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  4. Winter Woods
  5. Beach Home Rentals

Winter Woods Beach House Rentals & Places to Stay

Find the best beach rentals in Winter Woods - We found 108 exact matches

About Winter Woods Beach Home Rentals on PickleTrip

Looking for a pickleball stay or beach rental near Winter Woods? PickleTrip™ features more than 108 pickleball stays or beach rentals that are perfect for your next holiday. Discover properties that are within walking distance away from Winter Woods. Several of these vacation rentals in Winter Woods 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 Woods.

PickleTrip™ Offers 108 holiday homes and places to stay in Winter Woods. 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.

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Frequently Asked Questions About Winter Woods Beach Rentals

There are a lot of options in Winter Woods. If you plan on staying in the Winter Woods 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 Woods:

The average cost for a beach rental in Winter Woods is $297 per night. PickleTrip has a wide assortment of great beachfront homes near Winter Woods that would suit your needs.
Yes, we have 108 beach rentals with pools available in Winter Woods. Check our search bar to find a selection of vacation rentals available near Winter Woods.
Yes, here are the top beach rentals in Winter Woods that allow you to bring your pet:

See all pet-friendly beach rentals in Winter Woods 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 Woods to find one that works for you.
As of 2025, the data from PickleTrip shows that there are over 108 properties with private swimming pools or private homes with indoor pools in the Winter Woods area.
About 108 properties in Winter Woods boast of having access to hot tubs.