1. USA
  2. Florida
  3. Orlando
  4. Winter Springs
  5. Beach Home Rentals

Winter Springs Beach House Rentals & Places to Stay

Find the best beach rentals in Winter Springs - We found 44 exact matches

About Winter Springs Beach Home Rentals on PickleTrip

Looking for a pickleball stay or beach rental near Winter Springs? PickleTrip™ features more than 44 pickleball stays or beach rentals that are perfect for your next holiday. Discover properties that are within walking distance away from Winter Springs. Several of these vacation rentals in Winter Springs are kid-friendly & family-friendly, and are near top local attraction spots, to give guests an unforgettable travel experience. PickleTrip™’s rental listings come in all shapes and sizes for large groups, friends, or couples, or wedding retreats in Winter Springs.

PickleTrip™ Offers 44 holiday homes and places to stay in Winter Springs. The site provides unique Airbnb, VRBO, PickleTrip-style accommodations to fit your trip or get away with your friends and family.

PickleTrip™ beachfront rentals give you the best travel experience that makes it easy to find and book the best place to stay at the best destinations.

Show more
Show less

Frequently Asked Questions About Winter Springs Beach Rentals

There are a lot of options in Winter Springs. If you plan on staying in the Winter Springs area, consider making a reservation for a few nights at one of these properties as these have been rated the top Beach Home Rentals in Winter Springs:

The average cost for a beach rental in Winter Springs is $261 per night. PickleTrip has a wide assortment of great beachfront homes near Winter Springs that would suit your needs.
Yes, we have 44 beach rentals with pools available in Winter Springs. Check our search bar to find a selection of vacation rentals available near Winter Springs.
Yes, here are the top beach rentals in Winter Springs that allow you to bring your pet:

See all pet-friendly beach rentals in Winter Springs on PickleTrip

Most of the beach rentals we list are suitable for families or groups. Check out the complete list of the beach houses in Winter Springs to find one that works for you.
As of 2025, the data from PickleTrip shows that there are over 44 properties with private swimming pools or private homes with indoor pools in the Winter Springs area.
About 44 properties in Winter Springs boast of having access to hot tubs.