96+ Gulf Harbors Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Gulf Harbors

Discover more than 96 holiday rentals in Gulf Harbors. PickleTrip™ holiday homes has everything you need to find a place to stay near Gulf Harbors, FL.

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

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Frequently Asked Questions About Gulf Harbors Holiday Rentals

There are a lot of options in Gulf Harbors. If you plan on staying in the Gulf Harbors 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 Gulf Harbors:

There are many holiday rentals available in Gulf Harbors; however, here are a few of the most popular holiday homes listed in Gulf Harbors on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Gulf Harbors to find one that works for you.
Yes, there are 96 self-catering family homes and holiday rentals in Gulf Harbors.
There are more than 96 luxury holiday homes in or near Gulf Harbors, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 96 pet friendly rentals that are available in Gulf Harbors.