36+ Gulf Highlands Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Gulf Highlands

Discover more than 36 holiday rentals in Gulf Highlands. PickleTrip™ holiday homes has everything you need to find a place to stay near Gulf Highlands, FL.

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

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Frequently Asked Questions About Gulf Highlands Holiday Rentals

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

There are many holiday rentals available in Gulf Highlands; however, here are a few of the most popular holiday homes listed in Gulf Highlands 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 Highlands to find one that works for you.
Yes, there are 36 self-catering family homes and holiday rentals in Gulf Highlands.
There are more than 36 luxury holiday homes in or near Gulf Highlands, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 36 pet friendly rentals that are available in Gulf Highlands.