25 Best Places to Retire in Florida – Updated for 2019

At Florida for Boomers, we’ve written about many of the best places to retire in Florida.

Every year we take a look at our website analytics and go through the hundreds of emails we get from readers to figure out the places that people are reading about and asking us about the most.

If you are researching the best places to retire in Florida and feeling a little overwhelmed by all the options, I have two resources that can help.

The first is my book Florida for Boomers. This book covers Florida’s various regions and popular cities, types of communities, cost of living, property taxes, new home construction, and a whole lot more.

The second resource I’d like to share with you is called Pick the Right Place.

If you are not sure that Florida is even the right place for you, or want some help in zeroing in on what might be the best place for you, this is a great place to start.

52% of my website readers say that one of their greatest fears about retirement is moving to the wrong place.

Imagine if there was a book to walk you step-by-step through the process of figuring out where to retire, and guiding you through all the steps required to actually make it a reality.

That’s what I’ve put together for you here.

Without further ado, here are the 25 best places to retire in Florida today.

1. Sarasota/Bradenton

Located along the Gulf Coast just an hour south of Tampa and a little under two hours north of Fort Myers your will find the historic artist towns of Sarasota and Bradenton. Both of these communities combine the historic Old Florida feel with vibrant cultural districts to create one of the most perfect atmospheres anywhere.

Nearby communities you might like:

Del Webb at Lakewood Ranch is a 55+ active adult community located in the master-planned community of Lakewood Ranch near Sarasota, FL. Enjoy resort-style amenities and activities including a state-of-the-art fitness center, resort pool with lap lanes, grand clubhouse with full-time Lifestyle Director, social clubs, and group outings.

Del Webb at Lakewood Ranch offers a collection of single-family homes and low-maintenance attached villas designed to fit your lifestyle. There are currently 10 home designs to choose from starting in the mid-$200k’s.

Read: Spotlight on Sarasota & Bradenton

Read: Where to Eat, Stay, and Play in Sarasota & Bradenton

Read: Sarasota and Bradenton Community Profiles

2. Venice

Located just south of Sarasota, but not quite as far south as Fort Myers or Sanibel Island, Venice sits in a sweet spot along Florida’s southern Gulf Coast that makes it the perfect destination for anyone looking to make the most of 14 miles of stunning white sand beaches.

In addition to those beautiful beaches, Venice is also known for all kinds of exciting ways to enjoy the great outdoors. It is a fabulous destination for boomers interested in exploring arts and culture, boutique shopping, or a wide range of outstanding restaurant choices.

Nearby communities you might like:

The Floridian Club of Sarasota is a unique leasable community custom-tailored to the lifestyle of active adults seeking their next adventure. The spacious, low-density community consists of single-story villas and multi-story bungalows designed for individuals ages 55 and better. With 1-10 year lease options, you are welcome to stay as long as you like and come and go as you please. Make it yours with decor and upgrades that suit your personal tastes. Perhaps best of all, living at The Floridian Club includes maintenance both inside and outside of your home as well as a full-time on-site Activities Coordinator dedicated to making sure the social opportunities are abundant daily.

As a member, you will have exclusive access to the best amenities, such as a resort-style walk in pool, tropical club room and self-serve bar, fully loaded gym and numerous clubs and activities formed and planned by like-minded active adults just like you!

At The Floridian Club, you can have it all, without the obligations, time and hard work involved in owning a home. No large cash outlay to purchase means you don’t have to sell your current home or take on financial burden to enjoy the benefits of living in Florida either full or part time.

Get More Information About The Floridian Club Here.

3. Ft. Myers

Known for offering the perfect combination of recreation and relaxation, Fort Myers contains an endless amount of options including white sand beaches, first-class golf courses, exciting deep-sea fishing, and outstanding shopping.

There is an amazing selection of great local restaurants in just about every neighborhood, and baseball fans will be excited to know that both the Boston Red Sox and the Minnesota Twins host their spring training activities here.

