Photo by Anthony Martinez

Kendall County vacation rentals

We found 149 vacation rentals — enter your dates for availability

Discover a selection of 19 homes and other vacation rentals in Kendall County that are perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation homes have the amenities you need and want for your stay, which might include air conditioning and a pool. No matter what you're looking for, you'll be able to choose a rental that has what everyone needs, including accessible or non-smoking choices.

Popular Kendall County destinations on Vrbo

Setting Sun

Oswego

Oswego

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    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
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Book a vacation rental for your Kendall County getaway

Learn about the unique charm of Kendall County with a stay in a private vacation home. This city has something for everyone. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Kendall County

Do you want to discover attractions to see in the area? Venture out of your vacation home and check out everything that makes Kendall County a fun spot to vacation. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Fox Valley Winery (5 mi / 8 km)
  • Bolingbrook Golf Club (15.5 mi / 25 km)
  • Mistwood Golf Club (16 mi / 25.8 km)
  • Grundy County Speedway (16 mi / 25.8 km)
  • Cantigny Golf Club (20.7 mi / 33.4 km)
  • Seven Bridges Golf Club (21.3 mi / 34.3 km)

Exploring the natural landscape of Kendall County

Whether you're looking for fun outdoor activities or just want to take in the scenery, Kendall County is a great place to spend some time outside. Here are some of the area’s noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Fabyan Villa Museum & Japanese Garden (17.2 mi / 27.7 km)
  • Centennial Beach (17.4 mi / 28.1 km)
  • Riverwalk Park (17.5 mi / 28.1 km)
  • Shabbona Lake State Park (22.4 mi / 36 km)
  • Forest Preserve District of Will County (23.6 mi / 37.9 km)
  • Morton Arboretum (23.8 mi / 38.4 km)

Transportation to and around Kendall County

If you're traveling by train, the main station serving the city is Plano Station.

Frequently asked questions

What is the best area to stay in Kendall County when booking a vacation rental?
If you’re heading to Kendall County, Oswego is regarded as one of the most desired locations to stay. While you’re here, keep busy by discovering amazing sights like Fox Valley Winery and Hudson Crossing Park.
What is the most popular type of vacation rental accommodation in Kendall County?
Apartments are the most popular style of vacation rental in Kendall County, according to our data. Even if you have a different idea about what you’d like, Vrbo has properties in loads of shapes and sizes. Explore our options to find your perfect match.
How much does it cost to rent a vacation rental in Kendall County?
A range of things can influence the price of a vacation rental in Kendall County, like the type of property, season and length of stay. Still, all Vrbo homes have one thing in common — excellent value. Just enter your travel dates to find your dream escape.
How much does it cost to rent a beach house in Kendall County?
When you travel and the style and size of the property will help determine the cost of your beachside stay. Enter your Kendall County travel dates to see all your options on Vrbo. Did someone just say “private pool”? Use our filters to select the amenities and features you want in your rental.
Are there pet-friendly vacation rentals in Kendall County?
Happily, yes. Pick from six vacation rentals that allow pets in Kendall County on Vrbo. Our furry kids also need a break, so simply use our search function for pet-friendly vacation rentals to find a property where your pup can get in on the family fun.
Are there large group vacation rentals in Kendall County?
You’ll discover six properties in Kendall County that can sleep 10 or more people. Whether you’re organizing a trip with the family or a special event like a birthday party, there’s plenty of room to get your loved ones together under one roof.
What are the top attractions for families in Kendall County?
There are lots of exciting things to see and do with the family in Kendall County, including:

  • Richard E Klatt Memorial Field
  • Cedardell Golf Club
  • Hudson Crossing Park

Are there one-bedroom vacation rentals in Kendall County?
Yes, you’ll find 4 one-bedroom properties in Kendall County to choose from. A one-bedroom vacation property is a superb choice if it’s just you and your partner or if you’re vacationing solo. Toss in more space, privacy and convenience compared to a regular hotel, and you’ve got yourself an unforgettable getaway.
Can I find two-bedroom vacation rentals in Kendall County?
Gather your besties and relax in total privacy and comfort in one of the 12 two-bedroom vacation homes Kendall County has to offer.
Are there vacation rentals with WiFi in Kendall County?
Kendall County has 17 vacation rentals with WiFi, so you can stay connected when you’re away. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming Hollywood blockbusters to posting pics on social media, these Vrbo homes make it a cinch to get online.
How can I find vacation rentals with air conditioning in Kendall County?
Kendall County has 27 vacation rentals where you can relax in air-conditioned comfort. To find a property on Vrbo that has this amenity, enter your preferred travel dates and use the convenient filter tool to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Kendall County?
You’ll have to check with the Kendall County vacation home you’re considering on Vrbo as age restrictions vary. However, it’s typically 16, 18 or 21.
How long can I rent a vacation rental in Kendall County for?
It really depends on the Kendall County property. To see all available options offering extended stays, just enter your dates and number of guests into Vrbo’s search page. Look forward to having the whole property to yourself, as well as amenities such as a full kitchen, air conditioning and a yard to run around in. Be on the lookout for any long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Kendall County?
Whether you’re interested in one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some amazing deals and discounts on Vrbo. From weekend retreats to extended getaways, we’ve got the ideal place for your next Kendall County escape.

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