788+ Longboat Key Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Longboat Key

Discover more than 788 holiday rentals in Longboat Key. Rent By Owner holiday homes has everything you need to find a place to stay near Longboat Key, FL.

Whether you are looking for luxury villas in Longboat Key, 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. 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 Longboat Key with a whole family or group, RBO holiday accommodations make your trip memorable. We have plenty of places to stay in Longboat Key for families, large parties, or private owner accommodations for long or short trips. Longboat Key Pet-friendly holiday rentals are available. Book your favorite vacation rentals in Longboat Key with Rent By Owner. RBO makes it easy to compare and book holiday rentals today.

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Frequently Asked Questions About Longboat Key Holiday Rentals

There are a lot of options in Longboat Key. If you plan on staying in the Longboat Key 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 Longboat Key:

There are many holiday rentals available in Longboat Key; however, here are a few of the most popular holiday homes listed in Longboat Key on our website:
At Rent By Owner most of our places to stay are perfect for families. Check out the complete list of holiday homes in Longboat Key to find one that works for you.
Yes, there are 788 self-catering family homes and holiday rentals in Longboat Key.
There are more than 788 luxury holiday homes in or near Longboat Key, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: