Owner Direct Vacation
Rentals in Woodlawn

The Best Owner Direct Vacation Rentals in Woodlawn. Explore thousands of vacation home rentals, large cabins, and villas near Woodlawn

  1. Owner Direct
  2.  USA
  3.  Illinois
  4.  Chicago
  5.  Woodlawn

Explore the Best Woodlawn Vacation Homes

Looking for the perfect place to stay in Woodlawn? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Woodlawn character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.

  • vacation rentals
  • luxury villas
  • beachfront homes
  • pet-friendly rentals
  • condos
10 (10 Reviews)
Condo
Modern Apt Near U of Chicago!
  • Air Conditioner
  • Parking
  • Pet Friendly
US
View Availability
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3.6 (52 Reviews)
Hotel
Best Motel By OYO Chicago I-90
  • Air Conditioner
  • Parking
  • Bedding/Linens
US
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10 (10 Reviews)
Condo
Modern Apt Near U of Chicago!
  • Air Conditioner
  • Parking
  • Pet Friendly
US
View Availability
|
6.1 (12 Reviews)
Apartment
Charming 3BD 2BTH Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
US
View Availability
10 (10 Reviews)
Condo
Modern Apt Near U of Chicago!
  • Air Conditioner
  • Parking
  • Pet Friendly
US
View Availability

Why Travelers Love Using
Owner Direct to
Find Woodlawn Vacation Rentals

What makes our vacation homes stand out?

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Verified Properties

Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.

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Value You Can Trust

Compare a range of properties and find fair, transparent pricing—no hidden fees.

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Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Popular Neighborhoods for Woodlawn Vacation Rentals

What are the best areas to stay in Woodlawn

Discover the top neighborhoods in Woodlawn and choose a place that suits your stay.

Monday Feb 23

Woodlawn, Chicago

Sun
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-3.5°C
Mon
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-4.9°C
Tue
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-1.9°C
Wed
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-0.3°C
Thu
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-1.7°C
Fri
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-2.3°C
Sat
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2.6°C

Common Vacation Rental Amenities Typical Vacation Rental Amenities

What sort of amenities will be available at your stay?

Our Woodlawn vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.

Indoor Amenities

  • indoor-amenities-kitchenFully equipped kitchens
  • indoor-amenities-living-areaSpacious living areas with streaming TVs
  • indoor-amenities-wifiComplimentary Wi-Fi
  • indoor-amenities-acAir conditioning and heating
  • indoor-amenities-washerIn-unit washer and dryer
  • indoor-amenities-bedPlush bedding and comfortable furniture

Outdoor Amenities

  • outdoor-amenities-balconyBalconies or patios with coastal views
  • outdoor-amenities-poolPrivate or shared pools
  • outdoor-amenities-bbqBBQ grills and outdoor dining areas
  • outdoor-amenities-parkingOn-site parking
  • outdoor-amenities-beachEasy access to beaches and attractions

How to Reserve Your Woodlawn Vacation Rental

Booking Made Simple

Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.

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SEARCH PROPERTIES

Use filters for location, amenities, and budget.

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VIEW DETAILS

Check photos, reviews, and features for your top picks.

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BOOK SECURELY

Confirm your stay safely through our trusted travel partners.

Woodlawn Vacation Rental FAQs

1. What are the top vacation rentals in Woodlawn?

2. Which vacation homes in Woodlawn are best for families?

If you are looking for a family-friendly vacation home in Woodlawn, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Woodlawn:

3. How many vacation rentals are available in Woodlawn?

Currently, the total number of properties listed in 2026 is over 102 in the Woodlawn area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Woodlawn.