Condo vacation rentals in Oak Park

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Top-rated condo rentals in Oak Park

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Guest favourite

Condo in Chicago

4.86 out of 5 average rating, 334 reviews

Peaceful & Airy Modern-Chic Condo in Trendy Pilsen

Brand New Private Modern 2 bd 2bth apt for your stay in Chicago. We are located 2 blocks form the CTA line in the heart of Pilsen, a neighborhood Time Out labeled the 10th coolest in the world. Newly renovated, hardwood tiled floors throughout, chefs kitchen, toiletries, brand new furnishings including 2 queen beds, 1 twin sleeper, fresh linen, smart TV (HBO, Netflix, Hulu) wifi, tons of books,coloring books,board games & puzzles! We truly want you to feel like this is your home away from home.

Guest favourite

Condo in North Center

4.92 out of 5 average rating, 134 reviews

Spacious & Modern Family Friendly North Center Apt

Newly renovated, modern kitchen & bath, solar-powered, comfortable beds. Great location in safe neighborhood, Jewel Grocery store, Trader Joe’s, craft breweries, restaurants, bars, Wrigley Field nearby & brown line train to downtown Loop. Families with children are welcome. Owners with 2 young kids live upstairs, we are available to address guest needs. No smoking anything on property. Parties & excessive noise prohibited, max of 6 people allowed inside at anytime. Quiet hours 11 pm - 8 am.

Guest favourite

Condo in Andersonville

4.9 out of 5 average rating, 176 reviews

The Bright Retreat in Andersonville

Stay in the heart of Andersonville when you book this bright, newly renovated condo. The home is one block from Clark Street near some of Chicago's best restaurants. It is 3 blocks from the Argyle Red Line stop, which will get you to Wrigley in 15 minutes and downtown in 30 minutes. The home includes a fully stocked kitchen, free parking spot (small and medium size cars and SUVs only, not large vehicles), in unit washer & dryer, queen-size bed, and couch with queen-size memory foam mattress.

Guest favourite

Condo in East Rogers Park

4.9 out of 5 average rating, 123 reviews

Magnificent Place & A Parking Space

1 Bedroom with 1 bathroom This spacious, quiet condominium is located in the Rogers Park neighborhood of Chicago, 3 minute walk from the local pubs, restaurants, shopping, and tennis court. Great for weekend trips as the beach is a quick bike ride 5 minute bike ride. Metra UP-Northwest, a 17 minute train ride to Downtown Chicago (4 min walk West to catch this train). CTA Morse Red Line Train is also available, making multiple stops on its way Downtown (5 min walk East to catch this train).

Guest favourite

Condo in Humboldt Park

4.96 out of 5 average rating, 127 reviews

Stylish 3BR + Free Parking 10-15mins from Downtown

This apartment is located in Historical Humboldt Park, a residential area that is an easy 10-15mins drive to Downtown, Medical District, Wicker Park, West Town, Logan Square, and Ukranian Village. Due to the proximity, we host guests visiting for tourism, fests,concerts, sport events , work conferences, weddings, birthdays, and visiting family. There are grocery stores closeby. There’s street parking and a gated private parking available. Location wise, you are close enough to everything.

Guest favourite

Condo in Little Italy

4.97 out of 5 average rating, 145 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Guest favourite

Condo in Irving Park

4.85 out of 5 average rating, 105 reviews

Newly updated 1BD/1B in Old Irving Chicago!

Welcome to your home away from home in the heart of one of Chicago's safest and quietest neighborhoods! This beautifully updated 1 bedroom apartment offers everything you need for a comfortable and convenient stay. It is perfect for couples, solo travelers, and business visitors. Book now for a truly unforgettable experience in the Windy City! - 1 free parking spot - 400 MB Wifi - 2 smart T.V. with access to Netflix, Hulu, Amazon and more! - Desk - Easy app paid laundry in the building.

Guest favourite

Condo in Logan Square

4.98 out of 5 average rating, 246 reviews

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

Luxurious 1BR/2BA garden-level condo in vibrant Logan Square! Comfortably furnished with tons of light and amenities, conveniently located one block from the Logan Square Blue Line Station and located on a quiet street. Steps from all of the hip restaurants and nightlife in Logan Square. Huge back yard and patio with fire pit for guest use. Free on-site garage parking with remote. And, if using public transit, the Logan Square is 8 stops, ~15-20 minutes from the Loop downtown!

Guest favourite

Condo in Oak Park

4.88 out of 5 average rating, 173 reviews

Attractive Flat - Historic Oak Park

Attractive One Bedroom Flat for Rent in Historic Downtown Oak Park. Truly - one of the Best Locations in all of Chicago. Two Blocks from the Epicenter of this lovely city. Easy Access to Public Transportation to Downtown Chicago or the Greater Metro Area. The Elevated train -and- the Metra Train (15 Minutes by Train to Downtown) are each a quick walk. See “ property description “ For Important information for all perspective Guests:

Superhost

Condo in Humboldt Park

4.86 out of 5 average rating, 148 reviews

3D Tour! Designer Condo near Logan Square

Scan QR code in photos for a 3D Tour! What you’ll love: - Totally renovated garden unit, completed in 2021. Everything new. - Upscale furnishings & decor. - Gourmet, fully equipped kitchen w/ new appliances, coffee maker and spices. - Remote work station w/ super fast Wi-Fi (600mb). - Serta queen mattress in master. - Bunk beds w/ full and twin sized memory foam mattresses. - Heat & A/C.

Guest favourite

Condo in Oak Park

4.94 out of 5 average rating, 160 reviews

Picture Perfect 3Bed Steps from Train and FLW

Welcome to your beautiful 3 bedroom home-away-from-home! From the Instagram-worthy forest room to the cozy fireplace reading nook to the modern ice crusher in the kitchen, we've put so much thought into this home that we're sure you won't ever want to leave. Welcoming and newly updated, this unit is close to restaurants, shopping, the best of Frank Lloyd Wright, and the train to the city.

Superhost

Condo in Oak Park

4.79 out of 5 average rating, 329 reviews

Peaceful Oak Park Condo Next to Green Line Metro

Very private, quiet space amidst the activity of Downtown Oak Park. The layout of the space is ideal, as bedrooms are at one end, and the living space is at the other. Private outdoor deck. Oak Park is a beautiful neighborhood full of great places to eat, drink, and shop. Metro and Green line is steps away which means access to anywhere in the city of Chicago. Private parking too!