1. USA
  2. New York
  3. Olean
  4. Holiday Homes

38+ Olean Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Olean

Discover more than 38 holiday rentals in Olean. PickleTrip™ holiday homes has everything you need to find a place to stay near Olean, NY.

Whether you are looking for luxury villas in Olean, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, we can help you find the perfect place with private pickleball courts or nearby facilities. 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 Olean with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in Olean for families, large parties, or private owner accommodations for long or short trips. Pet-friendly holiday rentals are available as well. Book your favorite vacation rentals in Olean with PickleTrip™. Stay and play pickleball when you travel.

Show more
Show less

Frequently Asked Questions About Olean Holiday Rentals

There are a lot of options in Olean. If you plan on staying in the Olean 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 Olean:

There are many holiday rentals available in Olean; however, here are a few of the most popular holiday homes listed in Olean on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Olean to find one that works for you.
Yes, there are 38 self-catering family homes and holiday rentals in Olean.
There are more than 38 luxury holiday homes in or near Olean, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 38 pet friendly rentals that are available in Olean.