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Compare 143 Vacation Homes in Oconomowoc with updated reviews, rates, and availability.

Amazing Five Bedroom Milwaukee Vacation Home!!

10.0 out of 10, Exceptional, (37)
"Went for our annual golf trip. Perfect house for the 6 of us. Never had to leave the house after our rounds!"
Amazing Five Bedroom Milwaukee Vacation Home!!

Beautiful lakefront, Newly Remodeled Lower Level!

9.8 out of 10, Exceptional, (173)
"We had a wonderful stay; only complaint was that we couldn't get the outside light to work in the back, by the hot tub. Would definitely come again!"
Beautiful lakefront, Newly Remodeled Lower Level!

Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

10.0 out of 10, Exceptional, (321)
"Great house for being in the lake. Has a nice backyard that is fenced in and was perfect for our dogs. "
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

Pewaukee Lake Home: Sunsets, Dogs & Good Vibes

10.0 out of 10, Exceptional, (22)
"Kristen was an excellent host and made sure we had what we needed. The house and location were awesome and we all had a really great time."
Pewaukee Lake Home: Sunsets, Dogs & Good Vibes

Private estate with tennis court and more

10.0 out of 10, Exceptional, (38)
"We rented for a golf weekend! Close to Washington County course, Erin Hills and the Bog. Played Brown Deer on the way up. Property was everything needed and beautiful grounds! Would stay again!"
Private estate with tennis court and more

Relax Near Everything in Milwaukee

10.0 out of 10, Exceptional, (35)
"The property was exactly what we needed for a convenient extended weekend. Very spacious house with ample parking and all the amenities we were looking for. "
Relax Near Everything in Milwaukee

Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.

10.0 out of 10, Exceptional, (5)
"Beautiful home and property, lots of space to spread out and have privacy. "
Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.

Charming 3-bedrooms house/resort-like with Firepit and Deck.

2.0 star property
"He claimed it was too many people in the driveway and it was only 3 cars and 2 in the garage I also told him that it was family members from the wedding reception rehearsal and he popped up and kicked me out and sent me to jail"
The price is SAR 1,149
SAR 2,246 total
includes taxes & fees
1 Dec - 2 Dec
Charming 3-bedrooms house/resort-like with Firepit and Deck.

Modern and Convenient Waukesha Home with Hot Tub

8.0 out of 10, Very Good, (1)
"This home worked great for our group while in town visiting Carroll University. It was close to downtown and campus. I would stay here again."
The price is SAR 563
SAR 1,196 total
includes taxes & fees
2 Dec - 3 Dec
Modern and Convenient Waukesha Home with Hot Tub

4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!

9.6 out of 10, Exceptional, (157)
"Enjoyed being close to the wedding venue. Samantha was available to answer any questions. The bedrooms were large and living space great for family. "
4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!

Fall Deals! - Mins to Froedert/State Fair - Dogs!

9.6 out of 10, Exceptional, (8)
"Our family of 6 older adults (48-71) were in town for a funeral. CUTE home 20 minutes from everything we had to attend. Close to the interstate. Easy booking, quick response from the owner/host. The patio was a great gathering place as we had very comfortable weather. Mr. Ackley promptly addressed an issue that arised after hours on a Friday!!! That is a great host! Give this cozy home a try!"
Fall Deals! - Mins to Froedert/State Fair - Dogs!

Beautiful Waukesha Home

10.0 out of 10, Exceptional, (21)
"Beautiful home in a quiet neighborhood. Very clean property with all the amenities needed for our son’s wedding weekend. Host was very responsive and accommodating. Would definitely stay again if in the area. "
The price is SAR 939
SAR 2,053 total
includes taxes & fees
1 Dec - 2 Dec
Beautiful Waukesha Home

Family Friendly Sandy Beach Lake Home! Your 3Bed, 2Bath Escape For All Seasons!

