Holiday rentals with a fire pit in South Side

4.95 out of 5 average rating, 398 reviews

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

House is perfectly located within walking distance of Pilsen's best attractions. Home is furnished and newly renovated with the idea of making your stay as comfortable as possible. Walking distance from Thalia Hall and many other great restaurants and coffee shops. For your convenience there is a "corner store" steps from the home where you can purchase food and beverage items. The whole apartment is professionally cleaned after every guest no matter how many days they have stayed. Fresh sheets and towels are provided for all guests as well. Walking distance from local favorites: Simone’s, Honky Tonk BBQ, Dusek's/Punch House/Thalia Hall, 5 Rabanitos, Furious Spoon, S.K.Y and HaiSous. Located 2 miles South West of Downtown Chicago. Extremely close to South Loop and West Loop. Amenities: - Washer and Dryer (located in unit) - Granite counter tops - All new appliances - Tiled bathroom - Central Heat/AC - Private back deck - Closet space All access, full kitchen, washer and drier in apartment. Private entrance with Keyless entry. Available at any time, happy to answer any questions you may have. Interaction will be dictated by guests. This is a vibrant family neighborhood with character, art, great food, and culture. Walk to amazing restaurants, bars, and coffee shops, including local favorites Simone’s, Honky Tonk BBQ, 5 Rabanitos, Furious Spoon, S.K.Y, and HaiSous. Close to major Chicago highways: I-190: Kennedy Expressway I-290: Eisenhower Expressway I-55: Stevenson Expressway I-90/94: Chicago Skyway, Dan Ryan Expressway, Kennedy Expressway, Jane Addams Memorial Tollway Public transit easily accessible: CTA Bus #8, 18, 60 CTA Trains: Blue, Pink and Orange Lines Divvy Bike Rental Station one block away Permit Parking $6-10 dollar Uber to Downtown

4.96 out of 5 average rating, 123 reviews

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

1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard with exceptional landscaping. The property has a car port in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! NO CHORES! Please reach out with any questions you may have before booking Hot tub 5-6 Person Spa

4.9 out of 5 average rating, 216 reviews

Handicap accessible apartment w/Level-2 EV Charger

Just 12.5 miles from downtown in the extremely quiet Chicago neighborhood of Hegewisch. Walking distance to the South Shore train line, which can easily get you to Chicago museums and entertainment, or attractions in NW Indiana. Private parking in back also gives you the option of driving anywhere and then walking directly to your door, and outside cameras are present for security. Banks, restaurants, grocery, convenience, and liquor stores are all 1 block of the apartment for all your needs.

4.86 out of 5 average rating, 104 reviews

Skyline 2BR in South Loop Chicago Near McCormick

Welcome and Experience Chicago in style at our upscale corner suite nestled in the dynamic South Loop district—just steps from McCormick Place and minutes from top city landmarks. This modern, metropolitan 2-bedroom, 2-bathroom suite features soaring 10 ft ceilings, a spacious open layout, and curated interiors that set it apart from the average stay. From custom furnishings to thoughtful amenities, we’ve created an elevated home-away-from-home for families, professionals, and long-term stays.

4.97 out of 5 average rating, 310 reviews

Flat in Cicero

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

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

4.99 out of 5 average rating, 146 reviews

Home in Berwyn

Retro Modern Bungalow | fire pit | free parking

Experience the city in style at Retro Modern Bungalow—the perfect pad for up to 4 friends. Featuring two spacious bedrooms, each with a king bed and luxury linens, a propane fire pit and a fully fenced [pup-friendly] back yard. Enjoy central HVAC, hi-speed WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

4.87 out of 5 average rating, 247 reviews

Cottage in Merrillville

The Hideaway

This Christian friendly cozy cottage, located 30 minutes from Chicago is located on a private 3 acre property. It’s a private detached cottage from main house that sleeps four. One king size bedroom (2 air mattresses) (sheets supplied), large full bathroom with deep tub w/ handle (towels supplied), full kitchen (dishes, pots and pans ect supplied) private covered parking and yard (directly in front of cottage) w/ its own fire pit for enjoyment. No plug for electric cars (station 2 m away).

4.86 out of 5 average rating, 139 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

4.93 out of 5 average rating, 804 reviews

Treehouse in Schaumburg

Enchanted Garden Treehouse (Amenity*)

Summer is here, flowers are blooming, the treehouse is air conditioned and cozy, and the hot tub ready! Relax in our luxurious, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The running stream makes this a wildlife refuge, with tons of birds, squirrels, rabbits, foxes and hawks. We are 420 friendly. Come experience the magic and make a special memory!

4.9 out of 5 average rating, 110 reviews

Guest suite in Chicago

1 bed apartment + futon room bridgeport

Located at the geographic center of Chicago! Plenty of free street parking. Very safe and ~10 min walk to the 35th Orange line and 3 blocks from the Archer bus, both go directly downtown within minutes. Brand new lower level construction unit. Comfortable spacious rooms to relax in. Closet in both rooms for your use while here. The apartment has a separate entrance, bathroom, kitchen, dining space. Enjoy your own private space in Chicago with a back patio, grill, and laundry.

Guest house in Merrillville

4.92 out of 5 average rating, 111 reviews

Romantic Getaway Guesthouse/ Jacuzzi/Sauna/Pool

Romantic Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse/in-law suite offers ultimate relaxation with a private entrance, spa-like jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.

