Pewaukee holiday rentals

We found 1,059 holiday rentals — enter your dates for availability
Discover a selection of 20 homes and other holiday rentals in Pewaukee that are perfect for your trip. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and cable TV. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Pewaukee

Showing deals for:13 Nov - 20 Nov

Living area
Living area
Private kitchen
Dining
Exceptional
(9 reviews)

Kohl Manor Luxury Lake 8br year round retreat Pool, Cinema, Arcade on LacLaBelle

Oconomowoc

9% off
AU$34,655
for 7 nights, 1 home
AU$4,951 per night
includes taxes & fees
Kohl Manor Luxury Lake 8br year round retreat Pool, Cinema, Arcade on LacLaBelle
Fully equipped kitchen.
View of the lake from the upper level master bedroom.
Living room with large sectional and flat screen TV.
Lake side of home. Relax and enjoy views of the lake from upper and lower decks.
Exceptional
(55 reviews)

Waterfront Lake Ripley getaway. Kayak, paddleboard and fish from private pier!

Cambridge

8% off
AU$4,640
for 7 nights, 1 home
AU$663 per night
includes taxes & fees
Waterfront Lake Ripley getaway. Kayak, paddleboard and fish from private pier!
Living area
Lake
Dining
Private kitchen
Exceptional
(15 reviews)

"Five Bedroom Luxury by the River "

Milwaukee

8% off
AU$11,798
for 7 nights, 1 home
AU$1,685 per night
includes taxes & fees
"Five Bedroom Luxury by the River "
Living area
Property grounds
Dining
Living area
Exceptional
(12 reviews)

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

Pewaukee

8% off
AU$10,323
for 7 nights, 1 home
AU$1,475 per night
includes taxes & fees
Serene 4-bedroom Lake House in Pewaukee-Hot Tub!
Living area
Terrace/patio
Dining
Private kitchen
Exceptional
(7 reviews)

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

Milwaukee

6% off
AU$2,910
for 7 nights, 1 home
AU$416 per night
includes taxes & fees
Brady St Retreat! 4BR House w Patio & Fenced Yard
Dining room with beautiful woodwork and antique upright piano
Massive living room with Roku-enabled TV, wi-fi, comfy furniture, cozy woodwork
Landing looking down from 2nd floor
Front porch for relaxing or people watching
Exceptional
(8 reviews)

Huge Historic House Centrally Located in Milwaukee

Milwaukee

8% off
AU$3,803
for 7 nights, 1 home
AU$543 per night
includes taxes & fees
Huge Historic House Centrally Located in Milwaukee
Interior
Outdoor dining
Exterior detail
Private kitchen
Exceptional
(9 reviews)

Gorgeous space with huge porch.

Milwaukee

7% off
AU$2,245
for 7 nights, 1 home
AU$321 per night
includes taxes & fees
Gorgeous space with huge porch.
Living area
Private kitchen
Private kitchen
Property grounds
Wonderful
(6 reviews)

Quiet Retreat in Morgan Heights, Sleeps 6, 1.5 baths

Milwaukee

17% off
AU$2,031
for 7 nights, 1 home
AU$290 per night
includes taxes & fees
Quiet Retreat in Morgan Heights, Sleeps 6, 1.5 baths
Property grounds
Property grounds
Property grounds
Room
Exceptional
(25 reviews)

Spacious Rustic Log Home Retreat Near Madison & Milwaukee

Johnson Creek

8% off
AU$2,550
for 7 nights, 1 home
AU$364 per night
includes taxes & fees
Spacious Rustic Log Home Retreat Near Madison & Milwaukee
Room
Private kitchen
Living area
Interior
Exceptional
(23 reviews)

Cottage near Mt. Mary College

Milwaukee

7% off
AU$2,502
for 7 nights, 1 cottage
AU$357 per night
includes taxes & fees
Cottage near Mt. Mary College
Dining
Living area
Private kitchen
Room
Exceptional
(27 reviews)

Oak Park Bliss: 3BR, 2BA Gem

Milwaukee

7% off
AU$4,229
for 7 nights, 1 home
AU$604 per night
includes taxes & fees
Oak Park Bliss: 3BR, 2BA Gem
Exterior
Living area
Private kitchen
Dining
Exceptional
(25 reviews)

Green Valley Homes - 2 BDRM Lower Apartment

Milwaukee

7% off
AU$1,571
for 7 nights, 1 home
AU$224 per night
includes taxes & fees
Green Valley Homes - 2 BDRM Lower Apartment
Dining
Living area
Private kitchen
Room
Excellent
(22 reviews)

Spacious 4-bedroom home in quiet neighborhood

Milwaukee

8% off
AU$1,765
for 7 nights, 1 home
AU$252 per night
includes taxes & fees
Spacious 4-bedroom home in quiet neighborhood
Interior
Living area
Terrace/patio
Room
Exceptional
(9 reviews)

Barclay House in Walker's Point

Milwaukee

7% off
AU$2,811
for 7 nights, 1 home
AU$402 per night
includes taxes & fees
Barclay House in Walker's Point
Sliding Glass Doors leading to Deck.
House in Fall/Winter.
Stairs leading to Master Bedroom and Bedroom Two.
Roku T.V. in Living Room.
Exceptional
(18 reviews)

Whitefish Bay 3Bedroom Entire House Sleeps 4

Milwaukee

15% off
AU$3,134
for 7 nights, 1 home
AU$448 per night
includes taxes & fees
Whitefish Bay 3Bedroom Entire House Sleeps 4
Backyard and parking space
Dining table
Living room's tv
Kitchen
Exceptional
(70 reviews)

Eastside apartment with Private entrance and parking

Milwaukee

15% off
AU$1,395
for 7 nights, 1 apartment
AU$199 per night
includes taxes & fees
Eastside apartment with Private entrance and parking
Private kitchen
Living area
Terrace/patio
Interior
Exceptional
(36 reviews)

Newly renovated 3 bedroom home

Franklin

7% off
AU$3,241
for 7 nights, 1 home
AU$463 per night
includes taxes & fees
Newly renovated 3 bedroom home
Room
Private kitchen
Exterior detail
Dining
Exceptional
(43 reviews)

3 BR-2Q 2T Beds, 1 bath home walk to State Fair, close to Brewers, & Zoo.

Milwaukee

10% off
AU$1,670
for 7 nights, 1 home
AU$239 per night
includes taxes & fees
3 BR-2Q 2T Beds, 1 bath home walk to State Fair, close to Brewers, & Zoo.
Interior
Interior
Private kitchen
Dining
Exceptional
(18 reviews)

Huge condo in historic hotel near Lake Michigan/Parks/Festivals w/parking

Milwaukee

7% off
AU$3,144
for 7 nights, 1 apartment
AU$449 per night
includes taxes & fees
Huge condo in historic hotel near Lake Michigan/Parks/Festivals w/parking
Interior
Terrace/patio
Private kitchen
Room
Exceptional
(17 reviews)

Spacious 3BR/2BA Townhome w/ Private Parking & Walkable East Side

Milwaukee

7% off
AU$3,912
for 7 nights, 1 home
AU$559 per night
includes taxes & fees
Spacious 3BR/2BA Townhome w/ Private Parking & Walkable East Side
Dining
Exterior
Living area
Private kitchen
Exceptional
(18 reviews)

Milwaukee Bayview Getaway with Private Hot Tub

Milwaukee

7% off
AU$6,211
for 7 nights, 1 home
AU$887 per night
includes taxes & fees
Milwaukee Bayview Getaway with Private Hot Tub

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Head to the friendly city of Pewaukee

The lake and other outdoor surroundings create an inviting atmosphere in Pewaukee. This welcoming city is known for its water park, restaurants and sporting events. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Pewaukee

