Vacation rentals in Oak Park

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Oak Park vacation rentals

Stay near Oak Park's top sights

Frank Lloyd Wright Home and Studio184 locals recommend
Classic Cinemas Lake Theatre72 locals recommend
Ernest Hemingway Birthplace Museum70 locals recommend
Maya Del Sol67 locals recommend
FitzGerald's62 locals recommend
Spilt Milk57 locals recommend

Other great vacation rentals in Oak Park

Superhost
Home in West Lawn
4.92 out of 5 average rating, 38 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

AshleyRating, 5 stars1 month ago
Johanna made us feel warm and welcome. All amenities are included and work well. Excellent shower. She was very responsive and attentive.
Guest favorite
Apartment in West Town
4.85 out of 5 average rating, 129 reviews

Condo with private terrace, free WIFI and parking

SheaRating, 5 stars1 month ago
Loved this place! My three friends and I had plenty of space and felt right at home. The location in West Town is perfect -- not busy or loud at all, but very easy to walk to coffee shops or restaurants in less than 10 minutes. Plus, the hosts were very friendly and accommodating!
Guest favorite
Home in Chicago
5 out of 5 average rating, 5 reviews

Birthday?Anniversary?Showers?3500 sq ft, sleeps 16

ArissRating, 5 stars1 week ago
Vince’s place was amazing, it was such a good location, easy to drive to anywhere in Chicago. Vince was very easy to contact and was responsive within minutes. He made our stay very comfortable. The house was amazing and there was a lot of space, and there was a lot of amenities available for use, for example kitchen utensils and shower amenities. Overall this stay was amazing and I would book this again if I came back in the future
Guest favorite
Apartment in Albany Park
4.86 out of 5 average rating, 42 reviews

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars2 months ago
Wonderful stay as always, thank you so much!
Superhost
Apartment in Jefferson Park
4.63 out of 5 average rating, 24 reviews

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars3 weeks ago
Peaceful, felt like home, very spacious and comfortable
Superhost
Condo in East Rogers Park
4.79 out of 5 average rating, 29 reviews

Spacious condo with open floor plan and fireplace

TatianaRating, 5 stars3 months ago
This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.
Top guest favorite
Home in Lombard
5 out of 5 average rating, 25 reviews

Spacious Home in Chicago Suburbs

JenniferRating, 5 stars1 week ago
It was great! The house was lovely and looked newly renovated. It was much roomier than I expected. The beds were very comfortable.
Superhost
Home in Wood Dale
5 out of 5 average rating, 4 reviews

Home in the Woods!

MaikoRating, 5 stars1 week ago
We had such a wonderful time at Jazmin Airbnb. The place was clean and smell great! She was very responsive and we had no issue with checking into our Airbnb. Thank you for being such a great host!

Quick stats about vacation rentals in Oak Park

  • Total rentals

    320 properties

  • Total number of reviews

    19K reviews

  • Family-friendly rentals

    160 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wifi availability

    320 properties include access to wifi

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Oak Park?

    Yes! Work meets play with ease at over 180 vacation rentals in Oak Park featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in condo rentals in Oak Park?

    Experience the best of Oak Park with our condo rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Oak Park?

    Four-legged friends are welcome in Oak Park. Choose from more than 70 vacation rentals for guests traveling with pets.

  • Do guesthouse rentals in Oak Park have air conditioning?

    Absolutely! We offer over 10 guesthouse rentals with air conditioning in Oak Park. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in Oak Park have wireless internet?

    Absolutely! We offer over 10 guesthouse rentals with wireless internet in Oak Park. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Oak Park have a gym?

    Absolutely! We offer over 10 apartment rentals with a gym in Oak Park. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Oak Park have a bbq area?

    Absolutely! We offer over 10 apartment rentals with a bbq area in Oak Park. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Oak Park?

    Oak Park has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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