
Holiday rentals with outdoor seating in Caledonia
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Top-rated rentals with outdoor seating in Caledonia
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Popular amenities for outdoor seating rentals in Caledonia
House rentals with outdoor seating

Entire Modern Lakehouse, Steps to Lake Michigan
Beautiful property with a very friendly host who gave us a ton of great local recommendations. We loved our stay here.

Exhale, rest
We absolutely enjoyes our stay at Emily's. The home was clean and adorable in a beautiful location. Menomonee Falls is a wonderful place to explore and a perfect location to enjoy Milwaukee. Emily was a gracious host that reached out often and was quick to respond if needed. Her home had everything we could want or need. It felt like home! Highly recommend.

Michigan Blvd Custom Home with Lake Michigan Views
Luke’s place was perfect for our trip. We had plenty of room, everything was clean, and it was close to the lake. We enjoyed being able to walk to the park or walk along the lake. He was very responsive. I’d highly recommend staying here!

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

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.

"Magnolia Farmhouse" inspired 4-bedroom home
Spacious, good space for families. Convenient to Milwaukee and Chicago. Highly recommended.

6th Ave Harborside
We loved our stay at Amy’s place! Everything was as described & even better. The amenities were over the top, we rode the bikes on the lakeside trail (she even provided helmets), there were beach towels & 8 beach chairs that we used for our beach & pool days. The beds & furnishings were comfortable & clean. Our Goldens appreciated the dog bed, treats, toys & fenced yard. Our granddaughters loved the upstairs closet playroom! The little things were SO nice, luggage racks, a stool for the Littles, gates to block off areas, a well equipped kitchen, even an old Nintendo system that my 42 year old son enjoyed. 🤣 We were in the area for 10 days to visit our kids & grandkids, everyone enjoyed spending time there, off & on. We will definitely be back!

Historic cottage with fireplace. Pets Welcome!
This is a genuine find! The conveniences, small touches, and great communication would make this a great place to stay. But the charm and historic setting make this next level. A beautiful setting, nice location for Milwaukee access, and of course scrupulously clean. The owners have done a great job creating a very quaint place that also meets modern travel expectations. Highly recommend.
Apartment rentals with outdoor seating

Walk to downtown McHenry. Heart of the Fox River
This apartment was super cozy and warm. Everything was labeled nicely and everything we needed could be found in the kitchen and the bathroom.

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!

Cheerful Apartment in Downtown Arts District
The location was convenient and everything was within walking distance. Maureen was so helpful and responsive to whatever I needed. She is a great host and the trip was perfect!

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.

Inn on Billy Goat Hill
Cannot say enough good things about our stay at Billy Goat Hill! Fantastic location with a quick walk to the local shops, parks, and restaurants. The space was incredibly cozy and had everything you could need for your stay. Extremely affordable for a weekend getaway. Donna and Paul were so inviting and responsive. Cannot wait to return and visit again!

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