20725+ Hillcrest Estates Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Hillcrest Estates

Discover more than 20725 holiday rentals in Hillcrest Estates. PickleTrip™ holiday homes has everything you need to find a place to stay near Hillcrest Estates, FL.

Whether you are looking for luxury villas in Hillcrest Estates, 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 Hillcrest Estates with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in Hillcrest Estates 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 Hillcrest Estates with PickleTrip™. Stay and play pickleball when you travel.

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Frequently Asked Questions About Hillcrest Estates Holiday Rentals

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

There are many holiday rentals available in Hillcrest Estates; however, here are a few of the most popular holiday homes listed in Hillcrest Estates on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Hillcrest Estates to find one that works for you.
Yes, there are 20725 self-catering family homes and holiday rentals in Hillcrest Estates.
There are more than 20725 luxury holiday homes in or near Hillcrest Estates, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 20725 pet friendly rentals that are available in Hillcrest Estates.