317+ Long Island Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Long Island

Discover more than 317 holiday rentals in Long Island. PickleTrip™ holiday homes has everything you need to find a place to stay near Long Island, .

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

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Frequently Asked Questions About Long Island Holiday Rentals

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

There are many holiday rentals available in Long Island; however, here are a few of the most popular holiday homes listed in Long Island on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Long Island to find one that works for you.
Yes, there are 317 self-catering family homes and holiday rentals in Long Island.
There are more than 317 luxury holiday homes in or near Long Island, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 317 pet friendly rentals that are available in Long Island.