Holiday rentals with outdoor seating in Waukesha County

This cottage on Lake Pewaukee was a perfect place for our visit. We wanted to spend a few nights close enough to my mom's house that she could visit and spend some time with us on a trip back home after moving away from Wisconsin, and this place was wonderful! The deck was lovely, even in colder weather, and the kitchen had everything we needed to prepare a taco dinner and enjoy a night of games and quality time. I loved that there are two king beds and two full bathrooms. Pet friendly also for our two small dogs! Ample parking was great since we had a truck and a trailer. Kristen was responsive, kind, and professional- we will definitely rent here again and may make it a regular stop!

The property is just lovely, especially if you value peace when outdoors. We were just as pleased with our stay. It was first time we stayed in Pewaukee. The town itself and the neighboring towns had plenty to do. Howevere, we found ourselves at the airbnb mostly between the hot tub and sauna there was plenty to do.

We really enjoyed our stay. Denise was communicative and everything was easy. The house is beautiful. Its on a quiet street with lovely neighbors. Its directly off bike/walking trails, whis is why we chose it. The house is right off of the highway but it was never intrusive. We hung out at the fire pit and it was honestly just quiet background noise. The kitchen is perfect and had everything we needed and wanted. We cooked simple meals and everything was easy. The bed in the main bedroom was so comfy, all the linens and towels were plush. The hot tub was such a nice luxury. We were about 18-20 minutes from every restaurant we tried. Denise was super flexible about our timing, which we really appreciated. All in all it was a great experience and a place we would return.

This is an amazing spot with a great view! Aaron's home felt so cozy. Very comfy and unique. The jukebox was a hit! Thanks Aaron!

We had a great stay while visiting Wisconsin

We had such a wonderful Christmas at The Paddle House! The house was beautiful and Maria even had a Christmas tree set up for us! The view of the lake out of the huge living room window was amazing especially as it snowed! I would definitely recommend this property to anyone looking for a cozy oconomowoc getaway!

We had a great time staying at the Lake house. The location was perfect for walking to restaurants, the beach, and some shops. It was close to the freeway, for easy access to the city. Plenty of space for two families to stay. Jason was very responsive with anything we needed and was an excellent host. Thanks for sharing this property with us.

The house was super cute and cozy! It had two bedrooms, one bathroom, and an extra space in the basement. The kitchen was spacious, and it was perfect for three people to stay comfortably for a week. We really enjoyed our time here!

Loved the available basketball hoop

Such a wonderful stay! The apartment was extremely neat, tidy and perfect for our needs! My friend and I are on the taller side, so next time we’ll stay on the lower level, assuming the ceilings are slightly higher. But regardless, next time we’re in Port, we’re staying with Elle!! Thank you again for a great stay!!

By far this was my best experience throughout all of my years of using Airbnb. I’ve never had a host make me feel more at home & safe. Even one of the days by chance my girlfriend & I got to talk to Carlos in person because he was outside with his puppy when we were coming back to the Airbnb. He was super kind & sweet. Their place was comfy & cozy too just how I like & prefer it. LGBTQ+ friendly & very open about it. As someone who’s in a queer relationship this made me feel incredibly secure which is extremely important to me in today’s world. Also their location is walking distance from the Cactus Club which is one of our favorite local spots in MKE. My partner & I would definitely love to stay here again in the future sometime & recommend it to anyone. 🙂🌈

This place was nice and clean. Bigger than I expected from the pictures, very open and roomy. The host was very helpful, particularly with giving us heads up about street parking and such. She made every single effort to make sure we moved our car before it got towed. Which we did right in the nick of time. I'm definitely saving this place to stay next time I come to Milwaukee!

this is definitely a very comfy ,cozy , loving place.i met Jennifer,and her husband paul.theyre very nice people .the first thing they asked when I met them is everything ok,how awesome is that.the place is very quiet ,clean ,and very nice.definitely coming back next time I need an airbnb.paul ,and Jenifer are the best hosts,and the location is amazing.

had a very nice stay! Apartment was as described, very quaint, clean, and is in a great location.

