Family-friendly vacation rentals in Washington County

4.94 out of 5 average rating, 257 reviews

A charming red farmhouse is set against a snowy landscape, surrounded by a white fence. Leafless trees create a serene backdrop, enhancing the rural setting. The house features a mix of traditional and modern architecture with snow covering the yard.

Guesthouse in Richfield

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.

4.81 out of 5 average rating, 114 reviews

A charming brick house is surrounded by well-maintained landscaping, featuring various green shrubs and white flowering plants. The front yard offers a neat lawn and a flower bed with stones. The adjacent houses are visible, showcasing a friendly neighborhood vibe.

Guest suite in Milwaukee

Basement Bay View Suite,express bus airport-north

Bay View is a walking community. Our place is close to family-friendly activities, public transport, & the airport. You’ll love our place. It's a short walk to express bus from airport, past downtown, UW-M and to Bayside. Located across the street from Humboldt Park. We are about a 20 minute walk from Lake Michigan. Summerfest grounds a short bus ride away. Winter is fun in the park. Tobogganing (2), skates and cross country skis to use. Hope the sizes fit you. I find if one plays in snow ⛄️ 😌

4.98 out of 5 average rating, 130 reviews

The two-story home features a beige exterior with multiple windows, surrounded by a grassy yard. Two chairs are positioned in front on a small patio area. Large trees provide shade, while a view of the countryside and other structures is visible in the background.

Home in Glenbeulah

Stay at Sunrise LLC, Like being at Grandma's

Welcome to Stay at Sunrise LLC. We offer a clean and comfortable home for your vacation enjoyment. We are in a rural area, recreation trail head is 3 miles east of us as is the Wade House, 7 miles from Road America. Large yard, Fire pit, picnic table, child swing set. Garage parking on site if arranged in advance. We do not have WIFI Phone reception for Internet is good. No Cable or Satellite TV, Over 32 antenna channels. Smoking is allowed outside of the home. No pets allowed.

4.97 out of 5 average rating, 118 reviews

A red cottage is nestled among lush green trees, with a winding driveway leading to its entrance. Steps ascend to the upper level, and patches of sunlight filter through the leaves, highlighting the natural surroundings.

Guesthouse in Plymouth

Woodside Cottage Guest House-Close to Road America

Woodside Cottage in the Kettle Moraine forest of East Central Wisconsin offers a quiet private getaway for Road American race fans, golfers or those wanting just to have a break from the city and explore the area. This 2 bedroom guesthouse can host 8, with laundry, full kitchen, living room and outdoor fire pit. Due to family guest allergies, we are pet free. Located 4 miles from gate 4 at Road America and 20 miles from Whistling Straits golf course. WIFI available, but unreliable. 3 cars MAX

Apartment in Port Washington

The front exterior of the duplex showcases a charming farmhouse style with light grey siding and white trim. Two levels of porches with railings are complemented by doorways in vibrant turquoise. Flower baskets hang from the porch beams, and a garden with greenery enhances the inviting atmosphere.

5 out of 5 average rating, 239 reviews

Beautiful Port home short walk to town and lake

Enjoy Grace Guest house and the sights and sounds of Port Washington at our bright turn of the century duplex. Your private upstairs unit has 1.5 baths, a full kitchen and 3 bedrooms. Freshly renovated, our 1890 home is sure to charm with its many original features and large modern bathrooms and kitchen. Your second floor private walk-out deck is a great place to enjoy a morning coffee or cocktail and take in the Lake View. Port Washington’s shops and restaurants are a quick 4 minute walk.

4.96 out of 5 average rating, 291 reviews

A historic stone home is presented, featuring multiple windows that enhance its classic appeal. A well-maintained garden with colorful flowers surrounds the exterior, creating a welcoming entrance to the Butler Place. A sign displaying the property's name is held by two guests in front of the house.

Guest suite in Sussex

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.

4.99 out of 5 average rating, 143 reviews

Tall sunflowers bloom vibrantly in a garden, displaying bright yellow and orange petals. A wooden gazebo with hanging lights stands in the background, surrounded by lush greenery. Soft sunlight filters through the trees, enhancing the serene outdoor setting.

