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615+ Highlands County Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Highlands County

Discover more than 615 holiday rentals in Highlands County. Rent By Owner holiday homes has everything you need to find a place to stay near Highlands County, FL.

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

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Frequently Asked Questions About Highlands County Holiday Rentals

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

There are many holiday rentals available in Highlands County; however, here are a few of the most popular holiday homes listed in Highlands County 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 Highlands County to find one that works for you.
Yes, there are 615 self-catering family homes and holiday rentals in Highlands County.
There are more than 615 luxury holiday homes in or near Highlands County, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: