Vacation rentals with outdoor seating in Highland Park

Find and book unique outdoor seating rentals on Airbnb

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Popular amenities for Highland Park outdoor seating rentals

House rentals with outdoor seating

Guest favorite
A modern cabin exterior showcases large glass windows framed with dark wood, allowing natural light to fill the interior. Surrounding greenery and planted flower beds enhance the serene lakeside ambiance. A stone path leads to an additional structure, contributing to the secluded environment.
Home in Powers Lake
4.78 out of 5 average rating, 64 reviews

Powers Lakehouse Loft

AnthonyRating, 5 stars6 months ago
It was exactly what we were looking for. Very quiet with beautiful views. Being able to sit in the hot tub and take in the sunset was incredible. Any questions we had were answered quickly by this very kind host.
Guest favorite
A spacious outdoor area is presented, featuring a grassy lawn surrounded by trees. A playground with a slide and swings is visible alongside a trampoline. A fire pit with seating is centered on a gravel patch, with a red shed positioned in the background.
Home in Antioch
5 out of 5 average rating, 18 reviews

All seasons country house

ChrisRating, 5 stars5 months ago
Agnieszka's place was perfect for our visit with our son as he graduated boot camp. The home had everything we needed. The minimal decorations made it very easy to clean and easy to find all our stuff when we left. The home is beautifully remodeled on the inside. Much respect to the designer. We brought extra toiletries and paper products and dishwasher tabs because we were staying so many days. There was an adequate amount for a simple weekend stay. Plenty of sleeping space for several people. Just remember there is one bathroom. By the way, there is a great Jewel-Osco grocery store close by. We also visited an exceptional museum in Volo. It was perfect for a family, especially the boys! I really enjoyed the short drive to Kenosha, WI to gather stones by Lake Michigan.
Superhost
A small outdoor space features two blue chairs positioned on a light-colored area rug, surrounded by textured brick walls. Green vines adorn the wall on one side, adding a touch of nature. A white door provides access to the interior.
Home in Illinois Medical District
4.86 out of 5 average rating, 101 reviews

Casa PLZN Location | Entire Home | Garage Parking

RicardoRating, 5 stars2 weeks ago
Great place! I’ll definitely be coming back! The beds are amazing!
Guest favorite
Home in Logan Square
4.95 out of 5 average rating, 38 reviews

Gorgeous and Luxurious 3 BR Home

SeanRating, 5 stars6 months ago
This is a great house to stay for a family or two couples. Out of several ABNBs, this one gets the award for most clean. There is a fairly new Italian restaurant, Il Girasole Trattoria, that is walk-able and delicious. You will not be disappointed with your stay.
Top guest favorite
A modern living area is equipped with a wall-mounted television and a neutral sofa. A decorative coffee table and warm-colored accent chairs are positioned around the space. The room includes lush potted plants and framed artwork on the walls, enhancing the aesthetic appeal.
Home in Worth
5 out of 5 average rating, 16 reviews

3 x Queen Beds + Pull Out Sofa Bed - No Stairs !

SawsanRating, 5 stars1 month ago
Amazing house and location. Great host. Highly recommend.
Top guest favorite
Home in Elgin
5 out of 5 average rating, 22 reviews

Little Blue House

BriannaRating, 5 stars4 months ago
Alex is a great host! Dog friendly places are hard to find and his place made my dog feel super comfortable. Love this place and definitely will be back.
Superhost
A spacious backyard features a stone fire pit with a small fire burning inside. The grassy area is bordered by trees, and a multi-level home stands in the background. A wooden deck is visible above, with chairs arranged nearby for seating.
Home in Cary
4.83 out of 5 average rating, 92 reviews

Spacious 3 Bedroom

CoryRating, 5 stars2 weeks ago
The home is a great place for a family, we were able to stay a week comfortably with younger kids .
Superhost
A comfortably arranged living room features a gray sofa with multiple cushions and two teal accent chairs. Natural light enters through large windows dressed in light curtains, while a wooden floor adds warmth to the space. A flat-screen TV is mounted on the white wall.
Home in Markham
4.73 out of 5 average rating, 124 reviews

The Country Life! Entire House.

DeniseRating, 5 stars1 month ago
Cathy was a great host, very responsive! House was great, it accommodated our family size perfect. The only thing in my opinion that was missing was washer and dryer access in the home. We were traveling with toddlers and couldn’t wash a load of clothes. But aside from that everything else was great.

