Waterfront holiday rentals in Milwaukee

Charming home w/ fire pit, walk to Lake Michigan

Welcome to our home in a quiet neighborhood, a short walk to gorgeous views over Lake Michigan and two blocks to restaurants, shopping, and nightlife. Gather around the fire pit and grill dinner in the back patio. Listen to our vinyl collection or stream your own music while playing board games next to the smart TV. Super-fast internet, a fully equipped kitchen with coffee & tea, and in-unit laundry. Two comfy queen beds + a sleeper sofa. Here with kids? We have toys, a Pack n' Play, & more.

Beach · Check-in · Comfort

Milwaukees most coveted street! MKE Lake Life

Welcome to the Premier Lake View home located in Bay View, brought to you by NCL Properties. This gem is located on one of Milwaukee's most coveted streets with its absolutely stunning views of the lake, harbor and skyline. Experience the modern and vintage charm of this Bay View home, just 2 blocks from South Shore Park, beach and the beer garden. Enjoy direct, unobstructed views of Lake Michigan, the marina, and the city skyline. Also enjoy many near by walkable restaurants, bars and shopping.

View · Beach · Getting around

The Crows Nest Cottage 1

Welcome to our charming 1-bedroom cottage by a serene pond. This cozy retreat features a unique basketball/pickleball court, multiple outdoor patios, and a delightful treehouse lounge area. Perfect for relaxation ! Just 5 minutes away is The Rock Sports Complex, offering top-tier activities like Topgolf, minor league baseball, an umbrella bar, hiking trails,ski hills.Whether you’re seeking tranquility or adventure, our cottage provides the ideal getaway for both.washer,dryer BOAT TOURS AVAILABLE

View · Decor · Outdoor spaces

Let’s walk to the lake! Perfect4BR, Chef’s kitchen

This massive unit resides in the best location in the Upper East Side! Welcome to this gorgeous open concept contemporary duplex boasting 4 beds/2 bath + loft + full basement with dining table/chairs, real wood fireplace, full kitchen with Viking appliances, central AC/heat, vaulted ceilings! Accommodates up to 10 adults! Steps to the lakefront, Downer Ave, Bradford beach, and summerfest grounds. So close to art museum, trendy bars, wonderful restaurants, and many more that MKE has to offer!

Beach · Comfort · Wi-Fi

Exhale, rest

Exhale. The perfect combination. This home is right in the village of Menomonee Falls with great shopping and restaurants within walking distance. Close to the highway, it’s also a mere half an hour to anything Milwaukee so games, museums, festivals are all also at your fingertips. At the end of dead end road with views of the river, access to trails, and a secluded deck and fire pit, there is definitely also a rural feel. This location has it all. Go out, live life, come back, exhale and rest.

Beach · River · Family

Lake Dr Mansion

Downtown ~ Art Museum ~ Lake Experience a piece of Milwaukee’s rich history at an outstanding location on the prestigious N. Lake Drive on the vibrant Eastside. Nestled amongst beautiful single family mansions, this very spacious property is sure to please. Minutes from Fiserv forum, Summerfest, downtown, Art Museum, Discovery World, Harley Davidson museum, and many other city attractions. Short walk to Bradford Beach, Veteran’s Park, Lake Park, restaurants, cafes, Whole Foods, and much more.

Beach · Comfort · Laundry

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.

Beach · Accuracy · Access

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!

Beach · View · Pets

The Castor House. A hip riverside warehouse loft.

The Castor House is nestled above the popular cocktail joint Boone & Crockett and local music venue The Cooperage in the heart of Milwaukee's Harbor District. Walking distance from a diverse offering of bars and restaurants in the neighborhood, and central to various other popular bar districts within the City, our spacious warehouse loft is a perfect home base for taking in all that Milwaukee has to offer. If nightlife, great bites and local entertainment is your jam... you are here.

River · View · Air conditioning

English Tudor - Upper Flat blocks from the beach

Sophisticated 100 Yr Old English Tudor Upper Flat with hardwood floors, crown moldings, sunken living room, natural fireplace, built-in bookcases, and fully furnished. Spacious 2200 sq. foot 2nd-floor unit. Safe and QUIET neighborhood just blocks from Atwater beach. Cats are on the property and do not go any guest space. Make sure you have the correct number of guests on your reservation request. Bookings on a Friday or Saturday are required to include both nights.

Beach · View · Access

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.

Beach · View · Backyard

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

View · Beach · Outdoor spaces