Holiday rentals in Waukesha

4.97 out of 5 average rating, 348 reviews

Flat in Cedarburg

Cedarburg 2 br Apartment on prime Washington Ave

KelseyRating, 5 stars2 weeks ago

Kathy and Marty were very communicative. I knew without question if I needed anything they would answer right away. They were proactive with recommendations and directions for access. This is the second time I’ve stayed with them and will continue to do so any time I’m in Cedarburg! They are also close enough to Milwaukee for you to get multiple experiences if you are from out of town! Highly recommend a leisurely morning stroll to Boulangerie Du Monde and then Fiddleheads for coffee.

4.98 out of 5 average rating, 206 reviews

Apartment in Lake Geneva

Lake Geneva Cloud 9

LauraRating, 5 stars1 month ago

We were in Lake Geneva for a convention, so were mostly only in the condo for sleeping, but the place had everything we could possibly need and then some. There were plenty of extra supplies in the kitchen and bathroom. If we had been traveling with kids, there were toys and games. And if it had been a warmer season or we were there for relaxation, the location looks great for outdoor activities. Cheryl sent us good instructions for parking, unlocking the door, etc. And inside there was a whole binder of stuff to make anything we needed to do easy. Thanks, Cheryl...you made our brief stay easy and comfortable!

4.97 out of 5 average rating, 234 reviews

Apartment in Racine

Gorgeous Main Street Apt with Lake Views (APT2)

MandiRating, 5 stars2 weeks ago

We absolutely loved this condo! My husband and I stayed for 9 days and literally wanted to move in lol! We loved the open floor plan, the big multipurpose bar/kitchen table, and there were lots of little helpful touches such as the labels for all the lights and dimmer switches. There is a convenient laundry room right outside the front door to the condo with an extra large washer and dryer. Amy and David were excellent hosts and were available for any and all questions. The secure parking garage made us feel comfortable with our vehicle being right outside the door to the condo. If we’re able to come back to Racine we will definitely want to stay here again.

4.91 out of 5 average rating, 139 reviews

Flat in Port Washington

Lighthouse View -a real gem on Sweet Cake Hill

JohnRating, 5 stars1 week ago

Great hosts with a nice apartment, It was everything I remember about living in Port Washington. The older apartment made us feel right at home. Easy to find and within walking distance of downtown Port Washington. Thank you for providing our place to stay

4.97 out of 5 average rating, 141 reviews

Bungalow in Lake Geneva

Private Cozy Cottage Lake Geneva, WI

JasonRating, 5 stars1 month ago

We loved this place. It was an easy walk down to the water and into town for restaurants. The special touches of a bottle of wine waiting for us, the full basket of continental breakfast options, the gas fireplace, and the jacuzzi made this cozy little cabin feel like a resort. They raised the bar for what you AirBnbs should can. Perfect for a couple getaway.

4.98 out of 5 average rating, 144 reviews

Updated luxury country getaway short walk to lake!

KaitlinRating, 5 stars1 week ago

The house was cozy and clean! I am sensitive to fragrance and appreciated the home not being overly scented! Walkable to the lake and we loved seeing all the deer in the neighborhood. Shari was easy to get in touch with and we were provided with everything we needed during our stay.

4.98 out of 5 average rating, 146 reviews

Home in Elkhorn

Red Lodge - Game Room, Hot Tub, Near Lake

KatieRating, 5 stars3 weeks ago

This place was the perfect retreat for a few days away from home. Even in the off season we stayed entertained with the games and hot tub, making every moment enjoyable. Nestled in a charming yet private neighborhood, the home is spotless, thoughtfully maintained, and filled with warmth. It’s convenient location made exploring easy while still offering a peaceful escape. A truly wonderful stay.

4.97 out of 5 average rating, 153 reviews

NEW! Cozy Downtown Farmhouse, 5BR 3 BA Sleeps 15!!

MorganRating, 5 stars1 month ago

Highly suggest Brian’s place! Exactly like pictures and perfect for a weekend getaway. Home was beautiful and newly updated! Everything was walkable, perfect location to downtown. We had 14 guests and everyone was comfortable and beyond happy with accommodations! Brian was easy to work with and everything was clear for us. Thanks for a great stay! We will be back.

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Popular amenities for Waukesha holiday rentals

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Stay near Waukesha's top sights

Woodman's Food Market12 locals recommend

The Corners of Brookfield13 locals recommend

Taylor’s People’s Park8 locals recommend

Marcus Majestic Cinema of Brookfield7 locals recommend

Sendik's Food Markets6 locals recommend

Café Hollander - Brookfield5 locals recommend

Other great holiday rentals in Waukesha

Superhost

4.93 out of 5 average rating, 15 reviews

Large Geneva Home | 8 beds | Fenced Yard Walkable

IrisRating, 5 stars3 months ago

Overall, our experience was nothing short of amazing. We cannot recommend Bjorn and their property highly enough.

4.85 out of 5 average rating, 20 reviews

Guest suite in Wind Lake

Secret Garden Getaway

CassidyRating, 5 stars7 months ago

Sandy was such an amazing host! She was very kind and respectful. The place was beautiful! We went for a wedding and found that the location of the Airbnb was right around the corner, super convenient and so peaceful.

4.93 out of 5 average rating, 101 reviews

Home in Lake Geneva for your whole family

ScottRating, 5 stars1 month ago

Second time renting this house - it's like staying at home. Hosts are great to work with.

Superhost

Home in West Allis

4.77 out of 5 average rating, 153 reviews

★Cozy Beach Themed Home★2 Beds★Spacious Parking★

HélèneRating, 5 stars2 months ago

Tiare’s place was per the description and comfortable. The driveway was well shoveled/cleared after the snow. Place is conveniently located for our trip purpose.

4.91 out of 5 average rating, 114 reviews

Lake Geneva cottage with private beach access

ElenaRating, 5 stars3 days ago

Jennifer was very responsive and friendly. The house was adorable and was perfect for a overnight getaway

4.97 out of 5 average rating, 36 reviews

Home in Racine

Mid-Century Modern Dream Getaway

JasonRating, 5 stars1 week ago

We loved our stay in this beautiful mid-century modern home close to the lakefront. There was a bundle of firewood waiting for us when we arrived - perfect for a rainy, spring evening. Our time inside the house was relaxing and comfortable. We also took a few walks around the neighborhood. An old school supper club (Hob Nob) is just a few steps away and the lakefront is accessible as well. We would definitely stay here again.

4.89 out of 5 average rating, 132 reviews

Home in Slinger

Aprés House - On the slopes of Little Switzerland

CarolinRating, 5 stars3 months ago

We absolutely loved our stay. This was our second time at this place! Great space, walking distance to Little Switz skiing, and enough space to host friends for dinner!