Family-friendly vacation rentals in Shorewood

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Top-rated family-friendly rentals in Shorewood

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A charming red farmhouse is set against a colorful sky at sunset, surrounded by a picturesque yard filled with wildflowers. The property features a wooden fence and mature trees, contributing to a serene rural atmosphere.

Guesthouse in Richfield

4.94 out of 5 average rating, 254 reviews

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.

Guest favorite

Home in Bay View

4.95 out of 5 average rating, 111 reviews

This Must Be the Place- Bayview Bohemian Vibes

Perfect for families! We have a cozy light filled home in a quiet walkable neighborhood of Bayview. Enjoy the back porch with a coffee or local brew. We are a 5 minute drive from the airport, 10 min to downtown Mke and 5 minute walk to public transit. Parks are in walking distance as well as cafes & restaurants. Our home is a great place for couples, solo adventurers, business travelers, families, groups, and furry friends (Fee of $150 up to two well behaved dogs) Relax, unwind & enjoy our home!

Superhost

The exterior of the home features a stately design with prominent arched windows and a welcoming entrance. Lush greenery surrounds the property, while the evening sky casts a warm glow, enhancing the peaceful ambiance of the space.

Home in Walker's Point

4.89 out of 5 average rating, 231 reviews

Historic Home Sleeps 16 in MKEs Best Neighborhood

MAX of 16 guests! This luxury home has been designed especially for groups to gather and connect in-person. The huge second floor has ample space to gather everyone around a chef's kitchen and walk-out patio, while floors 1 & 3 are for sleeping Walk or bike everywhere! Minutes to Downtown, Third Ward, Bay View, Summerfest, and the best restaurants, breweries, trails, and music/sports venues. Just 5 blocks from easy freeway access and 12 minutes from airport! 2 driveway parking spots included

Superhost

A dining area features a large wooden table surrounded by eight brown leather chairs. Natural light fills the space through two windows, highlighting a decorative chandelier above the table. A wall adorned with greenery and a mirror adds elegance to the setting.

Home in Shorewood

4.85 out of 5 average rating, 110 reviews

Beautiful Luxury Suite A of Shorewood Home

Our home is perfect for a Milwaukee stay. Full of amenities and great location. This luxury home has two bedrooms, loft bed and two full baths. Large kitchen and dinning area and two living rooms areas. Two of the bedrooms are perfect couple retreats each with a plush king bed. This home has a lot of extra sleeping room if your family is large. Two large sectionals and a queen bed with the most comfortable cotton sheets and down comforters. Ask about parking and backyard patio for grilling.

Superhost

A comfortable living area is furnished with a brown sectional sofa and a wooden coffee table, displaying decorative items. A colorful area rug enhances the space. The walls feature a map design in various colors, adding character. An archway leads to a bedroom area in the background.

Apartment in Lower East Side

4.83 out of 5 average rating, 272 reviews

Best location in Milwaukee! Lower Duplex Unit

LONG TERM STAYS WELCOME. Unit is right off Brady Street, One of the best streets in Milwaukee. Over 70 places to eat or drink within walking distance, including bars with free shuttles to brewers games and Summerfest. There are many shops and grocery stores in the neighborhood and everything you could possibly want is a short Uber ride away. Best enjoyed by up to six people whether they be couples, friends, solo adventurers, business travelers, families (with kids), and furry friends (pets).

Guest favorite

A well-lit living room is shown, featuring a neutral couch facing a television on a wooden stand. A round coffee table sits in front of the couch. Natural light streams through the large window, highlighting a corner display of plants and decorative items.

Condo in Milwaukee

4.82 out of 5 average rating, 109 reviews

Full Condo&Garage in Trendy Bay View Milwaukee

This practical and cozy condominium is located in the heart of Bay View right on historic KK Avenue. It is next to the quaint Morgan Park and a bus stop, across the street from Sprocket Cafe, minutes from the lake and walking distance from the greatest trendy shops, bars, restaurants, and other Bay View classics. Whether you are totally new to the Milwaukee scene or just visiting "home", we are glad to welcome you to this charming condo, perfectly placed to meet all your traveling needs.

Top guest favorite

A spacious kitchen is equipped with modern appliances, including a stainless steel stove and hood. A large granite island complements dark cabinetry, and a window allows natural light to brighten the space. Two stools are positioned at the island, providing additional seating.

Townhouse in Bay View

4.95 out of 5 average rating, 407 reviews

Vintage Bay View - Big Backyard, Big 1 Bedroom

Welcome to your Milwaukee getaway! Located in the Bay View area, you're walking distance from the best farm-to-table restaurants, music venues, art fairs, and craft beer in the city. Not only that, but Lake Michigan's beaches, Miller Park, and downtown are a short drive away. The location is ideal. The place was created with a 70's midwestern feel, with wood-paneled furniture pieces and mod design. It also boasts a giant kitchen and backyard with grill. We can't wait for you to visit!

Top guest favorite

A bright living area is filled with natural light from large windows. A dark blue sofa is complemented by an armchair and a coffee table, which holds magazines. A decorative plant adds greenery, while a patterned area rug anchors the space.

Home in Wauwatosa

4.92 out of 5 average rating, 158 reviews

AVL-Entire Home-MKE/Tosa (next to Hart Park)

*Home is located in the heart of the Wauwatosa village! *One block walking distance to full service grocery store and numerous bars and pubs. *Charming patio with tables and gas grill . *Includes 2-car garage. Free off-street parking available. *Very quiet residential neighborhood with quick accessibility to highway. *2.3 miles to Miller Park or Miller Brewery. *12 minute drive to Milwaukee->Fiserv Forum, The Rave, Eastside, Brady Street, 3rd Ward, Summerfest grounds and Lake Michigan.

Superhost

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

4.83 out of 5 average rating, 101 reviews

Wonderful Family Home Across from Park

Extended Stays Welcome! Everything you could want in a home away from home. Our place is a comfortable and beautifully updated mid-century brick ranch on a quiet tree-lined street overlooking 36-acre Greene Park. Super convenient location, just 10 min from both the airport and downtown. Walkable to Lake Michigan and just down the road from Bay View's great restaurants and nightlife. Pet-friendly and perfect for families, small groups, or business travel. You'll feel right at home here!

Superhost

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.

Apartment in Bay View

4.92 out of 5 average rating, 117 reviews

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

Bright and airy two bedroom apartment in the center of one of Milwaukee's hottest neighborhoods! Situated between downtown Milwaukee and the airport/Amtrak hub, Bay View is the perfect place to enjoy all the best Milwaukee has to offer. This upper flat of a duplex is right off the action-packed triangle of KK and Lincoln Aves yet still quiet and tranquil enough for a good night's sleep. Book 3+ nights and receive a gift certificate to our restaurant right across the street!

Guest favorite

The exterior of the home features a charming back patio area surrounded by vibrant yellow flowers. A wooden deck is furnished with a dining table and seating, while a shaded area provides additional comfort. String lights enhance the inviting outdoor space, ideal for gatherings.

Home in Milwaukee

4.95 out of 5 average rating, 231 reviews

Spacious house, yard & hot tub easy drive downtown

My spacious home spreads out over three levels on 1/3 acre in a quiet residential neighborhood, and is about one mile from most downtown restaurants, bars, breweries, and entertainment venues. Having easy access to the freeway and downtown it's a perfect location from which to explore the city, or to relax and have fun in the home with its many included amenities. Don’t forget your swimsuits so you can enjoy the new salt water hot tub with moto massage seats.

Superhost

A comfortable living area is designed with a light palette, featuring a gray sofa and a matching love seat. A wooden coffee table rests in the center, accompanied by a beige armchair. Large windows allow natural light to illuminate the space.

Apartment in West Allis

4.77 out of 5 average rating, 191 reviews

Station No 06 Inn

Very spacious two bedroom condo style apartment completely remolded and updated. Located behind Wild Roots restaurant which offers fine dining in a casual setting. The Award Wining West Allis Cheese & Sausage Shoppe (deli & cafe), Station No 06 beer garden, and Becher Meats are across the street. Once you arrive you won't need to leave, and you get two free breakfast sandwiches and house coffee per adult per stay at the cheese shop are amazing!