Family-friendly holiday rentals in Milwaukee

4.98 out of 5 average rating, 237 reviews

A vibrant living room features a yellow sofa adorned with colorful throw pillows, paired with unique armchairs. A large mural in bold colors occupies one wall. Natural light filters through sheer curtains, illuminating plants and decorative shelves, creating an inviting atmosphere.

Home in Walker's Point

INSTA-worthy 2 Br Downtown Home Sleeps 8 Walkable!

Looking for a fun and vibrant place to stay in Milwaukee? The Pink Lady is the perfect rental for your next girl's weekend, bachelorette party, or birthday celebration. With an open-concept living space, pink kitchen, champagne bar, and private patio, you'll have everything you need for a fun-filled stay. With easy access to top restaurants, breweries, and cultural spots, come experience the best of Milwaukee with us. Book now and immerse yourself in the charm and excitement of Milwaukee!

FamilyKitchenCleanliness

A bright living area showcases a comfortable seating arrangement with decorative cushions. Potted plants add greenery, and light streams in through the large windows. Artwork adorns the walls, while a mix of textures is provided by the rugs and furnishings.

4.94 out of 5 average rating, 441 reviews

Bay View MKE Hideaway - with Parking!

Cozy, inviting, one bedroom apartment in the heart of Bayview, literally steps away from some of Milwaukee's best restaurants, bars and shops! One of two Airbnb guest spaces in our house, this downstairs apartment is our home base when we're in Milwaukee, and we love sharing it with guests when we’re on the road! We are within five minutes of Summerfest grounds and East Side & Historic Third Ward districts, and within 10 minutes of the airport, downtown, Marquette University, and Miller Park.

KitchenIndoor spacesDecor

A studio apartment is displayed with a spacious sleeping area featuring a cozy bed and a vibrant red couch. The kitchen area includes modern appliances and a dining space with wooden chairs. Natural light illuminates the warm wood flooring.

4.85 out of 5 average rating, 241 reviews

The LuLu Nest: Bay View Studio, 5 min to downtown!

Cozy and convenient studio apartment in the center of one of Milwaukee's hottest neighborhoods! Bay View, situated right betw downtown Milwaukee and the airport/Amtrak hub, is the perfect neighborhood to enjoy all the best Milwaukee has to offer. This studio apartment is only one of five in our building and is situated right above a popular neighborhood restaurant yet still quiet and tranquil enough for a good night's sleep. Book 5+ nights and receive a gift certificate to our restaurant!

KitchenIndoor spacesQuiet

4.98 out of 5 average rating, 134 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

FamilyIndoor spacesPets

4.92 out of 5 average rating, 153 reviews

The living room features a stylish tan sofa accompanied by a textured throw and decorative pillows. A round mirror hangs on the wall, reflecting the room's layout. A light fixture hangs overhead, and colorful artwork is displayed. A modern coffee table is positioned on a striped rug.

Home in Bay View

Funky 2BR in Prime Bay View - w/ Parking

Perfectly located on the main strip of KK in MKE's eclectic Bay View directly next to restaurants and bars. Minutes from downtown, Summerfest, art museum. You’ll have the entire first floor of this sunny duplex. Stylishly designed - 2 bedrooms with Casper mattresses, a bright kitchen with seating area, record player, a work space in the master, and a comfy living room with a smart TV. The space has a small backyard area, an in-unit washer & dryer as well as 1 off-street parking space.

Indoor spacesFamilyAir conditioning

4.89 out of 5 average rating, 266 reviews

Flat in Walker's Point

Bright Corner Studio Loft | King Bed + Parking

Welcome to your stylish Milwaukee retreat! This large corner studio loft blends historic Cream City charm with modern comfort. Soaring 15-ft ceilings, exposed brick, and oversized windows create a bright, open space. Enjoy a spacious king bed, fully stocked kitchen, and free off-street parking — rare in this neighborhood. Walk to the Third Ward, Walker’s Point, and Milwaukee’s best restaurants, breweries, shops, and the vibrant riverfront. Perfect for both work and play.

Indoor spacesKitchenQuiet

The exterior of a historical mansion is displayed, featuring intricate architectural details and multiple levels. Large windows and black front doors offer an inviting entrance. A grassy area with small shrubs lines the front, providing a well-maintained appearance against a cloudy sky.

