Holiday rentals in Bayside

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Top-rated holiday rentals in Bayside

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A spacious living area features a large smart TV mounted on the wall, with modern furniture arranged for comfort. A sectional sofa and accent chair provide seating options. Natural light streams through the windows, and artistic touches enhance the welcoming atmosphere.
Flat in Shorewood
4.9 out of 5 average rating, 109 reviews

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.

Guest favourite
The exterior of a charming house is showcased, featuring a welcoming front porch adorned with string lights. Lush greenery surrounds the home, with a flower garden displaying purple blooms. A pathway leads to the entrance, enhancing the inviting atmosphere of the property.
Home in Menomonee Falls
4.93 out of 5 average rating, 203 reviews

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.

Top guest favourite
The living room features a comfortable gray sofa adorned with decorative pillows, paired with a coffee table and two accent chairs. Natural light floods the space through large windows, highlighting the modern decor and a bookshelf with decorative items.
Home in Mequon
4.97 out of 5 average rating, 61 reviews

Quiet Escape | Lake Michigan | Milwaukee River

Big 2+ night discounts! Welcome to our spacious home nestled in the serene area of Mequon, WI. Escape the big-city crowds and enjoy the lovely ambiance from the backyard while being just a stone's throw away from the picturesque Milwaukee River, the grand Lake Michigan, and the vibrant city of Milwaukee. The relaxing setting and rich amenity list will leave you in awe. ✔ 4 Comfy BRs ✔ Cozy Living Areas ✔ Full Kitchen ✔ Fire Pit ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Washer/Dryer ✔ Free Parking

Top guest favourite
An open-concept kitchen and living area is showcased, featuring a modern kitchen island with wooden stools. Stainless steel appliances are complemented by white cabinetry, and natural light fills the space. A cozy seating area includes a light grey sofa and coffee table, adding comfort to the layout.
Apartment in Grafton
5 out of 5 average rating, 30 reviews

Eco-Conscious Luxury Condo | The Quarters Suite 4

Welcome to The Quarters at Mill Square, where luxury meets eco-conscious living in the heart of Downtown Grafton, Wisconsin. Our newly renovated suites have been reimagined to offer you a one-of-a-kind experience. With a modern, open-concept design and carefully curated furnishings, The Quarters exude a sense of airiness and comfort that will make you feel right at home. RNC 2024: July 15-18, 2024 dates are available but blocked for instant booking. Inquire for availability and rates.

Guest favourite
A modern living area features a comfortable seating arrangement with a light gray sofa and a wooden coffee table. The kitchen bar, equipped with three sleek black stools, is visible, showcasing a clean design. A large television is mounted on the wall, and greenery is present nearby.
Home in Fox Point
5 out of 5 average rating, 8 reviews

Fox Point living near the Lake!

Bring the whole family to this great home with lots of room for fun. Walking distance to Lake Michigan, Schlitz Audubon Nature Center and parks, you will never run out of things to do! Want to venture into the city? It is just a quick 15 minute drive to downtown MKE! Enjoy a Bucks game at Fiserv Forum, a beer at all your favorite breweries or explore historic Third Ward all while having the space to spread out in your home away from home. Come see what North Shore living is all about!

Superhost
Home in River Hills
4.67 out of 5 average rating, 9 reviews

Luxury 5BR | Indoor Pool + Theater | Sleeps 12+

Perfect for groups, this luxury 5BR home sleeps 12+ and is built for entertaining. Enjoy a heated indoor pool, private theater room, massive chef’s kitchen, and a stunning 4-seasons sunroom surrounded by nature. Unwind by the fireplace, relax in spa-style bathrooms, or spread out across multiple living areas—there’s space for everyone. Whether you’re here for a getaway, family gathering, or weekend with friends, this home delivers comfort, space, and unforgettable experiences.

