Family-friendly holiday rentals in Wauwatosa

4.98 out of 5 average rating, 252 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.

Bungalow in West Milwaukee

A dining area features a round table surrounded by black chairs with plush white cushions. Sunlight filters through large windows, highlighting the vintage sideboard and plant. An inviting living space is visible through an archway, showcasing a blend of decor and natural light.

4.97 out of 5 average rating, 194 reviews

Adorn Abode

Charming upper level hygge bungalow (2 unit home total). Ten minutes from anywhere. Tucked away in the quiet village of West Milwaukee. Full of natural light and curated vintage decor. Walking distance to a few restaurants and bars, as well as the American Family Field. Enjoy a cocktail on the front balcony and watch the sunset while indulging in a classic vinyl collection. Small balcony off of the kitchen to watch the sunrise and enjoy a cup of coffee. Perfect for adventuring or relaxing.

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.

4.88 out of 5 average rating, 116 reviews

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

4.98 out of 5 average rating, 378 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.

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

4.97 out of 5 average rating, 113 reviews

A cozy sleeping area features a wrought iron bed with white linens and several pillows. Two nightstands with lamps are placed on either side. A fan is mounted on the ceiling, while emerald green curtains frame a window beside a floral wall art piece.

Flat in West Allis

Nice 1 BR Apt, WIFI & Office, Near State Fair

This beautifully furnished upper duplex offers a cozy and comfortable living space in a safe and peaceful neighborhood. The kitchen comes fully equipped with all the necessary supplies for cooking and dining, and the garage and driveway provide convenient parking options. Stay connected with the included WIFI and watch YouTube TV. Nice Office space. Conveniently located near major freeways, downtown, hospitals, and the State Fair Grounds. Book now for a stress-free and enjoyable stay

4.96 out of 5 average rating, 229 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.

A newly remodeled kitchen features wooden cabinetry and a dark countertop, paired with modern appliances. A large sink and a stovetop are highlighted, along with a window that provides a view of the outside. The flooring is made of warm wood, enhancing the overall design.

4.98 out of 5 average rating, 206 reviews

Spacious Wauwatosa Home In Prime Location

We just finished remodeling the kitchen and all 3 bathrooms in our unique tri-level mid-century modern home. There are 4 bedrooms offering an array of accommodations as well as a couch with a pull-out queen bed. If you like to cook, our new kitchen is amazing! There is a fireplace room with a lovely view outside, a laundry room and a TV with cable, a DVR, and streaming apps like Netflix. WIFI is available. This is a quiet family neighborhood. No parties and please be respectful.

A single-story ranch-style home is presented, featuring a well-maintained exterior with a light-colored stone façade. Green grass surrounds the property, complemented by neatly trimmed bushes and a paved walkway leading to the front door. The roof is covered with gray shingles under a partly cloudy sky.

4.92 out of 5 average rating, 103 reviews

Relax close to everything in Milwaukee

Ranch Style home in a quiet Neighborhood. You will feel at home and comfortable! The home is well maintained and very clean. In the winters you could cozy up to a nice fire upstairs and relax with a glass of wine. Downstairs is a second fireplace you have going and play a game of pool. In The summer you can enjoy the three seasons room, with looking a cup of coffee and look at the planted flower garden. Close to the Wauwatosa village down town. Even closer to Elm Grove Village.

4.99 out of 5 average rating, 148 reviews

Tall sunflowers bloom vibrantly in a garden, displaying bright yellow and orange petals. A wooden gazebo with hanging lights stands in the background, surrounded by lush greenery. Soft sunlight filters through the trees, enhancing the serene outdoor setting.

Guest suite in Sussex

Garden Retreat in law Suite

Welcome to our in-law suite apartment featuring a full eat-in kitchen, living room, queen bed in large bedroom, walk in closet and full bathroom with walk-in shower. Our beautiful two acre yard has many areas to relax in, including a hammock and fire pit for the evenings. Twenty mins. to Erin Hills and Holy Hill and a half hour to most downtown Milwaukee attractions, as well as the RNC activities taking place this summer. Lots of city tips and suggestions for our guests.

