
Holiday rentals with outdoor seating in Milwaukee
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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!!

Private Home. Best stay for Brewers/Am Fam Field
I would stay there again. It was so pleasant, and peaceful. The host was helpful, instructions were useful. It was easy to get into. Very clean! Great location. If you’re ever in Milwaukee, this is a great place to stay.

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.

Charming Bayview House, steps from MKE Merriment!
Great 2 bedroom bungalow for a 2 night stay in Milwaukee. Attended a Brewers game with another couple. Location perfect for the game and dinner out on Tuesday night. Cooked in on Wednesday. House works perfectly for 4 adults and would work well for a family with 2 children. Deck in backyard was great for morning coffee and evening drinks. Very quiet neighborhood. Also being able to park in a garage was a big plus.

Large Luxury Home - Perfect for Groups - Downtown
Great location and stay. Bed count was a bit confusing as some of the beds are futons rather than actual beds which led to some of our guests moving around trying to find a comfortable spot but all in all nice spot.

Brewers Hill cottage, newly renovated near FiServ!
Great hosts with a fantastic place! They definitely made us feel at home and provided some helpful recommendations. Check-in & check-out were a breeze!
Apartment rentals with outdoor seating

Spacious+Mod Booth St Apt w Yard | Brewer’s Hill
What a lovely apartment! We're so glad we chose to stay at John and Jamie's place. It was spacious, clean, and beautifully-decorated. The kitchen was huge and had everything we needed, including coffee and half & half. The neighborhood is quiet and peaceful, and within walking distance of the riverwalk and Lakefront Brewery. We're sad we only got to stay one night. We would definitely stay here again next time we're in Milwaukee. Thanks, John & Jaime!

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.

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!!!!🫶🏽❤️

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!

Close to Stadium|Near Attractions|Parking|Sleeps 5
Dan and Catherine were able to accommodate us on short notice when our other accommodation had plumbing issues and had to cancel. Very comfortable home with everything you need. Very easy on and off I-94 near the Brewers Stadium.

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
the place was spacious and comfortable. loved the layout and the beds were comfy
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
The layout of unit 3 was exactly as described. It was spacious and perfect for our group of 10. There were plenty of towels, 12-cup coffee pot, and the laundry area was easily accessible. There are quite a few stairs but it was beautiful to have a balcony and sit out and drink your cup of coffee. We were 10 minutes driving distance from all our planned activities.

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!

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.

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.

Third Ward - High End 1 Bedroom up to 6 + Parking
The Airbnb was great—more spacious than it looks in the photos! Check-in was smooth with clear instructions, and it was super convenient having parking included. The parking lot entrance is right by the elevator, which made coming and going really easy. The unit itself had plenty of space for a one-bedroom and could comfortably fit 4+ people. It’s also in a nice, convenient area with easy access to everything we needed. Would definitely 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.
Quick stats about holiday rentals with outdoor seating in Milwaukee
Total rentals
710 properties
Nightly prices starting at
$46 AUD 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
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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
- Racine North Beach
- Grand Geneva Resort & Spa
- Milwaukee County Zoo
- Richard Bong State Recreation Area
- Wilmot Mountain Ski Resort
- Harrington Beach State Park
- The Bull at Pinehurst Farms Golf Course
- Milwaukee Country Club
- West Bend Country Club
- Heiliger Huegel Ski Club
- Springs Water Park
- Discovery World
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Blue Mound Golf and Country Club
- Sunburst
- America's Action Territory