1. USA
  2. Illinois
  3. Winslow
  4. Holiday Homes

60+ Winslow Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Winslow

Discover more than 60 holiday rentals in Winslow. Casai holiday homes have everything you need to find a place to stay near Winslow, IL.

Whether you are looking for luxury villas in Winslow, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartments for family holidays, or stylish accommodations for a business trip, we can help you find the perfect place. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to Winslow with a whole family or group, Casai holiday accommodations will make your trip memorable. We have plenty of places to stay in Winslow for families, large parties, or private owner accommodations for long or short trips. Winslow Pet-friendly holiday rentals are available. Book your favorite vacation rentals in Winslow with Casai. Casai makes it easy to compare and book holiday rentals today.

Show more
Show less

Frequently Asked Questions About Winslow Holiday Rentals

There are a lot of options in Winslow. If you plan on staying in the Winslow area, consider making a reservation for a few nights at one of these properties as these have been rated the top Holiday Home Rentals in Winslow:

There are many holiday rentals available in Winslow; however, here are a few of the most popular holiday homes listed in Winslow on our website:
At Casai.ca most of our places to stay are perfect for families. Check out the complete list of holiday homes in Winslow to find one that works for you.
Yes, there are 60 self-catering family homes and holiday rentals in Winslow.
There are more than 60 luxury holiday homes in or near Winslow, according to 2025 data from Casai.ca. Consider these homes for your next holiday:
Yes, there are 60 pet friendly rentals that are available in Winslow.