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

Lake Muskego House, Walk to Stores & Restaurants
I traveled for 20 years I've been in all kind of places and that was one of the nicest. The amenities were awesome they had everything you can ever imagine it was just a very pleasant trip I would return and I would advise everyone to go visit

Blair House 1890
This was a great stay! Annie was very communicative and accommodating the whole time. Would recommend!!

5th St. Retreat - Outdoor Oasis, Hot Tub, 8 Beds
Wonderful home, very responsive owner, made for a very enjoyable stay in Milwaukee! Highly recommend!

The Menlo Guesthouse
Savannah’s home was PERFECT in every way! Absolutely no complaints. Not only was it so homey and decorated with such charm, but it was completely spotless - so clean! AND she had snacks waiting us, so sweet! We were walkable to things, had enough space for 5 of us, and just felt like we were in a cozy home for the weekend. If we return to Shorewood, this is exactly where I’ll be staying!

The Little Gray House
This home is famtastic, it has everything you need and more. The back yard is a tranquil garden oasis. The landscaping is absolutely beautiful. The inside of the house is just as inviting and spectacular as the exterior. Very spacious with so many amenities. Our host Sarah was very responsive and left detailed descriptions and instructions for everything. We are already planning our next visit our next visit.

This Must Be the Place- Bayview Bohemian Vibes
Easy to access beautiful home which looks just like the photos. The host was extremely responsive when I had questions - would absolutely stay again.

Urban Loft 1558 - Industrial Walker's Point 3 Bdrm
A most charming little home! Came into town for a wedding and we truly could not have picked a better place! The location was better than I thought, we were only a 3-5 minute drive or within 10 minute walk away. The home was beautiful and clean. We absolutely look forward to coming back and staying here again!

Quiet Bay View Bungalow, Extended Family Stay
Great location, very comfortable and home like. Smart lock was very reassuring to see and simple to use. I would recommend this location!
Apartment rentals with outdoor seating

Private apartment on the Lower Eastside
I loved this little oasis right in the heart of Milwaukee! I stayed here for 10 days on the flat is clean, spacious and well decorated. Although it’s right in the middle of everything and so many places are walkable, the neighbourhood is nice and quiet and peaceful – exactly what I needed. I would be more than happy to stay here again on my return to Milwaukee.

Cozy private getaway, Hot Tub, Music theme
This was my first time staying in an Airbnb that was a part of someone's home when they were home. While I was nervous at first, this was a fantastic experience! Check in and check out was easy, the hosts ensured a private experience, the vibes and decor were top tier! The snacks and toiletries were great to have available. I truly wish we had more time to spend here, thanks so much for a great stay!

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!!!!🫶🏽❤️

Quiet 2br Retreat Minutes to MKE Summer Fun
Nice, sufficiently stocked home for nearly all your needs. Clean and uncluttered, nice smelling linens. Proactive and ample communication for check-in and check-out; friendly and helpful, albeit standard. Made use of the Collective Cafe 2 blocks away for breakfast and nearby playground for kids. Combined with the marked down price for a great value, this worked out great for us! Definitely recommended.

Tosa/MKE Charming, Clean and Inviting Upper Unit
Christine was a great host. The unit was well cleaned. I loved my stay and I will gladly stay again!

East Side Home
We stayed for the weekend for a family event and this was the perfect location with plenty of space. The home is very well appointed and comfortable with everything we needed. The beds are incredibly comfortable with lovely linens. Thank you so much!

Charming 1 bd upper level in great location!
The place met our needs well. Just as advertised, nice and clean ,easy to get in. Comfortable bed. Nice bathroom. We parked out front and unfortunately our car got broken into.

Center Street Retreat
This is an amazing spot in Milwaukee! This hidden gem was so clean, amazingly decorated, and all the personal touches by Jennifer and Lance were so thoughtful. We can’t wait to be back!
Condo rentals with outdoor seating

Private East Side Milwaukee flat with fenced yard
Loved our stay here - host was helpful with clear instructions. Location is great - right next to an awesome donut shop and a 10 minute drive from everything else! Check-in and check-out was a breeze and the bed was very comfortable. Would love to stay here again.

Brewers Hill Belle, 2 bed + Loft & balcony
We had a group of 5 women that stayed here for Summerfest. The location was ideal with quick Uber rides to downtown restaurants/ Milwaukee Public Market and Summerfest. We did not have a vehicle but the garage/off street parking is a nice amenity. Easy access with coded doors for the outside door and your unit door. We stayed in unit 3 which is on the top floor. It does have lots of stairs to get to the unit. We enjoyed coffee on the balcony a few mornings which was very pleasant. The weather was very hot (90’s) when we were there and the AC worked great. The hosts were quick to respond to any questions we had. We had a great stay and I would book again if I come this way.

Stylistic Condo Hot Tub Tosa Village 2 blocks away
Sarah was a wonderful host with a beautiful home! My friends and I had a great time at this spot. It was clean and comfortable. Sarah was accommodating and responsive. Also super easy to get around Tosa or easy to get downtown!

Charming 3BR Off Brady St
Timothy provided everything we needed days in advance to ensure a smooth check-in, and accommodated an early check-in which was much appreciated!

Riverfront 2BR • Outdoor Oasis • King Beds
Very responsive host. Host’s description of property matched reality of the booking, no surprises.

English Tudor - Upper Flat blocks from the beach
Amazing house in a fabulous location. Loved the neighbor and walkability to the lake and coffee shops and restaurants. Jodi made the best of a heat wave stay for us by having the air conditioners and fans on and everything cool when we arrived. I appreciated the labels/signage that provided clear communication about amenities/where things were stored if needed etc. I always appreciate a welcome binder and this was a nice through one. We really enjoyed some of the breweries Milwaukee had to offer, the Miller brewery tour was great and so was the Brewers game and this was a great home to enjoy all those things. Thank you Jodi for sharing your home with us.

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.

Private, quiet first floor condo in New Berlin
Samantha is a gem when it comes to communication! She was understanding and accommodating when we ran into a pickle w/ needing to add a pet to our stay, last minute. The condo had everything we needed, clean, calm neighborhood. We truly enjoyed our stay!
Quick stats about holiday rentals with outdoor seating in Milwaukee
Total rentals
710 properties
Nightly prices starting at
$50 NZD before taxes and fees
Total number of reviews
41K reviews
Family-friendly rentals
520 properties are a good fit for families
Pet-friendly rentals
260 properties allow pets
Rentals with dedicated workspaces
540 properties have a dedicated workspace
Destinations to explore
- Downtown Chicago Holiday rentals
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- Lake Geneva Holiday rentals
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- Holland Holiday rentals
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- Lake Michigan Beach Holiday rentals
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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
- Racine North Beach
- Bradford Beach
- Grand Geneva Resort & Spa
- Milwaukee County Zoo
- Richard Bong State Recreation Area
- Wilmot Mountain Ski Resort
- Harrington Beach State Park
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
- West Bend Country Club
- Heiliger Huegel Ski Club
- Springs Water Park
- Discovery World
- The Mountain Top Ski & Adventure Center at Grand Geneva
- America's Action Territory
- Blue Mound Golf and Country Club
- Sunburst