Holiday rentals in Glendale

4.79 out of 5 average rating, 256 reviews

Home in Mount Mary

Private Milwaukee Home-Great Location, Entire Unit

This private upper level unit is only 3 miles from Froedtert Hospital, 1.1 miles from Mayfair Mall, and only steps away from Mount Mary University; bordering Wauwatosa, a suburb with great places to roam! This home is spacious, yet cozy. Offers a secure bedroom for 2, living room with a comfy sofa bed that sleeps one, dining area, bathroom, & full kitchen with all the necessities. A Key Less entry makes your check-in quick and easy! Minutes from the highway, making getting anywhere a breeze.

4.97 out of 5 average rating, 226 reviews

Bungalow in Wauwatosa

Wauwatosa/Milwaukee “Inglewood Place”Classic Charm

Great location near all Milwaukee attractions and village of Wauwatosa.Cozy upper two-bedroom duplex with keyless entry in quiet east Tosa. Extras such as ironed sheets, snacks and personal items are included. Walk to popular restaurants and bars in the village and along North Ave. Full kitchen and new beds make this a home away from home. 10 min to Froedtert & The Medical College of WI & Children’s Hospital. Near AmFam Field (Brewers stadium) and the lakefront. 4 miles to downtown Milwaukee.

4.89 out of 5 average rating, 56 reviews

Apartment in Milwaukee

Relaxing 2-bedroom upper unit close to everything

Quiet, pet-friendly upper unit in a classic Milwaukee Lannon-stone home. Across from a country club and a couple blocks from beautiful Brown Deer Park, this comfy apartment is a wonderful jumping off spot for any Milwaukee visit. We are 15 minutes from the Deer District and downtown Milwaukee, 15 minutes to Miller Park, and 20 minutes to Summerfest grounds. Take a drive to surrounding areas-- 20 minutes to Cedarburg, 25 minutes to Port Washington, and 35 minutes to scenic Holy Hill.

5 out of 5 average rating, 23 reviews

Flat in Shorewood

Shorewood's Sunny Craftsman

Welcome to our beautiful, sun-filled, 2-bedroom flat in the amazing lakeshore community of Shorewood! Fully updated in 2023, this lower duplex unit is on a quiet block, and just two blocks from all the wonderful shops, restaurants, and bars on Oakland Ave. Shorewood is very walkable community, with parks, green spaces, beaches, and beer gardens within walking distance. Take advantage of the fully-stocked kitchen with stainless appliances, including dishwasher. Come visit us today!

4.82 out of 5 average rating, 76 reviews

Home in Glendale

4+2 bdrm house, quiet, spacious, great for groups

Welcome to my cozy and spacious 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+ to get a quote.

4.79 out of 5 average rating, 120 reviews

Home in Glendale

Retro Riverside Retreat, Backyard Oasis, Hot Tub

Escape to the retro riverside retreat! This large home sleeps 16+ and offers an incredible outdoor area with a hot tub, fire-pit, and river access. Your outdoor oasis and awaits. Inside, enjoy 6 bedrooms, 3 bathrooms, a huge dining table, and a game room. Perfect for large groups, family gatherings, or a peaceful oasis. Just a short 15-minute drive to vibrant Milwaukee attractions. Experience relaxation and adventure in our remarkable riverside getaway.

5 out of 5 average rating, 4 reviews

Home in Whitefish Bay

Whitefish Bay Beauty!

In the absolute center of Whitefish Bay -- walk to the library, toy store (Winkies), Stone Creek Coffee, Sendik's grocery store, and Lake Michigan from this 100 year-old charmer. 1st floor has a beautiful living room with a natural fireplace, TV room with cloud couch, and a gourmet kitchen. Stunning outside space with BBQ and fire pit. 2nd floor has 3 bedrooms, office, plus 3 full baths. Awesome shopping, restaurants, and beaches nearby.

4.96 out of 5 average rating, 539 reviews

Cabin in Hubertus

Hugel Hutte - Log Cabin Getaway

Welcome to the Hugel Hutte! This cute little cabin is perched on the hill top. It's feels like a tree house! You have the kitchen to use, but the famous Fox & Hound's restaurant is just steps away. It's literally right next door. So grab a few drinks and dinner...and walk home to your cabin retreat for the night. Enjoy the tranquil naturescape surrounding the house.