4.92 out of 5 average rating, 139 reviews

Home in Chicago Ridge

Quiet cul-de-sac with huge fenced in backyard

3 bedroom, 2 bath ranch home on a quiet cul-de-sac. Big fenced in backyard for the kids, dog, & adults to play during the day, then relax by the fire at night. Walking distance (50 ft.) to the bar/restaurant with private entrance. 15 miles (25 mins) from downtown Chicago. And for you couples, come back home from your busy day, sit back and relax in the 8 jet jacuzzi whirlpool tub that will comfortably fit both of you.

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Popular amenities for rentals with a firepit in South Side

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House rentals with a firepit

5 out of 5 average rating, 6 reviews

Home in Homewood

Modern Charming Home w/Pergola & games

KellyRating, 5 stars3 days ago

This place is definitely a gem! Excellent location and spacious house for a family! We will book here again when visiting the area. Very clean, accommodating and comfortable stay!

4.9 out of 5 average rating, 10 reviews

Cozy Modern Home w/Fireplace & Pond

JazsminRating, 5 stars4 months ago

The host was very nice and attentive. The place was very nice and clean. Great place to stay

4.72 out of 5 average rating, 54 reviews

Animal House near Sox stadium

ChristineRating, 5 stars1 month ago

If you're traveling with a pet I would highly recommend this place! Great location and great communication throughout our stay.

4.94 out of 5 average rating, 148 reviews

BoHo House - A Chic, 1903 Chicago Workers Cottage

niratiRating, 5 stars2 weeks ago

Adam was a great host and very responsive. We loved our stay. The house was clean and the house is easily accessible to everything. Would definitely recommend!

4.98 out of 5 average rating, 115 reviews

Entire first floor in Lincoln Square!

Mary BethRating, 5 stars1 week ago

This is our second stay at this location and we hope to return again in the future. It is a very well-maintained place in a safe location. Also, we love how clean it is!

4.83 out of 5 average rating, 122 reviews

Woodlawn Oasis: 5-15 Mins from Food, Fun, Dining

HaliRating, 5 stars1 month ago

This was a fantastic find! My whole party loved the place. It was clean and wonderfully located in a peaceful neighborhood close enough to transport to walk but far enough from the noise and bustle of downtown. Shawn was very responsive to any questions I had and was super kind and friendly! I absolutely would stay here again!!

4.83 out of 5 average rating, 71 reviews

Brand New Spacious Duplex

LillianRating, 5 stars1 week ago

I just wanna say thank to each other to host. It was nice and big. The bed downstairs was a little hard. The water stain around the basement floor area and it did smell like mold. Other than that. It was good value for your money. Parking was a challenge for us, but we figured it out. Have a great day if you stay.

4.83 out of 5 average rating, 23 reviews

Home in Burbank

Cozy getaway in the city.

CynthiaRating, 5 stars1 week ago

Juan was not only a great communicator but his home was beautiful and centrally located. If ever in the Chicago/Burbank area would definitely love to rent.

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Apartment rentals with a firepit

4.95 out of 5 average rating, 227 reviews

Flat in Berwyn

Spacious Oasis Berwyn with Free Parking

ZhongyuRating, 5 stars1 week ago

Safe and quiet location with easy access to various business and restaurants in very close proximity! Spacious and bright rooms that can literally sleep 8, making it especially spacious for 4 of us. All amenities listed in the ad are functional and easy to use. Plenty of parking spaces for up to 3 cars, a big plus in the Chicago area. Hosts are fantastic for providing all needed services without interfering privacy! We felt like at home!!! Great organic cup coffee is a huge plus to start the morning with! Extremely kids friendly with so many toys, games, and books offered, together with a fancy bunker bed set! Definitely our first choice whenever we visit Chicago!

4.92 out of 5 average rating, 197 reviews

iKlektik House Chicago / BlueJay

ARating, 5 stars2 weeks ago

We really enjoyed our stay here! Perfect for two people. This place is really cute and unique. Love the decor and seeing all the cool art projects. This place was within a couple miles of all the places we wanted to see, especially Soldier Field, so a Uber/taxi ride was cheap and very convenient. Super cute neighborhood too with beautiful row houses both modern and original. It is a nice quiet neighborhood as well and we felt very safe! We would recommend the Iklektik/Blue Jay house to anyone visiting Chicago that wants a comfortable and cozy experience!

4.97 out of 5 average rating, 123 reviews

Stylish 2BR stunner w/ unbeatable location

KathleenRating, 5 stars1 week ago

We had the absolute best experience staying at Eric’s place in Ukrainian Village. The parking was a huge plus, it was walkable and felt so safe and charming! The space was stunning and matched the listing perfectly. Will definitely be staying here next time we come to Chicago!

4.99 out of 5 average rating, 156 reviews

Flat in Forest Park

Sunny 1 bedroom apartment 1 block from restaurants

EleanorRating, 5 stars1 week ago

Jim was a fantastic host. Very responsive and timely in his communications and support for our needs during our stay in their place. Their home was comfortable and well appointed with additional amenities you don't often see in AirBnB spaces, like N'espresso appliances and supplies. We would definitely consider repeat visits! Thank you, Jim!