
Family-friendly vacation rentals in Pewaukee
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Top-rated family-friendly rentals in Pewaukee
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

YurtSimple
YurtSimple is where life slows down and people unplug. It’s forest bathing in nature. It’s getting away from it all to spend time with a partner, by oneself, and sometimes with pets. You’ll be driving past YurtCation (about 300 feet past YurtCation) to get to YurtSimple. YurtCation is 20’ in diameter and YurtSimple is 16’ in diameter. Wood and charcoal are provided. You may cook on the indoor wood stove top, or visit any number of great restaurants 2 miles away. You can even order pizza delivery

Peaceful weekend or extended stay, full amenities
The Country Retreat at the historic Schmitz Family Farm is close to many attractions, ideal for couples, families, girls' weekends, extended stays, business travel, and is dog friendly. Enjoy a sunrise or sunset, get cozy at the fireplace, or indulge in the many activities our area has to offer. We feature two beautiful bedrooms, living room with two sleeper sofas (can also be used as a third bedroom, as door closes for privacy), laundry room, full kitchen, coffee nook, quiet deck and backyard.

Stay With Horses Equestrian Escape Near Madison
Get ready for a quiet and peaceful stay. Take your pick: - 1King+1Queen Bed & 1 bath for 4 people - 1King+2Queen Beds & 2 baths for 6. (+$125 per night, contact host for payment) This home is attached to a barn with 6 Icelandic horses! Wake up to Icelandic horses just outside your window. A scenic escape with quiet mornings, fuzzy horses, and a one-of-a-kind IamGlytja experience - only 25 minutes from Madison - No horse riding allowed, owners to supervise all horse visits - No smoking / parties

Pet-Friendly Retreat•Sleeps 8•Huge Yard•Fire pit
Wake up to sunrise over a peaceful backyard and enjoy your morning coffee on the private balcony. Evenings are perfect by the fire pit under a starry sky. Just a 5 minute drive from Pewaukee Lake Pet-friendly home with a large yard and fire pit - ideal for relaxing and spending time together. Open-concept living, kitchen, and dining area creates a warm, inviting space to gather. Sleeps up to 8 and is best suited for small families or close-knit groups who prefer a more cozy, intimate layout.

Big Red Barn with a basketball court
A beautifully transformed dairybarn turned into a rustic Lodge with all the accommodations. Enjoy a full kitchen and bar filled with a gas fireplace, dart board and pool table. Head upstairs to the basketball court and onto a wraparound deck that over looks acres of wetlands with wildlife A birdwatchers paradise. If you need to detox we have a wood-burning sauna with all the wood and kindling for you to enjoy. We are located 2miles outside historic Cedarburg Wi and 25 minutes north of Milwaukee.

Modern Lake Country Farmhouse in Delafield
Just a half mile outside downtown Delafield, this charming, modern farmhouse is clean, updated and well stocked. There's plenty of space to have a peaceful, relaxing stay. Easy access to golf, lakes (like Nagawicka and Upper & Lower Nemahbin), parks (like Lapham Peak State Park), hiking, biking and x-country skiing. Enjoy walking access to restaurants and shops in Delafield. Just minutes off I-94 in Lake Country, conveniently located between Milwaukee and Madison. 30 minutes from Fiserv Forum.

Exhale, rest
Exhale. The perfect combination. This home is right in the village of Menomonee Falls with great shopping and restaurants within walking distance. Close to the highway, it’s also a mere half an hour to anything Milwaukee so games, museums, festivals are all also at your fingertips. At the end of dead end road with views of the river, access to trails, and a secluded deck and fire pit, there is definitely also a rural feel. This location has it all. Go out, live life, come back, exhale and rest.

Camp Wandawega: Lakeside 3 Bedroom Cabin
Overlooking the lake nestled right behind the main lodge, this cabin has 3 bedrooms, a half bathroom, a seating a room, a basic kitchenette & access to camp showers downstairs. One large bedroom has a queen bed, one room with bunkbeds, & one with a full bed to accommodate a max of 6 guests. (But the bunkbeds are best for kid-sized humans). Like all of Wandawega, it’s a back-to-basics, no-frills, primitive experience. Simple rooms, vintage furnishings. There is heat & a couple AC window units.

Cozy cottage in the heart of Lake Country
Entire cottage in the heart of Lake Country. Merryhill Cottage is nestled on two acres with mature trees. Included on the two acres- the host's farmhouse, a guest house and barn. The feeling of a country setting but with easy access to Hwys 16, 83 and I 94. Close to shopping, restaurants, parks, hiking, cross country skiing and snowshoeing, lakes, and beaches (10 min. to Delafield and Oconomowoc and 15 min. to Pewaukee.) Perfect for day trips to Madison (54 min.) and Milwaukee (30 min.).

