Pet-friendly holiday rentals in Homewood

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.

Entire home: Private, Cozy Oasis in a Quiet Locale

30 minute drive from Chicago's Grant Park. Near Little Calumet and Monon trails. Appeals to nature enthusiasts, cyclists, remote workers and brewery aficionados. This 2 bedroom, 1 bathroom retreat offers comfort and convenience. Full kitchen, private backyard and comfortable living space. 3 casinos, 6 breweries: 3 Floyds, 18th Street, Fuzzyline, Byway, New Oberpfalz & Wildrose within 7 to 20 min drive. Early check-ins offered/subject to availability. Feel free to inquire on availability.

Charming Garden Apartment

Make yourself at home in a charming apartment with all the amenities! Lose yourself birding or reading a book surrounded by lush gardens. Take a short walk to downtown Homewood to enjoy shopping & dining or catch the train to Chicago. 🏳️‍🌈 BLM Safe space! After a day of exploring, a king-sized sleep number bed & lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs welcome! This suite has a kitchenette with a convection toaster oven & induction cooktop.

Retro Modern Bungalow | free parking | fire pit

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 backyard. Enjoy central HVAC, speedy 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.

Modern 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. The property has a parking slab 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! Please reach out with any questions you may have before booking. NO CHORES! Hot tub 5-6 Person Spa

Warm and comfortable inviting Suburban home !

160 year old land mark community, Framed cedar bevel siding 2 story home, front porch , 10 ft high ceilings, kitchen canned lighting home. 6 feet fence In closed yard, whole house water filtration system , Quite neighborhood with sidewalks . 19 miles to downtown Chicago , Metra train station and bus route, in walking distance . driving to the city of Chicago 5 minutes to major expressways . Host is willing to be available for any and all information 24/7.

Cozy three bedroom home in Munster , Indiana.

Plan your next escape to Indiana or Illinois and stay in this beautifully renovated and thoughtfully appointed 3 bedroom and 1 bath home. Located in the quiet and safe suburb of Munster, Indiana, the property is just a 3 minute, easy access to the I-94 Highway. Exciting Downtown Chicago is just 30 minutes away! Walk to Riverside Park and take in the scenic view while enjoying a morning croissant and coffee from one of the quaint neighbourhood cafés.

Private Guest House, in Gated Nudist Resort.

Book your get away today. Make it a few days or a week. If you've ever thought of trying social nudity. This is the place to do it. Very private 200+ acre property. You can also USE GUESTHOUSE AS BASE FOR SHORT DAY TRIPS, to Indiana Dunes State Park, Michigan Wine Country, or Chicago. You won't find a more beautiful, cost effective setting for a get away. This listing is for Guest house only (see guest access below)...where NUDITY IS NOT REQUIRED.

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

This beautiful, newly remodeled, spacious, 3 bed 2 bath ranch style home is set back on a large lot. Located close to a major hwy, restaurants and a shopping. Just 15 minute to Midway Airport, 25 mins to O'Hare, and 25 mins to Downtown Chicago. Its a great spot to get to everything! Perfect for families, vacationers, and business travelers. You must be 21 or older to book. You must provide a valid photo of your D.L. or State ID upon request.

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.

Cozy Lakeview Studio with Private Access

Enjoy luxury and comfort in this cozy lakefront studio with a private entrance, attached to a home where the friendly hosts reside. The studio offers a plush queen bed, a kitchenette with a mini fridge, microwave, induction cooktop, and a full bathroom. Located in one of Naperville’s safest neighborhoods, it’s just moments from cafes, restaurants, markets, and a biking trail, with easy access to I-88.

Worth It! 3 bedroom ranch home

Relax with the whole family at this peaceful place to stay. Just minutes from walking parks, outdoor concert venue, golfing, and down town! Comfy and inviting Ranch style home offers 3 bedrooms, a fully equipped kitchen, flat screen TVs, and large windows. The private backyard has a patio, and bbq grill. A real home away from home, we look forward to your new booking.