Family-friendly vacation rentals in Wauwatosa

A living area features large windows with natural light filtering through sheer curtains. Comfortable seating includes a plush sofa with red accent pillows, a matching armchair, and an ottoman. A textured area rug adds visual interest to the hardwood floor.

4.98 out of 5 average rating, 399 reviews

Great Location, Wauwatosa (upper unit)

This bright & super clean upper (19 stairs) 2 bedroom duplex is in the heart of East Tosa. ( Bel Air Cantina, Cranky Al's, Rocket Baby, Rosebud Theater, il Mito, North Ave. Grill, Camp Bar and micro brewery within 1/2 a block to 4 blocks of this house) Centrally located for quick access to Medical College/Froedert, Am Fam Field, Milwaukee County Zoo, Downtown, Harley Museum, Milwaukee Art Museum & Summerfest/lakefront festival grounds. 1 space off street parking.(Owner does live on the property)

Indoor spacesKitchenParking

4.98 out of 5 average rating, 271 reviews

The exterior of a two-story brick duplex is shown, featuring a welcoming entrance. Lush green lawns are bordered by manicured flower beds. Steps lead to the front door, flanked by hanging flower baskets and illuminated by wall-mounted lanterns. A concrete pathway curves gently through the yard.

Bungalow in Wauwatosa

Wauwatosa/MKE “Inglewood Place” Historic Place

Great location! Near all Milwaukee attractions and village of Wauwatosa.Cozy, upper two-bedroom duplex with keyless entry in quiet east Tosa. Extras such as ironed sheets, snacks and personal items are included. Walk to popular restaurants and bars in the village and along North Ave. Full kitchen and new beds make this a home away from home. 10 min to Froedtert & The Medical College of WI & Children’s Hospital. Near AmFam Field (Brewers stadium) and the lakefront. 4 miles to downtown Milwaukee.

FamilyKitchenSleep quality

A well-lit living area features a large sectional sofa adorned with decorative pillows. A natural wooden coffee table is positioned on a soft area rug. Sunlight filters through the wooden blinds of the windows, illuminating the neutral-colored walls and the minimalist decor.

4.94 out of 5 average rating, 112 reviews

Charming Newly Renovated 2 BR in Village of Tosa

Come stay at this newly renovated upper bungalow duplex in the Village of Wauwatosa. Enjoy the many bars, restaurants, coffee shops and local establishments within walking distance in the vibrant and bustling Tosa Village. In addition to the easy access to local businesses, you can enjoy a stroll in Hart Park a walk, bike, or rollerblade down scenic Menomonee Parkway. Accessibility to many surrounding communities like downtown Milwaukee, Brookfield, Waukesha, Menomonee Falls, New Berlin.

FamilyIndoor spacesCondition

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

Come stay with us at West Allis Oasis in West Allis, WI, bring your pets too! Your cozy 2-bedroom, 1-bathroom home on a quiet street in a fantastic neighborhood. Dog-friendly and perfect for families or solo travelers, enjoy easy access to I-94 and the State Fair Park just a few blocks away. Our home offers a peaceful retreat with comfortable furnishings, a fully equipped kitchen, cozy bedrooms, and large fenced in yard. Book your stay today for the perfect blend of comfort and convenience!

KitchenIndoor spacesNearby

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!

Private, Renovated Home in Wauwatosa w/ Master Bedroom Suite, Workspace, Free Parking, Full Kitchen & Fitness Area 6 guests, 4 beds, 3 bedrooms, 2 full baths In walking distance of local restaurants & bars Near Hospitals 3.6 mi to State Fair Park 4.6 mi to Fiserv Forum 6.3 mi to Miller High Life Theater 6.9 mi to Summerfest Grounds -Washer & Dryer -WIFI -Smart TV -Fitness bike & equipment -Coffee bar -Towels -Toiletries -Dishes, Dishwasher -Games -Security System -Fenced Yard

Indoor spacesKitchenQuiet

A living area features a wooden futon adorned with colorful cushions, accompanied by a striped armchair. A flat-screen TV is positioned on a dark wood desk. Natural light filters through the window, highlighting the hardwood floor and a textured area rug in multiple colors.

4.88 out of 5 average rating, 191 reviews

MKE Bungalow, Driveway Parking, Long-Stays Welcome

Welcome to our comfortable 2 BR, 4-bed private upper unit bungalow apartment with an easy keypad for self check-in and off-street parking. There are 3 window AC units , one in both bedrooms and one in the living room. Only 12 min to downtown, 7 min to Miller Park, 9 to Froedtert Hospital, and a 3 minute ride (half-mile walk) to all that North Ave and East Tosa have to offer. Great for long term stays and families. We provide a stroller, a high-chair, a pack’n’play, board games and more.

KitchenIndoor spacesWifi

4.96 out of 5 average rating, 264 reviews

A spacious sleeping area is furnished with a large bed, complimented by soft white linens. A wooden dresser and a chair provide storage and seating options. Natural light filters through a nearby door, enhancing the welcoming ambiance of the room.

Bungalow in Wauwatosa

Tosa Respite (second floor, private suite)

Beautiful, private, second floor suite nestled in a quaint Wauwatosa neighborhood, Tosa Respite is a getaway within the city. Tosa Respite is conveniently located a stone’s throw from Interstate 94, Froetdert Hospital, The Medical College of WI, the Ronald McDonald House, State Fairgrounds, and biking/walking trails. Also walking distance to shops, cafés, restaurants, with a Bublr hub around the corner. Owner lives on premise and operates a private studio on the first floor.

FamilyKitchenView

A spacious bed is dressed in neutral linens, complemented by a decorative striped blanket and a pillow with 'relax' text. A wooden bedside table with a lamp rests nearby, and wall art is mounted above the bed, enhancing the room's inviting ambiance.

4.87 out of 5 average rating, 392 reviews

Tosa Village Studio Apartment

Tosa Village Studio. (Wauwatosa is the first suburb west of Milwaukee). Walk to the Village and explore the boutique shops, restaurants and bars. Enjoy summer concerts in Hart Park. Miller Park (Milwaukee County Stadium - Home of the Brewers) only 3.5 miles away. Close to the Medical Complex, Froedert and Children's Hospitals. 6.5 miles to the Fiserv Forum (Home of the Milwaukee Bucks). Six miles to downtown Milwaukee. Enjoy Summerfest at the Lake Michigan shore.

FamilyIndoor spacesDecor

4.87 out of 5 average rating, 100 reviews

A welcoming front porch features a rocking chair beside a small table. A decorative doormat lies at the entryway, and potted flowers add color to the space. The glass door allows natural light to enter, framing the comfortable indoor setting.

Townhouse in Wauwatosa

Central Location, Private Patio, Walkable, Quiet

Fun quiet central location. Space offers 2BRs 2 Baths & 2 living areas. Fiber internet and two working areas. Note that second space is in finished basement. Patio w/ fire pit. Kitchen fully stocked, stove, refrig, dishwsher & microwave (All Stainless steel). Washer and Dryer. Quiet neighborhood and walking distance to coffee shop, top restaurants, sports pubs, walking trail and more. Bus line right outside or 8 min by Uber to downtown Milwaukee. Parking available

FamilyKitchenAir conditioning

4.96 out of 5 average rating, 165 reviews

A spacious dining area features a wooden table surrounded by six chairs, complemented by an archway leading to a cozy living room. Natural light filters through large windows, illuminating the elegant combination of exposed brick and light-toned walls.

Home in Wauwatosa

Historic on The Avenue

Entire Home- 3 bedrooms This beautiful historic home is centrally located in the heart of Wauwatosa! Steps from the quaint village with restaurants, bars, coffee shops and boutiques! This property marries old world charm with modern amenities. Less than 15 minutes via freeway to downtown Milwaukee, the lakefront, Marquette University, less than 10 minutes to American Family Field, 5 minutes to the Milwaukee Zoo and Froedtert/Children's hospital.

KitchenIndoor spacesCheck-in

5 out of 5 average rating, 314 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

The Little Gray House is better than ever! This spring we completed many upgrades inside and out - check out our photos! We've got a few small openings left this summer, maybe they work for you? Time to book for fall and winter holidays so you can get in on the best little Airbnb around! The Little Gray House has attained rave reviews from travelers around the world for its comfort, cleanliness, and convenience. Happy to have you!

Indoor spacesFamilyPool

A well-appointed bedroom features a spacious bed adorned with soft linens and decorative pillows. A blue velvet headboard and artwork above add a touch of elegance. Natural light enters through a window draped with turquoise curtains, paired with a bedside lamp for evening ambiance.

4.83 out of 5 average rating, 129 reviews

Tosa Village | King Bed | Froedtert | Parking

This 1 bedroom 2nd Floor apartment has everything you need to feel at home with a location second to none. You will be staying directly on State St in the village of Wauwatosa - a wonderfully walkable neighborhood with amazing bars & restaurants, shops, and great proximity to Froedtert hospital. ✔ King Bed ✔ Fully Equipped Kitchen ✔ High-Speed Wi-Fi ✔ Free underground Parking ✔ Dedicated Workspace ✔ Roku Smart TVs ✔Parking + Elevator

FamilyKitchenCheck-in

Popular amenities for Wauwatosa family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 112 reviews

Brew City Inn with Hot Tub | Summerfest House

Indoor spacesKitchenCleanliness

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 spacesKitchenNearby

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.

4.91 out of 5 average rating, 314 reviews

Large Downtown Home w/ Hot Tub & Huge Backyard

KitchenFamilyWalkability

4.98 out of 5 average rating, 136 reviews

Belleview House: Hot Tub, Fire Table, Fenced Yard

KitchenIndoor spacesAmenities

4.86 out of 5 average rating, 116 reviews

Arcade Victorian Mansion · Sleeps 23 · 7 BR

FamilyIndoor spacesBackyard

4.93 out of 5 average rating, 289 reviews

Townhouse in Riverwest

The Hottest Tub in MKE • Skyline Views • Sleeps 8

Indoor spacesFamilyLaundry

4.84 out of 5 average rating, 115 reviews

Spacious Family Retreat w Hot Tub & Movie Lounge

Indoor spacesFamilyNearby

4.99 out of 5 average rating, 152 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 spacesFamilySleep quality

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 168 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

FamilyKitchenNearby

Apartment in Walker's Point

A stylish living area features large arched windows allowing natural light to fill the space. A vintage motel sign hangs prominently, enhancing the design. Two comfortable leather chairs are positioned around a wooden coffee table, with a plush ottoman nearby. A TV is mounted on a stone wall.

4.96 out of 5 average rating, 128 reviews

Vintage Motel Inspired 1BR City View, Free Parking

FamilyIndoor spacesLaundry

4.8 out of 5 average rating, 191 reviews

Home in West Allis

★Cozy Beach Themed Home★2 Beds★Spacious Parking★

Indoor spacesKitchenAccuracy

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, 107 reviews

Spotless, Walkable- Downtown, Fiserv Forum

Indoor spacesFamilyDecor

4.81 out of 5 average rating, 203 reviews

A cozy living area features a spacious sofa against a vibrant, textured wall. A colorful area rug adds warmth to the hardwood floor, while framed artwork decorates the surrounding walls. Access to the kitchen and stairway is visible in the background.

Home in West Allis

Designer Cottage-Parking, Patio, & New Kitchen

Indoor spacesFamilyNearby

A cozy living area features a light-colored sofa adorned with decorative pillows, accompanied by two wooden side tables. A television is mounted on the wall, and a small refrigerator stands nearby. A soft area rug adds comfort underfoot, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 155 reviews

That 70s Bungalow

FamilyIndoor spacesCheckout

4.92 out of 5 average rating, 174 reviews

A spacious living area features a cozy tufted sofa adorned with decorative pillows, complemented by a circular glass coffee table. A vibrant area rug with floral patterns enhances the warm wood floors. Colorful artwork decorates the walls, adding a playful touch to the room.

Home in Bay View

2BR Sunny Upper in Prime Bay View - w/ Parking

Indoor spacesKitchenQuiet

A comfortable living room is showcased, featuring a soft gray sectional couch and two blue accent chairs. A coffee table sits centrally on a decorative area rug. Natural light enters through large windows adorned with light drapes, framing a view of the exterior.

4.88 out of 5 average rating, 121 reviews

MKE 2BR Flat+PKG|5M to Brewers |15M to Airport

Indoor spacesKitchenGrill

Family-friendly home rentals with a pool

Location! Inground pool! Multi-month only.

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, 196 reviews

Brewers Hill Gem w/hot tub & seasonal shared pool

FamilyKitchenAmenities

4.95 out of 5 average rating, 19 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

KitchenFamilyHospitality

4.94 out of 5 average rating, 53 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

KitchenFamilyView

Home in River Hills

4.31 out of 5 average rating, 16 reviews

Luxury 5BR | Indoor Pool + Theater | Sleeps 12+

KitchenFamilyGetting around

Home in Sussex

Beautiful home in the country

Outdoor spacesValuePool

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.