Holiday rentals with outdoor seating in Woodlawn, Chicago

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!

perfect place to stay if you have pups, with a dog run so they can potty off-leash. clean and well-equipped. bathrobes, nice hot shower. appreciate that the shampoo, conditioner, and body wash were all provided. comfortable bed and quality air mattress w/ plenty of bedding. location could not have been more perfect for reaching chinatown, the museums, white sox stadium. there was always parking available on the street and for free (both things hard to come by in chicago). miranda provided names of some restaurants w/in walking distance w/ dog-friendly patios. and it was no issue leaving the pups for short stints, we just put them in their kennel and let miranda know by text (so she could keep an ear up for them in case they got distressed). will definitely book again when we visit chicago.

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!!

My family and I had a great stay at Bel’s powder blue house. The house matched the pictures and description posted on the website, and was very clean and cozy inside. Bel’s communication was very effective throughout the entire experience, I will definitely be booking with him again in the future!

It was a nice break from the hustle and bustle of the big city. A few great restaurants just a couple blocks away. And just a block away from bus stops.

KB was a great host, very responsive, and accommodating. I definitely recommend staying here!

I truly fell in love with this home. Spot on with the photos and descriptions. Very easy to communicate with Pam, and she offered as much assistance a needed, if needed. If you have a larger group needing accommodations this is a great space. The location was very close to the expressway and is 30 minutes from Navy Pier and downtown Chicago.

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.

A-MAZ-ING stay! My wife and I had such a blast in Chicago. GOGO was very kind and inviting, good energy! The place was exactly what we wanted with all the amenities. Sparking water in the fridge which was a treat after waking 18k everyday. As a runner, there was plenty of sidewalk and things to see. I recommend running up LEAVITT to 18th street and take 18th down for a nice 3 to 5 mile run. The L train “pink line “ was close and walking back at night we felt relatively safe. I would high recommend staying here in Pilsen area the next time you are in Chicago. Mahalo

Everything was great! From location to things to do, this is one of the best in the Windy City! 10 out of 10 would recommend!! 👍

It was very well maintained, and the apartment felt very peaceful. The area is also very nice, everything you could need is within 10 minutes walking distance.

Margarita was super accommodating to last minute adjustments and very responsive. The location was convenient, safe, and there was always parking!

We had a nice 2 night stay in Chicago. Place was affordable, comfortable and clean. 10 minutes from downtown Chicago and short walk to train. Hosts were friendly and great at communication.

Charming Victorian house in a peaceful and safe neighbourhood. So thankful for the really comfy queen bed - felt like my home mattress!

Joe’s place is exactly as described, and in a fantastic location. The unit is clean, easy to access and spacious. Proximity to the blue line is a major plus, and walkability to all the great things in the Logan Sq + adjacent neighborhoods is a major plus. Highly recommend.

Richard was very friendly with lots of knowledge about things to do. The place was very clean and inviting. Everything was provided for us as far as the extra towels and bedding. There was plenty to do in the area. And he was very outgoing and helpful. I had lost a screw on my glasses and he had a repair kit that he let me use to fix them. He goes above and beyond. Thank you Richard. When we return to Chicago we will definitely try to stay here again.

Wendy and Matt's place was comfortable and homey. The location was great, the apartment comfortable, and we had essential amenities. The building is mid-century modern and designed by famed architect Harry Weese that incorporates thoughtful references to Chicago architectural history throughout while still remaining visually cohesive. One minor issue is the stove, which is electric and somewhat underpowered. It's good enough for minor work like breakfast or heating leftovers but you may struggle producing more elaborate meals. It was a very minor quibble but worth noting for those culinarians wanting to prepare their own meals. The oven is decent but there is only one. Overall, my stay was excellent and I recommend Wendy and Matt's place wholeheartedly. They are excellent hosts as well.

Our group had (3) toddlers ages 1-4. Alex’s place was a great choice for us! There was plenty of room for kids to run around and with the bedrooms being below the main living areas, we felt comfortable that they would only be disrupting our own group and not the neighbors around us! The unit was very clean and stocked with the basics you would ever need. Alex was excellent at communicating access to building and parking rules all before we arrived. He even sent us a location for a park walking distance away for the kids. It was a comfortable neighborhood where we felt safe and were able to take a short drive into the city that felt like nothing! I would recommend this place to anyone, but especially families with children!

The condo was a couple’s dream. Made you want to just live there forever. Very clean and felt like home. Hosts were communicative and courteous. Will definitely book again in the future and would highly recommend!

This is our go-to place when we come to Chicago. On this trip, our flight landed early and John was willing to let us check in a couple hours early to accommodate us. John is always very responsive, and this time around was able to work with us on an issue with the electronic thermostat (previous renter had put it in ECO mode so that it would turn itself off when no one was home). The location can't be beat.

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!

The condo was very spacious and had everything we needed to stay right at home. Adrian was responsive to our questions. It was a perfect distance from the city for exploring through the day but staying in a peaceful place at night. The staircase in the house was a little steep but otherwise it was perfect.

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!

Supurb stay in Fulton Market! Seth was an outstanding host—responsive, welcoming, and accomidating. The apartment was spotless, well decorated, and thoughtfully stocked with everything we needed for a comfortable stay. The beds and linens were especially cozy, making it easy to relax and feel at home. The location is superb—just steps away from a variety of highly rated restaurants. The location is superb—just steps away from a variety of highly rated restaurants. We also felt completely safe throughout our stay. The neighborhood has a welcoming, upscale vibe, which added to our peace of mind. A quick heads-up: the unit is a second-floor walk-up accessed via a private entry. Inside, as you can see has the spiral staircase; a unique architectural feature, but if you’re traveling with heavy luggage, it’s something to keep in mind. Pack accordingly! 😉 Overall, we had a wonderful experience and would gladly stay here again and agai