Apartment
10.0(43 Reviews)
2 Bedrooms
4 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $276/Night
7 Nights - US $1,934
Oak Park Holiday Rentals
We compare holiday rentals from owners across Booking.com, Vrbo and Expedia.
- Up-front pricing
- No markup
- Trusted partners
Compare Villas, Resorts, & Rentals in Oak Park
10.0
Apartment
9.8(8 Reviews)
4 Bedrooms
10 Guests
- Parking
- Air Conditioner
Internet
Laundry
US $204/Night
7 Nights - US $1,425
Bed & Breakfast
9.8(135 Reviews)
1 Bedroom
Hot Tub
Breakfast- Parking
- Balcony/Terrace
US $286/Night
7 Nights - US $2,005
Apartment
10.0(13 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $282/Night
7 Nights - US $1,972
Bed & Breakfast
9.4(35 Reviews)
5 Bedrooms
10 Guests
- Breakfast
- Parking
- Balcony/Terrace
- Air Conditioner
US $323/Night
7 Nights - US $2,260
Apartment
9.6(12 Reviews)
1 Bedroom
- Parking
- Internet
Child Friendly
Security/Safety
US $330/Night
7 Nights - US $2,313
Apartment
10.0(11 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $361/Night
7 Nights - US $2,529
House
9.0(7 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Internet
- Security/Safety
US $345/Night
7 Nights - US $2,417
Apartment
9.6(12 Reviews)
1 Bedroom
- Parking
- Internet
- Child Friendly
- Security/Safety
US $386/Night
7 Nights - US $2,704
House
10.0(4 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $342/Night
7 Nights - US $2,395
House
9.0(4 Reviews)
4 Bedrooms
8 Guests
- Parking
Spa- Balcony/Terrace
- Internet
US $350/Night
7 Nights - US $2,450
Apartment
10.0(4 Reviews)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $217/Night
7 Nights - US $1,516
House
9.0(1 Review)
3 Bedrooms
6 Guests
- Parking
- Internet
- Child Friendly
- Security/Safety
US $330/Night
7 Nights - US $2,308
Apartment
10.0(3 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $155/Night
7 Nights - US $1,087
House
9.0(1 Review)
5 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $1,087/Night
7 Nights - US $7,607
Apartment
10.0(2 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $339/Night
7 Nights - US $2,376
Apartment
8.8(19 Reviews)
2 Bedrooms
4 Guests
EV Charge Station- Parking
View- Air Conditioner
US $378/Night
7 Nights - US $2,647
Apartment
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $322/Night
7 Nights - US $2,252
Apartment
8.7(16 Reviews)
3 Bedrooms
8 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $193/Night
7 Nights - US $1,353
Apartment
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $223/Night
7 Nights - US $1,560
House
8.7(3 Reviews)
2 Bedrooms
5 Guests
- Parking
- Internet
Accessibility
Sports/Activities
US $192/Night
7 Nights - US $1,344
Apartment
10.0(2 Reviews)
1 Bedroom
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $211/Night
7 Nights - US $1,478
Apartment
8.0(1 Review)
1 Bedroom
8 Guests
- Parking
- Air Conditioner
- Internet
Pet Friendly
US $239/Night
7 Nights - US $1,671
Apartment
10.0(2 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $127/Night
7 Nights - US $887
House
7.2(5 Reviews)
3 Bedrooms
9 Guests
- Parking
- Balcony/Terrace
- Internet
- Pet Friendly
US $195/Night
7 Nights - US $1,365
Apartment
10.0(1 Review)
2 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $2,972/Night
7 Nights - US $20,807
Apartment
4.3(3 Reviews)
2 Bedrooms
5 Guests
- Parking
- Internet
- Child Friendly
Wheelchair Accessible
US $136/Night
7 Nights - US $952
House
10.0(1 Review)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $748/Night
7 Nights - US $5,233
Apartment
1.5(2 Reviews)
4 Bedrooms
8 Guests
- Internet
- Child Friendly
- Security/Safety
US $244/Night
7 Nights - US $1,707
Apartment
10.0(1 Review)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $583/Night
7 Nights - US $4,081
Apartment
1.0(1 Review)
2 Bedrooms
3 Guests
- Parking
- Air Conditioner
- Internet
- Security/Safety
US $149/Night
7 Nights - US $1,043
Apartment
10.0(1 Review)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $303/Night
7 Nights - US $2,124
Apartment
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $205/Night
7 Nights - US $1,435
Apartment
10.0(1 Review)
2 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $287/Night
7 Nights - US $2,010
Apartment
4 Bedrooms
8 Guests
- Parking
- Internet
- Accessibility
- Security/Safety
US $205/Night
7 Nights - US $1,435
Apartment
10.0(1 Review)
1 Bedroom
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $222/Night
7 Nights - US $1,555
US $444/Night
7 Nights - US $3,109
Apartment
9.8(80 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $299/Night
7 Nights - US $2,096
Apartment
2 Bedrooms
6 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $294/Night
7 Nights - US $2,058
Apartment
9.8(80 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $151/Night
7 Nights - US $1,054
House
9.8(36 Reviews)
2 Bedrooms
4 Guests
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $288/Night
7 Nights - US $2,016
US $214/Night
7 Nights - US $1,499
Apartment
9.6(113 Reviews)
2 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $280/Night
7 Nights - US $1,963
Apartment
9.6(36 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $263/Night
7 Nights - US $1,842
Apartment
9.6(12 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $216/Night
7 Nights - US $1,509
House
9.6(8 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $220/Night
7 Nights - US $1,539
Condo
9.4(71 Reviews)
1 Bedroom
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $252/Night
7 Nights - US $1,763
Apartment
9.4(66 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $212/Night
7 Nights - US $1,487
Apartment
9.4(3 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $240/Night
7 Nights - US $1,679
Apartment
9.2(44 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $270/Night
7 Nights - US $1,891
Apartment
9.2(18 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $239/Night
7 Nights - US $1,671
Apartment
9.0(2 Reviews)
2 Bedrooms
- Parking
- Kitchen
- Air Conditioner
- Internet
US $282/Night
7 Nights - US $1,971
Apartment
8.8(8 Reviews)
2 Bedrooms
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $239/Night
7 Nights - US $1,670
Apartment
8.6(19 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $253/Night
7 Nights - US $1,773
Apartment
8.6(7 Reviews)
2 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $227/Night
7 Nights - US $1,590
Apartment
8.0(3 Reviews)
2 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $259/Night
7 Nights - US $1,811
Apartment
8.0(2 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $260/Night
7 Nights - US $1,819
Apartment
8.0(2 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $221/Night
7 Nights - US $1,548
Apartment
8.0(1 Review)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $126/Night
7 Nights - US $885
Apartment
5.0(2 Reviews)
2 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $266/Night
7 Nights - US $1,862
Apartment
5.0(2 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $141/Night
7 Nights - US $987
House
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,111/Night
7 Nights - US $7,777
Apartment
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $482/Night
7 Nights - US $3,374
Apartment
1 Bedroom
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $305/Night
7 Nights - US $2,137
Apartment
2 Bedrooms
2 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
- Child Friendly
US $218/Night
7 Nights - US $1,524
Apartment
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $187/Night
7 Nights - US $1,308
House
10.0(33 Reviews)
4 Bedrooms
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $555/Night
7 Nights - US $3,883
Apartment
10.0(17 Reviews)
3 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $588/Night
7 Nights - US $4,119
House
10.0(14 Reviews)
4 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $372/Night
7 Nights - US $2,604
House
10.0(11 Reviews)
4 Bedrooms
9 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,098/Night
7 Nights - US $7,685
Apartment
10.0(11 Reviews)
5 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $505/Night
7 Nights - US $3,534
House
10.0(7 Reviews)
6 Bedrooms
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $757/Night
7 Nights - US $5,298
About Casai's Private Villas and Holiday Rentals in Oak Park
Discover more than 221 vacation rentals available in Oak Park. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Oak Park.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Oak Park, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Oak Park. On average, places to stay near Oak Park offer 842.85 ft², with nightly prices averaging US $308.
With Casai, finding and comparing holiday rentals in Oak Park is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other places to stay near the Oak Park, IL
There are 221 Oak Park, IL Vacation Rentals
- Prices for a holiday home in Oak Park start at US $93
- Top rated vacation home in Oak Park is 8 MILES FROM DOWNTOWN CHICAGO!
- Most popular short term in Oak Park is Carleton of Oak Park
- Cheapest place to stay in Oak Park is Private Bsmt Apt W/Separate Entry- 1 Min to Subway
- Most expensive holiday rental in Oak Park is Modern Victorian With Old World Charm
Recently Booked Hotels, Resorts, or Rentals in Oak Park
Frequently Asked Questions About Oak Park?
What are the top holiday rentals in Oak Park?
With numerous options available in Oak Park, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Oak Park:
- 8 MILES FROM DOWNTOWN CHICAGO!
- Oak Park Victorian by FLW Studio
- Space&style New rehab, first flr + bsmt of duplex, driveway prkng, walk to train
- 4-bedroom townhome in Frank Lloyd Wright District-FREE PARKING, Patio, Yard
- 2-BR central Oak Park flat+near FLW homes+near trains to Chicago+pets ok+parking
- Elegantly decorated spacious 4 bedroom, 5 bathroom home in historic Oak Park
- 5 bedroom with 5 beds and 2 bathrooms
- The Oak Park Loft, Including Garage
- Oak Park 3000 sq ft, sleep 16
- Elevated Gem - Sleeps 12 - 20 mins to Downtown Chicago
How many Casai.com holiday rentals are available in Oak Park?
As of 2026, Casai boasts over 221 properties listed in the Oak Park area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Oak Park.
Nearby Neighborhood (3)
| Neighborhood | Property Count |
|---|---|
| Austin Vacation Rentals in Chicago, Illinois | 554 |
| South Austin Vacation Rentals in Chicago, Illinois | 563 |
| North Austin Vacation Rentals in Chicago, Illinois | 605 |
