Holiday rentals with outdoor seating in Milwaukee County

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

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Popular amenities for Milwaukee County outdoor seating rentals

Holiday House Rentals with Outdoor Seating

Superhost
Home in Milwaukee
4.75 out of 5 average rating, 16 reviews

2 Bedroom Home close to downtown

ZachRating, 5 stars2 months ago
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!
Guest favourite
Home in Milwaukee
4.9 out of 5 average rating, 214 reviews

Historic East Side Duplex, 3BD. No Cleaning Fee!

KevinRating, 5 stars1 week ago
Great host. Great location. Perfect space. Will look to use again when on Milwaukee’s Eastside.
Guest favourite
Home in Wauwatosa
4.96 out of 5 average rating, 103 reviews

Historic on The Avenue

DylanRating, 5 stars1 month ago
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!
Top Guest favourite
Home in Milwaukee
4.95 out of 5 average rating, 127 reviews

Large Luxury Home - Perfect for Groups - Downtown

JakeRating, 5 stars1 week ago
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
Guest favourite
Home in West Allis
4.9 out of 5 average rating, 78 reviews

3 Bedroom, 2 bath home, with gazebo By stadium

AmyRating, 5 stars1 month ago
This is a really nice location. Beautiful and very clean home. Would totally stay here again. Highly recommended and close to the stadium.
Superhost
Home in Milwaukee
4.88 out of 5 average rating, 267 reviews

Stunning Vintage/Modern! Brady St! Tons of Extras

KenRating, 5 stars1 month ago
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!
Top Guest favourite
Home in Wauwatosa
4.97 out of 5 average rating, 220 reviews

Wauwatosa/Milwaukee “Inglewood Place”Best Location

LisaRating, 5 stars1 week ago
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.
Top Guest favourite
Home in Milwaukee
5 out of 5 average rating, 125 reviews

Historic Brewery Tied-House in Bayview (Sleeps 12)

JulieRating, 5 stars2 weeks ago
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

Guest favourite
Apartment in Wauwatosa
4.85 out of 5 average rating, 318 reviews

Tosa Village Studio Apartment

DebbyRating, 5 stars4 days ago
One of our favorite places to stay. We like that we can walk to several restaurants when the weather is nice. Quiet and comfortable.
Guest favourite
Apartment in Milwaukee
4.94 out of 5 average rating, 104 reviews

Spacious+Mod Booth St Apt w Yard | Brewer’s Hill

MarkRating, 5 stars1 week ago
Great space! Convenient to everything. Great hosts.
Guest favourite
Apartment in Milwaukee
4.91 out of 5 average rating, 110 reviews

Charming 1 bd upper level in great location!

StaceyRating, 5 stars3 weeks ago
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?
Top Guest favourite
Apartment in Milwaukee
4.96 out of 5 average rating, 299 reviews

East Side Home

MarkRating, 5 stars4 weeks ago
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!
Superhost
Apartment in Milwaukee
4.85 out of 5 average rating, 233 reviews

Cozy Basement Space In Bay View by Lake Michigan

GeoffreyRating, 5 stars2 days ago
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!
Superhost
Apartment in Saint Francis
4.85 out of 5 average rating, 302 reviews

Cozy Apartment Nestled Across from Lakefront!

KelliRating, 5 stars1 day ago
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.
Guest favourite
Apartment in Milwaukee
4.91 out of 5 average rating, 180 reviews

Newport House -Walk to UWM- vintage upper+garage

MaggieRating, 5 stars7 months ago
This place was fantastic! Perfect for one person or a couple. A classic Milwaukee home with great charm.
Guest favourite
Apartment in Milwaukee
4.94 out of 5 average rating, 32 reviews

Apartment in Walkers Point

AnneRating, 5 stars1 month ago
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

Condo in Wauwatosa
4.63 out of 5 average rating, 113 reviews

Stylistic Condo Hot Tub Tosa Village 2 blocks away

IanRating, 5 stars9 months ago
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.
Condo in Milwaukee
4.66 out of 5 average rating, 32 reviews

Charming 2BR Off Brady St

AlexRating, 5 stars5 months ago
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.
Superhost
Condo in Milwaukee
4.91 out of 5 average rating, 34 reviews

Brewers Hill Belle, 2 bed, 2 bath, & balcony

JanetRating, 5 stars1 week ago
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!
Top Guest favourite
Condo in Milwaukee
5 out of 5 average rating, 102 reviews

Upper East Side, Designer Retreat w/large balcony

LauraRating, 5 stars8 months ago
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 🤙
Guest favourite
Condo in Shorewood
4.92 out of 5 average rating, 281 reviews

English Tudor - Upper Flat blocks from the beach

IngerRating, 5 stars1 month ago
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!!
Top Guest favourite
Condo in Milwaukee
4.99 out of 5 average rating, 217 reviews

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

CarolynRating, 5 stars1 week ago
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!
Condo in Milwaukee
4.63 out of 5 average rating, 41 reviews

Downtown Eastside gem near Fiserv Forum Bucks!

AlexRating, 5 stars1 month ago
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.
Guest favourite
Condo in Milwaukee
4.86 out of 5 average rating, 65 reviews

Spacious Bay View Historic Storefront Apartment

GraceRating, 5 stars6 months ago
No frills, exactly what we needed! Will definitely be back to explore Bay View more

Destinations to explore