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76+ Oakland Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Oakland

Discover more than 76 holiday rentals in Oakland. Casai holiday homes have everything you need to find a place to stay near Oakland, FL.

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

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Frequently Asked Questions About Oakland Holiday Rentals

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

There are many holiday rentals available in Oakland; however, here are a few of the most popular holiday homes listed in Oakland 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 Oakland to find one that works for you.
Yes, there are 76 self-catering family homes and holiday rentals in Oakland.
There are more than 76 luxury holiday homes in or near Oakland, according to 2025 data from Casai.ca. Consider these homes for your next holiday:
Yes, there are 76 pet friendly rentals that are available in Oakland.