Best Places to Rent in Florida during Winter

Here are the Best Places to “Snowbird” in Florida During the Winter and Enjoy the Warm Weather.

It’s easier to choose a great place to rent in Florida during the winter, than it is to decide where to move to live full-time. Why?

  • Because you won’t have to worry about hurricanes because the hurricane season ends November 30th. So you can snowbird in Florida’s hurricane evacuation areas near the coast without worry.
  • You “usually” don’t have to worry about avoiding flood zones along the beaches because it rains far less during the winter. Since you’re renting, you’re not obligated to carry a costly additional flood insurance policy to protect where you’ll be staying.
  • If any freak natural disaster does occur, you can just leave and go home. If the place was your full-time home, well…
  • When you book a seasonal rental for the winter (or just a month), you just pack your toothbrush and swimsuit and go!
  • So just choose a best place to rent in Florida during the winter that suits you, go, and leave your cares behind.

Choose a town that’s best for you, based on your interests…

The best places for winter rentals in Florida for golf enthusiasts

Naples in Southwest Florida

Naples is located in deep Southwest Florida and has more golf courses than just about anywhere in the US, especially for such a “small” town. It has a unique historic area right near the beach.

While homes and condos here are among the priciest in the state, winter rental “bargains” can occasionally be found.

The population here swells by about 300% during the winter because many home are owned by people who are only in town during the winter months..

Things to do in Naples Florida from Visit Florida

Other great places to spend winter in Florida if you love to golf

  • Bonita Springs- This town is just north of Naples and is a little less expensive.
  • Punta Gorda- You’ll find a small historic downtown here on the water and plenty of courses. It’s about an hour north of Naples and also less expensive overall.


The Best Places for Winter Rentals in Florida for Beach Lovers.

Siesta Key Beach Florida

Siesta Key has a beach rated as the best in the world, has a great little tropical village and is just minutes from upscale dining and shopping in Sarasota.

Things to do while in Siesta Key Florida from tripadvisor

Other ideal places to snowbird in Florida for the beach are…

  • Apalachicola- Located on Florida’s Panhandle coast. There’s still a little bit of old-time Florida in the area.
  • Bonita Springs- (also on the golf list above++) In Southwest Florida not far from Marco Island, Naples and the Everglades.
  • Dunedin- Beaches and a walkable downtown, a great place to meet people (single?)

florida move guide book cover and discription

Best Places to Spend the Winter in Florida for Those Who Love to Ride Bikes

Fernandina Beach, Florida

Fernandina Beach- Amelia Island biking, historic beach town. Close to the Georgia border, so closer but also a little cooler than south Florida during the winter months.

Has beaches and also a fantastic historical downtown that is one of the most walkable places in the USA. You can’t get a DUI if you’re walking, so enjoy yourself.

Just before writing this I found a fully furnished and equipped townhouse here, available for less than $2000 a month and just a short walk from the beach.

There are cheaper places than that too. Just bring your toothbrush, beach towel and cell phone so every time it snows in your home state, you can call the chumps back home and tell them how nice the weather was at the beach.

Watch the Fernandina Beach Florida Video

Things to do while in Fernandina Beach Florida from tripadvisor

Other places to find a winter home for your your bike…

  • Venice- Access to beaches, historic downtown and many miles of bike trails, many that go to the beach!
  • The Villages- This places has been described as “Disney” for the 55+ crowd.


The best places for winter rentals to just park the car at “home” and walk almost everywhere in a safe environment.

Dunedin Florida (also on our beach lovers and other lists)

Things to do while in Dunedin Florida from tripadvisor

Other Places to consider…

  • Fernandina Beach- It’s featured in another section in this article. Beach, bike, walk, historic downtown. Wow.
  • The Villages- Leave the car parked and walk, or ride your golf cart anywhere in this population 100,000+ retirement community “city”


The Best Places for Winter Rental in Florida if You Want a 55+ Active Adult Community.

The Villages Florida Near Ocala

After a quick online search, I found a fully furnished 3 bedroom 2 bath home with a garage for only $1200 a month in The Villages Florida. Guess what? There’s even a golf cart in the garage that’s included that you can use to travel just about anywhere you wish to go in this amazing “Disney for Adults” retirement community. Sure, almost every retirement community in Florida has a clubhouse and pool, but this place is a self contained city complete with more shops, restaurants and bars than you’ll likely visit.

If you want to guarantee you’ll enjoy warm weather, sunshine and fun this winter, this is the can’t miss choice. Sorry, this place isn’t for amateurs, you must be 55 or older. Make sure to bring a cell phone to send pics back home on particularly cold dreary days there, of you in your shorts, soaking up the sun.


The best places for winter rentals for boating and fishing enthusiasts.

Punta Gorda Florida (also on our golf and other lists)

Punta Gorda is where the river meets the Gulf of Mexico, so it offers a wide variety of boating and fishing adventure. Has a nice little historic village, waterfont park with tennis courts and a large covered wharf “Fisherman’s Village” filled with shops and restaurants. Many Events and festivals are held here too.

Things to do while in Dunedin Florida from tripadvisor

Florida has no shortage of places to enjoy fishing and boating while snowbirding. Here are some of the other best places…

  • Destin- The Florida Panhandle’s fishing, boating and beach paradise.
  • Cypress Gardens Area (freshwater)- Less expensive, less crowded and laid back even for Florida.


Best Places to Spend Winter in Florida Near the Theme Parks in Orlando

If all of Orlando’s theme parks, shopping and dinning options are what you like most about Florida, Winter Park may be your perfect place to snowbird this winter. I mean, it even has winter in it’s name. Renting a place in Winter Park means you can visit the madness of Orlando whenever you wish, but come home to a great town where you can enjoy a more relaxing and peaceful setting.

Winter Park has very a walkable part of town filled with places to eat, drink and shop, so you can enjoy the warm weather and have fun without even going to the city of Disney. I found a number of fully furnished and equipped homes and apartments just a block or two from Park Avenue (the town’s main entertainment area) for less than $2000.00 per month with all utilities included. Not a high price to pay to make the shivering folks back home jealous this winter.
Ron Stack “That Best Places Guy”

  • Want to be certain if moving to Florida is right for you or your family? You’ll know after reading the Florida Move Guide.
  • Is there a better state to relocate to or a better retirement lifestyle for you than moving to Florida? You’ll know after reading How to Retire Happier.