Nearby communities you might like:

Offering easy access to everything Southwest Florida is famous for, GL Homes is proud to introduce Valencia Bonita— a new standard of 55 plus living on Florida’s beautiful Gulf Coast. With an exciting vacation-inspired lifestyle that rivals the finest resorts, Valencia Bonita features an opulent 45,000 sq. ft. clubhouse and carefully designed single-family and villa home designs that are tailored to those looking for spacious layouts and sophisticated style. Valencia Bonita is located just minutes from pristine beaches, tranquil nature preserves, chic shops and fine dining. Plus, everyday conveniences including banks, grocery stores and top rated medical facilities are also just a short drive away. Homes start in the low $300k’s.

Get More Information About Valencia Bonita Here.

Read: Spotlight on Fort Myers

Read: Where to Eat, Play, and Stay in Fort Myers

Read: Fort Myers Retirement Community Profiles

4. The Villages

Located about an hour north of Orlando, The Villages was not even called “The Villages” when it first began. It started as a mobile home park called Orange Blossom Gardens.

Though it struggled in the early years, the community experienced staggering growth in the mid-1980’s because the community offered an impressive collection of amenities.

As that amenities-focused community continued to grow and develop, it eventually evolved into The Villages, which has become the premiere model for what a master-planned community should be.

Today, The Villages is known for having the largest and most diverse collection of amenities of any community on the planet. Residents have access to an amazing collection of golf courses, recreation centers, and town squares, as well as an unparalleled number of clubs covering just about any topic you can imagine.

With all of the advantages that The Villages offers to its residents, it is no wonder that it consistently ranks as the fastest growing community in the entire country. There were an astounding 2,231 new homes sold here in 2017.

Read: Retirement Spotlight: The Villages

5. Pensacola

Located at the very far end of the panhandle, Pensacola is a perfect location for anyone looking to enjoy Florida’s perfect weather and those beautiful Gulf Coast beaches, without relocating to one of the popular tourist destinations.

Between the outstanding fishing opportunities, the adventure of canoeing along the Blackwater River, and the history of the National Museum of Naval Aviation, there is a never-ending supply of activities to keep residents busy here. But at the end of the day, life in Pensacola is a pretty close match to the relaxing Florida retirement lifestyle you have alway envisioned for yourself.

Read: Retirement Spotlight: Pensacola

6. Naples

Like many southwest Florida communities, Naples brings together the best of shopping, recreation, and beautiful white sand beaches. But residents here would definitely argue that Naples offers the best versions of all three.

Historic downtown Naples is filled with with high-end shoppes and boutiques. The surrounding areas are littered with championship level golf courses. And this location along the southern Gulf Coast of Florida boasts some of the most stunning beaches you will find anywhere.

Read: Spotlight on Naples

Read: Where to Eat, Stay, and Play in Naples

Read: Naples Retirement Community Profiles

7. Kissimmee

If one of your concerns is that you move to Florida for retirement and your kids and grandkids never come to visit, that won’t be the case if you end up in Kissimmee. In fact, you might have a hard time getting them to leave!

Kissimmee is located just south of Orlando and is just minutes from popular attractions like the Walt Disney World Resort, Universal Studios, Sea World, and more. They call Kissimmee the “attraction zone” and it’s easy to see why.

Nearby communities you might like:

Solivita is a national award-winning retirement community in Central Florida’s attraction zone, offering great natural beauty, vast recreational amenities and enough to do to keep any active adult as busy as you care to be. No matter where you live within this lush gated 55-plus community in Kissimmee, you can easily walk, bike or drive your golf cart to indoor and outdoor dining venues, state-of-the-art spa and fitness complexes, pickleball or tennis courts, and other facilities for sports and games. You can also meet up with newfound friends, share the fun in social clubs, and enjoy lifelong learning classes and countless other amenities—inviting you to do it all, or nothing at all.

