Family-friendly vacation rentals in Wauwatosa

4.88 out of 5 average rating, 112 reviews

Apartment in Wauwatosa

Tosa Village | King Bed | Froedtert | Parking

This apartment is perfect for health care travelers, business travelers, singles, or couples looking for a hygenic, affordable location close to all the action. Businesses are welcome to book for their employees. This 1 bedroom 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

Guest suite in Brookfield

A two-story home is surrounded by vibrant autumn foliage, featuring large trees displaying rich yellow and orange leaves. A gravel driveway leads up to the house, with fallen leaves carpeting the ground. A garage is visible in the background, adding to the serene neighborhood setting.

5 out of 5 average rating, 251 reviews

In the Canopy (beautiful Brookfield/Milwaukee)

Relax “in the Canopy” of beautiful maples! If you’re looking for party central…this isn’t it. But if you want a comfortable place in a tree-filled neighborhood, just a few minutes from all the best Milwaukee has to offer, you’re in luck! Perfect location for quick access to the city—or to Lake Country to the west. Quiet, comfortable, safe, surrounded by beautiful gardens. We’re in a perfect launching spot to visit Summerfest, Brewers/Bucks games, or Milwaukee's western suburbs. Bring the kids!

4.98 out of 5 average rating, 244 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.

4.95 out of 5 average rating, 844 reviews

A spacious living room features a vintage-inspired green velvet sectional sofa paired with plush pillows. A glass coffee table rests on a soft area rug, with natural sunlight illuminating the room. Decorative plants and a round mirror add to the inviting atmosphere.

Apartment in Bay View

Beautiful Bay View MKE Flat - w/parking!

This is a bright, sunny apartment on the upper level of a sweet little 1870's "Polish Flat" in the heart of Bay View, one of the city's most desirable neighborhoods! We are just steps away from some of Milwaukee's best restaurants, bars, taprooms, boutiques and coffee shops. The space features an efficiency kitchenette, living room, beautiful bedroom and renovated bathroom with walk-in shower! Close to East Side, Walker’s Point, Historic Third Ward, Summerfest, Mitchell Park and the airport.

4.88 out of 5 average rating, 106 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

Apartment in Enderis Park

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.

4.89 out of 5 average rating, 171 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.

4.98 out of 5 average rating, 373 reviews

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.

Apartment in Wauwatosa

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, Miller park, Milwaukee County Zoo, Downtown, Harley Museum, Milwaukee Art Museum & Summerfest/lakefront festival grounds. 1 space off street parking. Bublr & bus stop nearby.

4.95 out of 5 average rating, 218 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.

4.95 out of 5 average rating, 113 reviews

A brightly colored living area features an orange couch with patterned cushions, complemented by a unique coffee table. A round ottoman sits nearby, while large windows allow ample natural light. Open shelving holds decorative items, enhancing the vibrant atmosphere of the open-concept space.

Home in Bay View

Bright 1.5BR in the Heart of Bay View - w/ Parking

Perfectly located in Milwaukee’s eclectic Bay View 4 blocks from the lake. Minutes from downtown, Summerfest, art museum, etc. You’ll have the entire second floor of this sunny duplex. The space is open concept - 1 bed with a King Casper mattresses, a bright kitchen with tons of space, a stylish living room with art throughout, and an office (with an air mattress). Fenced-in back yard that's great for pets and chill around the outdoor table for optimal hangs and BBQs.

4.86 out of 5 average rating, 352 reviews

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.

Apartment in Wauwatosa

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.

4.97 out of 5 average rating, 127 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.

5 out of 5 average rating, 282 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

Time to plan your fall and winter getaways! Stay with us and enjoy all the amenities of the Little Gray House including a shed bar with food truck style windows and TV, hot tub, comfortable bedrooms and more! We've also just added a tankless water heater - never run out of hot water! The Little Gray House has attained rave reviews from travelers around the world for its comfort, cleanliness, and convenience. Happy to have you!

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, 92 reviews

Home in Brewer's Hill

Brew City Inn with Hot Tub

4.89 out of 5 average rating, 192 reviews

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.

Home in Milwaukee

Happy Days Home close to all MKE attractions

4.95 out of 5 average rating, 241 reviews

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.

Home in Halyard Park

6BR house, yard, hot tub - 5 min drive downtown

5 out of 5 average rating, 71 reviews

An open-concept living area showcases contemporary design elements. A cozy seating area is complemented by a large sectional sofa. Bright yellow chairs surround a dining table, while modern lighting fixtures and unique wall art add character to the space. Large windows provide ample natural light.

