Villa holiday rentals in Chicago
Find and book unique villas on Airbnb
Top-rated villa rentals in Chicago
Guests agree: These villas are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago villa rentals
Private villa rentals
Villa in Alsip
New place to stay2 Full Beds | Non-Smoking
Villa in Bridgeview
New place to stay1 King Bed|Access|NS
Villa in Harvey
New place to stay2 Full Beds | Non-Smoking
Villa in Naperville
New place to stay2 Queen Beds|NS
Villa in Hammond
New place to stay2 Full Beds | Non-Smoking
Villa in Naperville
New place to stay1 Queen Bed|Deluxe
Villa in Lombard
New place to stay2 Queen Beds | Micfridge
Villa in Bridgeview
New place to stay2 Full Beds|Premium|Mini Fridge
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- South Side Holiday rentals
- Saugatuck Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Rentals with lake access Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with an accessible height bed Chicago
- Townhouse rentals Chicago
- Rentals with an EV charger Chicago
- Mansion rentals Chicago
- Loft rentals Chicago
- Rentals with a patio Chicago
- Guesthouse rentals Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Lakehouse rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- House rentals Chicago
- Rentals with a home theatre Chicago
- Rentals with outdoor seating Chicago
- Rentals with pools Chicago
- Rentals with a balcony Chicago
- Apartment rentals Chicago
- Smoking-friendly rentals Chicago
- Waterfront rentals Chicago
- Bed and breakfasts Chicago
- Rentals with beach access Chicago
- Beachfront rentals Chicago
- Rentals with a fireplace Chicago
- Rentals with a sauna Chicago
- Kid-friendly rentals Chicago
- Fitness-friendly rentals Chicago
- Ski-in/ski-out rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Private suite rentals Chicago
- Villa rentals Cook County
- Villa rentals Illinois
- Villa rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Flossmoor Golf Club
- Things to do Chicago
- Food and drink Chicago
- Art and culture Chicago
- Tours Chicago
- Sightseeing Chicago
- Things to do Cook County
- Tours Cook County
- Sightseeing Cook County
- Art and culture Cook County
- Food and drink Cook County
- Things to do Illinois
- Tours Illinois
- Art and culture Illinois
- Food and drink Illinois
- Sightseeing Illinois
- Things to do United States
- Tours United States
- Sightseeing United States
- Wellness United States
- Food and drink United States
- Nature and outdoors United States
- Art and culture United States
- Entertainment United States
- Sports activities United States