Get More Information About Solivita Here.

Read: Retirement Spotlight: Kissimmee

8. St. Augustine

Famous for being the oldest city in the country, St. Augustine is absolutely the perfect place for anyone who appreciates history. The city is located along the east coast of Florida just about 45 minutes south of Jacksonville, and a little over an hour north of Daytona Beach.

In addition to being a great location for history buffs, St. Augustine is also filled with tons of culture, great shopping, unique places to eat, and two really wonderful retirement communities. If you are passionate about any combination of those things, the Nation’s Oldest City could be a great option for your retirement!

Nearby communities you might like:

Freedom at San Salito is a 55+ neighborhood, located in St. Augustine, Florida that offers a low stress, low maintenance lifestyle. Located off State Road 16, residents will have easy access to a variety of public amenities. The community features include a gated entrance, private amenity center clubhouse and outdoor pool. Freedom at San Salito also has a part time Lifestyle Director who cultivates the ideal selection of clubs and events for homeowners.

The newly opened Freedom at San Salito’s amenities include an amenity center with a pool and covered patio, outdoor fireplace, two bocce ball courts, and a dog park. Residents of Freedom at San Salito also have access to the master community’s amenities which includes a clubhouse, multi-purpose room, pickleball courts, tennis courts, exercise room, and outdoor pool with patio. San Salito is close to the beach, golf courses, fantastic shopping, dining, music and entertainment!

Homes range in size from 1,585 to 2,033 square feet of living space, and include features like granite countertops, walk-in closets, and covered lanais. Prices start in the mid-$250k’s.

Get More Information About Freedom at San Salito Here.

Read: Retirement Spotlight: St. Augustine

9. Port Charlotte

Located almost exactly halfway between Sarasota and Fort Myers, Port Charlotte is one of the true hidden gems of Florida’s Gulf Coast, which makes it a natural destination for many boomers looking to enjoy their retirement years.

This small town community is located right on the water of Charlotte Harbor and offers access to more than 165 miles of waterways, so all kinds of water activities are extremely popular here.

Read: Cape Coral and Port Charlotte Make Forbes Best Places to Retire List

10. Tampa

As the third largest city in the state of Florida, Tampa offers residents all of the big city amenities they are looking for combined with the fantastic climate that draws people to the Sunshine State in the first place. In addition to tons of amenities and great weather, Tampa is also located right on the water and filled with outstanding shopping and dining options.

Nearby communities you might like:

Just a short drive from Tampa, the Villages of Citrus Hills is a Florida Retirement Community with single family homes and maintenance free villas that have been built with today’s demanding baby-boomer in mind. But what makes the promise of Florida Retirement in the Villages of Citrus Hills truly come together for today’s new breed of active adult retiree is its extraordinary collection of world-class community country club amenities and extensive social activities. Depending on the style and neighborhood you choose, home and home site packages range from the mid $300s to more than $1.2 million.

Get More Information About Citrus Hills Here.

Read: Retirement Spotlight: Tampa

11. Jacksonville

Located right on the Atlantic Coast in northeast Florida, Jacksonville offers its residents all of the amenities that come with a beachfront city for a fraction of the cost of some of the popular destinations nearby.

Known as the “River City on the Sea,” Jacksonville is packed with more than 22 miles of beaches, a scenic stretch of the beautiful St. Johns River, the largest urban park system in the nation, historic neighborhoods, and a thriving street art scene.

Nearby communities you might like:

Freedom at Arbor Mill and Freedom at Azalea Ridge are two 55+ active adult neighborhoods located practically next door to each other, in Jacksonville, Florida. Both communities offer a low stress, low maintenance lifestyle in a great location. The communities feature a gated entrance, private amenities, including a clubhouse and outdoor pool. Both communities will also have a Lifestyle Director who will cultivate the ideal selection of clubs and events for homeowners.

