
House holiday rentals in Shorewood
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Top-rated house rentals in Shorewood
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Holiday rentals for every style
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Popular amenities for Shorewood house rentals
House rentals with a pool

The Gem of Brewers Hill w/hot tub & seasonal pool
Excellent location and plenty of beds and bathrooms.

Family friendly & dogs welcome
We felt right at home at Jane's place. everything was as listed, the place was super homey, and Jane was a great host.

Cute and cozy 2 bedroom house perfectly located!
Our first time in Delafield and loved it!! Adorable little lake town with so many cute restaurants, coffee shop and ice cream just a short walk away. Elizabeth's home was exactly what we needed for a month long mother/daughter stay while attending treatment in the area. Meticulously clean at check-in and decorated so cute with finest attention to detail! So warm and cozy providing a perfect sanctuary. Elizabeth was flexible and responsive in all communication prior to and during our stay, and quickly addressed an Internet hiccup, ensuring the issue was resolved for us. Can't wait to return and highly recommend Elizabeth and this adorable gem of a home!!

Cozy cabin getaway near Lake Como and Lake Geneva
Sasha’s place was even better than expected. We all felt at home and it was very relaxing. We had plenty of room to accommodate all of the guests.

Vacation home: heated inground pool on 4+ acres
Was a wonderful stay at the home, will definitely go back again in the summer for a nice swim in the beautiful pool! If you are looking for a little getaway in a quiet area with a home that's both comfortable and modern I highly recommend this stay!

Oasis on Oak | Private In-Ground Pool | Hot Tub
House was great and matches the description and photos. House is spacious, good for a group of 6-7 people and private from other neighbors. It’s also less than 10 minutes from downtown Lake Geneva. It is an ideal house if you are looking for a quiet weekend retreat, close to the areas activities. In addition, the host is responsive and helpful. Looking forward to our next stay with you all!

Nestled in the Southern Kettle Moraine Forest
Jarvis and Chris are the kind of hosts who go above and beyond. We arrived after a chaotic day and were instantly welcomed with warmth, a surprise graduation cake and wine, and the peaceful reset we didn’t know we needed. The property is absolutely stunning—pictures do not do it justice. The trails are beautiful and serene, and the animals are the sweetest, most well-loved crew. You can feel how much care and heart goes into every part of this place. They also provided the best recommendations for dinners, hikes, and activities! If you’re thinking about booking—do it. You will not regret it. This place is a true Wisconsin gem. The love, care, and intention poured into it is obvious. We’re so grateful for this experience and already can’t wait to come back!

Wooded Hills/Indoor Pool/Hot Tub/Arcade
Great stay. Pool could have been cleaned better before our stay.
Weekly house rentals

Beautiful 4BR Home-Walk to Beach
There were six of us siblings traveling to Shorewood for a family memorial service, and we chose this house because it reminded us of our childhood home. It's a charming place filled with antiques and (probably) garage sale finds :-) We each had a room and appreciated the extra bathrooms and various spaces in the house which gave each of us enough privacy as well as plenty of togetherness. The house is located in Shorewood on a really cute street,and it's worth walking around to see the historic homes. It's nice and quiet and residential with restaurants, pubs, etc., nearby. Also appreciated Xavier's responsiveness on the one question I had - just a lovely trip overall.

Baby and Toddler friendly House by the Beach
We had a wonderful stay at Sitora’s house. The best house and location for ones with little kids. What a beautiful home. The distance to the beach was key for us. We enjoyed walking to both Atwood Park/beach and Shorewood nature preserve.

Charming Pet-Friendly 3-BR Home, Backyard, Firepit
This was the perfect house for our first trip with both kids and both dogs. The kids had their own bedrooms, the yard was fully fenced and large for the dogs to run around. The location seemed very nice and walkable to a few restaurants, and very close to the lake and beach. Maira also went above and beyond installing baby gates at the top and bottom of the stairs to keep the kids safe, which also helped us keep the dogs on the main level so we didn’t have to worry about them going on the beds! We would definitely stay here again!