Do you want to discover attractions to see while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Pewaukee a fun spot to go on holiday. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Springs Water Park (2.4 mi / 3.9 km)
  • Milwaukee County Zoo (11.6 mi / 18.7 km)
  • Milwaukee Mile Speedway (13.3 mi / 21.4 km)
  • Erin Hills Golf Course (13.7 mi / 22.1 km)
  • Cabela's (14.2 mi / 22.8 km)
  • Walter Schroeder Aquatic Center (16.8 mi / 27 km)

Exploring the natural features in Pewaukee

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Pewaukee is a great spot to appreciate mother nature. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Pewaukee Lake Beach (0.3 mi / 0.5 km)
  • Pewaukee Lake (2.4 mi / 3.8 km)
  • Frame Park Formal Gardens (4.7 mi / 7.5 km)
  • Holy Hill (11.8 mi / 19 km)
  • Lac La Belle (13.4 mi / 21.6 km)
  • Boerner Botanical Gardens (15.3 mi / 24.6 km)

Transport to and around Pewaukee

The nearest airport is in Waukesha, WI (UES-Waukesha County), located 3.2 mi (5.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Milwaukee, WI (MKE-General Mitchell Intl.), which is 20.3 mi (32.7 km) away.

Frequently asked questions

What is the best area to stay in Pewaukee when booking a holiday rental?
When considering a holiday rental in Pewaukee, Wisconsin, the area surrounding the lake is one of the best choices. This scenic neighbourhood offers stunning views and a tranquil atmosphere, making it great for a relaxing getaway. Here, you'll find a variety of properties, from charming lakeside cottages to modern family homes, suiting different tastes and budgets.Staying near Pewaukee Lake not only grants easy access to the water for activities like boating and fishing, but it also places you close to some delightful attractions. The lakefront park is a lovely spot for picnics and leisurely strolls, while the vibrant downtown area features a selection of quaint shops and eateries. Additionally, the nearby Pewaukee Lake Beach is a favourite among locals and visitors alike, providing a wonderful place to soak up the sun during the warmer months.
Where are the best areas for renting a beach house in Pewaukee?
For renting a beach house in Pewaukee, the area surrounding Pewaukee Lake is ideal. This picturesque setting offers a variety of holiday rentals that provide easy access to the lake's sandy shores and recreational activities. Many properties in this region come equipped with amenities such as private docks, outdoor patios, and fully equipped kitchens, making them great for families or groups wanting to enjoy lakeside living.The neighbourhoods along the western shore, particularly near the Pewaukee Lake Park, offer beach houses that allow guests to enjoy the scenic views of the water. Properties in this area often feature spacious living areas, barbecues for outdoor cooking, and sometimes even fire pits for evening gatherings. Additionally, the proximity to local shops, restaurants, and parks enhances the convenience for travellers.For those interested in water sports, rentals near the lake's public access points provide opportunities for boating, fishing, and swimming. Some houses may also offer amenities like kayaks or paddleboards for guests to use during their stay.
What is the most popular type of holiday rental accomodation in Pewaukee?
In Pewaukee, holiday houses are the most popular type of holiday rental, with approximately 57 available throughout the area. These properties often come with generous living spaces, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Many holiday houses also feature outdoor areas, such as decks or patios, where guests can relax and enjoy the scenic views of Pewaukee Lake. Additionally, there are several cottages available, offering a quaint and charming alternative for those seeking a cozier, more intimate setting.
Are there any family house rentals in Pewaukee?
In Pewaukee, Wisconsin, there are numerous family-friendly house rentals available—specifically around 16 options scattered throughout the area. This charming lakeside town is superb for families seeking both relaxation and adventure. Many of these homes boast spacious living areas, full kitchens ideal for preparing family meals, and outdoor spaces where children can play or where families can enjoy barbecues together.Properties near Pewaukee Lake often offer amenities like private docks for boating or fishing, while some may even feature game rooms for indoor entertainment. The area is also close to local parks, playgrounds, and walking trails, providing ample opportunities for outdoor activities.
Are there pet-friendly house rentals in Pewaukee?
