1868+ Highland Oaks Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Highland Oaks

Discover more than 1868 holiday rentals in Highland Oaks. Rent By Owner holiday homes has everything you need to find a place to stay near Highland Oaks, FL.

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

Show more
Show less

Frequently Asked Questions About Highland Oaks Holiday Rentals

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

There are many holiday rentals available in Highland Oaks; however, here are a few of the most popular holiday homes listed in Highland Oaks on our website:
At Rent By Owner most of our places to stay are perfect for families. Check out the complete list of holiday homes in Highland Oaks to find one that works for you.
Yes, there are 1868 self-catering family homes and holiday rentals in Highland Oaks.
There are more than 1868 luxury holiday homes in or near Highland Oaks, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: