Holiday rentals in South Milwaukee

Cozy Mid-century Ranch

My cozy home is on a peaceful dead-end street with a park at the end, offering both tranquility and convenience. Located along the Oak Leaf Trail, it’s a perfect location for a ride or bike in minutes to Grant Park or Bender Park beaches. You can easily walk to local bars, restaurants, and public transportation, providing quick access to shopping and downtown Milwaukee. Whether you're seeking a relaxing backyard retreat or outdoor adventures, this location truly offers the best of both worlds.

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.

BayView Beauty! So charming & trendy!

Enjoy a stylish experience at this centrally-located home! Completely remodeled down to the studs! Designer home features 3 bedrooms, 2 full bathrooms for your convenience and office. Amenities: AC, stainless steel appliances, coffee maker, hairdryer, linens & washer & dryer to make you feel right at home. The lower level is home to a game room: foosball table, dartboard and table top games, creating endless fun kickback & relax & enjoy everything Milwaukee and our fabulous house has to offer.

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.

Cozy Dog Friendly Home Near Airport & Downtown

Clean, stylish, cozy and quiet home, newly renovated 2 BD/1 BA Cape Cod near the airport and Bayview. Great restaurants, coffee shops, local bars, and parks within walking distance. A short drive to Lake Michigan, Summerfest, Fiserv Forum, 3rd Ward, Marquette, Harley Museum, and all the great things Milwaukee has to offer. A great rental for couples, solo travelers, business travelers, families, and your furry friends (max 2 - well behaved dogs, no puppies - an additional $100 fee per dog).

Farm House Retreat w/ Private Backyard & Garage

Comfort, convenience and country views await you! Relax on the private patio and soak up the beautiful scenery. Minutes from the lakefront, Racine Zoo and short drive to Milwaukee, you'll enjoy this completely updated home. Cook a meal in the fully stocked kitchen and kick back in the comfy family room. Whether you are here to visit family, attend special events or business travel, you'll find everything you need here. And if you're a little country at heart, the view will not disappoint.

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.

Spacious 3 Bedroom Townhouse

Forget your worries in this spacious and serene space. Your family will be close to everything when you stay at this centrally located place Located in Bay View /St Frances boarder. Three bedroom townhouse with all new furnishings. 1.5 Bath. Located close to Mitchell airport and downtown Milwaukee. Guest must have 5 star ratings to book this property. If you a new guest or below 5 star please message me to get approval. Absolutely no parties , events or gatherings. Thank you!

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.

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.

Swan City Cozy Boho in Bay View

Welcome to Swan City located in the heart of Bay View. With beautiful hardwood floors and a cozy boho-inspired decor, our space is designed to make you feel right at home from the moment you arrive. Centrally located, we are within walking distance of several restaurants, bars, and co-ops. This community is known for its lively atmosphere and friendly locals, and there's always something exciting to see, or an event to attend in the neighborhood.