1. USA
  2. Florida
  3. Naples
  4. Wing South
  5. Holiday Homes

1269+ Wing South Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Wing South

Discover more than 1269 holiday rentals in Wing South. Rent By Owner holiday homes has everything you need to find a place to stay near Wing South, FL.

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

Show more
Show less

Frequently Asked Questions About Wing South Holiday Rentals

There are a lot of options in Wing South. If you plan on staying in the Wing South 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 Wing South:

There are many holiday rentals available in Wing South; however, here are a few of the most popular holiday homes listed in Wing South 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 Wing South to find one that works for you.
Yes, there are 1269 self-catering family homes and holiday rentals in Wing South.
There are more than 1269 luxury holiday homes in or near Wing South, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: