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Vacation rentals with outdoor seating in Woodlawn, Chicago

Find and book unique outdoor seating rentals on Airbnb

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Popular amenities for Woodlawn, Chicago outdoor seating rentals

House rentals with outdoor seating

Guest favorite
Home in Chicago
5 out of 5 average rating, 10 reviews

The Modern Muse of Chicago! Close to everything!

VictoriaRating, 5 stars1 week ago
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!
Guest favorite
Home in Bridgeport
4.96 out of 5 average rating, 123 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

KristenRating, 5 stars1 week ago
Staying at Matt’s Air BnB was a fantastic experience. We stayed with our two kids and another couple and the space was perfect for our group. The spacious, fenced in yard made for a great hangout space for our toddler to safely run around. The house looks exactly like the pictures and was extremely clean. We will definitely stay here again! Thank you, Matt!
Guest favorite
Home in North Park
4.96 out of 5 average rating, 174 reviews

Chicago River House -BBQ Oasis now open!

ThomasRating, 5 stars2 weeks ago
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!
Top guest favorite
Home in Wilmette
4.97 out of 5 average rating, 154 reviews

Unique porcelain-enamel paneled "Lustron" home

JulietRating, 5 stars3 days ago
I enjoyed my stay here which enabled me to be close enough to Northwestern’s campus as I worked on a writing project. Being minutes from downtown Wilmette was a plus—be sure to check out Saint Roger’s Abbey bakery for wonderful French pastries! The house was neat, tidy, and matched the description. I also appreciated the record collection!
Top guest favorite
Home in Berwyn
4.99 out of 5 average rating, 146 reviews

Retro Modern Bungalow | fire pit | free parking

JenniferRating, 5 stars1 week ago
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!!
Guest favorite
Home in Pilsen Historic District
4.95 out of 5 average rating, 398 reviews

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

CarmenRating, 5 stars1 week ago
One of the best Airbnbs I have stayed at. It was beautifully decorated and super clean. Had everything I needed to feel comfortable and at home. The host was extremely responsive. The parking was a bit difficult but would not deter me from staying there again. Very close to downtown, about 10 minutes. Highly recommend.
Guest favorite
Home in Chicago Ridge
4.91 out of 5 average rating, 143 reviews

Quiet cul-de-sac with huge fenced in backyard

MeganRating, 5 stars4 days ago
Tom's place was really nice and exactly as described. The backyard was perfect for our pup and the neighborhood was really nice to take him on the walk. We would defintely stay there again if we are in the area.
Guest favorite
Home in Whiting
4.85 out of 5 average rating, 157 reviews

The Spa of Downtown Whiting

MeganRating, 5 stars5 days ago
My partner and I absolutely loved our stay at Steven’s place. It was exactly what we were looking for. The spa tub was amazing. Walking distance to the beach and the local shops! Steven gave several recommendations for places to check out. We went to dinner at a local bar and walked 119th street to check out the small businesses! It is the perfect in between spot to stay for Chicago and The Dunes! The place was just like the pictures, with comfortable beds, nice couches and surround sound! Definitely one of our best stays! We hope to visit again before the end of summer!

Apartment rentals with outdoor seating

Guest favorite
Apartment in Hammond
4.84 out of 5 average rating, 149 reviews

Plant MOOD FREE Wi-fi, parking, washer & dryer!

AdamRating, 5 stars1 month ago
We really enjoyed our stay. The place was very clean and welcoming. The bathroom had a nice shower with good water pressure. The bed was comfortable and provided a restful sleep. Any questions I had, Siobhan responded very quickly and pleasantly. We went to a beer festival in nearby Munster and this was a great location to stay in.
Top guest favorite
Apartment in Forest Park
4.98 out of 5 average rating, 233 reviews

Walk to Oak Park from this Newly Remodeled Gem

BeverlyRating, 5 stars3 weeks ago
Uncommonly well supplied and furnished, this is one of our favorite Airbnbs anywhere. We’ve stayed a few times, and our experience has always been exceptional.
Superhost
Apartment in Near West Side
4.84 out of 5 average rating, 126 reviews

*A Happy (City) Glamping- walk to train FREE park

KeishaRating, 5 stars1 week ago
The space is exactly as described. Loved how close it was to public transportation. The space is great for a weekend away.
Guest favorite
Apartment in Avondale
4.97 out of 5 average rating, 162 reviews

Designer Avondale Attic

JaninaRating, 5 stars2 weeks ago
Just wonderful. That was one of the nicest places I've ever been. The apartment is totally lovingly furnished. Everything was super clean and tidy. There are even toothbrushes, toothpaste and a sleeping mask if you need them. The kitchen is also super equipped with everything you need. The short walk to the metro was also very convenient. We would definitely come back.
Top guest favorite
Apartment in Blue Island
4.94 out of 5 average rating, 299 reviews