4.91 out of 5 average rating, 772 reviews

Historic Lower East Side Apartment with Lake Views

This is one unit in a historical mansion with lake views! Layout is shotgun, open concept with a SMALL functional kitchen. Definitely gives off a pied-à-terre vibe. You have direct access to the back patio and a dedicated parking space around the corner. This unit is in the heart of the lower east side- close to the art museum, cathedral square, Brady st, 3rd ward, as well as the best restaurants and bars in MKE .

Indoor spacesKitchenGetting around

Superhost

4.85 out of 5 average rating, 369 reviews

Modern Luxury 1BR Apt with Rooftop+Gym+Parking

Experience Milwaukee like a VIP! This luxury one-bedroom apartment offers the ultimate convenience with direct access to the Fiserv Forum through the building's enclosed skywalk. Whether you're in town for a game, a concert, or simply to explore, you'll love taking in the skyline views from the rooftop patio, working up a sweat in the fitness center, or relaxing in your sleek and comfortable private space.

FamilyIndoor spacesAccuracy

4.74 out of 5 average rating, 111 reviews

A spacious living area with exposed wooden beams and a cream-colored brick wall. A comfortable blue sofa is complemented by a gray accent chair. A coffee table sits in front, and a 55" flat-screen TV is situated across from the seating. An office desk is positioned nearby.

Flat in Walker's Point

1 bed | Sleeper Sofa | 5 Min to AdeptiCon

Be where the action is in this stylish 1 bedroom in Walker's Point with Milwaukee's historic cream city brick! With just a few steps from hip taverns, restaurants, museums, breweries, jazz clubs & more! Adventure through Milwaukee easily from this prime location! ✔ Fully Equipped Kitchen ✔ Comfortable Bedroom w/Queen Bed ✔ Pets Welcome ADDITIONAL FEE (SEE HOUSE RULES) ✔ Office Desk & High Speed Wi-Fi

KitchenIndoor spacesCleanliness

4.99 out of 5 average rating, 155 reviews

A well-appointed bedroom features a black metal bed frame with soft white linens and decorative pillows. A wooden bench sits at the foot of the bed, complemented by a nightstand with a lamp. Natural light enters through a window, casting a bright ambiance.

Home in Lower East Side

Luxe Brady St home, 5 min to Bucks/Marquette!

Walk to restaurants, bars, coffee & the lake! Free shuttle to Brewers & Bucks 1 block away. Fully renovated property w/backyard oasis. 2 parking spots provided Located in lively entertainment district Squeaky clean home with tons of amenities! 5 min to Fiserv Forum, Third Ward, Summer fest, Breweries, Art Museum, Children's Museum, Parks etc. Perfect for friends, families & colleagues!

Indoor spacesKitchenAmenities

A spacious living area features large windows providing views of Lake Michigan. A light wood dining table is paired with white chairs, and a cozy sectional sofa invites relaxation. Artistic pieces adorn the walls, enhancing the bright and airy atmosphere.

4.99 out of 5 average rating, 235 reviews

Lakeview Downtown Milwaukee Condo

This charming one bedroom offers a full kitchen, king bed, private full bathroom, dining and living room area. Conveniently located in Milwaukee's East Side - close proximity to lake paths and trails, Juneau park, Brady Street, Fiserv Forum, the Art Museum and Summerfest grounds! Stay here and start your day with a beautiful sunrise in one of the best locations Milwaukee has to offer.

KitchenFamilyAccess

A spacious living area is highlighted by large windows, allowing natural light to fill the room. A cozy sofa, two chairs, and a television are arranged to create a welcoming atmosphere. Modern stainless steel appliances are visible in the kitchen area, providing convenience.

4.94 out of 5 average rating, 137 reviews

MKE#210 - Explore Downtown/Fiserve/3rd ward/River

Overlook Wisconsin Avenue in stylish luxury, Experience Milwaukee at this centrally-located place. Close to everything; the Theater District just blocks from the Wisconsin Center and Convention Center. Walk along the Wisconsin River to the Infamous Third Ward or still down the skyway to the 3rd St Market. Health Club Access and free parking for one vehicle is provided.

Indoor spacesKitchenGetting around

Popular amenities for Milwaukee family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 287 reviews

Townhouse in Riverwest

The Hottest Tub in MKE • Skyline Views • Sleeps 8

Indoor spacesFamilyBiking

4.99 out of 5 average rating, 150 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 spacesGetting around

5.0 out of 5 average rating, 312 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 spacesKitchenWifi

An open concept kitchen features a large white island with seating, accompanied by modern cabinetry. The living space extends into a bright dining area, enhanced by natural light from a window. Decorative artwork and a wall clock add character to the surroundings.