In Pewaukee, there are several pet-friendly house rentals available, making it an excellent choice for travellers looking to bring their furry companions along. Many of these properties are conveniently located near Pewaukee Lake, offering easy access to outdoor activities such as swimming, fishing, and boating. The rentals often come with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, providing a homely atmosphere for families and groups.The surrounding areas also feature parks like the Pewaukee Lake Park, which has walking trails and picnic spots, superb for enjoying the outdoors with pets. Additionally, the nearby village offers charming cafes and shops that welcome pets, enhancing the overall experience for both you and your furry friends.
Are there any remote work holiday rentals in Pewaukee?
In Pewaukee, Wisconsin, there are plenty of remote work-friendly holiday rentals available, with around 60 options to choose from. This picturesque lakeside town provides a conducive environment for those looking to combine work and leisure. Many properties come equipped with essential amenities such as free Wi-Fi, dedicated workspaces with desks and comfortable chairs, ensuring that remote workers can be productive during their stay.The area is known for its charming waterfront, where guests can enjoy scenic views and outdoor activities during breaks. Nearby attractions include the beautiful Pewaukee Lake, which offers opportunities for fishing, boating, and relaxing by the shore. The local dining scene features a variety of establishments ranging from casual cafes to more upscale restaurants, making it easy to unwind after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Pewaukee?
In Pewaukee, popular rental amenities include kitchens, which allow guests to prepare their own meals at their convenience. Many properties also feature decks or patios, providing outdoor spaces for relaxation and enjoying the fresh air. Onsite parking is another common amenity, making it convenient for travellers with vehicles. Additionally, some rentals may come equipped with blenders, great for those looking to whip up smoothies or other beverages during their stay.
When is the best time to visit Pewaukee for a holiday rental?
The best time to visit Pewaukee for a holiday rental is during the peak season from June to August, with July being particularly popular among travellers. This vibrant period attracts those looking to enjoy the beautiful lakeside setting, engage in outdoor activities like swimming and boating, and take advantage of the warm weather.In July, you can expect delightful temperatures averaging around 24 to 30 degrees Celsius, creating a great environment for sun-soaked days by the lake. The atmosphere is bustling with summer events, including music festivals and local markets, making it an ideal time for families and friends seeking a lively getaway.For those who prefer a quieter experience, consider planning your visit in October when the summer crowds have dispersed. This month offers a serene escape with the added charm of autumn foliage, great for leisurely walks along the scenic trails and enjoying the crisp air.Ultimately, the best time to book your holiday rental in Pewaukee depends on your preference for a lively summer atmosphere or a peaceful autumn retreat.
What are the top attractions in Pewaukee?
In Pewaukee, visitors can enjoy a range of attractions centred around its picturesque lake. Pewaukee Lake itself is a prime spot for swimming, boating, and fishing, with several parks along its shores offering picnic areas and playgrounds for families. The nearby Pewaukee Lake Beach is particularly popular during the summer months, providing a sandy area for sunbathing and water activities.For outdoor enthusiasts, the Lake Pewaukee Park features trails for walking and biking, as well as facilities for sports like volleyball and basketball. The charming downtown area offers local shops, cafes, and restaurants where visitors can experience the community's friendly atmosphere.In addition, the nearby Retzer Nature Centre provides opportunities for hiking and wildlife observation, showcasing the natural beauty of the region.
Are all fees included in the Pewaukee holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Pewaukee holiday homes with parking?
Stayz offers a wide selection of holiday homes in Pewaukee with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Pewaukee holiday homes?
You can find great discounts on holiday homes in Pewaukee on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Pewaukee holiday home booking on Stayz?
To find Pewaukee holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Pewaukee?
A long-stay holiday home in Pewaukee is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Pewaukee holiday home?
Book your Pewaukee holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pewaukee?
Prices for holiday homes in Pewaukee vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Pewaukee to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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