New homes are single story, thoughtfully designed and feature many upgrades and covered lanais to enhance your Florida lifestyle. All yard maintenance is included in the monthly HOA fee. The central aspect of each community will be an amenity center with an exercise room and covered patio, outdoor fireplace, pickleball courts, bocce ball courts, and a dog park.

Get More Information About Arbor Mill & Azalea Ridge Here.

12. Stuart

Known as “The Sailfish Capital of the World,” Stuart is located along the Atlantic Coast of Florida, north of West Palm Beach and just south of Port St. Lucie. This area of Florida is also known as “The Treasure Coast” because so many ships have been lost here fighting to survive storms over the years.

Nearby communities you might like:

As soon as you enter Vitalia at Tradition, you’ll know you have found the ultimate active adult lifestyle. From the welcoming palm-lush and Mediterranean-inspired entrance to the passionate attention to detail in every resident home, Vitalia at Tradition has taken the art and science of resident-centered community planning to new levels.

With bicycles and golf carts as the preferred method of transportation, active adult residents can join friends within the neighborhood or explore the vast 8,300 acres of Tradition. While the scale may be large, the feel is still small town America with a Town Hall, boutique restaurants and shops, spas and salons, along with the town center, Tradition Square. It’s the lively hub where residents gather for year-round events, entertainment, and concerts.

For those who want to stay in to enjoy the quaintness of their own neighborhood, Vitalia unveiled an outstanding 24,000-square-foot clubhouse encompassing everything from tennis and bocce courts to great lawn with fire pits and a putting green to a ballroom, fitness rooms and more! The Captiva Club is a private lakefront facility offering year-round recreation and social activities for Vitalia residents, complementing an active lifestyle.

Get the Vitalia at Tradition Information Here

13. Amelia Island & Fernandina Beach

Located in the far northeast corner of the state, just north of Jacksonville, Fernandina Beach and Amelia Island are stunningly beautiful and filled with history, culture, great shopping, championship level golf, world-class resorts, and a collection of incredible restaurants. That is a pretty impressive list when you consider that the island is only 13 miles long and two miles wide!

Read: Retirement Spotlight on Fernandina Beach and Amelia Island

14. Delray Beach

Located just an hour up the coast from Miami you will find one of the best small town communities in the entire country. VisitFlorida.com describes Delray Beach as a “small and intimate town with big-city sophistication.”

This is obvious to anyone who visits based solely on the number of art galleries, restaurants, and nightly entertainment events available throughout the popular downtown area. Delray Beach is the place where you can find big city culture in a small town environment…which is why so many people have decided to make their homes here.

Read: Delray Beach Was Built For Boomers

Read: Spotlight On Delray Beach

Read: Where to Eat, Stay, and Play in Delray Beach

Read: Delray Beach Retirement Community Profiles

15. Dunedin

Located west of Tampa and just north of Clearwater, Dunedin offers residents the perfect hybrid lifestyle that allows them to be close to the big city action, but also far enough removed that they can find some peace and quiet as well.

As one of the oldest cities along the West Coast of Florida, there is a fantastic amount of history that exists here, and more to come as the locals are continually improving their quality of life with world-class dining options.

Read: Retirement Spotlight: Dunedin

16. Daytona Beach

Because of its popularity among race fans, motorcycle enthusiasts, spring breakers, and summer vacationers, Daytona Beach is often overlooked by many boomers as they search for a Florida retirement destination that will fit their ideal lifestyle. However, those popular reasons for visiting Daytona Beach are really just scratching the surface of what residents enjoy here throughout the year.

Read: Retirement Spotlight: Daytona Beach

17. Cape Coral

When most people think about Southwest Florida, they typically associate it with Fort Myers, Sanibel Island, or Naples. But just across the way from Fort Myers is the quiet community of Cape Coral, which offers up the ideal destination for many retiring baby boomers.

With more than 400 miles of canals and an equally impressive number of outstanding golf courses, Cape Coral is a prime destination for anything water-related, and the golfing is top-notch as well.