Cabin in Pewaukee

Pewaukee Serenity Cottage: Whimisical by the Lake

4.92 out of 5 average rating, 256 reviews

A spacious living area features a comfortable sectional sofa and a mounted flat-screen TV. Natural light floods through multiple windows, revealing views of the city skyline. A cozy gas fireplace adds warmth, while a dining area can be seen in the background.

Townhouse in Riverwest

Amazing view, Modern Space

4.94 out of 5 average rating, 158 reviews

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.

Home in Halyard Park

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

4.99 out of 5 average rating, 96 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

4.78 out of 5 average rating, 132 reviews

An outdoor area features a hot tub and a fire-pit surrounded by several white Adirondack chairs. A spacious wooden deck is visible, along with a well-maintained lawn and trees providing a natural backdrop.

Home in Glendale

Retro Riverside Retreat, Backyard Oasis, Hot Tub

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 101 reviews

A spacious living room features a light-colored sofa adorned with decorative pillows, accompanied by a wooden coffee table. Two large windows allow natural light to fill the space, while a mix of wall art and plants adds character. The room showcases rich wooden accents and flooring.

Townhouse in Bay View

Bright & stylish home in Bay View

4.9 out of 5 average rating, 276 reviews

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.

Home in Riverside Park

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

4.98 out of 5 average rating, 239 reviews

A charming two-story green cottage is featured, with white window shutters and a peaked roof. A small front porch hosts a bistro table and chairs, while a flowering window box adds a touch of color. The property is surrounded by lush trees and a well-maintained lawn.

Home in Greendale

Guesthouse on Clover - Historic Greendale

4.89 out of 5 average rating, 123 reviews

A cozy living room area features a grey sectional sofa, a pair of round wooden tables, and a large television. Natural light streams in through three windows, illuminating the hardwood floors. A decorative rug adds texture to the space, complemented by a plant and lamp arrangement.

Home in Bay View

The Bay View BoHo

Townhouse in Halyard Park

The living space features a bright seating area with two dark sofas facing a clear coffee table, surrounded by framed artwork on the walls. A circular light fixture hangs above, while a dining table for two is visible in the corner, accentuated by a well-equipped kitchen in the background.

4.81 out of 5 average rating, 277 reviews

Remodeled Victorian | Downtown | AC | Full Kitchen

4.9 out of 5 average rating, 164 reviews

Home in Walker's Point

Cream City Loft • Sleeps 6 + Large Deck

4.98 out of 5 average rating, 133 reviews

A historic cottage is set amidst lush greenery, featuring a mix of stone and siding on the exterior. A gravel driveway leads to the entrance, surrounded by well-maintained landscaping and mature trees that provide a tranquil atmosphere.

Home in Mequon

Historic cottage with fireplace. Pets Welcome!

4.9 out of 5 average rating, 356 reviews

A living room area features a cozy sofa complemented by a patterned chair and a wooden coffee table. Natural light filters through three windows adorned with stained glass, illuminating the hardwood floor. An archway leads to a dining area furnished with wooden chairs and a table.

Apartment in West Allis

The Cheese House

Family-friendly home rentals with a pool

5 out of 5 average rating, 13 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

4.93 out of 5 average rating, 41 reviews

A spacious living area is highlighted by natural light streaming through large windows. Light-colored furniture is arranged around a central coffee table on a decorative rug. An inviting dining space is visible, along with a modern kitchen area in the background.

Home in Racine

Cedar Hot Tub•Spacious Home•Quite Neighborhood

Apartment in Milwaukee

New place to stay

Keefe Avenue-Upscale Queen Bedroom/Full Office

4.89 out of 5 average rating, 18 reviews

A cozy living room features a light-colored sectional sofa complemented by colorful throw pillows. A plush, vibrant area rug adds warmth to the space. Two windows with light-filtering shades allow natural light, while a recliner and wooden table provide additional seating and surface space.

Home in Riverwest

Big BLUE Skyline VIEW

A bright and airy living space features a soft-toned sofa and a wall-mounted TV. A small work area with a chair and desk aligns against the wall, while large windows allow natural light to fill the room, providing a sense of openness. Two additional communal areas are visible, showcasing varied seating arrangements and decorative plants.

Apartment in Milwaukee

4.87 out of 5 average rating, 38 reviews

Charming 1BR Apt with Balcony+Pool+Gym

4.89 out of 5 average rating, 123 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

4.86 out of 5 average rating, 77 reviews

An aerial view captures the spacious outdoor area featuring a heated pool surrounded by lounge chairs. A fully stocked fishing pond is visible alongside a grassy yard, with a trampoline and fire pit area situated near the residence. Lush trees add to the greenery.

Home in Caledonia

7 1/2 Acre Private Estate MSG Owner for Discounts