Charming Unique 2 Bdrm Apartment in Victorian Home

KatharynRating, 5 stars1 week ago
Charming Victorian house in a peaceful and safe neighbourhood. So thankful for the really comfy queen bed - felt like my home mattress!
Guest favorite
Apartment in Near South Side
4.94 out of 5 average rating, 172 reviews

South Loop 3Br/2Ba Condo with Balcony & Parking

KeithRating, 5 stars2 weeks ago
Got lucky finding this place. Excellent experience. Great owner. Everything was neat, clean, and super easy. We will gladly be back. Great job!
Guest favorite
Apartment in Cicero
4.97 out of 5 average rating, 311 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

PatriciaRating, 5 stars1 week ago
5 star for sure! This place is a hidden gem, its so clean and has so many little extras to make you feel at home. I found seasoning to cook with,.coffee, tea, cream and sugar..and even a couple of pods for laundry. All of that plus an easy check-in, great parking space in the back (which you will need since street parking can be dicey) and the friendly neighbors made my stay wonderful. I stayed 7 nights and it is quiet at night so I felt very safe and got a good nights rest each night. I will definitely book again!!!
Guest favorite
Apartment in Berwyn
4.91 out of 5 average rating, 388 reviews

Private apartment with retro vibe

BeckyRating, 5 stars1 day ago
Place was centrally located with lots to do in walking distance for food and entertainment. We could walk to the venue where we saw our live music. The host is very kind and had a lot of information about the area to share with us. We felt very safe the house was peaceful very clean. The outdoor garden area is really pretty too. We definitely wanna stay here the next time we’re up for a show.

Condo rentals with outdoor seating

Guest favorite
Condo in Evanston
4.95 out of 5 average rating, 108 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

StaciRating, 5 stars3 weeks ago
Always responded quickly. When we had trouble with front door lock they came out quickly and addressed the problem.
Guest favorite
Condo in Humboldt Park
4.94 out of 5 average rating, 180 reviews

3 BR Summer GetAway, 15mins to Loop+Gated Parking

ThaddeusRating, 5 stars3 days ago
Close to the green line for easy transportation.
Guest favorite
Condo in Pilsen Historic District
4.94 out of 5 average rating, 127 reviews

The Urban Oasis | Outdoor Lounge • Sleeps 10+

BridgetteRating, 5 stars1 day ago
The unit was as described, clean, affordable, easy to get to and home base from, and the neighborhood felt safe. There’s a coffee shop right on the corner we walked to in the mornings. We had a big group for a bachelorette and there was plenty of spaces to sleep downstairs (3 bedrooms with beds and one shared space with four beds), get ready (2 full bathrooms including two baths for kiddos), and lounge all together (large couch, big kitchen table, island seating, and outdoor covered area). Big thing for me is ceiling fans the bedrooms so that was super satisfying. Highly recommend this unit and we’d go back!
Top guest favorite
Condo in West Town
4.97 out of 5 average rating, 146 reviews

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

MichaelRating, 5 stars1 week ago
Great place! Everything was clean, in a good location and they communicated well.
Guest favorite
Condo in Lincoln Park
4.91 out of 5 average rating, 110 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

NicolasRating, 5 stars1 week ago
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.
Guest favorite
Condo in Ukrainian Village
4.93 out of 5 average rating, 139 reviews

Modern Chicago Movie Themed Apt

LechelleRating, 5 stars2 weeks ago
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!
Guest favorite
Condo in West Town
4.98 out of 5 average rating, 165 reviews

Spacious 4 Bedroom Condo

ScottRating, 5 stars1 month ago
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.
Guest favorite
Condo in Logan Square
4.93 out of 5 average rating, 105 reviews

Wicker Park/Bucktown condo with large balcony

ErinRating, 5 stars1 month ago
We enjoyed our time at this apartment! Nestled in the Bucktown neighborhood of the city, which is peaceful and surrounded by beautiful homes. Nearby Wicker Park and Logan Square have a lot to offer, as well as Lincoln Park (the neighborhood) not being too far away either. While the bedroom and bathroom are on the smaller side, that’s just city life and it is a perfect retreat for 1-2 people. It’s very stylish yet cozy with the decor and all updated appliances and bathroom. I would take note of the stairs for this unit in particular, as it’s on the second level but they were fine and the patio deck was nice! We really appreciated Lauren being accommodating to our late booking. We would definitely stay here again!

Quick stats about vacation rentals with outdoor seating in Woodlawn, Chicago

  • Total rentals

    40 properties

  • Nightly prices starting at

    G$6,276 GYD before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    40 properties include access to wifi

Destinations to explore

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  3. Illinois
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  5. Chicago
  6. Woodlawn
  7. Rentals with outdoor seating