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Compare 146 Vacation Homes in Oconomowoc with updated reviews, rates, and availability.

Beautiful lakefront, Newly Remodeled Lower Level! ^^
Large deck, expansive FLAT yard

Beautiful lakefront, Newly Remodeled Lower Level! ^^

9.8 out of 10, Exceptional, (175)
"Everything listed was as advertised. The home was wonderful and the hosts were responsive and accommodating. Definitely recommend if staying in the area."
Beautiful lakefront, Newly Remodeled Lower Level! ^^
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River
Elm Island Bay From Pier

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

10.0 out of 10, Exceptional, (325)
"We had a great time! The cabin had everything we needed. We just sat around the fireplace, went for walks and thoroughly enjoyed ourselves! We will definitely be coming back!"
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River
Eclectic Hubertus Home w/ Game Room & Fire Pit!
Hubertus Vacation Rental | 3BR | 3.5BA | 3,833 Sq Ft | Stairs Required

Eclectic Hubertus Home w/ Game Room & Fire Pit!

9.8 out of 10, Exceptional, (7)
"We loved the property, it had plenty of room and was perfect for what we needed. On top of that, the aesthetic was just amazing and the nature and peace surrounding the house put it over the top. "
Eclectic Hubertus Home w/ Game Room & Fire Pit!
Modern lake house with a double lot. The views are amazing inside and out!
Dining

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

10.0 out of 10, Exceptional, (17)
" Very clean and updated. Great stay for visiting family over the holidays. "
The price is SAR 1,446
SAR 2,516 total
includes taxes & fees
1 Jan - 2 January 2025
Modern lake house with a double lot. The views are amazing inside and out!
Amazing Five Bedroom Milwaukee Vacation Home!!

Amazing Five Bedroom Milwaukee Vacation Home!!

10.0 out of 10, Exceptional, (40)
"I went to detox, relax, and swim for a few days and did not bring family, but this is a terrific place for a family getaway with amazing pool, video games, plenty of beds, etc. Pleasant neighborhood as well. "
Amazing Five Bedroom Milwaukee Vacation Home!!
Modern Lake House: Sandy Floor, Breathtaking Views
Miscellaneous

Modern Lake House: Sandy Floor, Breathtaking Views

9.4 out of 10, Exceptional, (8)
"We stayed for two nights and communication was excellent before and during our stay. Really enjoyed the updated kitchen for cooking meals and the easy access to the road for walking around the area. "
Modern Lake House: Sandy Floor, Breathtaking Views
Beautiful Waukesha Home
Exterior

Beautiful Waukesha Home

10.0 out of 10, Exceptional, (23)
"This property has everything a large group would need, is sparkling clean and has some extra special perks like a fireplace and outside seating/fire pit area. Would recommend wholeheartedly!"
Beautiful Waukesha Home
Family Friendly Sandy Beach Lake Home! Your 3Bed, 2Bath Escape For All Seasons!
Aerial view

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

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

10.0 out of 10, Exceptional, (6)
"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.
🌊 Well Appointed Home Steps from Pewaukee Lake + KING Bed 🌊
Pewaukee Lake House

🌊 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
Kitchen to Dining Open Concept

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

9.8 out of 10, Exceptional, (64)
"My wife and stayed with our son and wife along with our grandson. We had plenty of room. Would've liked another shower but all was good. Food next door at the watering hole was excellent too !"
Cottage On The Canal - An All Seasons Getaway - Waterford - Lake Tichigan
Historic, Vintage, Classy, 11 bed, 5+ bath!
Exterior

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!
Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle
Exterior

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!"
The price is SAR 1,502
SAR 3,322 total
includes taxes & fees
12 Jan - 13 January 2025
Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle
✨Chic Retreat near Wedding Venues, Downtown & Lakes with King Bed✨
Fully stocked kitchen with counter seating and built in breakfast nook

✨Chic Retreat near Wedding Venues, Downtown & Lakes with King Bed✨

10.0 out of 10, Exceptional, (11)
"Great location and beautiful home. Super clean, well-stocked and looks so well-cares for!"
✨Chic Retreat near Wedding Venues, Downtown & Lakes with King Bed✨
W172-Lannon · Charming Muskego House, Walk to Lake & Restaurants

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 1,036 total
includes taxes & fees
5 Jan - 6 January 2025
W172-Lannon · Charming Muskego House, Walk to Lake & Restaurants
Beach House
Terrace/patio

Beach House

10.0 out of 10, Exceptional, (24)
"We celebrated my mom's 70th Birthday. I would absolutely rent this property again!!"
Beach House
Quaint & Family-Friendly Watertown Farmhouse!
Watertown Vacation Rental | 3BR | 2BA | Stairs Required | 2,000 Sq Ft

Quaint & Family-Friendly Watertown Farmhouse!

10.0 out of 10, Exceptional, (12)
"We traveled out for my son's wedding. The accommodations were outstanding and helped us relax from the busyness of the rehearsal and wedding. The home was very clean, and the hostess was an absolute delight. Everything we needed for a stress-free visit was provided. The beds were very comfortable, and the home gave off a cozy vibe. I would definitely stay here again."
Quaint & Family-Friendly Watertown Farmhouse!
Waterfront Executive Home sleeps 14
View from shore

Waterfront Executive Home sleeps 14

10.0 out of 10, Exceptional, (17)
"My siblings and I LOVED every aspect of this home! The kitchen was beyond the pale. We cooked every evening. The lake access was amazing and we kayaked to the lake twice. We could not get over how wonderful this property was. For most VRBOs the pictures look so much better than the reality. In this case, the reality was better than the pictures! Bob was wonderful and responded promptly to all our questions. I highly recommend this property!"
Waterfront Executive Home sleeps 14
New! Modern River & Lake House. Book Now!
Miscellaneous

New! Modern River & Lake House. Book Now!

9.4 out of 10, Exceptional, (3)
"Great view. Comfortable furnishings. Clean and relaxing. Nice amenities. Good for dogs and people alike. "
New! Modern River & Lake House. Book Now!
Fireside Charm on Strawberry Hill – A Tranquil Escape! Hot Tub, Pet Friendly
Cozy up in the living area and stream all your favorite shows

Fireside Charm on Strawberry Hill – A Tranquil Escape! Hot Tub, Pet Friendly

10.0 out of 10, Exceptional, (1)
Fireside Charm on Strawberry Hill – A Tranquil Escape! Hot Tub, Pet Friendly
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

Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle
Exterior

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!"
The price is SAR 1,502
SAR 3,322 total
includes taxes & fees
12 Jan - 13 January 2025
Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle
✨Chic Retreat near Wedding Venues, Downtown & Lakes with King Bed✨
Fully stocked kitchen with counter seating and built in breakfast nook

✨Chic Retreat near Wedding Venues, Downtown & Lakes with King Bed✨

10.0 out of 10, Exceptional, (11)
"Great location and beautiful home. Super clean, well-stocked and looks so well-cares for!"
✨Chic Retreat near Wedding Venues, Downtown & Lakes with King Bed✨
3 Bedroom Okauchee Lake
Outdoor dining

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
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.