1427+ Sleepy Hollow Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Sleepy Hollow

Discover more than 1427 holiday rentals in Sleepy Hollow. PickleTrip™ holiday homes has everything you need to find a place to stay near Sleepy Hollow, FL.

Whether you are looking for luxury villas in Sleepy Hollow, 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 with private pickleball courts or nearby facilities. 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 Sleepy Hollow with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in Sleepy Hollow for families, large parties, or private owner accommodations for long or short trips. Pet-friendly holiday rentals are available as well. Book your favorite vacation rentals in Sleepy Hollow with PickleTrip™. Stay and play pickleball when you travel.

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Frequently Asked Questions About Sleepy Hollow Holiday Rentals

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

There are many holiday rentals available in Sleepy Hollow; however, here are a few of the most popular holiday homes listed in Sleepy Hollow on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Sleepy Hollow to find one that works for you.
Yes, there are 1427 self-catering family homes and holiday rentals in Sleepy Hollow.
There are more than 1427 luxury holiday homes in or near Sleepy Hollow, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 1427 pet friendly rentals that are available in Sleepy Hollow.