Best Florida Beach Towns for Winter Travel

So, will you have a car? How many nights/weeks? Ages? Likes? BUDGET? House? 2 hotel rooms? Condo apartment?
All of these factors help determine which coastal Florida beach town is right for your winter vacation.
With an abundance of hidden getaways on both the Gulf and Atlantic sides, it’s hard to find the best places to visit, but the Florida shoreline just might be the perfect escape from cold winter weather.
While we are partial to Naples, Florida we do love the other quaint beach towns Florida has on its sandy shores welcoming visitors to warm water in the winter months of December, January and February.

Our favorite Florida Beach Towns:


For some travelers, the best winter beach vacations are in Florida. One of the most beloved destinations on the Gulf Coast is Naples. Here you will find a variety of relaxing rentals. Beaches can be empty in places, Naples delivers plenty of pools, hot tubs, golf courses, and activities to make up for it. The Everglades are also nearby for adventurous travelers that want to discover local Florida wildlife.

Key West

Key West is part of the Florida Keys archipelago. It’s also Florida’s southernmost point, lying roughly 90 miles north of Cuba. Famed for its pastel-hued, conch-style houses, it’s a cruise-ship stop also accessible from the mainland via the Overseas Highway. Famous residents who have called Key West home include Ernest Hemingway, Tennessee Williams, Kelly McGillis, Jimmy Buffet, David Allen Coe, Calvin Klein, Shel Silverstein and Judy Blume.

Marco Island

With an abundance of warm weather year round, its no surprise Marco Island has some of the top beaches in the world. The largest Island in Florida’s chain known as Ten Thousand Islands, Marco Island features two public beaches, as well as offshore island beaches and proximity to the popular beaches in Naples, Florida.

Boca Grande

Located on Gasparilla Island off the Gulf Coast, northwest of Fort Myers, Boca Grande is an affluent residential community recognized for excellent fishing. Among Boca Grande’s many charms is the Gasparilla Inn & Club, a hidden gem. Built in 1911 but maintained through renovations and updates, this luxurious resort preserves its old Florida charm.


Clearwater Beach dazzles with impeccable beaches and inviting waters. Caladesi Island, off the north end of the beach, was recognized as the nation’s best by Dr. Beach (2008). Besides the beaches, there is Clearwater Beach’s inviting, small-town atmosphere. At the Clearwater Marine Aquarium, you will find Winter the Dolphin, star of the movie Dolphin Tale.

Peak Season

With mild winter temperatures, January and February in Central and South Florida is peak season. Many vacation rentals and hotels book up to a year in advance. So you may be limited by your dates and availability if this is a last minute trip.

Types of Beaches

When it comes to picking a Florida beach your choices can fall into two different categories. Since Florida is rimmed by water on almost every side you can choose to vacation in castaway solitude or metropolitan mayhem.
City Beaches: Big built up city beaches include places like Miami, Ft Lauderdale, Clearwater, Palm Beach and Melbourne?
Low Key Beaches: With an abundance of open spaces and coastline Florida has its fare share of mellow out of the way places like Anna Maria, Gasparilla/Boca Grande, Cabbage Key, Siesta Key, Lido Key and Marco Island.

Come Inside to the Comfort of Your Naples Florida Vacation Home

When you stay in one of our stunning rentals, you can relax knowing that you’ll have everything you need for the perfect vacation. You and your family will love the beauty of the Paradise Coast, and our homes are complete with the amenities you deserve for a luxurious getaway. All you have to do is arrive and enjoy! Contact us today! We are looking forward to helping you find your luxury vacation home!

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Naples Florida Vacation Homes LLC
2805 Horseshoe Drive S #10
Naples, Florida 34104
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