House holiday rentals in Shorewood

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Popular amenities for house rentals in Shorewood

House rentals with a pool

Guest favourite
Home in Brewer's Hill
4.92 out of 5 average rating, 140 reviews

The Gem of Brewers Hill w/hot tub & seasonal pool

GerryRating, 5 stars2 weeks ago
Excellent location and plenty of beds and bathrooms.
Guest favourite
Home in Mequon
5 out of 5 average rating, 10 reviews

Vacation home: heated inground pool on 4+ acres

AvremiRating, 5 stars1 month ago
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!
Superhost
Home in Sussex
4.88 out of 5 average rating, 112 reviews

Wooded Hills/Indoor Pool/Hot Tub/Arcade

KaitlynRating, 5 stars1 week ago
Great stay. Pool could have been cleaned better before our stay.
Home in Caledonia
4.85 out of 5 average rating, 75 reviews

7 1/2 Acres! Pool! Hot Tub! Fishing Pond!

SherriRating, 5 stars2 months ago
I think this was my favorite place I’ve rented. I’m glad I found it just an hour outside the suburbs of Chicago. It’s a country feel with a ton of activities as described, plus a few extra. My boys really enjoyed the game room. There’s a TV so we played music videos while playing darts, billiards, and I enjoyed throw back video games like Donkey Kong, Centipede and Dig dug. It was cooler outside so I definitely want to return in the summer to enjoy the pool, bonfire, fishing pond, but we had one nice day so still got to enjoy the large property, paddle boat, swings, bocce ball and hot tub. The house has very comfortable furniture, like the beds and couches. We watched movies at night and slept well. Robert was a great host and I appreciated all the helpful notes around the house. I almost felt guilty it was just me and my boys, but it was a perfect getaway. Plenty to do, or do nothing and enjoy the views.
Guest favourite
Home in Cudahy
4.78 out of 5 average rating, 152 reviews

Make Yourself At Home! Close to Lake & Airport!

TanyaRating, 5 stars2 months ago
Ann went above and beyond to be a fantastic host!!! Her listing gives a very accurate overview of the living space and what to expect during this airbnb experience. She makes you feel at home and like you're staying at a friend or family member's house vs. an impersonal hotel. Her wonderful pets are an added bonus. There was a furry welcoming committee there to meet us at the door and to offer snuggles :) I would recommend this airbnb to anyone! It's in a peaceful neighborhood and only a short drive to shopping centers and restaurants galore.
Top guest favourite
Home in Brewer's Hill
4.97 out of 5 average rating, 174 reviews

The Peacock Place w/ Seasonal Outdoor Heated Pool

MikeRating, 5 stars2 weeks ago
We cant say enough about our stay with Stephanie and Jesse. We were only there for a night, but we found the place to be spacious, comfortable and well maintained. The house itself was gorgeous and it felt like an authentic Milwaukee home. The surrounding neighborhood was walkable and beautiful as well. The morning we left we noticed our tire was flat. Stephanie and Jesse were super proactive in helping us fix the flat. Jesse, who was extremely handy, was able to take the nail out and fill the hole so that we could return the rental car. We were all super thankful for their help as they took all the stress out of what would have otherwise been a somewhat stressful situation. They were great hosts and we cannot recommend them enough!
Home in Milwaukee

Townhome Villa private oasis

Home in Riverside Park
New place to stay

Cooler by the Lake - MKE

Weekly house rentals

Superhost
Home in Whitefish Bay
5 out of 5 average rating, 4 reviews

Whitefish Bay Beauty!

TaylorRating, 5 stars10 months ago
This cute street is everything you are looking for a peaceful enjoyable getaway! This property is not just a rental property, but a home that is being shared by a wonderful host! The kitchen and backyard are fully equipped beyond expectations. This historical house has amazing charm and very comfortable beds. The backyard is a slice of heaven and a great retreat away. The host is very responsive and was able to tend to any request! I am a property manager with 19 properties in upstate NY and I only wish would be if this house was in my area so I could be part of this wonderful rental.
Guest favourite
Home in Shorewood
5 out of 5 average rating, 29 reviews

Beautiful 4BR Home-Walk to Beach

EmilyRating, 5 stars3 weeks ago
Home away from home! Some family and I road tripped over to the Milwaukee area to attend a Twins vs Brewers game and celebrate my 40th Birthday. This house was just right for us, with lots of charm and eclectic art. We really felt like we lived there comfortably for a weekend. The neighborhood is darling, you basically take a tour of lovely old houses while you the walk to the lakeshore. Good times were had by all❤️
Guest favourite
Home in Whitefish Bay
4.9 out of 5 average rating, 20 reviews

Whitefish Bay Getaway; steps from Starbucks!

