Holiday rentals in Milwaukee County

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Top-rated holiday rentals in Milwaukee County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Guest suite in Milwaukee

4.88 out of 5 average rating, 250 reviews

Vibrant 2BR Hillside Hideaway in charming Bay View

2nd floor of 1921 duplex in Milwaukee's lively Bay View neighborhood. Walk to restaurants or take a short bike ride or car ride to local well-loved taverns. Downtown is a 5 minute ride on the highway. 2 bedrooms, a cozy living room, and an eat-in kitchen. Beautiful Lake Michigan and multiple award-winning Milwaukee County Parks nearby offer year-round scenic walks, and seasonal farmers markets, ice skating and live music. Close enough to the action of the city with the comfort of a quiet street.

Guest favourite

Townhouse in Milwaukee

4.86 out of 5 average rating, 88 reviews

*CLEAN* Craftsman Lakeside 3 Bedrm Bay View Duplex

**Sparkling Clean** newly renovated historic 100 year old UPPER duplex in the highly desirable South Shore Park neighborhood of Bay View. Resembles northern Wisconsin cabin with all of the creature comforts of being close to the city of Milwaukee. Just a block off the lake/park/beach/restaurants. Super spacious living room & full size dining room with 3 separate bedrooms and a bathroom with two vanities gives all of your guests ample room to be comfortable. Pull out beds avail Sorry, no pets

Superhost

Flat in Milwaukee

4.84 out of 5 average rating, 270 reviews

Best location in Milwaukee! Lower Duplex Unit

LONG TERM STAYS WELCOME. Unit is right off Brady Street, One of the best streets in Milwaukee. Over 70 places to eat or drink within walking distance, including bars with free shuttles to brewers games and Summerfest. There are many shops and grocery stores in the neighborhood and everything you could possibly want is a short Uber ride away. Best enjoyed by up to six people whether they be couples, friends, solo adventurers, business travelers, families (with kids), and furry friends (pets).

Guest favourite

Home in Greenfield

5 out of 5 average rating, 5 reviews

Charming 3 bed, 1.5 bath, fenced yard & parking!

Relax at this peaceful home, tastefully decorated in a fun boho chic style! Just a short drive to downtown and area attractions. Enjoy the quiet tree-lined neighborhood. With 3 levels, 3 bedrooms, 1.5 bathrooms & bonus space on the lower level, this is the perfect getaway with enough room for everyone! Kitchen offers plenty of counter space & is well-stocked. A fenced-in backyard, patio and plenty of parking (garage & pad) make this an easy place to stay. Max 2 dogs allowed, no cats allowed.

Guest favourite

Home in Milwaukee

4.9 out of 5 average rating, 10 reviews

Cream City Escape *Sleeps 8* Walkable

Relax and recharge with the whole family, a group of friends or your loved one at this fully renovated home in one of Milwaukee's favorite neighborhoods, BAYVIEW! This modern and clean space has three levels, 5 beds, a queen pullout and two full baths leaving plenty of space for everyone. To make it even better, it's less than 10 minutes to downtown Milwaukee and just a short walk to the beach or the popular Kinnickinnic strip, which is loaded with restaurants and boutique shops to explore.

Guest favourite

Flat in Milwaukee

4.89 out of 5 average rating, 9 reviews

4 real w/ benefits, vintage MKE 2bdr bungalow

Simplify your MKE visit with sunny 1st flr convenience in this circa 1923 Milwaukee 2bdr bungalow. Recombine fond memories, or create new, with the mellow original wood tones and AUTHENTIC furnishings by Heir Apparent. Enjoy WiFi, smart TV/lighting, new beds, full kitchen, dual Keurig. Secure Sprinter/rig parking options. Abundant retail, parks, trails nearby. Easy streets and freeway access to everything: Lakefront, Art Museum, Summerfest, FiServ, stadium, Chicago, Madison, and Green Bay.

Top guest favourite

Flat in Wauwatosa

4.99 out of 5 average rating, 334 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, Miller park, Milwaukee County Zoo, Downtown, Harley Museum, Milwaukee Art Museum & Summerfest/lakefront festival grounds. 1 space off street parking. Bublr & bus stop nearby.

Superhost

Home in West Allis

4.77 out of 5 average rating, 152 reviews

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

Welcome to this cozy 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 spot with plenty of parking on premises (up to 3 cars!) Amenities include: - Parking - TV - WiFi - Self Check in - Fresh Sheets and Towels - Additional Pillows - Shampoo & Conditioner - Soap & Hand Sanitizer - Fully Stocked Kitchen

Guest favourite

Home in West Allis

4.9 out of 5 average rating, 143 reviews

KING BED/Amazing Location/Free parking/Wi-Fi

Enjoy a fun and relaxing stay with family or friends in this stylish, cozy, and comfortable lower unit, which features: 2 bedrooms (1 king, 1 queen ) 1 bathroom Fully equipped kitchen with dining table and designated coffee bar Living room with a 65” smart TV (Netflix included) Home office space Free parking spot Located just a short drive (4 min) from I94, this home offers easy access to all the city's major attractions * the ideal base for exploring the best of Milwaukee

Guest favourite

Home in Wauwatosa

4.94 out of 5 average rating, 51 reviews

Park View Townhouse

Bring the whole family to this great place with lots of room for fun. A quiet location on a cul-de-sac. A Well equipped Kitchen. A gas fireplace. Close to park, restaurants, shopping, activities, which include, golfing, visiting a premier zoo, festivals, Major League Baseball games, museums, concerts and more. Please note; this property is adjacent to another like it (Townhouse With a Park View). They can be booked together (calendar permitting) for a combined capacity of 18

Top guest favourite

Flat in Milwaukee

4.9 out of 5 average rating, 527 reviews

Thomas Hideaway

Near great views, great restaurants/cafés, cinema, bowling, beach, festivals, colleges, hospital, Whole Foods, Milwaukee River, parks, trails, bus lines, shops, breweries, art, climbing gym, nightlife! 30-minute walk to festivals. Convenient East Side location, urban feel, cozy loft apartment, sunny balcony. 2 flights of stairs. Suits couples, friends, solo adventurers, business travelers. King-sized bed in bedroom. Futon in living room. Parking spot included

Top guest favourite

Flat in Glendale

4.95 out of 5 average rating, 38 reviews

Apple Blossom Retreat: Cute, cozy 2 bedroom rental

Adorable upper apartment in an owner-occupied duplex at the end of a quiet street. Mature trees in a peaceful neighborhood make it feel like a cozy retreat, and it’s just minutes away from shopping, downtown, and beautiful Lake Michigan. Whether you’re visiting family, coming for business, or exploring the attractions of the city, this will feel like a home away from home!