4.95 out of 5 average rating, 191 reviews

Downtown Oasis: Hot Tub, Garage, 2 King Huge yard!

KitchenIndoor spacesDecor

4.95 out of 5 average rating, 112 reviews

Brew City Inn with Hot Tub | Summerfest House

FamilyIndoor spacesHospitality

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.

4.93 out of 5 average rating, 183 reviews

Spacious Farmhouse with Large Yard and Hot Tub

FamilyKitchenLocation

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, 131 reviews

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

Indoor spacesKitchenDecor

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

Indoor spacesKitchenWalkability

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 138 reviews

A modern kitchen features sleek cabinetry and stainless-steel appliances. A spacious island with four bar stools offers ample seating, while a bowl of fresh fruit adds a pop of color. Natural light enhances the airy atmosphere, complemented by understated lighting fixtures.

Flat in Lower East Side

Brady St Apt - 2 Master Suites, Free Parking

KitchenIndoor spacesValue

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.

4.98 out of 5 average rating, 104 reviews

Spotless, Walkable- Downtown, Fiserv Forum

Indoor spacesKitchenCheckout

A warm dining room features a round wooden table surrounded by six chairs. Natural light filters through large windows adorned with light curtains. Original woodwork highlights the charm of the space, complemented by decorative wall sconces and a sideboard with stained glass details.

4.97 out of 5 average rating, 101 reviews

Historic Bay View Home

FamilyKitchenGetting around

4.95 out of 5 average rating, 165 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.

Flat in Riverwest

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

Indoor spacesKitchenWalkability

4.88 out of 5 average rating, 130 reviews

A spacious living area features a blue sectional sofa and a yellow accent chair, offering an inviting seating arrangement. A brown coffee table sits on a patterned rug, while large windows allow for natural light. A desk with a chair is positioned nearby for work or leisure.

Home in West Allis

West Allis Oasis

FamilyIndoor spacesCheck-in

4.89 out of 5 average rating, 124 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!

Indoor spacesFamilySleep quality

The living area features a stone fireplace and a flat-screen TV mounted above it. Two dark armchairs and a comfortable sofa create a cozy seating arrangement. Natural light enters through multiple windows, highlighting the original woodwork and a vibrant area rug on the hardwood floor.

4.97 out of 5 average rating, 168 reviews

Spacious & Private 2 bdrm in the heart of Bayview

Indoor spacesKitchenLaundry

5.0 out of 5 average rating, 164 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

KitchenIndoor spacesParking

Family-friendly home rentals with a pool

A charming duplex stands with a triangular roof, featuring a colorful facade and multiple balconies. Stairs lead up to the front porch, where seating areas are present. Lush greenery and colorful flowers are visible in front of the stone boundary wall, complementing the vibrant exterior.

4.96 out of 5 average rating, 241 reviews

The Peacock Place w/ Shared Seasonal Outdoor Pool

FamilyIndoor spacesLaundry

4.79 out of 5 average rating, 163 reviews

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!

Indoor spacesKitchenHospitality

4.87 out of 5 average rating, 703 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

Indoor spacesFamilyParking

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, 119 reviews

Rosie’s Eastside Garden Bungalow

FamilyKitchenComfort

4.93 out of 5 average rating, 58 reviews

The exterior of a mid-century modern tri-level home is showcased amidst a spacious green yard. Surrounding trees provide shade, contributing to the peaceful ambiance of the property. A large driveway is visible, accommodating multiple vehicles.

Villa in Hales Corners

Beautiful 6 bedroom with Heated Pool & Jacuzzi

KitchenFamilyAccuracy

4.94 out of 5 average rating, 18 reviews

A spacious outdoor patio surrounds the inviting swimming pool, featuring lounge chairs, umbrellas, and shaded seating areas. Lush greenery and trees frame the scene, enhancing the tranquil atmosphere. The bright blue sky is dotted with clouds, offering a relaxing space for sunbathing or gathering.

Home in Mequon

Vacation home: heated inground pool on 4+ acres

Indoor spacesKitchenTV

The exterior of the two-story townhouse is visible, featuring a beige facade with dark brown trim. Large windows allow for natural light, while a patio area is accessible through a glass door. Lush greenery surrounds the property, adding a tranquil feel to the entrance.

Townhouse in Milwaukee

4.67 out of 5 average rating, 3 reviews

2 Story - 2Br Condo

KitchenIndoor spacesHeating