
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.

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.

Beautifully Restored Historic Victorian
Whether this is for a single, couple, or small group, your stay at this historic home will truly be memorable. You’ll love the MBR suite featuring a gas fireplace, whirlpool tub, and double walk-in custom tile shower. There is an additional very nice full bath/shower on the main floor. The finished lower level has two separate rooms, each with a quality double futon with bedding available for your guests. For this attractive price, the upper 4 bedrooms are locked but may be opened for more

Lace & Woods Farm "Hammer Hideaway"
HEATED POOL MAY-SEPT FOR ADDITIONAL CHRG. Cozy designer custom built guest house nestled amongst a 10 acre hobby farm. come for a relaxing getaway. This home is an artistic gem! Boasting an open concept, with a queen bed on main level and twin mattress underneath , a full kitchen, cozy living area, wood burning fireplace. The loft has extra sleeping with a double bed and twin bed.Custom designed. Great location winter and summer, enjoy snowmobiling trails and skiing near by or beaches & hiking

In the Canopy (beautiful Brookfield/Milwaukee)
Relax “in the Canopy” of beautiful maples! If you’re looking for party central…this isn’t it. But if you want a comfortable place in a tree-filled neighborhood, just a few minutes from all the best Milwaukee has to offer, you’re in luck! Perfect location for quick access to the city—or to Lake Country to the west. Quiet, comfortable, safe, surrounded by beautiful gardens. We’re in a perfect launching spot to visit Summerfest, Brewers/Bucks games, or Milwaukee's western suburbs. Bring the kids!

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.).

Cozy 2BR charm | Big Yard, Fire pit, Replenishing!
Cozy gem sleeps up to 5. Renovated Interiors w/ large balcony overlooking serene yard. Enjoy an eastern sunrise during your morning coffee, or a starry night next to the warmth of a fire. 1 mile from 94 - 20 minutes from Milwaukee. Fully stocked kitchenette. Gas burning stove/oven, microwave, coffee maker, full size fridge/freezer, in unit washer/dryer, wifi, smart tv, wireless printer, private large balcony w/ heater for cooler nights. Perfect space for a couple or traveling profesional.

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.

Family friendly farmstay just outside Milwaukee
The Inn at Paradise Farm is an original 1847 log homestead in rural Wisconsin just a short drive from Milwaukee and close to many attractions, especially for nature lovers. Our very spacious private 4-room suite with private entrance is comfortable for couples, families, or business travelers who long to unwind in a pastoral setting. Visit with, and even help care for, our friendly animals! We are licensed and inspected. Paradise Farm welcomes all.

Okauchee Lakefront Cabin Escape
The perfect lake house for a family or a group of friends: kayaks, fire pit, gas grill, bags, jukebox, darts, bumper pool and sunsets on the deck. Near Erin Hills for golfers (15 minutes). Down the road from the Kettle Moraine hiking trails (10 minutes) and the Nashotah dog park (5 minutes). Several bars and restaurants within 5 minutes. The very best in lake life, outdoor life and night life.

Chic Loft Surrounded by Nature
This charming shabby chic loft sits in the heart of the country between Madison and Milwaukee. The Lighthouse Farm is also a wedding/event venue (please inquire for more details) . A quiet relaxing environment, with lots of open space, natural sunlight and lush green landscape. Great for those looking to get away with easy access to metropolitan areas, lakes, rivers and hiking/biking trails.

Clean 1bd/1bath close to everything!
Charming 1 bedroom 1 bath with private entrance and parking. Close to downtown, Shopping malls, Zoo, Hospital, Airport,Main freeways. Full kitchen with stove, microwave, coffee pot, dishes. Unit has tv and wifi. Coin operated laundry is accessible on premis. Why stay at a hotel when you can feel at home in this lovely unit.
Popular amenities for Pewaukee family-friendly rentals
Family-friendly home rentals with a hot tub

Happy Days Home close to all MKE attractions

Clementine Cottage

Beautiful Victorian in Historic District

5th St. Retreat - Outdoor Oasis, Hot Tub, 8 Beds

Cabin Outdoor HotTub Sleeps 7 Pet Friendly

Amazing view, Modern Space

Wooded Hills/Indoor Pool/Hot Tub/Arcade

Downtown Oasis: Hot Tub, Garage, 2 King Huge yard!
Family- and pet-friendly home rentals

Our Cozy Bay View Bungalow Getaway

Peaceful weekend or extended stay, full amenities

Lake Michigan Writer’s Cabin

Vast Lake Koshkonong Views from Pier, Deck, & Home

Lakeside Getaway

Charming A-Frame - Dog Friendly!

2BR Sunny Upper in Prime Bay View - w/ Parking

Cozy Basement Space In Bay View by Lake Michigan
Family-friendly home rentals with a pool

Vessel: Irish Mist V - 32' @ Reefpoint W1-3

Serene Lakefront condo with magnificent view, pool

LakeView-SummerPool-FamilyFriendly-CloseToTown

Relaxing Villa with Amazing Amenities!

Luxury Log Cabin retreat home

Lake Geneva relaxation!

Lake Geneva Cloud 9

Lake Geneva Retreat! Fireplace! WiFi!
Quick stats about vacation rentals that are family-friendly in Pewaukee
Total rentals
30 properties
Nightly prices starting at
R695 ZAR before taxes and fees
Total number of reviews
940 reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Destinations to explore
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- Six Flags Great America
- Alpine Valley Resort
- Kohler-Andrae State Park
- Erin Hills Golf Course
- Geneva National Resort & Club
- Illinois Beach State Park
- Harrington Beach State Park
- Milwaukee County Zoo
- Racine North Beach
- Grand Geneva Resort & Spa
- Wilmot Mountain Ski Resort
- Richard Bong State Recreation Area
- West Bend Country Club
- Bradford Beach
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
- Discovery World
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Milwaukee Public Museum
- Springs Water Park
- Heiliger Huegel Ski Club
- America's Action Territory
- Sunburst
- The Rock Snowpark