Apartment rentals with outdoor seating

Top guest favorite
An outdoor balcony is featured with wooden railing and a small round table surrounded by two wrought iron chairs. The space is sunlit, offering views of neighboring brick buildings and clear skies.
Apartment in Ukrainian Village
4.9 out of 5 average rating, 518 reviews

iKlektik House Chicago / Robin

RitaRating, 5 stars3 weeks ago
The Iklektik House is an absolute gem! Everything we needed for a relaxing and comfortable stay, just enough space for two in a bright, clean, and cozy space with tons of charming little historic details and charm, while still perfectly accomodating for a modern stay. The neighborhood was fantastic with lots to do and see, and we much appreciated the amenities Mindy and Tony offer in their clean and welcoming space (coffee! Plenty of fresh linens and we could have cooked a meal if we had more time) Parking on the street was always easy but we ended up walking a lot since there are so many shops and places to eat in the neighborhood. 11/10 - would absolutely book again!
Guest favorite
A private rooftop patio is displayed, featuring a seating area with bright orange cushions on a dark wicker couch. A glass table is centrally placed, surrounded by panoramic views of the Chicago skyline under a partly cloudy sky.
Apartment in Near North Side
4.91 out of 5 average rating, 137 reviews

Modern 3BR with Private Rooftop & Free Parking

ChunguangRating, 5 stars5 days ago
A great place to stay for a family to explore downtown Chicago. The location is convenient, with easy access to major attractions, and restaurants. The home was clean, cozy, and well-equipped — we truly felt like we were at our own home. The host was responsive and thoughtful, which made our stay even more comfortable. Highly recommended!
Guest favorite
A modern living space features a dark sofa adorned with colorful cushions. A round coffee table sits in front, accompanied by a small side table with a decorative vase. A large mirror reflects the cozy atmosphere, while a vibrant city skyline artwork adds visual interest to the wall.
Apartment in Avondale
4.97 out of 5 average rating, 107 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

DarenRating, 5 stars3 days ago
A very nice and welcoming place to stay!
Superhost
A spacious living area features a cream-colored sofa near a large mirror. A round dining table with four chairs is set in the center, accompanied by a wooden desk and a lamp. Natural light flows in through the window, illuminating the light decor.
Apartment in Evanston
4.83 out of 5 average rating, 178 reviews

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

SkylarRating, 5 stars3 weeks ago
Craig was extremely nice and accommodating when it came to my birthday weekend. He responds quickly to all questions asked and makes sure we’re comfortable at all times. This home was clean, accurately described, and had the perfect “home feeling”. Overall, when visiting the area I will be booking here again !
Superhost
A spacious outdoor terrace is shown, featuring comfortable seating arrangements with orange cushions and a circular table. Potted greenery lines the space, and decorative string lights enhance the ambiance. A neutral rug adds warmth to the seating areas, inviting relaxation.
Apartment in East Rogers Park
4.89 out of 5 average rating, 166 reviews

Executive Apartment on Lake Michigan with parking

DebraRating, 5 stars1 month ago
This was a beautiful place with an excellent view of Lake Michigan. Both rooms had comfortable beds and setup with everything you need. Kitchen is well stocked, but we mostly ordered Grub Hub, lol. Loved spending time here and great place to hangout and chat with friends. It is right on the water and we really enjoyed watching the waves crash against the barrier. It is on the 2nd floor, but the stairs are not bad at all. Felt very safe and having the parking space is a great perk. Very commutative and checked in with us to make sure everything was fine. Would definitely stay here again!
Guest favorite
A living area features a cozy orange sofa and two gray armchairs set around a round coffee table. Natural light enters through large windows dressed in floral curtains, while a colorful area rug adds warmth to the space.
Apartment in Oak Park
4.92 out of 5 average rating, 182 reviews

Large sunny 3BR apt. in downtown Oak Park

CraigRating, 5 stars1 month ago
This was a beautiful place! it had everything we needed. Oak Park downtown is walkable and has everything you could want. It is an upstairs unit so be prepared for some steps. Parking was easy. Michelle was great! Downtown Chicago is only 15m (if there's no traffic.). We would definitely come back!
Guest favorite
The living area is characterized by a vintage fireplace and mid-century furniture. A large artwork hangs above the mantel, and a round dining table is partially visible in the adjacent area. Natural light brightens the space through windows draped with sheer curtains.
Apartment in Lincoln Park
4.93 out of 5 average rating, 505 reviews

Victorian Home in Old Town

AlexRating, 5 stars5 months ago
I really enjoyed my stay! I loved the art and decor of the space. I am a solo traveler and I felt safe being here. There are written instructions on the door and in the home that explain almost everything I needed. I felt safe in the neighborhood! I would get back late and felt safe doing so. There are multiple stores within walking distance so it was easy to grab food or any items I may have needed. I didn't have a car and found it very easy to get to everywhere I wanted to go. Shampoo/Conditioner/Body Wash was a pleasant surprise to have! Along with the teas and coffee items. The space was a great size and I had everything I needed. It was easy to come and go and check in was very easy. I would stay here again, Lynn was super responsive, helpful, and kind! The bedroom area doesn't get much light, but it wasn't an issue for me. Bed was comfy, home was beautiful, and I loved my stay. Thank you so much Lynn!
Guest favorite
A cozy living area features a green sectional sofa adorned with yellow accent pillows. A wooden coffee table sits in the center, complemented by a light grey armchair. Natural light streams in through a skylight, highlighting the rich brown flooring.
Apartment in Avondale
4.9 out of 5 average rating, 104 reviews

Avondale Cozy 1 Bedroom Attic Apartment 4th FL

CatherineRating, 5 stars4 weeks ago
Great place, beautiful attic and great amenities from host!

