Holiday houses in Milwaukee County

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.

Eastside Upper 4BR w 2 Garage Spots

Welcome to Murray Hill in MKE. This 4BR, 1BA unit offers everything for a wonderful fun stay in MKE. Enjoy the L-shaped balcony facing in front + a smaller balcony in rear. Good sized rooms w high ceilings, main BR has desk. Use (at your own risk) grill/fire table. CHILDREN MUST BE SUPERVISED. Bike rental w/in 3 block walk, tour local parks, lakefront, and nightlife on nearby Brady St. A variety of nearby restaurants + coffee shops await your visit. We look forward to hosting your stay!

The Waypoint Victorian 4BR Bay View Residence

Built in 1909, The Waypoint Victorian has welcomed more than a century of arrivals. Today, it continues that tradition as a place to pause between adventures; a warm, collected home designed for comfort, connection and exploration. Each room reflects the spirit of travel through rich colors, vintage trunks, layered textures and thoughtful details gathered with intention. Whether you're here for a weekend escape, a family gathering, or a longer stay, The Waypoint is your place to settle in.

Prairie style home on Stratford

Unique Arts and Crafts lower flat with turn of the century charm. Natural cherry woodwork with a spacious living and dining area—with seating for 10. Includes three bedrooms – one with a king bed, and two with queen beds. Updates Includes a modern kitchen, bath and shower, washer/dryer, and central air. Additional features include high-speed Internet with meshed WIFI, a 65" 4K TV, full surround sound—and Roku. Outdoor patio has seating for 12+, a Weber Summit grill, great for entertaining!

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.

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.

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.

Shorewood house - near shops w/ WiFi & parking

Just down the road from Lake Michigan, this charming duplex upper is the perfect space for a relaxing getaway. After a day of shopping, eating good food, and exploring Milwaukee, look forward to kicking back in the cozy living room, or on the patio. This duplex has 2 bedrooms; a King bed master, and one bedroom with two Twins. There is one charming bathroom with a bathtub. Well stocked kitchen, and plenty of backyard space. The lower tenant is respectful of guests.

English Tudor -Floor 3 Suite blocks from the beach

Total 4 beds - 2 Queen, 1 twin, 1 full Floor 3 is a private, peaceful, comfortable suite. Newly tiled bathroom and renovations throughout. Comfortably Sleeps 6 beds (2 queen, 1 double, 1 twin. There is 1 full bathroom. I have a cat that goes in the lower level stairway to access their restroom in the basement. But they do not go in the 3-floor unit. I also have 2 lovely dogs you may see when coming in.

Lake Michigan Views • Private Cedar Sauna

Just steps from Lake Michigan, this cozy home offers a private cedar barrel sauna, fireplace, and seasonal outdoor spaces. Spend an evening under the string lights in the Garden Lounge, gather around the chimenea, or walk the nearby bluff trails along the lake. Downtown Milwaukee, beaches, breweries, restaurants, museums, festivals, and sporting events are all just minutes away.

Beautiful Bayview 2 Story Loft w/Skylights, Wetbar

Beautiful huge 2 story Bayview Loft with skylights - best location in Milwaukee right next to South Shore Park includes wet bar and two living spaces with huge master suite. Vintage antique styling meets modern amenities with Memory-Foam mattresses, toilets with heated seats and bidets, Reverse Osmosis drinking water system, Nespresso coffee maker, natural gas fireplace.

Downtown-2 King Beds-hot tub-Double Shower-Parking

Discover luxury in historic Brewers Hill, close to all of Milwaukee's main destinations. Newly renovated 3-bed haven with 2 king beds, an 86" TV, and a fully stocked kitchen. Host in style with a dining table for 10. Indulge in 3 bathrooms, featuring a double main shower and a claw tub for a spa-like feeling. Your retreat for modern comfort and historic charm awaits!