Guest suite in Sussex

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.

4.8 out of 5 average rating, 303 reviews

The studio features hardwood floors and exposed wooden beams adding character. A spacious bed is centrally positioned, accompanied by soft bedding. A small dining table and kitchenette with essential appliances are visible. A modern light fixture provides illumination near a cozy reading chair.

Apartment in West Allis

Kegel's Inn - Studio - Classic Apartment #3

Quaint little studio with lots of old-world character. This one-room studio has original hardwood floors, heavy wood ceiling beams and 1930's tile work in the bathroom. The apartment looks down on 59th street, which for the summer months between May and November, hosts the Kegels Beer Garden on the street! We're one of the last Authentic German restaurants and Inn's left in country and the studio apartment is right above it! We hope you love this place as much as we do!

4.98 out of 5 average rating, 145 reviews

A warm living area features exposed log walls and a stone fireplace. Comfortable leather seating is arranged around a coffee table. A television sits on an entertainment unit, and framed photographs decorate the mantle. Natural light enters through windows near the ceiling.

Cabin in Campbellsport

Log Cabin Luxury on a Lake

Enjoy a 1,400 sq.ft. home in the Northern Unit of the Kettle Moraine Forest on 50' of shore. Enjoy the lake for swimming, kayaking, fishing, and floating! Lots of trails for hiking nearby and other fun summer activities! Updated home with a log cabin feel. Modern kitchen and great room—perfect for game night or sitting by the fireplace. Lake views from the master bedroom and sun room. Beautiful bathroom with big walk in shower. Come see for yourself!

A spacious living room features a large gray sectional sofa, an armchair in burgundy, and a dark wood TV stand with a flat-screen television. Natural light enters through the window, complemented by light-filtering shades. A neutral wall displays a framed cityscape artwork.

4.83 out of 5 average rating, 150 reviews

Mid-century Lower in Riverwest

This 2 BR duplex lower apartment is located in Milwaukee's Riverwest neighborhood, 2 miles directly north of downtown. It is furnished with many vintage mid-century furnishings, including a working HiFi. There is a garage space for your use during your stay, and ample street parking right in front making it easy to come and go. The kitchen has dishes, pots, pans, and all the utensils you will need during your time here.

The airy living space is adorned with colorful string lights and features a cozy seating arrangement. A large window allows natural light, with a view of the balcony. A workspace with a desk, a comfortable chair, and plants enhances the inviting atmosphere.

4.87 out of 5 average rating, 419 reviews

Riverwest Loft with city skyline view

This amazing loft space has one of the best views in Milwaukee! Once you get upstairs, you won't want to leave! We offer a full kitchen, bathroom with shower, private bedroom and a single bed and futon in the common area. On the 3rd floor of a 3 unit building. Very close to breweries, Bucks Stadium, downtown, Brady St, East side, festivals, etc. We've enjoyed fun times here and know you will too!

Guest suite in Helenville

The spacious loft features a modern open layout, with a kitchen area showcasing white cabinetry and a large granite countertop. Natural light floods the space through multiple windows, highlighting a cozy seating area beside a fireplace and a unique handcrafted couch that doubles as a bed.

4.95 out of 5 average rating, 366 reviews

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.

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Popular amenities for Washington County family-friendly rentals

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Family-friendly home rentals with a hot tub

Three wooden Adirondack chairs are positioned on a dock, facing a serene lake at sunset. A person is visible kayaking in the distance, with mountains silhouetted against the colorful sky.

Home in Plymouth

4.92 out of 5 average rating, 13 reviews

the getaway at crystal lake!

MikeRating, 5 stars46 months ago

This is a warm, inviting home with a terrific location in the lake. Jana and Josh’s house was very comfortable, clean, spacious and stocked with everything we needed for our vacation. An absolutely beautiful spot on the lake. Jana and Josh were extremely helpful and generous hosts who really anticipate what guests may need. We loved our stay!