4.87 out of 5 average rating, 364 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.

Flat 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.

4.88 out of 5 average rating, 166 reviews

The kitchen features dark cabinetry and modern appliances, complemented by a central wooden island with seating for two. Pendant lights hang above, illuminating the area. A window offers natural light, and open access to a hallway is visible in the background.

Townhouse in Story Hill

Central, Game Room, Quiet Walkable Area

Beautiful luxurious 4 bedroom (bonus sunroom) home central to everything Milwaukee has to offer. Located in sought after quiet community due to its proximity to all main attractions while providing safety and peace for residents and visitors. Our property is less than 10mins from heart of Milwaukee, walking distance to main attractions such as Brewers stadium and state fair. We do our absolute best to be exceptional hosts so hope you decide to stay with us

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.

4.96 out of 5 average rating, 140 reviews

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.

Popular amenities for Wauwatosa family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 106 reviews

Home in Brewer's Hill

Brew City Inn with Hot Tub

4.89 out of 5 average rating, 199 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

4.91 out of 5 average rating, 286 reviews

An outdoor space is illuminated by decorative string lights, featuring a large wooden dining table surrounded by ten metal chairs. A hot tub and a spacious lawn are visible, accompanied by a wooden shed in the background. The setting is designed for relaxation and gatherings.

Home in Halyard Park

5th St. Retreat - Outdoor Oasis, Hot Tub, 8 Beds

4.97 out of 5 average rating, 113 reviews

Home in Murray Hill

Belleview House: Hot Tub, Backyard, Fire Table

4.93 out of 5 average rating, 269 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, 174 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, 120 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

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 109 reviews

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.

Flat in Walker's Point

Vintage Motel Inspired 1BR City View, Free Parking

4.95 out of 5 average rating, 283 reviews

A charming red farmhouse is set against a snowy landscape, surrounded by a white fence. Leafless trees create a serene backdrop, enhancing the rural setting. The house features a mix of traditional and modern architecture with snow covering the yard.

Guest house in Richfield

Peaceful weekend or extended stay, full amenities

4.98 out of 5 average rating, 247 reviews

The well-appointed kitchen features wooden cabinetry, stainless steel appliances, and a sleek black countertop. A dining table with vibrant red chairs accommodates a gathering, while a striking light fixture adds a modern touch. Natural light fills the space through multiple windows.

Apartment in Bay View

Bay View - Lake View on the Park w/Secret Lounge

4.97 out of 5 average rating, 176 reviews

A red barn stands prominently amid a snowy landscape, bordered by lush green grass. A tree casts a shadow, and a silos is visible to the left. A gravel path leads to the barn, while a white fence outlines the property in the background.

Guest house in Hubertus

Quiet retreat-golf, bike, hike, motorcycle

Superhost

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.

Townhouse in Halyard Park

4.81 out of 5 average rating, 277 reviews

Remodeled Victorian | Downtown | AC | Full Kitchen

4.98 out of 5 average rating, 146 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!

4.91 out of 5 average rating, 362 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.

Flat in West Allis

The Cheese House

4.94 out of 5 average rating, 134 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

Family-friendly home rentals with a pool

A modern living space features a light-colored carpet underfoot. A gray sofa with decorative cushions is positioned across from a sleek coffee table. A dining area is visible with a round table and upholstered chairs, while large windows allow natural light to fill the room.

Flat in Lower East Side

North End 519

4.94 out of 5 average rating, 173 reviews

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.

Home in Brewer's Hill

Brewers Hill Gem w/hot tub & seasonal shared pool

4.98 out of 5 average rating, 123 reviews

An inviting outdoor space showcases a wooden deck with two striped chairs positioned beside a large double door. A barbecue grill rests nearby, and a sign reading 'Hammer Hideaway' is mounted on the wall. Lush greenery and a clear sky provide a relaxed atmosphere.

Farm stay in Germantown

Lace & Woods Farm "Hammer Hideaway"

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.

Flat in Milwaukee

4.84 out of 5 average rating, 51 reviews

Charming 1BR Apt with Balcony+Pool+Gym

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

4.78 out of 5 average rating, 156 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!