better than the photos, nice private location. We did not have a chance to check out the amenities, like the hot tub and pool at the near by resort but will definitely stay again to check it out!

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.

Poolside Lookout at the Cove Hotel |Downtown LG
If you're looking for a relaxing, peaceful yet close to everything getaway....Samantha's place is it!! From the minute you walk into the Cove, you guide yourself straight into a restful oasis. Entering Samantha's place, I was amazed at how spacious it all was. From the very modern kitchen, all of the utensils and kitchen necessities to the wide tub in the bathroom and big bed in the bedroom, everything felt like home. Relaxing in the living room with a beautiful view to the outdoors and the balcony was enjoyable. I highly recommend Samantha's place for your next stay in Lake Geneva.

Lake Geneva Cloud 9
We were in Lake Geneva for a convention, so were mostly only in the condo for sleeping, but the place had everything we could possibly need and then some. There were plenty of extra supplies in the kitchen and bathroom. If we had been traveling with kids, there were toys and games. And if it had been a warmer season or we were there for relaxation, the location looks great for outdoor activities. Cheryl sent us good instructions for parking, unlocking the door, etc. And inside there was a whole binder of stuff to make anything we needed to do easy. Thanks, Cheryl...you made our brief stay easy and comfortable!
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- Milwaukee Public Museum
- Racine North Beach
- Wilmot Mountain Ski Resort
- Six Flags Great America
- Erin Hills Golf Course
- Geneva National Resort & Club
- Grand Geneva Resort & Spa
- Milwaukee Country Club
- Alpine Valley Resort
- Springs Water Park
- Moraine Hills State Park
- Illinois Beach State Park
- Harrington Beach State Park
- Bradford Beach
- Lake Kegonsa State Park
- Richard Bong State Recreation Area
- Heiliger Huegel Ski Club
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Milwaukee County Zoo
- West Bend Country Club
- America's Action Territory
- Sunburst
- Blue Mound Golf and Country Club
- Discovery World
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