Family-friendly holiday rentals in Shorewood

4.91 out of 5 average rating, 117 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.

FamilyIndoor spacesCheckout

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!

FamilyIndoor spacesAmenities

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.

Indoor spacesFamilyCleanliness

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.

KitchenIndoor spacesParks

4.98 out of 5 average rating, 141 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

KitchenFamilyHospitality

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, 147 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.

FamilyKitchenBiking

4.94 out of 5 average rating, 109 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!

FamilyIndoor spacesCondition

A cozy living room features a dark leather sofa and armchairs arranged around a coffee table with a warm wood finish. Large windows allow natural light to fill the space. A patterned area rug adds texture to the hardwood floor, enhancing the room's welcoming ambiance.

4.9 out of 5 average rating, 108 reviews

Cream City Home - Shorewood

Welcome to our spacious and stylish Airbnb in the heart of Shorewood! This lower unit of a duplex offers two comfortable bedrooms, a fully equipped kitchen, a cozy living room, and a private backyard patio. Our home is located in a quiet and friendly neighborhood, just a short walk away from Lake Michigan and local restaurants and shops. With modern amenities and classic decor, our Airbnb provides a comfortable and convenient home base for your next Wisconsin adventure.

KitchenFamilyHospitality

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, 145 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.

KitchenFamilyValue

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.

FamilyKitchenGetting around

4.89 out of 5 average rating, 209 reviews

A spacious living area features mid-century furnishings, including a blue sofa and wooden coffee table. A large television is positioned on a side table. A dining table with several chairs is visible in the background, along with natural light filtering through the window treatments.

Apartment in Riverwest

Mid-century Upper in Riverwest

This 2 BR duplex upper 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.

KitchenIndoor spacesAmenities

4.85 out of 5 average rating, 130 reviews

A sturdy entrance door with multiple glass panels is framed by textured stone walls. The door features a decorative wreath adorned with sunflowers and autumn accents, creating a welcoming entry point.

Apartment in Shorewood

English Tudor -Floor 3 Suite blocks from the beach

Total 4 beds - 2 Queen, 1 twin, 1 full Floor 3 is a private, peaceful, comfortable suite. Newly tiled bathroom and renovations throughout. Comfortably Sleeps 6 beds (2 queen, 1 double, 1 twin. There is 1 full bathroom. I have a cat that goes in the lower level stairway to access their restroom in the basement. But they do not go in the 3-floor unit. I also have 2 lovely dogs you may see when coming in.

KitchenIndoor spacesAmenities

Popular amenities for Shorewood family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 116 reviews

Brew City Inn with Hot Tub | Summerfest House

FamilyKitchenBarbecue

5.0 out of 5 average rating, 320 reviews

Home in Wauwatosa

The Little Gray House

Indoor spacesFamilyTV

4.93 out of 5 average rating, 293 reviews

Townhouse in Riverwest

The Hottest Tub in MKE • Skyline Views • Sleeps 8

Indoor spacesFamilyDecor

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

KitchenFamilyComfort

4.98 out of 5 average rating, 154 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

FamilyIndoor spacesAccess

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, 252 reviews

6BR Home•Hot Tub•Game Room•Near Downtown•Sleeps 14

Indoor spacesFamilyBathroom

A spacious hot tub is positioned under a wooden structure, surrounded by a concrete slab. Sturdy steps lead up to the hot tub's entry, which is equipped with comfortable seating. Utility equipment is displayed on the wall, enhancing the outdoor setting.

4.9 out of 5 average rating, 133 reviews

Quiet, Comfy Craftsman 2-BR with Private Hot Tub!

KitchenFamilyHospitality

A spacious living room features a large leather sofa and two armchairs, positioned around a decorative coffee table. Natural light filters through large windows, illuminating the space. A neutral area rug adds warmth to the hardwood flooring, while soft curtains frame the windows.

4.92 out of 5 average rating, 319 reviews

Large Downtown Home w/ Hot Tub & Huge Backyard

KitchenFamilyBackyard

Family- and pet-friendly home rentals

Superhost

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.

4.88 out of 5 average rating, 354 reviews

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

FamilyIndoor spacesBeach

4.91 out of 5 average rating, 129 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

Indoor spacesKitchenAir conditioning

4.98 out of 5 average rating, 108 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

FamilyIndoor spacesLayout

5.0 out of 5 average rating, 172 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

FamilyIndoor spacesLocation

4.9 out of 5 average rating, 106 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

FamilyKitchenPets

4.95 out of 5 average rating, 171 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

Indoor spacesKitchenAmenities

4.89 out of 5 average rating, 126 reviews

A spacious living area features a cozy seating arrangement with a dark blue sofa and two patterned armchairs around a glass coffee table. A decorative rug lies on the hardwood floor, while a modern light fixture hangs from the ceiling. A fireplace and TV are positioned on the wall.

Home in Wauwatosa

Entire Wauwatosa Home!

FamilyIndoor spacesOutdoor spaces

4.98 out of 5 average rating, 122 reviews

A modern kitchen features sleek cabinetry and open shelving. The space is illuminated by natural light through multiple windows. A wooden countertop extends into a dining area with bar stools, while brick accents add a touch of character.

Home in Lower East Side

Cream City Lounge | Parking| AC | Patio | Pets

KitchenIndoor spacesBathroom

Family-friendly home rentals with a pool

4.87 out of 5 average rating, 713 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

KitchenFamilyBackyard

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, 198 reviews

Brewers Hill Gem w/hot tub & seasonal shared pool

Indoor spacesKitchenCheck-in

4.88 out of 5 average rating, 145 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

Indoor spacesFamilyAccess

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

4.78 out of 5 average rating, 171 reviews

Close to Lake with Great Ammenities & Breakfast!

KitchenFamilyPets

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

FamilyIndoor spacesBackyard