A salt water hot tub is illuminated with soft blue lights, showcasing gentle water jets. Surrounding greenery and trees are visible in the background, providing a natural setting. A few metallic cups rest at the edge, enhancing the inviting atmosphere.

4.95 out of 5 average rating, 233 reviews

6BR house, yard, hot tub - 5 min drive downtown

FrankRating, 5 stars2 weeks ago

If i could give Paul and his home 6 stars I would. He was an excellent host. The home had everything and more than our group expected. It was close enough to down town but far enough to feel like we were away from the city.

A spacious deck is furnished with a dining table beneath a sun umbrella, alongside several lounge chairs. A hot tub is positioned on one side, with a view of the backyard and a garage in the distance under clear skies.

Condo in Wauwatosa

4.63 out of 5 average rating, 114 reviews

Stylistic Condo Hot Tub Tosa Village 2 blocks away

IrelandRating, 5 stars10 months ago

Sarah was a wonderful host with a beautiful home! My friends and I had a great time at this spot. It was clean and comfortable. Sarah was accommodating and responsive. Also super easy to get around Tosa or easy to get downtown!

A cozy living area is highlighted by a bookshelf filled with various books and a stylish armchair adorned with a decorative pillow. A potted plant adds a touch of greenery, while framed artwork and a small window create a warm and inviting space.

Home in Oconomowoc

4.77 out of 5 average rating, 30 reviews

Lake home on Lower Nehambin Lake

KappieRating, 5 stars2 weeks ago

We had a wonderful stay at the lake cabin. It was a great spot for our family of 5. We brought our children, ages 4, 2, and 4 months old and thought the cabin worked well for our needs. It is not particularly childproof, but we had no issues and our children loved the yard and the lake. I loved sitting on the back deck to enjoy the beautiful view in the early mornings when my infant had woken me up :) The bathroom was spacious, and the beds were comfortable. The kitchen had everything we needed and more. Everything about the stay was smooth and easy.

An aerial view of a spacious home reveals a well-manicured lawn surrounded by lush greenery. The two-story house features a light-colored exterior and a front porch, with a red car parked in the driveway. Nearby trees and open fields create a serene setting.

Home in Plymouth

5 out of 5 average rating, 15 reviews

Country Retreat, Close to Road America and Golfing

RandyRating, 5 stars23 months ago

Matt's house was awesome! Everything you needed for your stay and more. He made us feel more than welcome and we felt right at home. Thank you again for a great stay.

4.92 out of 5 average rating, 245 reviews

A luxurious hot tub is positioned on a spacious deck, offering panoramic views of the Milwaukee skyline. The bubbling water reflects the blue sky, while greenery borders the area, creating a serene environment for relaxation.

Townhouse in Milwaukee

Amazing view, Modern Space

TammyRating, 5 stars1 month ago

This place was súper clean and beautiful. We were very comfortable and never heard the neighbors downstairs. The only thing that happened was the that the thermostat stopped working and they weren’t able to come and fix it. Then the bathroom switch kept tripping and we had to find the fuse box and various times the light didn’t work. But it was such a nice place and I would totally stay there again. We had a very comfortable experience.

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Family- and pet-friendly home rentals

A serene backyard is showcased, featuring a well-maintained lawn and a cozy seating area. A hammock hangs between two trees, while potted plants are arranged on a wooden fence. A dog is seen exploring the space, adding a sense of warmth.

4.93 out of 5 average rating, 188 reviews

HGTV Renovated Home with GREAT backyard!

JoshRating, 5 stars2 weeks ago

This place was stunning and Jenni was fabulous to work with. Literally zero complaints! Thank you so so much for everything ❤️

4.98 out of 5 average rating, 279 reviews

A quaint living space features an antique-style fireplace made of dark wood, with a circular mirror above it. A flat-screen television is mounted on the wall opposite a small table and a suitcase rests on the hardwood floor, accompanied by a decorative flower arrangement.

Apartment in Waldo

The Blue Cobb House

MikeRating, 5 stars1 month ago

My wife and I were celebrating our 45th Wedding Anniversary- Jewel made it so special for us! And her place? WOW! We’ve stayed in AirBnb’s from Olympia to Siesta Key, from Zagreb to Dubrovnik- and Jewel’s place and her hospitality outshines them all! Beautiful accommodations, spotless, every possible provision, comfortable and supportive bed, - it was simply heavenly!!! Thanks to Jewel!!!

