
Holiday rentals with outdoor seating in Milwaukee County
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Milwaukee County
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
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Popular amenities for Milwaukee County outdoor seating rentals
Holiday House Rentals with Outdoor Seating

2 Bedroom Home close to downtown
Jacob has done a great job with this place! It’s comfortable and well furnished and makes you feel right at home. I was here for an extended stay and am definitely sad to leave such a great spot. Great location, nearby grocery, quick access to the highway, very easy to get downtown, good restaurants nearby as well. Jacob and Austin were great cohosts, very accommodating and professional - their responsiveness was stellar! Overall a great stay, highly recommend staying here!

Historic East Side Duplex, 3BD. No Cleaning Fee!
Great host. Great location. Perfect space. Will look to use again when on Milwaukee’s Eastside.

Historic on The Avenue
Finding a place for a big group of guys that's conveniently located near serval bars and restaurants isn't the easiest thing to do in tosa. But, thankfully, Matt's place met all of our needs. It's a super comfy and large space—perfect for a weekend get together. I would 6/5 recommend this place!

Large Luxury Home - Perfect for Groups - Downtown
Cool place awesome location have no complaints except a lot of the “beds” are actually couches and not sleeper sofas but other than that had a great time the basement with beer pong table video games putting greens and football is VERY fun

3 Bedroom, 2 bath home, with gazebo By stadium
This is a really nice location. Beautiful and very clean home. Would totally stay here again. Highly recommended and close to the stadium.

Stunning Vintage/Modern! Brady St! Tons of Extras
Dustin was a great hose and communicated with us effectively. Very responsive. The house was great with all the amenities: 3 twin mattresses that you could have folks sleep on the floor in comfort. There is a pack and play there as well. The photos don't show it but both bathrooms have showers. There were plenty of linens and towels and he also provided shampoo and soap. The location is awesome, several food and bar options you can easily walk to. There is a full service grocery store nearby as well. If you have to go downtown, it's very walkable, about a 30 min walk or a quick 8 min drive. Absolutely enjoyed our stay here!

Wauwatosa/Milwaukee “Inglewood Place”Best Location
We could not believe all the extras Barbara & Fritz had available. They even personalized some treats for us! The place is very homey and comfortable. We felt safe in this beautiful neighborhood. We met Barbara & Fritz, they are a charming couple but not intrusive. I would have loved to sit and chat with them longer had our schedules allowed. We highly recommend their place and would stay again.

Historic Brewery Tied-House in Bayview (Sleeps 12)
We’ve stayed in LOTS of Airbnbs, but this one “takes the cake!” It was SO clean, spacious, and comfortable. Kyle was absolutely the most responsive and proactive host we’ve ever met (and yes, we got to meet him and talk a bit which was just delightful!). He really did think of everything between the treats in the refrigerator, cupboards, and coffee/tea bar and the toiletries basket. Don’t hesitate! Book the Schlitz Castle today…and tell Kyle that Julie sent you!
Apartment rentals with outdoor seating

Tosa Village Studio Apartment
One of our favorite places to stay. We like that we can walk to several restaurants when the weather is nice. Quiet and comfortable.

Spacious+Mod Booth St Apt w Yard | Brewer’s Hill
Great space! Convenient to everything. Great hosts.

Charming 1 bd upper level in great location!
We very much enjoyed our stay here! Nice bed, top notch shower, close to interstate and many cool things. A great home base for exploring Milwaukee. Did I mention the shower was awesome?

East Side Home
Josie & Dave were fantastic hosts! Instructions on getting in, parking, amenities, etc were clear and generous. The home itself was clean, comfy and super cool! Location is stellar, you're minutes from countless restaurants and attractions, but still in a beautiful neighborhood. We had everything we needed and a few extra and surprise perks as well. We would recommend this to anyone, and also stay again as well. Thank you for a wonderful weekend!

Cozy Basement Space In Bay View by Lake Michigan
The location was very clean, organized, and the check-in and check-out instructions were very simple and easy to follow. The accommodations matched the description accurate and was a very nice space! The environment was welcoming and the neighborhood felt safe and quiet. It was also very convenient to popular areas in the city. Carlos’ communication was thorough, detailed, and made for a calm and relaxing experience. I would stay at this same location again if I am in the area!

