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77+ Lake Mary Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Lake Mary

Discover more than 77 holiday rentals in Lake Mary. PickleTrip™ holiday homes has everything you need to find a place to stay near Lake Mary, FL.

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

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Frequently Asked Questions About Lake Mary Holiday Rentals

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

There are many holiday rentals available in Lake Mary; however, here are a few of the most popular holiday homes listed in Lake Mary on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Lake Mary to find one that works for you.
Yes, there are 77 self-catering family homes and holiday rentals in Lake Mary.
There are more than 77 luxury holiday homes in or near Lake Mary, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 77 pet friendly rentals that are available in Lake Mary.