10.0 out of 10, Exceptional, (31)
"We loved our stay here. We wanted a quiet place to stay for an extended weekend and this was the perfect spot. My kids loved the pier, the kayaks, and the bikes. I loved the giant couch and the view! The pictures didn't show off how amazing this house really is so when I walked in I literally said "Wow!". The house had everything you could possibly need. Thank you for letting us stay at your property. We will definitely be back again. "
Family Friendly Sandy Beach Lake Home! Your 3Bed, 2Bath Escape For All Seasons!

🌊 Well Appointed Home Steps from Pewaukee Lake + KING Bed 🌊

9.6 out of 10, Exceptional, (10)
"Lovely unit very clean, and great hosts!"
🌊 Well Appointed Home Steps from Pewaukee Lake + KING Bed 🌊

Cottage On The Canal - An All Seasons Getaway - Waterford - Lake Tichigan

9.8 out of 10, Exceptional, (62)
"Good location, great host, nice break!"
Cottage On The Canal - An All Seasons Getaway - Waterford - Lake Tichigan

Historic, Vintage, Classy, 11 bed, 5+ bath!

10.0 out of 10, Exceptional, (6)
" We were immediately impressed with the property! It was beautiful and well appointed.The host was responsive."
Historic, Vintage, Classy, 11 bed, 5+ bath!

Classic Brookfield Home ~ 14 Mi to Milwaukee!

9.2 out of 10, Wonderful, (13)
"Plenty of space and beautiful landscaping that we all enjoyed. The woodwork and decorations add so much character. "
Classic Brookfield Home ~ 14 Mi to Milwaukee!

Newly remodeled Lauderdale Lakes waterfront home-hot tub, sauna, pickleball!

10.0 out of 10, Exceptional, (7)
"Great property right on Lauderdale Lakes and next door to Lauderdale landing. House was new, clean, and great for entertaining a large group. Briana was a fantastic host with lightning-quick responses. Couldn't recommend this property enough for larger groups looking to spend a few days on the lake."
Newly remodeled Lauderdale Lakes waterfront home-hot tub, sauna, pickleball!

W172-Lannon · Charming Muskego House, Walk to Lake & Restaurants

9.6 out of 10, Exceptional, (5)
"Home needs a few fixes, but easy to do. Overall good property . Convenient placement with lots to do and many restaurants and convenient stores for provisions. "
The price is SAR 454
SAR 1,032 total
includes taxes & fees
2 Dec - 3 Dec
W172-Lannon · Charming Muskego House, Walk to Lake & Restaurants

The views are amazing inside and out. Modern lake house with a double lot.

10.0 out of 10, Exceptional, (16)
"We were in town with family to celebrate a birthday. The home was exactly as described, super clean & well furnished. We were comfortable, had plenty of space, the host offered great communications and we didn't have a single complaint! Highly recommend!"
The price is SAR 1,543
SAR 2,685 total
includes taxes & fees
26 Nov - 27 Nov
The views are amazing inside and out. Modern lake house with a double lot.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Oconomowoc

3 Bedroom Okauchee Lake

9.2 out of 10, Wonderful, (10)
"Property description is accurate, yes you are staying above a very popular bar so you will hear the music late into the evening. We were there for a holiday weekend so this was just fine for us and our adult kids! Hosts communicated promptly and even provided a waffle bar and snacks! Loved being able to go downstairs and order food and drinks. We also walked to nearby restaurants, a perfect location to experience some lake life. Thank you!"
3 Bedroom Okauchee Lake

Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle

10.0 out of 10, Exceptional, (30)
"The house was beautiful. Well equipped and comfortable. Had a few elderly individual staying at the home, they were just a little scared of the stairs. (narrow stairs and curvy). Great location to the function all had to attend. Close to town and walkable. I would gladly use this VRBO again I loved the home!"
Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle

Luxury Lakefront Home, Okauchee Lake's Finest Swim Frontage, 3 levels LakeViews

10.0 out of 10, Exceptional, (14)
"Our family had a fun stay at this property. Many amenities and a great location. Thank you!!"
Luxury Lakefront Home, Okauchee Lake's Finest Swim Frontage, 3 levels LakeViews
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.