3555+ Jackson Square Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Jackson Square

Discover more than 3555 holiday rentals in Jackson Square. Rent By Owner holiday homes has everything you need to find a place to stay near Jackson Square, FL.

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

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Frequently Asked Questions About Jackson Square Holiday Rentals

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

There are many holiday rentals available in Jackson Square; however, here are a few of the most popular holiday homes listed in Jackson Square 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 Jackson Square to find one that works for you.
Yes, there are 3555 self-catering family homes and holiday rentals in Jackson Square.
There are more than 3555 luxury holiday homes in or near Jackson Square, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: