487+ Island Oaks Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Island Oaks

Discover more than 487 holiday rentals in Island Oaks. Rent By Owner holiday homes has everything you need to find a place to stay near Island Oaks, FL.

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

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Frequently Asked Questions About Island Oaks Holiday Rentals

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

There are many holiday rentals available in Island Oaks; however, here are a few of the most popular holiday homes listed in Island 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 Island Oaks to find one that works for you.
Yes, there are 487 self-catering family homes and holiday rentals in Island Oaks.
There are more than 487 luxury holiday homes in or near Island Oaks, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: