Family-friendly vacation rentals in Shorewood

4.91 out of 5 average rating, 116 reviews

A spacious living area features a large smart TV mounted on the wall, with modern furniture arranged for comfort. A sectional sofa and accent chair provide seating options. Natural light streams through the windows, and artistic touches enhance the welcoming atmosphere.

Apartment in Shorewood

Charming home w/ fire pit, walk to Lake Michigan

Welcome to our home in a quiet neighborhood, a short walk to gorgeous views over Lake Michigan and two blocks to restaurants, shopping, and nightlife. Gather around the fire pit and grill dinner in the back patio. Listen to our vinyl collection or stream your own music while playing board games next to the smart TV. Super-fast internet, a fully equipped kitchen with coffee & tea, and in-unit laundry. Two comfy queen beds + a sleeper sofa. Here with kids? We have toys, a Pack n' Play, & more.

KitchenFamilyGetting around

A uniquely decorated bathroom features a white sink with a black rim, positioned beneath an oval mirror. Bright tropical wallpaper displays vivid greenery and animal motifs. A yellow towel hangs on a gold ring, and a white toilet paper holder is positioned nearby.

4.88 out of 5 average rating, 184 reviews

The Prospect House - Shorewood / Milwaukee, WI

From activities and attractions to fairs and festivals, Milwaukee, has something for everyone in your travel group! After each adventure-filled day, look forward to returning to this 3-bed, 1.5-bath lower duplex house featuring a fully equipped kitchen, bright living space, classic creaky wood floors, comfy accommodations for 6. There's a variety of things to do in MKE including award winning dining, pro Sports, Brewery tours, music festivals and more! Indoors or outdoors, the fun is endless!

KitchenFamilyDecor

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.

4.84 out of 5 average rating, 114 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.

FamilyKitchenAmenities

The exterior of the bungalow is highlighted by a charming front porch with a blue door. Vibrant flowers and greenery flourish along the stone landscape, providing a welcoming entrance. Large windows invite natural light into the home, complementing its classic design.

4.97 out of 5 average rating, 122 reviews

Rosie’s Eastside Garden Bungalow

Classic 1920's bungalow 10 minutes from Fiserv Forum, and across from the Oak Leaf trail— Rosie’s is truly a hidden gem on the East Side of Milwaukee. Wake up to birds chirping and enjoy your morning coffee on the air conditioned sun porch. Walk to Collectivo on the Lake, Bradford Beach, UWM, North Avenue, Brady Street, among countless cafes, restaurants, pubs, and more. This is your home away from home with welcoming hosts living next door for any recommendations or questions during your stay.

FamilyIndoor spacesValue

4.98 out of 5 average rating, 137 reviews

Belleview House: Hot Tub, Fire Table, Fenced Yard

Welcome to Belleview House, a delightful pet-friendly 3-bedroom home nestled in the heart of the vibrant Murray Hill/East Side neighborhood. We have renovated and redecorated the entire home and backyard (November 2025)! ✔ Hot Tub - closed during quiet hours ✔ Fast Wi-Fi ✔ Workspace ✔ Smart TVs ✔ Comfy king, queen, and twin beds ✔ Fenced Backyard with outdoor fire table ✔ Lawn bowling, horseshoe & cornhole ✔ Outdoor dining table ✔ 0.9 mi to Bradford Beach on Lake Michigan ✔ Stocked kitchen

Indoor spacesKitchenCheckout

The living room features a comfortable sectional sofa and a light-colored couch, accented with colorful pillows. A round wooden coffee table sits at the center, complemented by a decorative rug. Natural light filters through large windows with stained glass detailing.

4.99 out of 5 average rating, 145 reviews

The Menlo Guesthouse

A vintage, lower flat in a 100-year-old duplex with modern comforts and conveniences. Perfect for short or long stays while visiting Milwaukee. Situated in the walkable/bikeable Milwaukee neighborhood of Shorewood. The flat is located just a few blocks north of UWM and a few blocks east of the Oak Leaf Trail. Three minutes from Atwater Beach. Ten minutes or less to Bradford Beach, museums, and Summer Fest. Fifteen minutes or less to Fiserv Forum, Panther Arena, and American Family Field.

FamilyIndoor spacesWalkability

4.93 out of 5 average rating, 107 reviews

A charming upper unit of a bungalow is surrounded by lush green trees and well-maintained landscaping. The exterior features a combination of brick and stone, with decorative patriotic bunting adorning the porch. A pathway leads to the entrance, framed by vibrant foliage.

Apartment in Riverwest

Charming Bungalow Unit Just North of Downtown Milw

Here’s an opportunity that can’t be beat! This fully furnished upper unit in a charming bungalow is ready to be your home base while in Milwaukee. Two bedrooms, one fitted with a king size bed and one with a queen. Full kitchen. Plenty of street parking in this walk able niche neighborhood. Near Downtown, UW-Milwaukee, MSOE, The Milwaukee RiverWalk as well as a quick hop, skip and jump to museums, tours and arenas/stadiums. Easy access to public transportation. No cleaning fees!

FamilyKitchenParking

A cozy living area is presented with two dark leather sofas, accompanied by bright red cushions. A glass coffee table occupies the center, while light enters through two large windows adorned with navy blue curtains. A stylish lamp and a decorative piece complete the room.

4.89 out of 5 average rating, 349 reviews

Historic East Side Duplex, 3BD. No Cleaning Fee!

Minutes from downtown Milwaukee by car or bus, the whole group will enjoy easy access to the city from this central location less than a mile from the UWM campus. A block from the Urban Ecology Center and Oak Leaf Trail access and easy walking distance to North Avenue's restaurants, bars, and the Oriental Theater, there's no shortage of activities, entertainment, and dining options around this historic and charming East Side abode. Or stay in with our grill and fire pit.

FamilyKitchenHospitality

A well-equipped kitchen features white cabinetry, stainless steel appliances, and green tile backsplash. The space is illuminated with recessed lighting and includes a dining area with a wood table. An open doorway leads to another room, enhancing the overall flow of the layout.

4.93 out of 5 average rating, 161 reviews

Shorewood house - near shops w/ WiFi & parking

Just down the road from Lake Michigan, this charming duplex upper is the perfect space for a relaxing getaway. After a day of shopping, eating good food, and exploring Milwaukee, look forward to kicking back in the cozy living room, or on the patio. This duplex has 2 bedrooms; a King bed master, and one bedroom with two Twins. There is one charming bathroom with a bathtub. Well stocked kitchen, and plenty of backyard space. The lower tenant is respectful of guests.

Indoor spacesKitchenLayout

A welcoming hallway is displayed, featuring light-colored walls and a combination of wooden and tile flooring. An ornate mirror hangs on one wall, while decorative hooks are mounted nearby. Natural light streams in through a window beside the front door, enhancing the inviting atmosphere.

5.0 out of 5 average rating, 144 reviews

Bright Eastside MKE cottage w/ FREE Parking

Welcome to our peaceful little cottage in the heart of Milwaukee. This adorable 2 bedroom, 1 bathroom home will meet all of your needs with 1 king bed, 1 queen bed, a fully stocked kitchen, wifi, driveway for off street parking, and bikes to use on the nearby Oak Leaf Trail. This is the perfect place to enjoy the friendly city of Milwaukee with a comfortable place to sleep at the end of the day. Enjoy all of the restaurants and shops on the Eastside of Milwaukee.

KitchenIndoor spacesQuiet

4.89 out of 5 average rating, 185 reviews

A cozy bedroom area is presented with two twin beds, each adorned with green plaid bedding and yellow patterned cushions. A shared dresser is positioned between the beds, topped with two table lamps. Natural light enters through two windows with blinds, illuminating a floral area rug on the wooden floor.

Apartment in Riverwest

Seven Swans Inn - The Perch

This bright little charmer is situated within one of Milwaukee’s friendliest, most vibrant and walkable neighborhoods. This apartment has all you need to enjoy every moment of your time in the city. Start your day with by wandering downstairs for crepes and coffee (Thursday-Sunday 8-3) at Seven Swans Creperie! Only 5-10 minutes from Downtown, Fiserv Forum, Deer District, Brady Street, the Third Ward, Milwaukee Public Market, and Milwaukee’s famed lakefront!

Indoor spacesFamilyAir conditioning

4.97 out of 5 average rating, 324 reviews

A spacious living area features a mix of seating options, including a leather couch and armchairs. Large windows allow natural light to brighten the room, highlighting the hardwood floors and area rug. A coffee table sits centrally, providing a functional gathering space.

Apartment in Milwaukee

East Side Home

Upper flat located on Milwaukee's Historic East Side! We hope your stay with us feels like home. Spacious layout for most any kind of group. Stones throw to UWM, Lake Park, and Historic Downer Avenue shopping. Ten minute drive to downtown Milwaukee. We have been so lucky to have great guests, and we are constantly looking to improve your time here. If there is anything you might want for your trip please ask and we will do our best to accommodate.

FamilyIndoor spacesQuiet

Popular amenities for Shorewood family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 109 reviews

Downtown-2 King Beds-hot tub-Double Shower-Parking

KitchenIndoor spacesGetting around

4.95 out of 5 average rating, 114 reviews

Brew City Inn with Hot Tub | Summerfest House

Indoor spacesFamilyOutdoor spaces

4.93 out of 5 average rating, 291 reviews

Townhouse in Riverwest

The Hottest Tub in MKE • Skyline Views • Sleeps 8

Indoor spacesFamilyDecor

5.0 out of 5 average rating, 316 reviews

A hot tub is positioned on a wooden deck with a view of a fenced backyard, featuring charming seating areas surrounded by lush greenery. Potted plants line the space, and a geometric-patterned rug adds a pop of color beneath outdoor furniture.

Home in Wauwatosa

The Little Gray House

Indoor spacesKitchenHot tub

An inviting game room is showcased with a variety of entertainment options. A dartboard, two basketball hoops, and arcade machines with colorful controls are visible. Comfortable seating is arranged around a central play area, creating a space for relaxation and fun.

4.86 out of 5 average rating, 118 reviews

Arcade Victorian Mansion · Sleeps 23 · 7 BR

KitchenIndoor spacesOutdoor spaces

The exterior of a historic red farmhouse is displayed, featuring a welcoming porch with green steps leading up to the entrance. Nearby, a wooden fence and landscaped yard with several plants are visible, providing a charming and well-maintained outdoor space.

4.94 out of 5 average rating, 185 reviews

Spacious Farmhouse with Large Yard and Hot Tub

Indoor spacesFamilyQuiet

4.99 out of 5 average rating, 153 reviews

A cozy living room is centered around a modern fireplace framed by built-in shelves filled with decorative items and books. Light-colored sofas surround a glass coffee table atop a patterned rug. A ceiling fan provides airflow while natural light streams through nearby windows.

Home in Walker's Point

Barclay House in Walker's Point

Indoor spacesFamilyNearby

A cozy living area is captured, featuring two patterned armchairs and a blue sofa arranged around a light coffee table. A stone fireplace anchors the space, complemented by a colorful floral artwork on the wall. Natural light filters through the windows, enhancing the inviting ambiance.

4.89 out of 5 average rating, 207 reviews

Happy Days Home close to all MKE attractions

KitchenFamilyWifi

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 107 reviews

A cozy living area is highlighted by a light-colored sofa and a circular coffee table at the center. Two windows allow natural light to fill the space, illuminating a decorative rug. A mirror enhances the sense of openness, while potted plants and stylish furniture add softness.

Apartment in Milwaukee

Spotless, Walkable- Downtown, Fiserv Forum

KitchenIndoor spacesCheck-in

4.95 out of 5 average rating, 169 reviews

The kitchen features a blend of modern and vintage elements, with a checkerboard floor and wooden accents. A central wooden table is flanked by a gas stove and a decorated countertop. Natural light fills the space through multiple windows, enhancing the inviting atmosphere.

Apartment in Riverwest

Spacious+Mod Booth St Apt w Yard | 5 min to Fiserv

FamilyKitchenGetting around

4.88 out of 5 average rating, 121 reviews

Cozy East Side | Sauna |Parking | Near Downtown

Indoor spacesKitchenHospitality

4.91 out of 5 average rating, 128 reviews

A cozy living area is highlighted by a red futon, complemented by decorative pillows. A small coffee table with magazines sits in front of the seating. Natural light filters through the window shades, illuminating the inviting space. A bookcase is positioned near the entrance.

Apartment in Milwaukee

Eastside 4BR w Parking, Treadmill

FamilyKitchenTV

Apartment in Lower East Side

Modern Brady St Apt, 3 Private Baths, Free Parking

FamilyIndoor spacesComfort

4.95 out of 5 average rating, 139 reviews

5.0 out of 5 average rating, 171 reviews

A stylish living room features a combination of modern and vintage decor. A leather sofa and two vibrant red chairs are arranged around a wooden coffee table. Decorative plants and unique light fixtures add character, while floral wallpaper and a colorful dining area can be seen in the background.

Home in Walker's Point

Fabulous Walkers Point Mansion w/ Bar andFireplace

FamilyKitchenCheck-in

Superhost

A spacious living area is highlighted by two leather sofas adorned with decorative pillows. A circular coffee table sits in the center on a light rug, while wall-mounted lighting and a chandelier provide illumination. Large windows offer natural light and a view of the outdoors.

Home in Walker's Point

Cream City Victorian | Parking | AC | Patio | Walk

KitchenIndoor spacesParking

4.97 out of 5 average rating, 167 reviews

4.9 out of 5 average rating, 105 reviews

A functional kitchen area is highlighted by modern appliances, including a stainless-steel refrigerator and microwave. White cabinetry contrasts with the tiled backsplash. A wooden work table is positioned beneath hanging pots, while a colorful rug adds a welcoming touch to the tiled floor.

Home in Wauwatosa

Family friendly, Private Patio, Walkable, Quiet

FamilyIndoor spacesValue

Family-friendly home rentals with a pool

4.87 out of 5 average rating, 708 reviews

The entrance features a charming facade with three large windows and a decorative door. A set of stairs leads up to the front door, flanked by a wrought-iron railing. Lush greenery surrounds the base, enhancing the welcoming appearance of the home.

Loft in Riverwest

The Dragonfly Loft

KitchenFamilyBiking

A historic Victorian-style home is showcased with a blue exterior and ornate architectural details. Bright green foliage frames the entrance, leading to the front steps. The sky is clear, enhancing the home's inviting appearance.

4.92 out of 5 average rating, 197 reviews

Brewers Hill Gem w/hot tub & seasonal shared pool

Indoor spacesKitchenRiver

4.88 out of 5 average rating, 144 reviews

An indoor pool area is showcased, featuring a large, clear pool with a projector screen positioned above. Natural stone walls and wood beams enhance the space, complemented by soft lighting. Large windows allow natural light to brighten the inviting environment.

Home in Sussex

Wooded Hills/Indoor Pool/Hot Tub/Arcade

KitchenIndoor spacesDecor

Superhost

An outdoor patio space is presented, featuring a paved area surrounded by various seating options, including green chairs and a red umbrella. A grilling station is visible, and the background includes a garage with an open door. Lush greenery provides a natural border.

Home in Cudahy

Close to Lake with Great Ammenities & Breakfast!

FamilyKitchenAccuracy

4.77 out of 5 average rating, 168 reviews

4.94 out of 5 average rating, 54 reviews

A landscaped patio area features a circular arrangement of seating around a fire pit. Paved pathways meander through lush greenery and flowering shrubs, leading to a charming ranch-style home with a covered entrance, set against a backdrop of mature trees.

Home in River Hills

Exclusive Milwaukee Home

Indoor spacesKitchenBackyard