Waukesha Vacation Rentals

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Vacation Rentals in Waukesha

NEW! Experience the Serene & Unique Blue Tree House – Hike, Relax & Lake Nearby

Richfield WI

Located in Hubertus, this vacation home is on a lake, a 2-minute drive from Heiliger Huegel Ski Club and 6 minutes from Holy Hill.

Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Waukesha WI

$282 nightly

$319 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

With a stay at this vacation home in Waukesha, you'll be within a 5-minute drive of Monkey Joe's and Prairieville Park.

Family Paradise 3 bedroom, Cozy Home + Game Room.

Brown Deer WI

$269 nightly

$312 total

Dec 26 - Dec 27

Total with taxes and fees

With a stay at this vacation home in Milwaukee (Brown Deer), you'll be within a 10-minute drive of Lake Michigan and Walter Schroeder Aquatic Center.

Sunset Lake House w Hot Tub, 4 fireplaces & kids bunkroom!

Oconomowoc WI

Located in Oconomowoc, this vacation home is on the waterfront, a 3-minute drive from Aurora Medical Center Summit and 6 minutes from Oconomowoc Memorial Hospital.

Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find

Milwaukee WI

$370 nightly

$436 total

Dec 19 - Dec 20

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Milwaukee, within a 5-minute drive of Lake Michigan and Fiserv Forum.

Charming Vintage Farmhouse 1 bedroom Garden Oasis

Milwaukee WI

With a stay at this vacation home in Milwaukee (Bay View), you'll be a 1-minute drive from Lake Michigan and 8 minutes from Fiserv Forum.

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

New Berlin WI

$1,610 nightly

$1,819 total

Dec 22 - Dec 23

Total with taxes and fees

With a stay at this vacation home in New Berlin, you'll be within a 10-minute drive of Waukesha Springs Park and Minooka Park.

Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!

River Hills WI

With a stay at this vacation home in Milwaukee, you'll be within a 15-minute drive of Lake Michigan and Fiserv Forum.

Remodeled Home - Steps from Brady Street!

Milwaukee WI

$226 nightly

$266 total

Jan 7 - Jan 8, 2026

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Milwaukee, within a 5-minute drive of Lake Michigan and Fiserv Forum.

Brady St Retreat! 4BR House w Patio & Fenced Yard

Milwaukee WI

With a stay at this vacation home in Milwaukee (Lower East Side), you'll be within a 5-minute drive of Lake Michigan and Fiserv Forum.

Serene 4-bedroom Lake House in Pewaukee-Hot Tub!

Pewaukee WI

With a stay at this vacation home in Pewaukee (Starke Peninsula), you'll be a 1-minute drive from Pewaukee Lake and 5 minutes from Two Brothers Wines.

Erin Hills Area Perfect Getaway - NEW Fall Color and Winter Pricing!

Rubicon WI

Located in Rubicon, this vacation home is in a rural location, within a 15-minute drive of Erin Hills Golf Course and Heiliger Huegel Ski Club.

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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.