Condo rentals with outdoor seating

Guest favorite
A cozy living space is highlighted by a warm fireplace surrounded by decorative artwork. A large couch is positioned centrally, offering an inviting view of the flickering flames. Soft curtains frame the window, allowing natural light to fill the room.
Condo in Lake Geneva
4.92 out of 5 average rating, 518 reviews

Charming, Cozy & Eclectic Condo in Lake Geneva!

EricRating, 5 stars1 week ago
Tricia's place was wonderful. It was a close 5 minute drive to William's Bay, where we spent most of our time. The home was perfect, quiet, and we'd love to stay here again!
Guest favorite
A modern living area features a light-colored sectional sofa adorned with blue accent pillows. A round black coffee table is positioned in the center, resting on a decorative rug. Two lamps and a piece of coastal-themed artwork complement the bright, airy atmosphere.
Condo in Bridgeport
4.89 out of 5 average rating, 112 reviews

Convenient & Spacious 3BR Condo w/Free Parking

RachelRating, 5 stars2 weeks ago
Convenient stay right outside of the heart of downtown Chicago! Easy to drive into town for the day. Very comfortable beds and very clean as well. Would recommend
Guest favorite
A bright living area is illustrated with large windows allowing natural light to fill the space. A comfortable beige sectional sofa provides seating, while a wooden coffee table sits on an area rug. A desk with modern design and a chair are present, enhancing the workspace.
Condo in West Town
4.92 out of 5 average rating, 113 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

SearaRating, 5 stars2 weeks ago
Great place to stay! Quiet neighborhood and walkable distance from a few shops and food places. We enjoyed our stay very much!!
Top guest favorite
Condo in Lake Geneva
4.97 out of 5 average rating, 148 reviews

Magnificent waterfront views & cozy fireplace

xueRating, 5 stars2 days ago
"5-star stay! Clean, convenient, and great value. Would book again!"
Guest favorite
A sliding glass door opens to a private balcony featuring outdoor seating with a round table and four chairs. Lush greenery and a view of the lake are visible in the background, while the interior space includes comfortable striped seating and a cozy area rug.
Condo in Lake Geneva
4.96 out of 5 average rating, 138 reviews

LakeView-SummerPool-FamilyFriendly-CloseToTown

DaynaRating, 5 stars1 month ago
We loved our stay at this beautiful location. It was close by to everything we wanted to do and the condo was exactly what we were hoping for! Rachel gave great recommendations and was so responsive to our questions. We will definitely stay here again!
Guest favorite
A modern living area showcases a coffered ceiling and stylish furnishings. Plush sofas and accent chairs are arranged around a coffee table, with a large wall-mounted television and a decorative painting enhancing the aesthetic. Natural light enters through multiple windows, illuminating the space.
Condo in West Town
4.98 out of 5 average rating, 160 reviews

Spacious 4 Bedroom Condo

IzabelRating, 5 stars2 weeks ago
Had a great time with friends and we were all able to comfortably hang out in communal spaces, get around the city. The bathroom to room ratio was ideal for a group of girls to get ready and the neighborhood made us feel safe walking around at all times of the day. Would recommend
Guest favorite
An outdoor patio space is showcased, featuring a large table surrounded by several chairs. String lights hang overhead, illuminating the area. A gas grill is positioned nearby against a backdrop of exposed brick and wood fencing, creating a secluded atmosphere.
Condo in River North
4.99 out of 5 average rating, 134 reviews

Luxurious River North 3BR/2BA- Free Onsite Parking

JoelRating, 5 stars6 days ago
Neel went above and beyond for my family and I during our stay. The unit was quiet, fun to hang out in, extremely clean, great layout for a family, very convenient parking, and quiet. I would highly recommend staying here! Thank you Neel!
Guest favorite
A spacious living area showcases a light-colored sofa paired with dark green accent chairs. A glass coffee table sits atop a patterned rug, while decorative elements, including candles and potted plants, are arranged on a wall shelf. Natural light enters through large windows.
Condo in Logan Square
4.93 out of 5 average rating, 103 reviews

Wicker Park/Bucktown condo with large balcony

JaneRating, 5 stars3 weeks ago
Lauren’s condo is nestled in a quiet peaceful neighborhood. It is an ideal location for us just a 12 minute walk from our family’s condo. It is within walking distance to coffee shops, restaurants, and shopping. Lauren was very responsive to any questions. The condo is pleasing and tastefully decorated. Her condo was clean with a comfortable bed and bed linens. We love the neighborhood and look forward to our next visit.

Quick stats about vacation rentals with outdoor seating in Highland Park

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ184 before taxes and fees

  • Total number of reviews

    1.4K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

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