Photo by Tanesha Thompson

Woodlawn holiday rentals

We found 79 holiday rentals — enter your dates for availability

Discover a selection of 27 apartments, 11 flats and other holiday rentals in Woodlawn that are perfect for your trip. Holiday rentals provide the best amenities for your family, friends or furry companion, such as a fireplace and a washer and dryer. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday home accommodation in Woodlawn?
According to our data, apartments are the most sought-after property type in Woodlawn. But of course, everyone's idea of an awesome trip can vary. Stayz has holiday homes in a variety of sizes and shapes, so you're bound to find your ideal fit.
How much does it cost to rent a holiday home in Woodlawn?
The average price for a holiday home in Woodlawn depends on several factors, including property type, season and length of stay. Whether you're in search of a villa with space for extended family or a cosy cabin perfect for just you and the kids, just enter your dates of travel to see stays with terrific value.
How much does it cost to rent a beach house in Woodlawn?
Prices for beach houses in Woodlawn can vary depending on the style and size of the property and time of year you're travelling. Simply enter your travel dates into Stayz and how many guests to see your options and prices. From there you can use our filters to tailor your search results by ratings, nearby activities and more.
Are there pet-friendly holiday homes in Woodlawn?
Yes, there are. Pick from 14 holiday homes that welcome pets in Woodlawn on Stayz. Our furry friends also need a break, so simply use our search function for pet-friendly holiday homes to book a perfect pad where your puppy can get in on the family fun.
What are popular home amenities in Woodlawn?
The most popular home amenities people search for in Woodlawn include a garden, nearby museums and a barbecue grill. Whether you're going on holiday with family, pals or even pets, Stayz holiday properties include the best amenities for hanging out with the people that matter most.
Are there holiday homes in Woodlawn that welcome kids?
With 14 family-friendly holiday homes to select from in Woodlawn, now is a superb time to introduce your little ones to the wonders of travel. Check our "Properties good for families" filter to browse stays that come with conveniences perfect for travelling families, like living rooms, swimming pools, entertainment areas and hot tubs.
What are the top attractions for families in Woodlawn?
There are tons of wonderful things to see and do with the family in Woodlawn, such as:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Can I find two-bedroom holiday homes in Woodlawn?
Gather your family and experience complete comfort and privacy in one of the five two-bedroom holiday properties Woodlawn has to offer.
Are there holiday homes with WiFi in Woodlawn?
Woodlawn has 11 holiday homes with WiFi, so you can stay connected during your holiday. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movies with your family to writing and sending emails, these Stayz homes make it a breeze to get online.
How can I find holiday homes with air conditioning in Woodlawn?
Woodlawn has 12 holiday homes where you'll be able to relax in air-conditioned comfort. To find a stay on Stayz that provides this perk, enter your desired travel dates and use the filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Woodlawn?
The minimum age requirements can vary across properties on Stayz, so be sure to check the rules of the holiday home in Woodlawn you're interested in. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Woodlawn for?
The amount of time you can rent a Woodlawn holiday home for depends on each property. Just enter your travel dates to see options offering extended stays. They have all the things you need to make your extended trip more enjoyable and comfortable, such as laundries and air conditioning. Some properties may also offer discounted weekly or monthly prices, so you can stick around for longer for less.

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