Vacation rentals with a patio in Plainfield

Find and book unique patio rentals on Airbnb

Top-rated patio rentals in Plainfield

Guests agree: these patio rentals are highly rated for location, cleanliness, and more.

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Guest favorite

A spacious living room features a classic brick fireplace and large windows adorned with sheer white curtains, allowing natural light to brighten the space. An inviting white sofa and a cozy armchair are complemented by a textured area rug, creating a comfortable environment for relaxation.

Home in Lincoln Park

5 out of 5 average rating, 11 reviews

Top Floor in Historic Old Town!

Unbeatable Location in Historic Old Town Triangle! This charming top-floor apartment is on a quiet cul-de-sac in the heart of Old Town Triangle, steps from St. Michael’s Church, North Ave Beach, Lincoln Park Zoo, and Wells Street’s entertainment district. The sun-filled space features an oversized private patio, and 3 bedrooms with queen beds, closets, and dressers. The spacious kitchen and dining areas are perfect for gatherings. The “L” stop is just two blocks away for easy access to the city.

Top guest favorite

A spacious rooftop patio features a covered bar with four stools, surrounded by lush greenery and views of the city skyline. Soft lighting hangs above, and sheer white curtains provide a touch of elegance while maintaining a connection to the outdoors.

Home in Near North Side

4.98 out of 5 average rating, 43 reviews

Private Downtown Retreat with Rooftop Oasis

Welcome to your exclusive retreat in the heart of the city, where urban sophistication meets unparalleled comfort. Nestled in between Magnificent Mile and Gold Coast, this luxurious Airbnb offers a haven of style and tranquility amidst the hustle and bustle. The rooftop patio offers incredible views of the city skyline, with touches of lush greenery. The spacious living areas boast oversized windows that flood the space with natural light. Each bedroom is a sanctuary where luxury meets comfort.

Superhost

Home in Highland Park

5 out of 5 average rating, 28 reviews

Sanctuary on the Ravine

Take it easy at this unique and tranquil get away, walking distance to Ravinia and Beaches 3 Blocks.This historic, beautifully decorated and well maintained home has a lovely, peaceful & serene setting. Multiple indoor and outdoor seating arrangements. Fully stocked kitchen that opens to family room looking out onto several multilevel brick patios and a quiet, private ravine. The extra large living room has a down feathered sectional couch that seats up to 10 people. No parties or gatherings

Superhost

An outdoor space features a gazebo and comfortable seating, framed by vibrant flowers. The heated above-ground pool is visible, surrounded by a wooden deck. Lush greenery serves as a backdrop, creating a serene setting enhanced by soft evening light.

Home in Carol Stream

4.42 out of 5 average rating, 24 reviews

Amazing Summer Pool Awaits You!

Vacation, Staycation or Business, you will love your stay at this beautiful paradise with heated pool and tri-level entertainment deck equipped with grill and outside seating and gazebo! Semi-secluded backyard, walking distance to bike path, playground, skate park, walking trails, restaurants and even the gym! Relax on the magnificent deck while watching the sunset This home is pet free and smoke free. Pool is available May-Sept. WiFi is available throughout and Smart TV in the family room.

Guest favorite

A vibrant living area features two orange armchairs positioned around a decorative wooden table. A floral wallpaper adorns the wall behind a wall-mounted television, while a rich area rug anchors the space. Natural light filters through sheer curtains, highlighting the room's colors.

Apartment in Wicker Park

4.96 out of 5 average rating, 144 reviews

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Location! Location! Location! Prime Wicker Park Location on Milwaukee! This spacious, cool, vibrant, eclectic, fully equipped apartment is close to everything, making it easy to plan your visit. Bright top floor unit with a private patio to just chill and unwind or walk downstairs and your literally in the heart of Wicker Park. Super easy access to downtown nightlife/lake/museum all within 15 minutes and super easy commute to O'hare. CTA busses all around and a 2 minute walk to the Blue Line.

Top guest favorite

A spacious patio area is configured with a large dining table and six chairs, shaded by a green umbrella. The backdrop features a well-maintained lawn and a portion of the house, showcasing a blend of light-colored siding and a sliding glass door.

Home in Elgin

4.89 out of 5 average rating, 18 reviews

Chic, Cozy & Beautiful w/2 King Beds & BBQ/Patio

Kick back & relax in this serene, stylish retreat. Furnished w/handpicked treasures from exquisite estate sales from some of the most beautiful homes in the area. This space is a blend of comfort & elegance, the perfect place to unwind! 3 good-size bedrooms, 2 w/King Size Beds, master on-suite bath, 75" 4K TV in the stylish living room... a huge backyard w/patio & Weber BBQ Grill. A very nice home updated in July 2024 - brand new doors, lighting, plumbing fixtures, fresh paint...Don't miss!

Guest favorite

A cozy sitting area features a blue armchair and a light gray sofa adorned with yellow accent pillows. A wooden coffee table sits in front, placed on a patterned rug. A wall art piece of a toucan against floral imagery adds a touch of color.

Apartment in Oak Park

4.85 out of 5 average rating, 103 reviews

Circle Back Modern Apartment

Sit on your leafy private patio and enjoy your coffee before heading out to the city- or wind down at the end of the day with a cold beer. Steps to coffee shops, neighborhood pubs, and the Blue Line train this beautifully updated and decorated apartment is the perfect landing pad for your Chicago adventure. FREE off-street parking, free in-unit laundry, a cute coffee station- basically every amenity we could think of! This will be the place you want to stay every time you visit Chicago.

Superhost

A cozy living area features a gray sectional sofa positioned across from a light coffee table. A tall indoor plant adds a touch of greenery, while natural light filters through the window, adorned with sheer curtains. A dining area is visible in the background.

Apartment in Lake View

4.82 out of 5 average rating, 116 reviews

Chic Penthouse In Perfect Wrigleyville Location

Bright and open top floor apartment within easy walking distance to many of the best sites in Chicago: Wrigley Field, Lake Michigan, Lincoln Park, top notch neighborhood restaurants, pubs, and entertainment, and many more! With so much to do in the area and easy access to public transit you're sure to have jam-packed days of exploring and enjoying the city. After a long day, come back to this peaceful apartment to relax, recharge, and prepare to do it all again tomorrow. Book today!

Top guest favorite

A well-designed outdoor space features a paved patio area with multiple seating options, including blue chairs and a table. Wooden deck steps lead to an entrance, while vibrant green and orange decorations add color to the surrounding fence. A clean and spacious environment is offered.

Home in Avondale

5 out of 5 average rating, 11 reviews

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

Guest favorite

A spacious living area features a large, cozy couch with warm, muted tones. A round black coffee table sits in front of the couch, adorned with a vase of fresh tulips. Natural light enters through two windows, with simple gray curtains providing a soft accent.

Apartment in Logan Square

4.82 out of 5 average rating, 103 reviews

Bucktown Garden Suite 7 min walk to train

Bucktown Garden Apartment in A+ location on quiet neighborhood street. Private suite equipped with full bath, fridge, snacks, large couch, and queen-sized bed + free public laundry with soap provided. Walk in any direction to get to some of Chicago's best bars and restaurants or hop on the blueline subway 3 blocks away and zip downtown to explore some tourist attractions. Very easy, free street parking on the block. NO SMOKING/VAPING OR DRUG USE ON THE PROPERTY

Guest favorite

A spacious outdoor patio area is surrounded by wooden buildings, featuring a circular table with four chairs. A grill is positioned nearby, and a large, blue umbrella provides shade. Planters with greenery add a touch of nature to the space, enhancing its relaxing atmosphere.

Condo in Wicker Park

4.83 out of 5 average rating, 338 reviews

Lively Wicker Park 2br, Steps to Damen Blue Line

Rehabbed 2BR 1BA garden unit in the very popular neighborhood of Wicker Park/Bucktown! 2 queen beds and full of amenities. Just a block from everything this neighborhood has to offer and 2 blocks from the 'L' to take you downtown or to O'hare Airport. Premium location to effortlessly walk from our quiet side street and be in the heart of all the entertainment! I provide all the essentials to make your stay easy and comfortable!

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, 135 reviews

Modern 3BR with Private Rooftop & Free Parking

A beautiful and modern 2450 sq feet apartment with a private rooftop deck, a rooftop firepit, an additional private patio and yard, brand new appliances, and bright spacious interior. Free private on-premise parking (1 garage spot and one driveway spot) in the heart of Chicago and a blocks walk to the L-transit system provides easy access to both downtown, the greater Chicago area, and both major airports.

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What guests are saying

Floresitas Oasis, your home in Chicago

4.94 out of 5 average rating, 34 reviews4 days ago

Lizbeth is a very responsive and proactive host. She is quick to answer and she is very welcoming. I highly recommend her as a host! The house is very cozy and tidy as well. It is well kept and everything you would need is available in there. It was a pleasure staying there.

Home in Chicago

What guests are saying

Evergreen Retreat

5 out of 5 average rating, 22 reviews4 days ago

This is a very beautiful house with TONS of space, big and perfect for my healing retreat, I hosted 9 ladies, the backyard is huge plus there was an outdoor event area. The place looked exactly like pictures, clean, host was responsive and polite. The house is very relaxing and peaceful. I would definitely recommend!

Home in Aurora

What guests are saying

Loft on Lake in Oak Park

5 out of 5 average rating, 6 reviews1 month ago

I had the most incredible stay at Jay’s Loft on Lake Street. From the moment I walked in, I was blown away by the beautiful décor. Every detail was thoughtfully curated, creating a warm and inviting atmosphere. The space was not only stunning but also incredibly comfortable and clean, providing everything I needed for rest and relaxation - including a fully stocked gourmet kitchen. The master bedroom, with its luxurious ensuite bathroom, was a true highlight. The plush bedding, calming ambiance, and spa-like bathroom made it feel like a private retreat — the perfect way to unwind after a long day. Every aspect of my stay exceeded expectations, and I can’t recommend this place enough for anyone seeking a peaceful, stylish, and rejuvenating getaway. I’ll definitely be back!

Apartment in Oak Park

What guests are saying

Skip the hotel! Relax here!

4.8 out of 5 average rating, 35 reviews3 days ago

Great location for our family in Aurora and Oswego that we were visiting. The neighborhood was nice and quiet. I enjoyed walking down to the Fox River Trail in the mornings and we loved siting out on the patio in the evenings. The kitchen was fully equipped with everything you could possibly need to cook any meal! The beds were a little too soft for us, but overall it was a great stay.

Home in Montgomery

What guests are saying

Cozy Countryside Cottage with private patio

5 out of 5 average rating, 10 reviews2 weeks ago

My wife and two small children stayed with me at this home of 1 week. We had an excellent stay and have zero complaints. Access to the home was easy yet secure. The home was spotless and tidy. It had all mentioned amenities and was more than comfortable for my family. We had zero issues. Rita was an attendant and pleasant host to have. We will stay here again if we are in the area. Highly recommend.

Guest suite in Carpentersville

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