
Vacation rentals with outdoor seating in Gary
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Top-rated outdoor seating rentals in Gary
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Popular amenities for Gary outdoor seating rentals
House rentals with outdoor seating

Pet friendly stylish retreat with sauna, hot tub
My wife and I have stayed at many vacation home rentals over the years, this one was one of the very best! First, I booked they house late afternoon on the day we wanted to arrive. Sarah responded immediately, accepted our booking and got me the access code to the property. It was all done within a few minutes! The house was beautifully decorated (my wife loved it and she is a designer!), well appointed and located very conveniently to all of the places we wanted to spend our time. We loved the hot tub, used the sauna almost every morning and our Golden Doodle loved the big fenced in back yard. Sarah and Brady are unbelievably responsive to needs too! One evening we wanted to enjoy the fire pit, but they were out of fire starters. I contacted Sarah at 7:36p, she responded at 7:37p and by 7:51 Brandy had already dropped a box of fire starters on the front porch! What?!?!?! Amazing. I HIGHLY recommend this place, we will be back!

South Shore Studio Apartment {National Park}
I absolutely adored Robert’s place! What a beautiful/peaceful space :) Everything was clean and tidy, loved it right away. I was also lucky enough to check out the open mic event Robert hosts from 2 to 8pm on Sundays :) Will definitely be back!

Chicago River House -BBQ Oasis now open!
Even more spacious than in the photos! Well-kept place, with a fully stocked kitchen, projector, BOSE speaker, and great backyard. Double shower in the master bedroom, and strong water pressure. Entry is easy with a code. Finally, the host is VERY accommodating, flexible, and responsive. Recommended!

Peaceful Getaway in Miller Beach
The house was absolutely lovely—very clean, comfortable, and just minutes away from the beach. It was exactly as described, and even better in person. The space was accessible, which made our stay even more convenient. The host was also very responsive and attentive throughout our visit. We had a great experience and would definitely stay here again!

Cozy at The Walter
I thoroughly enjoyed my recent stay at this home. The home itself was filled with everything we could have needed and saved us from trips to the store when we needed something quickly. It also felt to me like it was nicer than the photos and felt extremely safe and comfortable. All in all I would 100 percent stay here again!

Retro Modern Bungalow | fire pit | free parking
This exquisite MCM GEM in Berwyn was the perfect home base for us while visiting Chicago. Every corner is curated with unique and authentic MCM touches, all with the contemporary creature comforts one could want and then some. Everything was sparkling clean and April was a superb host. We hope to come again, & highly recommend!!

Cozy House with Gazebo
We stayed for almost a week with three dogs. Sarah's place was perfect for our needs - great backyard, comfortable beds, clean and equipped kitchen, and awesome location - close to Chicago, Indiana dunes and easy to navigate thru, no traffic. Sarah and her family (and their amazing dog Chandler) are super friendly and helpful. We will definitely stay there again once back in the area.

Perfect for Dunes! Special Spring Rates!
I absolutely adore this listing! It looks just like the photos, very easy instructions to follow, and a cute little neighborhood! Definitely check this place out the decorations and overall aesthetic of this house is adorable, not to mention it was very clean and homey definitely coming back :)
Apartment rentals with outdoor seating

Modern Apt with style & comfort in Pilsen Chicago
Gogo was great. We misread checkout time at 11, when it was actually 10, and he was so friendly about it. It was our second time staying there because we liked it so much the first time!

Cute Skylar: Valparaiso University ShortTerm Stay
Super clean, quiet, and cozy but stocked with everything you need and just a few blocks from Valpo campus and the downtown eateries. Really just a perfect spot, and only about 30 minutes drive from all parts of Indiana Dunes NP. Also, Diana was a very gracious and kind host! Would love to stay here again the next time I'm in town!

Charming Unique 2 Bdrm Apartment in Victorian Home
Carol’s place was very comfortable for our family of 4! Amenities were all as listed and everything was clean and inviting. We hope to stay here again the next time we visit family in Blue Island!

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
We loved our stay! It was so clean and very close to public transit! We navigated the trains to and from Cicero into Chicago NP! We will definitely be back and we would definitely recommend staying at this Airbnb!!!

ValpoVilla: Location, location, location!
We had another great stay at Mari-Beth’s place, and we look forward to staying a third time in the future.

Home in Forest Park Upstairs.
He was available without delay and really seemed like a kind person. The location is wonderful whether you're looking for safe and simple stay or a trip into city. Highly recommend!

Second Floor Apartment sitting on Pine Lake
We had an amazing time! Me and my boyfriend stayed for one night, the patio and dock were super cozy and we really enjoyed sitting out there at night just listening to music and having some drinks. Super nice area, the beach isn't too far and they have some fun bars and restaurants in the area. Overall, we really enjoyed our stay.

Handicap accessible apartment w/Level-2 EV Charger
Richard was great and very helpful. He was in constant communication with us and provided helpful tips for our visit to Chicago. Highly recommend staying at this place
Condo rentals with outdoor seating

A Stones Throw from U Chicago South Campus!
Everything was great! The location was perfect—close to most of the attractions we visited during our stay. We really appreciated how well everything was set up. The honey was a lovely touch, and we especially enjoyed the peaceful, quiet atmosphere away from the city. Thank you for a wonderful experience!

3 BR GetAway, 15mins to Loop + private parking
Planned a trip to Chicago for a weekend get away and Michael’s house did not disappoint. Free parking with unlimited parking passes, probably the most friendly/sweet neighbors you’ll find and just a very beautiful home 100% recommend very close to the green line train which we used to get to the loop every day book this house before it’s gone!

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Our stay in Evanston was great! The apartment is close to all of downtown Evanston, the Metra, and the L. Also easy access to NU. Everything was just as it says and the free underground parking is a HUGE plus!

Downtown Chicago - Spa Bath, Patio, 3 blocks to L
This is our 3rd time staying at Thomas and Cynthia place. We would have it no other way. Home away from home every single time.

Renovated 2 Bed Condo Lincoln Park w/ Free Parking
John's place is great, just as described. Very clean and location is perfect (across the street from Pequod's). Check in/out was easy and communication was good.

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!
One of my favorite Aibnbs of all time. The location is FUN - right in the center of the action in Northalsted. The space itself is beautiful and clean. The bedrooms are spacious, and the kitchen is well equipped. Allan was awesome and left us a bottle of prosecco to welcome us. Best part of the house is the huge covered front balcony - a front row seat to the joyous crowds, especially on the weekend. We saw a concert, walked to a Cubs game, spoiled the kids on Michigan Ave - and everyone agreed the balcony was our fave part of the trip. The rear deck is icing on the cake. We were in town so our kids could go to a concert and they also loved the area. If you're sensitive to noise, bring earplugs - all the action brings a bit of music - but really it's a steady din so super easy to tune out at bedtime. We love this place and can't wait to come back!

Modern Chicago Movie Themed Apt
We had a fantastic stay at this Airbnb during our Chicago trip! The location was perfect — close to everything we wanted to see and do with our kids. The apartment was clean, well-equipped, and exactly as described. It felt like a home away from home. Check-in was smooth, and the host was responsive and helpful throughout our stay. Highly recommend for families or anyone visiting the city!

Spacious 4 Bedroom Condo
We had a great stay for an extended wedding weekend with our entire family. Adrian's home was clean, modern, and well appointed. The beds were all very comfortable and linens were very soft. We felt very safe and the garage parking spot was a nice addition. I would highly recommend his home and would not hesitate to rebook there in the future.
Quick stats about vacation rentals with outdoor seating in Gary
Total rentals
80 properties
Nightly prices starting at
R897 ZAR before taxes and fees
Total number of reviews
4K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Warren Dunes State Park
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Wicker Park
- Willis Tower
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Chicago Cultural Center
- Medinah Country Club
- The Beverly Country Club