Family-friendly holiday rentals in Greenfield

4.95 out of 5 average rating, 228 reviews

A living room is presented with a gray sofa, a minimalist table, and wooden chairs. Natural light enters through large windows, accentuated by decorative curtains. A patterned area rug covers the floor, while a ceiling fan hangs above, contributing to the room's comfortable ambiance.

Flat in West Allis

Sunny State Fair Sojourn!

Newly renovated upper unit in a 1902 Victorian home. 2 bedroom, one bath, kitchen, dining area, living room, and office space! Less than one block from Wisconsin State Fair Park, The Milwaukee Mile and local bus routes! Minutes from American Family Field, Milwaukee County Zoo, and more! Local shuttle to Summerfest and other concerts and sporting events withing walking distance! Private balcony, free parking for one car, private laundry in the unit. Owner occupied lower for over 25 years!

4.98 out of 5 average rating, 262 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.

A cozy living room is highlighted by a light gray sofa adorned with decorative cushions. A small blue coffee table sits in front, complemented by a candle and a framed picture. Natural light enters through a window, brightening the neutral-colored walls.

4.79 out of 5 average rating, 184 reviews

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

Cozy and quaint two bedroom beach themed home located in the heart of West Allis. Close to public transportation and a few minutes driving to State Fair Park, Milwaukee County Zoo, Potawatomi Hotel & Casino, bars, restaurants, and more! Peaceful and quiet residential spot with plenty of parking on premises (up to 3 cars.) Amenities include: Spacious Parking, Smart TV, WiFi, Self Check in, Fresh Sheets & Towels, Hairdryer, Fully Stocked Kitchen, Washer & Dryer, Reading Material and much more!

4.94 out of 5 average rating, 893 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.

Flat 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.

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.

4.87 out of 5 average rating, 123 reviews

West Allis Oasis

Welcome to our 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. Relax and unwind in a tranquil environment after a day of exploring. Book your stay today for the perfect blend of comfort and convenience!

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, 198 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 light-colored sofa and a rustic wooden coffee table, complemented by a textured area rug. Large windows, dressed in sheer white curtains, allow natural light to fill the room, which includes a television mounted on the wall.

4.94 out of 5 average rating, 103 reviews

The Stallis Palace

Discover modern comfort in this 3BR, 1.5BA gem in central West Allis, WI. Spacious and fully furnished, enjoy craftsman woodwork, modern decór, and an abundance of light flooding through oversize windows. Walk to shops, dining, and nightlife. Within 5 miles of several major regional medicals centers! Master BR with office, porch, and outdoor dining area. Local, experienced hosts, ultra high-speed internet, and smart TVs make this the perfect blend of style and convenience. Book today!

4.96 out of 5 average rating, 121 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

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.

4.83 out of 5 average rating, 192 reviews

Designer Cottage-Parking, Patio, & New Kitchen

LOCATION, LOCATION! • Fast Fiber Internet TIME (MIN) 5-10 McCarty Park (Water Park, Trails, B-Ball Court) STATE FAIR TOSA 10-15 Brewers, Bucks Harley, 3rd Ward Breweries, Zoo ATTN MEDICAL Near All Hospitals PRIVATE PATIO & FENCED-BACKYARD • Seating for 4 w/ table • 🐶 can roam • Safe & secure kids play • Space for games & bags SAFE PARKING • Allows 2-4 vehicles inc. trucks & boats • 100FT off street • driveway widens LAUNDRY • W&D • Pods & D-Sheets • Util. Sink • Iron+Board

4.96 out of 5 average rating, 152 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, 299 reviews

A secluded outdoor patio is highlighted by a well-equipped hot tub, surrounded by lush greenery and wooden fencing. Comfortable seating is arranged nearby, with a patterned rug beneath a shaded area. Decorative plants and a charming umbrella enhance the relaxing atmosphere.

Home in Wauwatosa

The Little Gray House

Spring is here and it's time to share what we've been up to! Those of you staying with us after April will be treated to new kitchen counter tops, roof, windows and siding :) It'll still be the LGH, but with a little something more! We'll update the photos as soon as it's completed! The Little Gray House has attained rave reviews from travelers around the world for its comfort, cleanliness, and convenience. Happy to have you!

4.96 out of 5 average rating, 219 reviews

A welcoming living area features a dark leather sofa and loveseat, complemented by a wood coffee table atop a plush area rug. Natural light enters through two windows, enhancing the space's warmth. Artwork is displayed on the wall, adding a touch of character.

Flat in West Allis

Clean 2 bedroom/1 bath close to everything!

Charming, recently and tastefully furnished 2 bedroom 1 bathroom apartment with private entrance and parking. Close to downtown, shopping malls, zoo, hospital, airport, and main freeways. Full kitchen with stove, microwave, coffee pot, toaster, and kitchenware. Unit has TVs and WiFi. Coin operated laundry is accessible in building. Why stay at a hotel when you can feel at home in this lovely unit?

Popular amenities for Greenfield 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, 111 reviews

Brew City Inn with Hot Tub | Summerfest House

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.

4.9 out of 5 average rating, 202 reviews

Happy Days Home close to all MKE attractions

4.98 out of 5 average rating, 227 reviews

A private hot tub is set in a shaded outdoor area, surrounded by wooden fencing. The tub features jets and is filled with bubbling water. Steps lead up to the hot tub, and a patterned area rug lies nearby, enhancing the relaxing space.

Cottage in Racine

Clementine Cottage

4.91 out of 5 average rating, 288 reviews

A wooden deck features a partially covered jacuzzi, emitting steam amid a rainy backdrop. A stone fire pit, with a glowing flame, stands nearby, providing warmth. A patio set, including a chair, complements the serene outdoor setting surrounded by greenery and trees.

Guest suite in Racine

Racine theme Airbnb at the Red Birch on Erie

4.98 out of 5 average rating, 126 reviews

Belleview House: Hot Tub, Backyard, Fire Table

4.93 out of 5 average rating, 279 reviews

Townhouse in Riverwest

The Hottest Tub in MKE • Skyline Views • Sleeps 8

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.

4.94 out of 5 average rating, 181 reviews

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

4.85 out of 5 average rating, 109 reviews

Spacious Family Retreat w Hot Tub & Movie Lounge

Family- and pet-friendly home rentals

4.84 out of 5 average rating, 231 reviews

A comfortable living area features a gray sectional sofa adorned with decorative pillows. A round coffee table is situated in front, with a plant centerpiece. Light streams from the kitchen area, which includes modern appliances and a dining table in the background. Wall art adds a touch of character.

Home in Muskego

Lake Muskego House, Walk to Stores & Restaurants

4.96 out of 5 average rating, 124 reviews

A log cabin sits perched on a grassy embankment, framed by trees. The exterior features large windows and a spacious deck with steps leading down to the water's edge. Two red chairs are placed near the shoreline, reflecting the cabin's warm colors on the water.

Home in Nashotah

Okauchee Lakefront Cabin Escape

4.94 out of 5 average rating, 140 reviews

A comfortable living area features a black leather sofa and an accent chair, complemented by a long ottoman. A decorative lamp stands on a glass side table, and large windows allow natural light to fill the room. A television is mounted on the wall.

Home in Bay View

Charming Bayview House, steps from MKE Merriment!

4.97 out of 5 average rating, 253 reviews

Cabin in Lake Geneva

Dog friendly - A-Frame adventure

4.9 out of 5 average rating, 251 reviews

A rustic cabin with dark wooden logs is situated among tall green trees. The spacious porch features a railing and several chairs, inviting relaxation. Sunlight casts warm tones across the facade, while the surrounding grass and woods enhance the cabin's natural setting.

Guest house in Racine

Charming log cabin in the woods

4.97 out of 5 average rating, 181 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

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

4.89 out of 5 average rating, 100 reviews

Family friendly, Private Patio, Walkable, Quiet

4.92 out of 5 average rating, 142 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

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 22 reviews

An inviting outdoor area features a private pool illuminated in a calming blue hue, surrounded by lounge chairs and lush greenery. A multi-level deck is visible, offering seating options. Soft lighting enhances the relaxing atmosphere as dusk approaches, with trees providing natural privacy.

Home in Burlington

Spacious Home Near Lake Geneva - Heated Pool

4.94 out of 5 average rating, 48 reviews

A single-story house is presented with a light exterior and a welcoming porch. A shaded area is provided by the overhanging roof, and a bench is positioned on the porch. A well-maintained lawn stretches in front, framed by lush green trees.

Home in Delafield

Cute and cozy 2 bedroom house perfectly located!

4.98 out of 5 average rating, 43 reviews

A refreshing pool surrounded by a wooden deck is visible, complemented by several loungers for relaxation. Lush greenery frames the area, providing a serene backdrop. Colorful flowers in the foreground add a touch of vibrancy to the peaceful outdoor setting.

Home in Lake Geneva

Cozy cabin getaway near Lake Como and Lake Geneva

Superhost

Home in River Hills

4.63 out of 5 average rating, 8 reviews

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

4.93 out of 5 average rating, 74 reviews

A cozy living area features a red sofa adorned with decorative pillows, a wooden coffee table, and a round dining table surrounded by six chairs. Light illuminates the space, creating a warm atmosphere. The kitchen area is visible in the background.

Flat in Waterford

Cozy lower level 2 bedroom apartment.

4.85 out of 5 average rating, 134 reviews

A white motor yacht, named 'Irish Mist,' is docked at Reefpoint Marina. The boat features a spacious top deck with a black canopy and is surrounded by other yachts in the water, with a soft sunset glow illuminating the scene.

Boat in Racine

Vessel: Irish Mist V - 32' @ Reefpoint W1-3

Superhost

An expansive outdoor area features a refreshing in-ground pool adjacent to a wooden deck. A hot tub sits nearby, sheltered under a pergola. Lush trees form a green backdrop, creating a natural setting for relaxation and outdoor activities.

Home in Lake Geneva

5 out of 5 average rating, 11 reviews

Private Inground Pool Hot Tub