Find hotels in Winter Beach, FL from $106

For most travelers seeking a mix of convenience and classic Florida charm, the best area to stay in Winter Beach is along Ocean Drive, particularly between the 500 and 1000 blocks.This stretch of Ocean Drive is the heart of Winter Beach's hospitality and dining scene. It's characterized by its direct beachfront access, a manicured boardwalk superb for strolls, and a collection of boutique shops and restaurants. You'll find many accommodations offering ocean views and easy access to the public beach.Ocean Drive is especially well-suited for couples looking for a relaxing getaway with dining and entertainment options within walking distance. The area allows for leisurely days on the beach, followed by evenings enjoying waterfront meals and sunset views.Families traveling to Winter Beach will also find this area appealing due to its proximity to the beach and numerous family-friendly dining choices.

The best time to go to Winter Beach is during the dry season, specifically from November to April, for optimal weather and fewer chances of rain.This period avoids the heat and humidity of summer and the higher likelihood of afternoon thunderstorms. Travelers looking for comfortable temperatures for outdoor activities like beach walks, golf, or exploring the botanical gardens will find these months ideal.For those seeking a quieter experience and potentially better value on accommodations, late spring (April and May) or early fall (October and November) can be good options.

With Expedia, you earn OneKeyCash™* on eligible Winter Beach hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.