GabrielaRating, 5 stars3 weeks ago
Tim and Karen were amazing hosts—very responsive and helpful with all of my questions and concerns. Their place was spacious, clean and felt like home, making it perfect for my group of 10 friends. There’s plenty to do in the area, and downtown Milwaukee is just a short 10–15 minute drive away. I highly recommend staying at Tim and Karen’s if you’re planning a group trip and want a comfortable place to stay with easy access to local activities.
Guest favourite
Home in Milwaukee
4.96 out of 5 average rating, 28 reviews

Vintage UWM Duplex on Downer - Pet-friendly 2BR

BrendenRating, 5 stars3 weeks ago
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.
Top guest favourite
Home in Whitefish Bay
4.95 out of 5 average rating, 20 reviews

Whitefish Bay 3Bedroom Entire House Sleeps 4

MalaineRating, 5 stars3 days ago
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!).
Guest favourite
Home in Bay View
4.94 out of 5 average rating, 96 reviews

2BR Sunny Upper in Prime Bay View - w/ Parking

KristiRating, 5 stars1 week ago
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.
Top guest favourite
Home in Riverside Park
5 out of 5 average rating, 11 reviews

East Side Duplex-Cozy Lower Unit

TinaRating, 5 stars2 months ago
Had a great weekend stay in Milwaukee! Came to town because my son ran the half marathon and we had a great time! Jarrid's place was super convenient and perfect for where we wanted to be. Clean, homey, and made out of towners feel super comfortable! Thanks for the bottle of wine, Jarrid!!
Superhost
Home in Shorewood
4.83 out of 5 average rating, 36 reviews

Prairie style home on Stratford

SusanRating, 5 stars2 weeks ago
Perfect location close to the lake parks, restaurants, cafes. Fully stocked kitchen. Comfortable beds. Spacious dining and living room. Beautiful patio. Clean and comfortable. Friendly host!

Private house rentals

Guest favourite
Home in Glendale
4.9 out of 5 average rating, 48 reviews

Retreat w/hot tub Fmly/Pet Frdly No Clean fee

AlexRating, 5 stars1 month ago
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!
Top guest favourite
Home in Bluemound Heights
5 out of 5 average rating, 73 reviews

Entire Cozy Cottage! Pet Friendly, No Cleaning Fee

KateRating, 5 stars3 days ago
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!
Guest favourite
Home in Glendale
4.92 out of 5 average rating, 25 reviews

Bass & Sparrow - Spa Retreat on the MKE River

CamilleRating, 5 stars2 weeks ago
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!
Superhost
Home in Lower East Side
4.95 out of 5 average rating, 20 reviews

Style and Luxury | Unbeatable Location

MiryeaRating, 5 stars3 weeks ago
Great location and space! Walking distance to many restaurants and bars. We enjoyed how spacious it was and having the parking spot was really convenient. The hosts were very communicative and helpful when some things came up. Overall, would definitely stay here again!
Guest favourite
Home in Riverwest
4.96 out of 5 average rating, 56 reviews

The Good Life Milwaukee (Riverwest)

RyanRating, 5 stars2 weeks ago
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!
Top guest favourite
Home in Brewer's Hill
5 out of 5 average rating, 93 reviews

Near Downtown w/ Rooftop Patio & Game Room!

KristaRating, 5 stars1 week ago
Michael was an over the top host! He was very responsive and made the process very easy and comfortable. We hosted a bachelorette here and it was perfect! Everyone commented how clean the house felt and loved all the sleeping accommodations. The roof was a beautiful addition. If you are looking for a place to stay in Milwaukee Michaels place is perfect!
Top guest favourite
Home in Shorewood
5 out of 5 average rating, 26 reviews

Charming Mediterranean Lower Flat

RhondaRating, 5 stars5 months ago
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!!!
Top guest favourite
Home in Milwaukee
4.98 out of 5 average rating, 91 reviews

Charming Pet-Friendly 3-BR Home, Backyard, Firepit

NicoleRating, 5 stars6 days ago
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!

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

  • Wifi availability

    40 properties include access to wifi

Destinations to explore

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  2. United States
  3. Wisconsin
  4. Milwaukee County
  5. Shorewood
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