Beautiful home on Okauchee Lake, WI
I have a beautiful home on a fun lake. It is just 25 mins from Milwaukee and 50 mins from Madison. There are several bars and restaurants on&off the water; you can either walk, drive or boat to. I have a boat slip available if you want to bring your own 18' or smaller boat. There is a fire-table on the patio for those quiet nights sitting out under the stars. Winter is spectacular here too. Nearby is the Nashotah Park, with a dog park and hiking trails. Lions park has an area for parties.

The Loft @ The Butler Place. 1846 homestead.
The Loft at the Butler Place is a beautiful, quiet retreat set in the rural suburb of Sussex, just 30 minutes west of Milwaukee. The home is the 1846 homestead of the William Butler family, making the home older than the State of Wisconsin! The 2019 remodel of the Loft is in sophisticated farmhouse style and pays tribute to the history of the home in its furnishings, up cycled pieces, and beautiful setting. "Broken becomes blessed" both tells and compells as an invitation to all.

Garden Retreat in law Suite
Welcome to our in-law suite apartment featuring a full eat-in kitchen, living room, queen bed in large bedroom, walk in closet and full bathroom with walk-in shower. Our beautiful two acre yard has many areas to relax in, including a hammock and fire pit for the evenings. Twenty mins. to Erin Hills and Holy Hill and a half hour to most downtown Milwaukee attractions, as well as the RNC activities taking place this summer. Lots of city tips and suggestions for our guests.
Popular amenities for Pewaukee family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury Lakehouse 6 Bed with Private Pier

Walk 2 lake, HOT TUB, pool table, bikes & kayaks

Clementine Cottage

Secluded in the Woods, Hot Tub

Living the Lakehouse Dream

3BR Home w/ Hot Tub 1.5 blocks from Lake Como

Meracle Acres

Cabin Outdoor HotTub Sleeps 7 Pet Friendly
Family- and pet-friendly home rentals

Cozy Lake Geneva Cottage | Near Lake & Town

Black Squirrel Farmhouse - (Downtown Oconomowoc)

Oconomowoc Downtown River View

Magnificently-restored, charming, 8+ Bed-Victorian

Lake Michigan Writer’s Cabin

Local Landmark CF / Coffeehouse / Kettle Moraine

Charming log cabin in the woods

Cozy Lake Cottage With The Best View & Pontoon!
Family-friendly home rentals with a pool

LakeView-SummerPool-FamilyFriendly-CloseToTown

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD

LG Quaint Condo on Lakeshore Dr.

Relaxing Villa with Amazing Amenities!

Luxury Log Cabin retreat home

Lake Geneva Cloud 9

Lakeview at CasaComo

The Peacock Place w/ Shared Seasonal Outdoor Pool
When is the best time to visit Pewaukee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ779 | ﺩ.ﺇ742 | ﺩ.ﺇ753 | ﺩ.ﺇ826 | ﺩ.ﺇ995 | ﺩ.ﺇ1,212 | ﺩ.ﺇ1,425 | ﺩ.ﺇ1,285 | ﺩ.ﺇ1,113 | ﺩ.ﺇ955 | ﺩ.ﺇ870 | ﺩ.ﺇ815 |
| Avg. temp | -4°C | -3°C | 3°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 12°C | 5°C | -1°C |
Quick stats about vacation rentals that are family-friendly in Pewaukee

Total vacation rentals
Explore 30 vacation rentals in Pewaukee

Nightly prices starting at
Pewaukee vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

Verified guest reviews
Over 1,010 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Pewaukee vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Pewaukee rentals

4.9 Average rating
Pewaukee stays are highly rated by guests—averaging 4.9 out of 5!
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- Six Flags Great America
- Alpine Valley Resort
- Kohler-Andrae State Park
- Wilmot Mountain Ski Resort
- Illinois Beach State Park
- Milwaukee County Zoo
- Baird Center
- Milwaukee Public Museum
- Bradford Beach
- Discovery World
- Marquette University
- Riverside Theater
- American Family Field
- Gurnee Mills
- Fiserv Forum
- American Family Insurance Amphitheater
- Pabst Mansion
- Lake Geneva Public Library
- Lake Geneva Cruise Line
- South Shore Park
- Betty Brinn Children's Museum
- Holy Hill National Shrine of Mary
- Atwater Park
- Lake Geneva Ziplines & Adventures