I had a wonderful stay at this charming and cozy apartment! The space was exactly what I was looking for—comfortable, clean, and full of character. The host’s instructions were clear and made check-in a breeze. I truly felt at home and will definitely stay here again next time I’m in town. Highly recommend!

I had a wonderful stay! The place was exceptionally clean, very comfortable, and located close to all the main attractions in Milwaukee. It was also quiet, which made it easy to relax after a day of exploring. The host was incredibly kind and very reliable; communication was smooth and thoughtful from start to finish. I’d absolutely stay here again and highly recommend it to others!

Amazing place! Beautifully decorated and tons of amenities. We loved the location and being able to walk to lots of restaurants. Would love to stay again!

John and his wife had great hospitality! They greeted us when we walked in and truly welcomed us to the area. The unit was well equipped, and is capable of handling several people for sleeping accommodations.. fantastic location and accessible to lots of restaurants, etc.

Lori’s place was amazing! The location was perfect, peaceful, yet centrally located near tons of things to do. Whether you want to explore or just head back to relax, it’s the ideal spot. I highly recommend taking your coffee out onto the balcony to enjoy the beautiful view, it was one of my favorite parts of the stay. Lori was incredibly responsive and checked in often to make sure I had everything I needed. I would 100% stay here again in a heartbeat!

Once we landed in Milwaukee, we texted Jodi to let her know when we expected to arrive at her place. She quickly responded that she had some errands but provided the entry code and made us feel welcome. We got settled in and then she reached out via text to let us know she had returned. She came up to meet us in person and helped us understand the city requirements for parking on the street. She had already provided the URL to the registration site and just made sure we were comfortable with what needed to be done. She later informed me that I'd parked on the wrong side of the street so that I could move the vehicle so that it didn't get a ticket. I appreciated that. We were out and about most of the time we were there. The notes that she had placed throughout were very helpful. The booklet that she printed was very clear and her expectations were reasonable and easy to meet. It's an older home, but very quaint and pretty cool.

We had an incredible stay at this beautiful Lake Geneva Airbnb! The home felt so welcoming from the moment we walked in. The location couldn’t have been better. Just minutes from the lake and downtown, we were able to enjoy charming local shops, great restaurants, and stunning lakeside views without needing to drive far. It was the perfect blend of peaceful retreat and convenient access to everything Lake Geneva has to offer. Our host was outstanding—friendly, responsive, and truly committed to making our stay comfortable. They provided excellent local recommendations and made sure we had everything we needed. Whether you're looking for a romantic weekend, a family getaway, or just some time to relax by the water, this place is a gem. Wehighly recommend it to anyone visiting Lake Geneva!

We rented this entire house, both upper and lower units (separate listings) for our wedding across the street at South Shore Pavilion. This rental was outstanding and created a beautiful and stress free home-base for our wedding guests and weekend. The bridal party was able to get ready here before the ceremony and guests from out of town had clean private bedrooms to stay in. Awesome eclectic vibe and plenty of places to relax, with plenty of extra room. I recommend this rental to anyone spending an important weekend in Bayview, like a wedding. The next door neighbors were courteous and very tolerant of our busy weekend. Instructions were clear for how to stay out of their way and how to be good guests in the neighborhood of mostly homeowners. I would not consider this a “party house” given the context of the neighborhood and rather a beautiful relaxing domain to enjoy the best neighborhood in Milwaukee.

We enjoyed our stay here! It has a comfortable king bed and unique decor which made our visit fun. The location is very close to the lake and walkable to several downtown restaurants, coffee shops, Lake Geneva Shore Path and lake tour boats. We enjoyed getting custom-make breakfast wraps downstairs. We had a college reunion event at the Geneva Taphouse a couple blocks away. Lots to do and see in downtown Lake Geneva!

We had a fantastic long weekend at this Airbnb! The location was absolutely perfect for exploring the area – everything we wanted to see and do was within easy reach. The place itself was wonderful; clean, comfortable, and had everything we needed for a relaxing stay.