Vacation rentals in South Milwaukee

4.97 out of 5 average rating, 142 reviews

An outdoor patio area features a circular fire pit surrounded by four chairs on a stone surface. The lawn is well-maintained, bordered by wooden fencing with greenery in the background, enhancing the outdoor space's charm.

Home in Thiensville

Quaint & Cozy Town Cottage Desirable N. Shore

Adorable small Town Cottage walkable to coffee shops, restaurants, parks & the riverwalk…bring the pup and experience something sweet. Everything you need to get away, business trip or extended stay. Well appointed kitchen, 2 small but cute baths with heated floors(1) and fast WiFi. Urban-like walk-ability w/ small town charm! Walk to (excellent) authentic Himalayan food at the Cheel or a glass of wine at Glaze and paint a new coffee mug! Go out or kick back with the fire/grill and s’mores!

4.86 out of 5 average rating, 437 reviews

Home in Hubertus

Bark Lake, Entire Home, Private Lake Frontage 50ft

A 1,700 sqft home with 3 bedrooms, 2 baths, sofa bed and couch, large outdoor deck, hot tub, grill, 50 feet of lake access. Enjoy the morning sunrise from the East and relax by the waterfront and watch the sunset on the West. Bring the family and enjoy some lake life where the days linger on longer. During the Summer months we have a pier available to fish off of. There are two fire pits, one by the lake and another tucked away near the house. You will love it here, it is very calm and relaxing.

4.87 out of 5 average rating, 93 reviews

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

The exterior of the beach home is shown, featuring a spacious porch with white adirondack chairs. Beautiful landscaping surrounds the house, while large windows provide ample natural light. The architectural details include a mix of siding styles and a welcoming front entry.

5 out of 5 average rating, 26 reviews

The Beach house! Enjoy Beachfront Living!

BEST HOUSE ON THE BEACH! Close to marina, harbor, restaurants, downtown stores! Sip your morning coffee enjoying the beautiful sunrise from the porch of this Historical Nautical Beach home! Plenty of sleeping for up to 15 guests. Owner has 2nd lake home 2 blocks away to share in the fun w larger group! Just a short walk to the lake, concessions, 1 mile beach, charter fishing, Zoo, Walking/bike paths. Whether looking for peace and quiet or an exciting fun-filled vacation, this home has it all!

4.97 out of 5 average rating, 235 reviews

A modern mini kitchen features gray cabinetry and stainless steel appliances, including a refrigerator and microwave. A spacious custom island with natural wood finish is accompanied by four brown seating chairs. Under-cabinet lighting enhances a functional cooking area, with cookware and utensils visible.

Condo in Racine

Gorgeous Main Street Apt with Lake Views (APT2)

Gorgeous, open concept Main Street apartment on 3rd level, with views of downtown and partial views of the lake and harbor. New mini kitchen with 2 induction stove top burners, a microwave, toaster, and all the cookware and utensils needed for a getaway. Supersize custom island, comfy furnishings, and convenient to everything downtown. Unique building is connected to parking garage. Drive up to the 3rd floor - walk just 10 steps to your door - enjoy the views from above, without the climb.

4.91 out of 5 average rating, 268 reviews

A Finnish sauna constructed with natural wood stands adjacent to a stone fire pit, which contains a gentle flame. The transparent glass doors of the sauna reveal its warm interior, while the stone surface surrounding the fire pit adds a rustic touch.

Guest suite in Racine

Racine theme Airbnb at the Red Birch on Erie

Home is set in a quiet neighborhood with a working vegetable farm for a backyard where deer, squirrels, geese and birds entertain. You will enjoy unobstructed, amazing sunsets along with Racine themed artwork and memorabilia, all retro and eclectic in design. It's a short drive to the Lake Michigan shoreline and just minutes away from downtown and the finest beaches! You're host has props from his Old Times photo studio that are available for photography on the grounds in special settings.

Superhost

A long horizontal painting hangs on a beige wall, depicting gentle waves and three sailboats on a serene blue sea. The sky is bright with soft clouds, and the shoreline features scattered birds, creating a calming coastal scene.

Home in West Allis

4.77 out of 5 average rating, 155 reviews

★Cozy Beach Themed Home★2 Beds★Spacious Parking★

Welcome to this cozy beach themed home located in the heart of West Allis. Close to public transportation and a few minutes driving to State Fair Park, Milwaukee County Zoo, Potawatomi Hotel & Casino, bars, restaurants, and more! Peaceful and quiet spot with plenty of parking on premises (up to 3 cars!) Amenities include: - Parking - TV - WiFi - Self Check in - Fresh Sheets and Towels - Additional Pillows - Shampoo & Conditioner - Soap & Hand Sanitizer - Fully Stocked Kitchen

4.9 out of 5 average rating, 149 reviews

Home in West Allis

KING BED/Amazing Location/Free parking/Wi-Fi

Enjoy a fun and relaxing stay with family or friends in this stylish, cozy, and comfortable lower unit, which features: 2 bedrooms (1 king, 1 queen ) 1 bathroom Fully equipped kitchen with dining table and designated coffee bar Living room with a 65” smart TV (Netflix included) Home office space Free parking spot Located just a short drive (4 min) from I94, this home offers easy access to all the city's major attractions * the ideal base for exploring the best of Milwaukee

A modern fire table sits on a wooden deck, surrounded by black stone and greenery. Flames rise gently from the center, providing warmth and ambiance. In the background, Lake Michigan glimmers under a soft gray sky, and a well-maintained lawn extends toward the water.

5 out of 5 average rating, 7 reviews

Scenic Waterfront Lake Michigan Escape

This stylish 1913 craftsman is perfect for family vacations, group trips or a couple's escape. Situated directly on Lake Michigan you can enjoy breathtaking views from the home and recently constructed deck. The primary bedroom features a new bathroom and magnificent views of the lake. There are three workspaces perfect for "work from home". Finish your day by relaxing in the hot tub, hammock or by the fire. The home is close to city amenities but feels like it's a world away.

A spacious living area is featured, highlighted by a gas fireplace with a television mounted above. Comfortable seating options are arranged around a decorative rug, with large windows providing natural light. Neutral tones create a calm ambiance, complemented by greenery in the corner.

5 out of 5 average rating, 66 reviews

Beautiful home with amazing Lake Michigan views

Historic home with modern upgrades that has gorgeous views of Lake Michigan. The home was recently upgraded with amazing features including two gas fireplaces, high end kitchen finishes, and a spa style primary bathroom with heated floors. The house is located in the Southside Historic District, steps from the lake, and a short walk to downtown Racine. You can enjoy the local restaurants and shopping, explore the lakefront, or stay in and relax in the peaceful home.

4.94 out of 5 average rating, 53 reviews

A spacious living area features a large sectional sofa arranged around a decorative area rug. Exposed wooden beams and a high ceiling contribute to an open atmosphere. A coffee table holds a magazine, while a bar seating area is visible in the background.

Condo in Racine

Beautiful Downtown Home - 2 Blks from Lake

Experience the ultimate in relaxation and convenience at this charming vacation rental in Racine. Perfect for a family vacation, romantic getaway, or weekend trip with friends. This 2-bdrm, 2-bath offers a top-notch location just 2 blocks from Lake Michigan and the downtown area. Step inside and discover a beautiful space with all the amenities you could need for your stay. Relax in the cozy living room or whip up a feast in the fully stocked gourmet kitchen.

The kitchen showcases modern cabinetry with sleek handles, a spacious countertop, and stainless steel appliances. Natural light filters through the window with blinds, illuminating a round dining table with wooden chairs. A textured rug adds warmth, complementing the contemporary design.