Guest favourite
The open living area features a modern design with large windows allowing natural light to fill the space. A soft gray sofa and accent chairs provide comfortable seating, while a stylish coffee table sits in front. The kitchen, equipped with wooden cabinetry and sleek appliances, is visible in the background.
Townhouse in Thiensville
5 out of 5 average rating, 8 reviews

500 House - Unit C

 Welcome to your modern retreat in a sustainably built property that blends comfort, style, and convenience. This thoughtfully designed unit offers a bright open floor plan, private patio, and access to beautifully shared community spaces—including a fire pit and outdoor lounge area. Whether you're here for a solo getaway, a family vacation, or a group gathering, the 500 House provides the perfect balance of privacy and connection.  Relax, explore, and feel right at home.

Guest favourite
The spacious living room is characterized by rich wooden flooring and a decorative area rug. A wood-burning fireplace is situated within a brick surround, complemented by a variety of artworks on the walls. Windows are dressed with elegant curtains, allowing natural light to fill the room.
Home in Glendale
4.81 out of 5 average rating, 86 reviews

6 bdrm house, quiet, spacious, great for groups

Welcome to my cozy and spacious 6 bedrooms, 9 beds house! While I am out of town, you can enjoy all the comforts of home away from home. The kitchen is fully equipped, so you can cook and dine together at your convenience while saving money on restaurants. The fenced-in private yard and two level deck add convenience and privacy, a tankless water heater assures that noone in your group will have to take a cold shower in the morning. Please message me for quantities 16+.

Top guest favourite
A quaint two-story building is set amidst a well-maintained green lawn, surrounded by mature trees. A gravel driveway leads to the side of the structure, with additional buildings visible in the background, contributing to a peaceful rural ambiance.
Guest suite in Germantown
4.93 out of 5 average rating, 162 reviews

1853 Farmhouse Apartment

Welcome to a two-bedroom apartment. The space includes a private bathroom, kitchen and living area. There is no kitchen/dining table. The apartment is on the second floor of the house and has an outside staircase leading up to it. The entrance/staircase is not shared by the hosts and there are no shared spaces in the home. The staircase may be steep for persons who have difficulty navigating stairs. Guests are welcome to use the patio area on the property.

Guest favourite
An open living area features a modern style with a gray sofa and a wooden coffee table at the center. A dining space with a dark table and chairs is visible to the left, while a staircase leads to the upper level in the background.
Home in Milwaukee
4.89 out of 5 average rating, 106 reviews

Cozy 2-bedroom cottage close to everything!

This newly remodeled, cozy cottage has been called a hidden gem. It’s walking distance from Bayshore Mall. Five minute walk to biking/hiking trail, Milwaukee River for fishing and kayaking and Whitefish Bay. Twelve minutes from Lake Michigan, Downtown and the Historic Third Ward! Booking requirements: Full/Complete Air BnB profile. Government ID check for pre-approval and upon arrival. No parties or events. Active noise monitoring device. No pets allowed.

Superhost
An open-concept living space features a modern kitchen with a large island and stainless steel sink, complemented by pendant lighting. A comfortable seating area with a light-colored sofa and large windows invites natural light, while a dining area with white chairs is visible in the background.
Home in Mequon
4.88 out of 5 average rating, 213 reviews

Mequon Ranch Experience

Escape to our stunning vacation home in Mequon, WI for a peaceful group getaway. Completely renovated and fully furnished, our home comfortably accommodates up to 8 guests. Enjoy complete privacy on our one-acre lot, and relax on the patio, grill up a delicious meal, or gather around the fire pit. Only blocks away from the Milwaukee River and minutes to downtown Mequon, our home offers easy access to nearby attractions. Book now for an unforgettable stay!.

Guest favourite
Home in Whitefish Bay
4.83 out of 5 average rating, 23 reviews

Berkeley Bungalow | Blocks from the Lake | Parking

Relax with the whole family just blocks from Lake Michigan in this peaceful Whitefish Bay retreat. Enjoy a bright, stylish home with three spacious bedrooms, two full baths, and a modern kitchen. Walk just 8 minutes to the lakefront and Big Bay Park Beach, or explore nearby cafés, boutiques, and parks on Silver Spring Drive. Only 10 minutes to downtown Milwaukee, museums, lakefront festivals, and the zoo! Comfort, charm, and calm near the water await.

Popular amenities for Bayside holiday rentals

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  2. United States
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  4. Milwaukee County
  5. Bayside