
Holiday rentals with outdoor seating in Pewaukee
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Top-rated rentals with outdoor seating in Pewaukee
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Popular amenities for outdoor seating rentals in Pewaukee
House rentals with outdoor seating

Okauchee Lakefront Cabin Escape
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!

Guesthouse on Clover - Historic Greendale
This lovely home in Greendale was one of our favorite Airbnb stays. The house has character, was very clean and cozy, had comfortable beds and actually had comfortable pillows! My twin boys gave the stamp of approval and said they’d slept so good. Greendale itself was adorable with breakfast, coffee, lunch and dinner spots a nice short stroll away. This location was six minutes to the baseball complex for our son’s tournament and couldn’t have been handier. And the host, Jody, was wonderful and helpful. My fingers are crossed this place will be available for our next tournament!

Beautiful home on Okauchee Lake, WI
Lovely house on the lake, as advertised. House was tastefully furnished and everything worked. Good restaurants nearby, but a special shout out to Smoke on the Water BBQ. It was in Cathy's recommendations, but we ate there a lot. We hope to stay there again next time we are in the area!

5th St. Retreat - Outdoor Oasis, Hot Tub, 8 Beds
We’ve stayed at more than one of Bradley’s listings and they never disappoint! Their attention to details, including customer satisfaction is very well managed. I would recommend people to stay and time!!

The Little Gray House
Wow! What a beautiful home, backyard, and surrounding areas. Sarah thought of everything that you might need at a home away from home. We enjoyed every minute of the property and didn’t want to leave! We hope to make this a recurring family trip to Wauwatosa :)

Lakeside Getaway
We had a great stay at Lexi’s place. The view is great and the house had everything we needed to make ourselves at home for the week. We would definitely stay here again when we are in the area.

Cheerful, open space, and relaxing 1 bedroom home.
Exciting stayng in a wonderful Place. Okochee Is a stunning Little Town on the lake where you can find relax, peace and beautiful panorama. In the house of Kathy, Everything Is studied and smart. We Hope to come back to this Amazing accomodatiion. Thank you tò Kathy and Jacky .

Pewaukee Lake Home steps from water & restaurants!
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!
Apartment rentals with outdoor seating

Spacious & Private 2 bdrm in the heart of Bayview
The hundreds of reviews are accurate! This spot is a GEM. Thoughtful amenities, warm and inviting energy through the entire space and walkable to some great restaurant/bars! Will be staying here every time we visit! Peace and love!!!!🫶🏽❤️

Silvers Four-Six-Four *A home away from home*
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!!

East Side Home
As previous residents of Milwaukee, we're always so happy to return and stay at Dave and Josie's place for our visits. Dave and Josie are exceptional hosts, real pros that take pride in their historic home and make it so comfortable for guests. It's clean and quiet with no necessity overlooked. The bed is sooooo comfortable and I love having my coffee in the delightful sunroom at the front. And you can't beat the location. You are a few blocks from Lake Park/Lake Park Bistro and just a short pleasant walk to our fave coffee shop, Stone Creek, not to mention Cafe Hollander for brunch and Sendiks if you need a grocery stop! The check in/out is seamless. Dave and Josie are so responsive and friendly. Already looking forward to our next visit!

Cozy Basement Space In Bay View by Lake Michigan
My husband and I had a lovely stay at Carlos's. The space was exactly like the photos, and we had more resources than we even planned on. It's a well-insulated basement space, so even on our last day when the weather was very warm outside, it was downright chilly inside. There was plenty of hot water for the shower, parking was easy to find with clear instructions provided, and enough space for what we needed. We realized our first night that we forgot toothpaste, and Carlos and his wife were so generous to bring some down for us to use until we could get to the store the next morning. Some other reviews mentioned the low ceiling, and while my husband is over 6 ft tall, he had no issues. The space was very affordable for the location, and Carlos and his family are gracious hosts. Absolutely would recommend staying here.

Cozy Apartment Nestled Across from Lakefront!
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.

Inn on Billy Goat Hill
Cannot say enough good things about our stay at Billy Goat Hill! Fantastic location with a quick walk to the local shops, parks, and restaurants. The space was incredibly cozy and had everything you could need for your stay. Extremely affordable for a weekend getaway. Donna and Paul were so inviting and responsive. Cannot wait to return and visit again!

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

Beautiful Port home short walk to town and lake
Eileen was a phenomenal host! Great location, everything you need, walkable to all the wonderful things in Port. Great place - very welcoming! Visit!
Apartment rentals with outdoor seating

Private East Side Milwaukee flat with fenced yard
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!

DElafield Rivers Gateway Luxurious Condo
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.

English Tudor - Upper Flat blocks from the beach
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.

LakeView-SummerPool-FamilyFriendly-CloseToTown
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!

Bay View - Lake View on the Park w/Secret Lounge
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.

Top location, no cleaning fee, everthings close B
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!

Third Ward - High End 1 Bedroom up to 6 + Parking
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.

Relaxing Villa with Amazing Amenities!
Great place! Loved that we were tucked away in a more quiet area but still a short drive away from the hustle and bustle of Lake Geneva. Quiet, clean, and spacious.
Quick stats about holiday rentals with outdoor seating in Pewaukee
Total rentals
20 properties
Nightly prices starting at
₹3,446 before taxes and fees
Total number of reviews
790 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Six Flags Great America
- Erin Hills Golf Course
- Milwaukee Public Museum
- Alpine Valley Resort
- Kohler-Andrae State Park
- Geneva National Resort & Club
- Illinois Beach State Park
- Bradford Beach
- Grand Geneva Resort & Spa
- Racine North Beach
- Richard Bong State Recreation Area
- Milwaukee County Zoo
- Wilmot Mountain Ski Resort
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
- Harrington Beach State Park
- Heiliger Huegel Ski Club
- West Bend Country Club
- Springs Water Park
- Discovery World
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Sunburst
- America's Action Territory
- Blue Mound Golf and Country Club