Holiday rentals in Cudahy

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Top-rated holiday rentals in Cudahy

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

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Top guest favourite

The kitchen features dark cabinetry complemented by white subway tile. A farmhouse sink is positioned below a wooden shelf, while appliances include a black refrigerator and a red microwave. A round clock hangs on the wall, adding practicality to the space.

Townhouse in Bay View

*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

4.88 out of 5 average rating, 125 reviews

Top guest favourite

A welcoming living area features a brown leather couch and an armchair, arranged comfortably around a plush ottoman. The wall is adorned with a collection of framed artwork, while natural light illuminates the space. A dining area is visible in the background with wooden bar stools.

Home in St. Francis

South Shore Guesthouse

Find tranquility and peace within this lush garden home. South Shore Guesthouse located two blocks from Lake Michigan has all the amenities you need, and will feel like a retreat away from the hustle and bustle. Quiet family neighborhood close to downtown Milwaukee and near the dining scene of Bayview and Third Ward. This home has been curated with vintage finds and unique art for those who enjoy history and luxury. Walk/bike along Lake MI and find yourself on the beautiful beach of Grant Park.

5.0 out of 5 average rating, 39 reviews

Superhost

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!

I want you to be able to do things here that you can't do in a hotel. If you're grillilng out, having a bonfire or watching movies all night long, you can turn up that volumn as loud as you want all night long! I posted my listing under "entire home" as you do get so much more than just renting "a room". When I have guests I stay in my office or bedroom so my guests feel more comfortable utalizing entire home & yard. In fact, if you don't ask for breakfast, you may not even see me at all.

4.78 out of 5 average rating, 171 reviews

Top guest favourite

A stylish living room is highlighted by a large window providing views of the park. Two navy blue armchairs and a matching sofa surround a striped coffee table. Rich red carpets and green plants add warmth to the space, complemented by an elegant chandelier above.

Home in Bay View

Gorgeous Bayview 2Story Loft w/Upper Deck/Firebowl

Located right on South Shore Park with views of Lake Michigan. Just a 3 minute walk to South Shore Beach and the Oak Leaf Trail, and just a 6 minute drive to downtown Milwaukee. This two story treetop loft occupies the upper two levels of a large historic house and has a large 400 sqft 2nd story deck overlooking the park and lake with a 4' natural gas fire bowl. Also features indoor bioethanol fireplace and full bar with a wine-chiller. The perfect place to kick back and relax with friends!

4.99 out of 5 average rating, 291 reviews

Guest favourite

A spacious back yard overlooks Lake Michigan, featuring a manicured lawn and five comfortable seating options. Sailboats are visible on the water, with a breakwater in the distance. The serene setting is framed by lush greenery, inviting relaxation and enjoyment of the scenic view.

Flat in Bay View

Lakeside Beauty

Stunning lower duplex on Lake Michigan in beautiful Bay View WI. Exceptionally large 2 bedroom unit boasts back yard overlooking Lake Michigan with fire pit for cozy evening fires. Unit is a mix of new and classic vintage. Walking distance to South Shore Yacht Club, South Shore Terrace Beer Garden, Award Winning restaurants, a unique European grocery store, and the second largest Farmer's Market in the state. Seven minutes to downtown Milwaukee. Owner lives upstairs. Two bikes available.

4.86 out of 5 average rating, 325 reviews

Guest favourite

A cozy living space features a floral-patterned couch accompanied by a wooden coffee table. The walls are adorned with warm wood paneling, complemented by soft lighting from a wall sconce. Greenery is present with potted plants, adding a touch of nature to the space.

Home in Oak Creek

Spacious Ranch Home Oak Creek close to Airport

Chalet style ranch home is fully furnished and offers 2400 square feet of private usable space. The 3 bedrooms, living room, dining room, family room, 1 1/2 bathrooms, kitchen, and kitchen table area are all located on one floor. You will love waking up in the morning in this quiet suburban neighborhood and looking out the many windows at the park across the street. Close to the heart of Oak Creek Drexel Town Square, 4.6 miles from the airport, & 15 minutes from Downtown Milwaukee.

4.87 out of 5 average rating, 114 reviews

Top guest favourite

Guest suite in South Milwaukee

Historic Hawthorne House

Nestled just steps from Grant Park Beach & Lake Michigan, the scenic Seven Bridges Trail, and the lush Grant Park Golf Course, this unique rental offers a blend of history, charm and comfort. Only a 10 minute drive to Mitchell International Airport and an easy 20 min drive to downtown Milwaukee. Whether you're here to unwind in nature, explore the local parks, enjoy a peaceful lakeside stay, or enjoy the best that Milwaukee has to offer this home has everything you need.

4.99 out of 5 average rating, 117 reviews

Top guest favourite

Home in Cudahy

Lake Michigan Views • Private Cedar Sauna

Just a short walk from Lake Michigan and the scenic bluff trails, this cozy home is a comfortable place to settle in while exploring Milwaukee and the lakefront. Enjoy your private cedar barrel sauna, curl up by the fireplace, or spend an evening in the seasonal Garden Lounge. With vintage pieces, cozy spaces, and thoughtful extras throughout, the home has a relaxed feel, with downtown Milwaukee, beaches, restaurants, breweries, festivals, and more nearby.

5.0 out of 5 average rating, 68 reviews

Guest favourite

A vibrant yellow wreath adorns a red door, leading into a welcoming space. Inside, a dining area is visible, featuring a round table surrounded by wooden chairs. A circular mirror reflects the textured wall with blue floral patterns, creating a lively and inviting atmosphere.

Bungalow in Bay View

Our Cozy Bay View Bungalow Getaway

Our relaxing, clean, fully equipped Bay View bungalow delivers a perfect getaway. We are equipped with 1g wifi, 4K smart TV, dimmers, and a washer/dryer. Tastefully decorated, uncomplicated, and comfortable. There are cozy coffee shops, restaurants, and local bars just a few blocks from the house. The Bay View Dog Park is one block away. We have parking for two cars. We follow an Enhanced Cleaning Protocol, and are 100% smoke free without exception.

4.96 out of 5 average rating, 367 reviews

Guest favourite

A comfortable living room features a large corner sectional couch with accent pillows. A wooden coffee table rests in the center, adorned with a small decorative tray. Natural light enters through multiple windows dressed with bamboo shades, enhancing the inviting environment.

Home in Bay View

Sunny 3BR Craftsman Bungalow | Bay View

🌿 Updated 3 bedroom 2 bath home welcomes you to one of Milwaukee’s favorite neighborhoods: Bay View. 🚶‍♂️ Steps away from beloved Humboldt Park and its seasonal beer garden, plus a bevy of fantastic local restaurants in this foodie mecca. 📍 Quick access to and from downtown, the airport and the lakeshore. 🛏️ King bed master suite upstairs with dedicated workstation makes working remotely a breeze. 🔥 Awesome backyard with fire pit and gas grill.

4.83 out of 5 average rating, 104 reviews

Guest favourite

A dining nook is highlighted, featuring two high-backed black bar stools surrounding a small round table. A wall-mounted sign lists several cities, and natural light filters in through nearby windows, illuminating the wood-like flooring and creating a bright atmosphere.

Home in Cudahy

Upgraded! 4BR in Milwaukee near Airport & Downtown

Bring the whole family to this upgraded home with lots of room for fun. Located directly across the street from Warnimont Golf Course & Lake Michigan, this home has plenty to do and see. The large, fenced in yard is perfect for your pets to run around. It's the perfect place to stay in Milwaukee! 12 mins to General Mitchell Airport, 14 mins to downtown, 16 mins to American Family Field and Fiserv Forum, 13 mins to Henry Maier Festival Park.

4.9 out of 5 average rating, 125 reviews

Top guest favourite

A spacious bedroom features a white bed adorned with decorative pillows and a textured throw blanket. A striking lion portrait hangs above the bed. Natural light fills the room through a nearby window, with soft curtains partially drawn, complementing the warm brown walls.

Home in Milwaukee

Mid-Century Inspired Upper Duplex in Bay View

Step through the carpeted private entrance of this 2nd floor home, and into a mid-century interior with a modern twist. Eye-catching touches include the collection of retro radios that give it its name, stylish decor and a subway-tiled bathroom. This cozy apartment is decorated in a mid-century theme with a modern twist. It's on the second floor of a duplex. You will have your own carpeted entrance located in the back of the property.

4.95 out of 5 average rating, 262 reviews