Cozy Apartment Nestled Across from Lakefront!
Very roomy, good value for the accommodation, very safe neighborhood within a short walk to the waterfront and the cutest little coffee shop just down the street. It was so cozy in the bar downstairs, and if you are looking to experience the charm of Wisconsin hospitality, you must meet Paul. We felt at home but also didn’t get bogged down by the laundry list of rules that many airbnb homes expect their guests to accomplish before they leave. We genuinely felt like guests.

Newport House -Walk to UWM- vintage upper+garage
This place was fantastic! Perfect for one person or a couple. A classic Milwaukee home with great charm.

Apartment in Walkers Point
The place was in a central location for our visit – easy to get to Marquette, downtown and the third ward. The place was as described and was great for our family of five.
Condo rentals with outdoor seating

Stylistic Condo Hot Tub Tosa Village 2 blocks away
We booked for 2 weeks and enjoyed each day! Great neighborhood for walking our dog and loads of restaurants nearby to try out. The home was furnished with everything you could need. Sarah was accommodating to meet our needs and we would definitely come back here.

Charming 2BR Off Brady St
Many thanks to Timothy for providing us with such a wonderful apartment in the heart of Milwaukee. The location is perfect, nestled in a beautiful area with a bustling street full of pubs, cafes, and restaurants, and close to both a river and a lake. We truly enjoyed our stay and felt a warm sense of home, especially during the cool December evenings. Thank you for your thoughtful touch in making this experience unforgettable.

Brewers Hill Belle, 2 bed, 2 bath, & balcony
Great location while visiting with friends! The home was beautiful and had more room than expected! We loved all the extra touches! Would stay again!

Upper East Side, Designer Retreat w/large balcony
Cory’s place is a gem! We loved staying in this condo. Walking to great places around, close to the beach and enjoying the beautifully decorated space. Every detail in this place is thoughtfully located and curated. I was able to add one more guest that joined us after booking and had a nice exchange with Cory. She is a FANTASTIC host, my experience here reminded me why I like staying in Airbnb, due to the human connections you can make :) and of course, the unique places that you get so appreciate. Thanks Cory and hope to be back one day 🤙

English Tudor - Upper Flat blocks from the beach
Jodi's place was just as described. This is an older house with lots of charm. The beds were comfortable and the kitchen and bathrooms were well-stocked. Jodi was so easy to work with--very communicative, very responsive, a true delight. I would absolutely stay here again!!

Bay View - Lake View on the Park w/Secret Lounge
Beautiful home and incredible location. Every day we walked across the street to the South Shore beach to kick off the afternoon with beers by the lake. Club Garibaldi is an easy walk, where we had fantastic wings and caught a Thin Lizzy cover band. The apartment’s interior is stunning and simultaneously very cozy. We all enjoyed the fully stocked coffee and tea bar. Thank you, 10/10 highly recommend!

Downtown Eastside gem near Fiserv Forum Bucks!
Wonderful space, if you're to go out on Brady and or water/3rd street... lots of bars and restaurants in both areas, you'll be pleasantly surprised with how walkable it is to both areas. Amazingly secure, key fob to get into the lobby, standard key to use the elevator and then the actually unit also locks aswell. Don't have much to say other than there's plenty of space for 6 people, great balcony with walls on either side and a roof, tub with jet, and a nice projector down the spiral staircase. I hope you get to enjoy your space as much as I did.

Spacious Bay View Historic Storefront Apartment
No frills, exactly what we needed! Will definitely be back to explore Bay View more
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- Milwaukee Public Museum
- Erin Hills Golf Course
- Kohler-Andrae State Park
- Wilmot Mountain Ski Resort
- Alpine Valley Resort
- Racine North Beach
- Illinois Beach State Park
- Milwaukee Country Club
- Richard Bong State Recreation Area
- The Bull at Pinehurst Farms Golf Course
- Springs Water Park
- Bradford Beach
- Heiliger Huegel Ski Club
- Harrington Beach State Park
- Pine Hills Country Club
- Milwaukee County Zoo
- Discovery World
- Sunburst
- America's Action Territory
- West Bend Country Club
- Blue Mound Golf and Country Club