A spacious living area features high ceilings with exposed beams. A curving staircase leads to an upper level, while large windows provide ample natural light. A comfortable sectional sofa is arranged around a coffee table, and a decorative area rug adds color to the wooden floor.

4.89 out of 5 average rating, 231 reviews

Historic Home Sleeps 16 in MKEs Best Neighborhood

LynneRating, 5 stars8 months ago

Always love staying with Daniel and Anne's place! Not only are they always super responsive, but their property is beautiful and well set up for large groups. walk friendly, and lots of nearby food options. 100% would recommend, and we definitely hope to be back in the future!

A cozy living space features a large sectional sofa adorned with colorful pillows. A round coffee table sits in the center, complemented by a textured rug. Natural light enters through a nearby window, illuminating the plants and decor against a warm, inviting wall.

4.95 out of 5 average rating, 116 reviews

This Must Be the Place- Bayview Bohemian Vibes

KristenRating, 5 stars1 week ago

Easy to access beautiful home which looks just like the photos. The host was extremely responsive when I had questions - would absolutely stay again.

4.94 out of 5 average rating, 470 reviews

A charming guest house exterior is framed by manicured landscaping. The entrance is highlighted by large wooden doors, with a welcoming porch illuminated by soft lighting. A one-car garage is present on the side, and lush trees provide a natural backdrop.

Home in Plymouth

Country Guest House - Beautiful Gardens!

PahouaRating, 5 stars1 week ago

Joe and Alyssa 's property was amazingly beautiful ! All my siblings us came from out of town and state , to see our baby brother walk for his high school graduation in Sheboygan . This home housed us all with the main house and guest house . Very fast communication with the owners and they were able to adjust our reservation so quick for us to book the guest house that last minute too . The grilling space was wonderful , as we had kids who ran around the yard - Safely without any concerns . Will definitely look forward to booking with Joe and Alyssa again in the future !

4.83 out of 5 average rating, 102 reviews

A bright living room features two lightweight armchairs, a round coffee table, and a comfortable sofa with neutral tones. Natural light fills the space through a large window, enhancing the ambiance. A ceiling fan hangs above, and a world map artwork adds a touch of style.

Home in Cudahy

Wonderful Family Home Across from Park

TimerieRating, 5 stars2 months ago

We loved this house!!! It had absolutely everything we needed. Great location in a nice neighborhood across the street from a park, but just a few minutes from all the fun in Bay View and a very easy drive to downtown. The house was spotless and comfortable, and it was so nice being able to bring our dogs. We really felt at home. Thank you!

A bright living area features large windows letting in natural light, decorated with elegant dark curtains. Two red-accented chairs are positioned beside a small table and a lamp. A light-colored sofa faces a modern television atop a light wood stand.

4.92 out of 5 average rating, 117 reviews

Allis in Dairyland-2 Bdm flat in heart of Bay View

ninaRating, 5 stars5 months ago

The perfect location for my stay!! The hosts were quick to respond if I had any issues and the actual place itself was so cute.

4.84 out of 5 average rating, 429 reviews

An open loft space features light-colored walls and wooden beams, providing a spacious atmosphere. A large painting hangs above a cozy seating area with a fabric sofa and armchair. A simple bedside table is placed next to a spacious bed, creating a restful setting.

Loft in Milwaukee

Charming Loft - sparkling clean-walk everywhere

AllisonRating, 5 stars1 month ago

My husband and I stayed here for a quick Milwaukee getaway. We loved the space and felt like we were at home. The location is perfect and walkable to everything we needed. Jori was ultra responsive and very helpful. We already talked about booking this place again!

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Family-friendly home rentals with a pool

A comfortable living area features a large coffee table at its center, surrounded by a variety of seating options, including two patterned sofas and two armchairs. Bright artwork adorns the walls, and large windows provide natural light and a view of the outdoors.