
Holiday rentals with outdoor seating in Caledonia
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Top-rated Holiday Houses with Outdoor Seating in Caledonia
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Holiday House Rentals with Outdoor Seating

Hot tub getaway Extra Large capacity home
This was a wonderful place for our family get together. The house has a few different places for a large group to hang out and was close to the beach.

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

Lake it Easy at this beautiful 2 bedroom lake home
We had a great stay! Everything was as described and we were cozy from the moment we walked in! Neighborhood is cute, neighbors were friendly, and you can’t beat the lake views! (just a few short steps from the driveway and you’re right at the boat launch) We didn’t bring our kayaks with but we could have easily walked them down. It was a great week here and we would absolutely stay again!

Cozy historic Cream City Brick Workers Cottage
This Is a nice older historic home a few blocks from the lake, where there is a nice beach and walking paths- we even walked several times to downtown to eat at the various waterfront restaurants. The house is nicely kept, the two bedrooms are quiet and comfortable, extra space with a full living room with larger table as well as kitchen with table to eat at- Kitchen well equipped. We had some initial worries on the neighborhood but after staying 4 days we felt more comfortable and had no problems. its more of an urban environment and on some nights more people are out and about on their porches or on the street. Strangely not many people at the beach or waterfront when it's so nice there. Would stay there again for sure

Renovated Luxury Retreat Near Lake•Peaceful Escape
we loved staying here! we loved how everything was labeled and knew where everything went, we loved the extra pickleball and volleyball equipment. over all very beautiful and felt right at home!

Brand New Studio w. Private Entry + Garden Patio
Hubby and I stayed Friday and Saturday night. The room was perfect for us. Not too big and not too small. Plenty of amenities in the room to make us feel welcome. We didn't get a chance to sit out on in the backyard, but the view was beautiful.

Sunny Upper Flat in Shorewood Near UWM & Downtown
ok so i’m picky. and this place knocked my socks off. it is VERY well taken care of, no mold/mildew like a lot of older homes begin accumulating. SUPER clean and just so comfortable. they were crazy flexible with my checkin (why do i think i’m still 20 and try to take a red eye?!) and were really easy to communicate with. will stay here every time i’m in milwaukee if it’s available!!

The Rawson House
The house was perfect for the six adults and one child in our party. The house is minutes from the airport and downtown Milwaukee. It has a great backyard with lots of room to play. I highly recommend this house to anyone visiting Milwaukee.
Apartment rentals with outdoor seating

J’s Farmhouse Cottage. 2 bedroom duplex.
Jones home was immaculate and very cozy and comfortable. it was very close to the Illinois Beach State Park on Lake Michigan which is why we were in the area. highly recommend.

Silvers Four-Six-Six *A home away from home*
We loved staying here! We came for Memorial Day weekend and had never been to Port Washington. It is a beautiful small town on the water with a great downtown. The place was super clean and cozy! We thought it was even better in person than it looked in the pictures. Elle was very responsive, left good recommendations for town, and even had eggs, yogurt and fruit for us to make breakfast in the morning. 10/10 highly recommended staying here!

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!!!!🫶🏽❤️

Cozy 2 Bed Apartment
We had a lovely 4 night stay while visiting Six Flags Great America and the surrounding area. The apartment was exactly as described and had everything we needed for a comfortable stay. Hugo was very quick to respond to us when we reached out and was very communicative. We would definitely stay again when traveling to the Chicago area!

The Hive 2BR Apt | Downtown Racine Escape!"
The hive was great! Would absolutely stay here again. Angela is a wonderful, responsive and accommodating host.

Downtown-Treetop Deck-2Bd/2Bth
Couldn't ask for a better place to stay in Kenosha. SOOo private. There is no one on either side of the apt and a store is below so no one is there at night. GREAT back deck w grill. Super clean. Great shower. Hosts are the nicest people!! They greeted me when I arrived and gave me detailed instructions on how TV worked, how to get onto back deck etc. They have thought of EVERYTHING someone might need. Beach towels and beach bag...even a big wide brim hat in case you forgot yours. Magnified make up mirror, great TV w movie channels, super comfortable bed, AC units in every room. Loved it and will stay again whenever I am in Kenosha!!

MKE-Spa Airbnb
Nicely decorated with ample shared spaces for up to 4 adults though we only had 2. One phone call was all it took to register to park on the city street. Neighborhood is up and coming though we felt There is upstairs noise as others have commented.

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

Beautiful Villa with Amenities Galore
We were lucky to find Amy's place as many only book two-night minimum and we were only in town for one. Her condo was clean and comfortable. We entered on a hot day to a well-air-conditioned home and to jazz music playing. It was such a great way to start our stay. She gave recommendations for the area and had very few requests for checkout - just take trash and start the dishwasher. We three women took a late-night walk in the area and felt perfectly safe. Be aware that check-out is 10AM while most places are 11:00. It was fine with us as we were getting on the road by then but some would care. I don't know if there's any flexibility as it didn't matter. Amy was very proactive about ensuring we were all settled in and asked if there were questions. We had a great stay and recommend Amy's condo.

Magnificent waterfront views & cozy fireplace
This cozy little condo on lake Como/Geneva was outstanding! Easy access to all the things in the area! Lori was extremely communicative and we enjoyed her as a host. If we find ourselves in Geneva again we will certainly stay here on repeat!

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.

LakeView-SummerPool-FamilyFriendly-CloseToTown
Rachel’s place was very clean and a short drive to everything we did in the area. It was the perfect size for our family of 4. The pool was nice as well.

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
This was a great stay. We parked our car and never used it- walked to the beach, to restaurants, etc. The decore wasn't my style, but the space was nice , the shower was great, and we had everything we needed.

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!
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- Six Flags Great America
- Erin Hills Golf Course
- Alpine Valley Resort
- Milwaukee Public Museum
- Geneva National Resort & Club
- Illinois Beach State Park
- Bradford Beach
- Moraine Hills State Park
- Racine North Beach
- Harrington Beach State Park
- Milwaukee County Zoo
- Grand Geneva Resort & Spa
- Richard Bong State Recreation Area
- Wilmot Mountain Ski Resort
- Milwaukee Country Club
- West Bend Country Club
- Discovery World
- Heiliger Huegel Ski Club
- Springs Water Park
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Old Elm Club
- Shoreacres
- Sunburst
- Blue Mound Golf and Country Club