4.99 out of 5 average rating, 238 reviews

Home in Milwaukee

Sunny Upper Flat in Shorewood Near UWM & Downtown

Beautiful two bedroom upper flat in Shorewood with great light. New carpet, pillow top mattresses, coffee brewer, and many more amenities. 5 minutes from UWM and close to lakefront, downtown, I43 and much more. A short ride to Summerfest grounds. Close to many restaurants of many different styles. You will feel at home in our cozy two bedroom flat.

4.92 out of 5 average rating, 245 reviews

Townhouse in Riverwest

Amazing view, Modern Space

Soak your cares away in a luxurious 7-person hot tub while taking in breathtaking panoramic views of the Milwaukee skyline! This chic two-level condo, nestled on a hill above the Milwaukee River, puts you just a 10-15 minute stroll away from the vibrant energy of North Ave, Brady St, and downtown—where the action is always happening.

4.9 out of 5 average rating, 48 reviews

Home in Glendale

Retreat w/hot tub Fmly/Pet Frdly No Clean fee

Experience comfort and convenience in this cozy suburban house on a quiet street. With a serene atmosphere, modern amenities, and nearby attractions, it's your ideal retreat. Whether you're looking for a relaxing getaway or a convenient base for your adventures, this house promises the perfect balance of comfort and convenience.

4.9 out of 5 average rating, 150 reviews

Flat in Riverwest

Cozy Garden Apartment in Eclectic Riverwest

Stay in this cozy studio garden apartment located in the eclectic Riverwest neighborhood! Located within a block of neighborhood staples like Art Bar and Café Corazon and a quick 10 minute drive to downtown, this is the perfect spot for any visit to the Good Land! Ample street parking is available.

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Other great holiday rentals in Glendale

Private room in Riverwest

4.96 out of 5 average rating, 643 reviews

Bremen Street House | Private Room

MarthaRating, 5 stars4 days ago

Loved staying here. Communication was great. Everything was clean, organized and a relaxing space. It was nice to soak in the cute bath tub after a long day of exploring. I'd love to stay here again and would recommend.

Private room in Milwaukee

4.82 out of 5 average rating, 497 reviews

Cozy spacious basement w/private entry & bathroom

ThomasRating, 5 stars2 weeks ago

Jennifer's place was excellent. The concise yet very clear & easy-to-follow instructions made check-in and check-out a breeze. It was a nice place. I liked that the TV had already some recorded shows on it. Pretty close to downtown Milwaukee. I couldn't have asked for more. I certainly would stay again. 10/10

Flat in Milwaukee

4.66 out of 5 average rating, 539 reviews

Kasa | Central 1BD, Visit Westown | Milwaukee

VeronicaRating, 5 stars1 week ago

Loved our stay at Kasa in Westown Milwaukee. It was close to enough to get to the main attractions in under 15 minutes. The space is perfect for 2 people and worth getting the parking space at the building. Will stay again.

Private room in Whitefish Bay

5 out of 5 average rating, 235 reviews

Private room in lovely, comfortable home

FarrahnRating, 5 stars2 months ago

I highly recommend Kathy's place. it literally has everything you could think of in terms of items you need or want. We will definitely be back if we can! ✨️😊❤️☕️✨️

5 out of 5 average rating, 12 reviews

Flat in Shorewood

The Little Blue Bungelow

MicheleRating, 5 stars4 days ago

Pam was a delightful host at her charming Little Blue Bungalow. My first impression was how clean it was with a nice window breeze and beautiful decor. The bed was super comfy and supplies needed were provided. A beautiful garden in the back was the perfect place to sip coffee or wine. The neighborhood is charming with welcoming sidewalks and an easy walk to great restaurants and to the lake. I'll definitely be staying there next time I'm in Milwaukee.

Townhouse in Glendale

4.59 out of 5 average rating, 32 reviews

Riverfront Townhouse Near Downtown Milwaukee

MagdalisseRating, 5 stars4 months ago

Keith was responsive. My kids had a blast!

Flat in Milwaukee

4.6 out of 5 average rating, 20 reviews

Cozy Quaint Convenient @ MKE 2bdr bungalow

SofiaRating, 5 stars1 month ago

This was truly my favorite Airbnb experience. The place is gorgeous, and host provided weekly cleanings during my month stay. I would return to the unit and there would be fresh flowers and fruit restocked. The unit is better than pictures shown! I felt right at home and would absolutely recommend to others. Thanks Stephen!