Vacation rentals in Milwaukee County

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.

Lake Michigan Views • Private Cedar Sauna

Private cedar barrel sauna, cozy fireplace, and peaceful outdoor spaces just steps from Lake Michigan. Unwind beneath the string lights in the seasonal Garden Lounge, gather around the chiminea, or stroll scenic bluff trails along the lake. Just minutes from downtown Milwaukee, beaches, breweries, restaurants, museums, festivals, and sporting events, this thoughtfully designed getaway is the perfect home base to relax, recharge, and explore year-round

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.

Historic Lower East Side Apartment with Lake Views

This is one unit in a historical mansion with lake views! Layout is shotgun, open concept with a SMALL functional kitchen. Definitely gives off a pied-à-terre vibe. You have direct access to the back patio and a dedicated parking space around the corner. This unit is in the heart of the lower east side- close to the art museum, cathedral square, Brady st, 3rd ward, as well as the best restaurants and bars in MKE .

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?

Modern Brady St Apt, 3 Private Baths, Free Parking

Brand-new, architecturally designed modern retreat steps from vibrant Brady Street, Milwaukee. This luxury home features sleek finishes, built-in Bluetooth audio, 3 master suites, a private patio, and 2 free on-site parking spaces. Comfortably sleeps 9 guests, offering easy access to city life, dining, shopping, and lakefront activities. Perfect for an upscale urban escape.

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.