
House holiday rentals in West Side
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Top-rated house rentals in West Side
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Popular amenities for house rentals in West Side
House rentals with a pool

Munster hide away
Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.

Rosemont 4BD2BA house with Pool
Mike was very responsive leading up to our stay and very helpful whenever I had any questions about the property. The home was very clean and well maintained. Would recommend!

Now Open: Heated Pool with Entire House
Really great place to stay, super responsive host! The pool was pretty great and so was the hot tub! Great location too, lots of stores, restaurants around, and parks like the Busse Woods (it’s huge and lots of walking paths)!

Schaumburg Oasis:Private Pool & Enchanted Garden
They were a fantastic host, very responsive to every question and anything we needed. The location is quiet and amazing, great place to relax and enjoy time. love the pool! Will definitely stay again. 100% recommend!

Luxury Loft with Private Pool and Movie Theater
Damani was a great host, really responsive and easy to communicate with! The house was exactly as advertised and really nice! The pool was great!

Luxury fenced in modern ranch
It was a chaotic start to our vacation stemming off my daughter's graduation from Northwestern; however, Jennifer immediately took the stress off my shoulders and welcomed our family to a fabulous stay at her home. Words cannot express how grateful my family is and without Jennifer's help it would not have been as successfull. I highly recommend staying at any of her properties. She will go above and beyond to make sure you're stay is wonderful!

LUXE - Movie Theater + Spa House
Great getaway place to stay at. Beautiful patio area as well!

Spacious 4 Bed/3.5 Bath Sleeps 8+
Beautiful house very clean and comfortable. We'll be back very soon
Weekly house rentals

Entire 2 BR home w/ office, deck & no clean fee!
Great host. Very responsive and clear with instructions. Highly recommended

Animal House near Sox stadium
If you're traveling with a pet I would highly recommend this place! Great location and great communication throughout our stay.

Floresitas Oasis, your home in Chicago
Lizbeth was an amazing host. She’s responsive and attentive. The place was exceptional clean and had an amazing smell. I was there to celebrate my birthday and was pleasantly surprised upon entry when I was greeted with a personalized birthday message, fresh flowers and a bottle of wine. Anytime I reached out to Lizbeth, she responded expeditiously. Again, very attentive. My husband and I will definitely stay at her beautiful Oasis again. We felt comfortable and completely safe. Everything we wanted to do was a quick drive from the location. If you’re considering staying at her home, you will not regret it. If I could give more than 5 stars, I would. Thanks Lizbeth for being an incredible host Until the next time…

Sunny Historic Cottage on the Park
We loved Megan’s place! It’s adorably decorated and very cozy. We felt at home during our stay. The beds were comfortable and the kitchen was great for cooking dinner one night. Checking in and out was really simple. You’re not immediately by the train, but it’s a quiet safe neighborhood and there’s a little park across the street and a cute coffee shop a short walk from the house. As was clearly indicated by the hosts, it’s notably warmer upstairs than it is downstairs (we stayed in November) but it wasn’t a real issue. Would happily stay here again.

Spacious whole apt near shopping and city
Host was very nice and helpful with our questions, nice neighborhood some noise but nothing too extreme & house was clean.

Vintage Urban Retreat | Oak Park
We had a great time at Gabriela's place. The listing was accurate, the location was great, and we were pleasantly surprised by how new and clean everything felt. Would stay again.

Luxury-Near Downtown & United Center-Sleeps 14
Dan is a gracious host! He takes great pride in his property and making sure guests are comfortable and satisfied with their stay. I recommend this property to anyone who truly wants a home away from home stay! My family and I will book again next year!

Mid-Century Gem By United Center: Hot Tub & Sauna
Had a great time at Sebastian’s place! The house was better than expected. Highly recommend staying here if you’re visiting Chicago.
Private house rentals

The Modern Muse of Chicago! Close to everything!
Jasna was an amazing host! The house was absolutely spectacular—truly even better than the photos. Every room felt thoughtfully designed and full of warmth, making it feel just like home. We had all the amenities we needed, which made our stay super comfortable and stress-free. It was the perfect setting for a special girls’ trip with my mom and sister. The neighborhood was peaceful and beautiful, adding to the relaxing vibe. We’ll definitely be back! Thank you again for everything, Jasna!

Family Friendly Duplex/9 min from MDW/Free Parking
Very nice space to bring friends over

Chicago Home (1st floor) by Midway near Downtown
My friends and I had a great time staying at Joanna’s place! It was super clean, the neighborhood was nice, and there were lots of stores and restaurants around the area too! We would definitely stay again :)

Spacious Designer Oasis: Game Room - Yard - Garage
Rameez was an amazing host! Making the experience even more enjoyable with his quick responses & fast accommodations. The home is more spacious than it looks in the photos and it truly exceeded my expectations. I had a great stay for my birthday!

Cheerful two bedroom home with patio/deck
Beautiful home in a quiet neighborhood with responsive and helpful hosts.

Private 3rd Floor Apartment
Very comfy apartment in a great neighborhood. We were in town for a baseball game and it’s a terrific place for that, just about a 20-minute walk to Wrigley Field. The only thing to be concerned about is the stairs: there are two flights to get into the apartment and they’re fairly steep and small, so if you have mobility issues that would be a concern. I don’t and had no problem. Karen is a lovely host and was very helpful when I was getting into the place and unloading my stuff from my car. There are tons of restaurants and coffee shops in the area, so it’s a great place to explore and hang out.

Perfect Location Across from Park & Train Station
The house was beautiful and was perfect for our group. Everything was spotlessly clean and just as described. Access to the El was convenient but also created quite a lot of noise especially in the front of the house. This, of course, is completely out of the host’s control and we got used to it after 24 hours or so. The location was also convenient to the interstate that flows right into downtown, which was great for us as we were participating in a conference in a hotel on Michigan Avenue. Overall we had a great experience with the house and the host. Would recommend this location very highly.

Big house in the BEST Location!
The house is lovely! Better than the pictures, just as all of the reviews say. The showers are incredible. The master bathroom is a dream. We had everything we needed & more. We don’t have a single complaint. We definitely plan on booking here again.
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Moraine Hills State Park
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