1. USA
  2. Florida
  3. Fort Myers
  4. Oak Run
  5. Holiday Homes

416+ Oak Run Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Oak Run

Discover more than 416 holiday rentals in Oak Run. Casai holiday homes have everything you need to find a place to stay near Oak Run, FL.

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

Show more
Show less

Frequently Asked Questions About Oak Run Holiday Rentals

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

There are many holiday rentals available in Oak Run; however, here are a few of the most popular holiday homes listed in Oak Run 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 Oak Run to find one that works for you.
Yes, there are 416 self-catering family homes and holiday rentals in Oak Run.
There are more than 416 luxury holiday homes in or near Oak Run, according to 2025 data from Casai.ca. Consider these homes for your next holiday:
Yes, there are 416 pet friendly rentals that are available in Oak Run.