Whitefish Bay Getaway; steps from Starbucks!
Adorable neighborhood - super charming and peaceful vibe - very family friendly

Vintage UWM Duplex on Downer - Pet-friendly 2BR
Great location. We happened to be there after school ended so it was a peaceful neighborhood at the time. Easy to get to the lake and not far from other areas in the city. We were able to check in a little early and it was nice being able to bring our dogs. Lacy was a great host and we’d definitely stay again. One thing I’d say is that if it was during the peak summer months, it would have been very hot with no air conditioning.

2BR Sunny Upper in Prime Bay View - w/ Parking
This was our second stay here, and our second time hosting an out-of-town guest in this fun space. Our hosts went above and beyond. I made a major mistake in my booking date, and I could have had a major scramble to find an alternative, and they responded immediately, and with such grace, flexibility, and kindness. On top of that, this is such a great location for seeing Bay View and the rest of the city. We sampled more restaurants, we took walks, and we had everything we needed to be comfortable when we were back at the apartment for downtime. Highly, highly recommend.

4 Mins Walk Lake Michigan Atwater Park Beach. Pets
Our stay was great. Location was awesome. Lokesh communicated with us and accommodated our needs.

Prairie style home on Stratford
Alan and Sarah were great hosts. The house matched the pictures and description exact and was perfect for our needs. My only concern was having to meet on site for a physical key as I normally book keyless entry. However, the process was easy and met my travel timeline and there were extra keys once on site. The homemade cookies were a delicious and kind touch!
Private house rentals

Retreat w/hot tub Fmly/Pet Frdly No Clean fee
Candace was very responsive with any questions we had and did her best to get us in early. The place was perfect for us and the hot tub was a nice adde amenity!

Entire Cozy Cottage! Pet Friendly, No Cleaning Fee
Amanda and Troy’s place was a great little bungalow for our first trip to Milwaukee. It was quick and easy to get to the highway, yet far enough to be situated it a quiet little neighborhood. Amanda and Troy really thought of everything! We took their recommendation and enjoyed walking to Blue’s Egg Cafe & Bakery. Would recommend their place for your next trip!

Bass & Sparrow - Spa Retreat on the MKE River
You would have no idea this place is in Milwaukee. It truly felt so secluded, like you were hours away from downtown. The hot tub, sauna, river right there…might has well been at a resort. Truly one of the most memorable weekends and we can’t wait to reserve another stay with Brad!

Style and Luxury | Unbeatable Location
My group of friends and I had a great stay. There was plenty of room and the place matched the description perfectly. We would definitely stay here again in the future!

The Good Life Milwaukee (Riverwest)
We were in Milwaukee for a wedding and Jeanie’s place was perfect for our group of 7. Plenty of space, a nice quiet neighborhood, very comfortable beds, and had everything we needed!

Charming Mediterranean Lower Flat
Can’t rave enough. The easiest Air B and B adventure we’ve been to. I really appreciated the cleanliness and clear instructions. Gorgeous flat! Made our daughter’s graduation from nursing school an even more memorable event!!!

Auburn Place: Cozy 3BR Home in Wauwatosa
Nice property with off street parking, close to everything you want to do in Milwaukee. *Almost* walking distance to watch a Brewers game (2.5 miles). Great grocery stores and restaurants nearby - some within walking distance. Check in earlier than most properties - and check out instructions were easy and reasonable. The hosts communicate well and any questions or concerns I had were answered promptly. Tosa is a quiet, safe, family suburb. This is a good option if your plans bring you to Milwaukee.

Whitefish Bay 3Bedroom Entire House Sleeps 4
My family and I had a very comfortable stay here. It had everything we required to make our time here feel like home. An added bonus: only a 5-minute drive to Kopp’s Frozen Custard! (A must stop for us whenever we’re in the Milwaukee area.) James is an ideal host—pleasant, organized and responsive (vielen Dank!).
Quick stats about house rentals in Shorewood
Total rentals
40 properties
Total number of reviews
1.1K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wi-Fi availability
40 properties include access to Wi-Fi
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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
- Richard Bong State Recreation Area
- Milwaukee County Zoo
- Wilmot Mountain Ski Resort
- Harrington Beach State Park
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
- West Bend Country Club
- Pine Hills Country Club
- Heiliger Huegel Ski Club
- Springs Water Park
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Discovery World
- Sunburst
- Blue Mound Golf and Country Club