18. Boynton Beach

Located just about halfway between West Palm Beach and Boca Raton, Boynton Beach offers residents a lifestyle that is far-removed from all of the popular Florida tourist destinations without actually being all that far away from those places.

Nearby communities you might like:

Swim, play, dine, relax or socialize – you can do as much or as little as you want at Valencia Sound in Boynton Beach. The nearly 39,000 square-foot Clubhouse with upscale indoor and outdoor amenities, including a full-service restaurant, sports lounge and multiple pickleball, tennis and bocce courts, provides the ultimate 55+ lifestyle in Boynton Beach. Hundreds of clubs are available to join, Broadway-style shows and entertainment are found in the Social Hall, classes on everything from art to fitness are scheduled at the Clubhouse, and tournaments are held at the world-class Racquet Club. Home prices start in the $400k’s.

Get More Information About Valencia Sound Here

19. Vero Beach

Located just a bit north of Fort Pierce and Port St. Lucie, Vero Beach is one of the most underrated destinations along Florida’s Atlantic Coast. Known for outstanding golf, water sports, and fishing, this is the perfect community for active boomers that are looking to pack some adventure into their retirement years.

20. Ocala

The Ocala area represents a unique combination of history, horses, and culture that is surrounded by some of the most beautiful natural environments you will find anywhere. Sprinkle in the collection of interesting shops and restaurants in Ocala’s downtown district and you will find Ocala to be the type of place where no one struggles to find something to do.

Nearby communities you might like:

At On Top of the World Communities, active adults will find all they dream about and so much more. Located in beautiful Ocala Florida (just down the road from Leesburg), On Top of the World residents can enjoy any schedule that suits their tastes – from activity packed to unhurried.

Leisure amenities include 54 holes of golf on three courses, indoor and outdoor swimming pools, tennis courts, a 14-acre R/C flying field, bocce, racquetball and basketball courts, fitness center, health club and spa, restaurants, cultural venues, and much more.

Residents can also participate in over 175 clubs, leagues, hobbies, and lifelong learning opportunities.

New homes are of quality construction, often exceeding ENERGY STAR criteria while offering comfort, convenience, and a wide variety of design elements.

There are 22 floor plans available with prices ranging to suit every budget starting in the mid $100k’s.

Get more info. from On Top of the World Here.

Read: Retirement Spotlight: Ocala

21. Port St. Lucie

Port St. Lucie and other neighboring towns in St. Lucie County promote themselves as offering “the real Florida,” which they describe as a perfect atmosphere for golf lovers or anyone looking for a small, friendly, beach town.

Nearby communities you might like:

Valencia Cay at Riverland is the newest 55+ community on Florida’s East Coast. Located in Port St. Lucie, Valencia Cay brings together GL Homes’ famous 55+ resort-style living with an amazing master site plan to create a Florida lifestyle that’s second-to-none!

 At this new community, you’ll find a million ways to have fun. Walk to nearby shops and restaurants, spend the day at the beach or simply enjoy all the amenities right within your own neighborhood.

Get in on the ground floor of Florida’s next top master planned community with prices starting in just the $200s.

Get More Information About Valencia Cay Here.

Read: Retirement Spotlight: Port St. Lucie

22. Clearwater

Located west of Tampa and just north of St. Petersburg, Clearwater makes up the third leg of one of the most popular tourist destinations in all of Florida. Known for its white sand beaches and the fabulous Clearwater Marine Aquarium, this is the ultimate destination for baby boomers that want to feel like they are forever on vacation.

Because it is located so close to Tampa, Clearwater residents enjoy close access to a major international airport. They also enjoy some of the most beautiful beaches that you will find anywhere along the Gulf Coast.

Read: Retirement Spotlight: Clearwater

23. Lake Nona

Located just inside the city limits in southeastern Orlando, Lake Nona is the ultimate combination of everything that most Baby Boomers are looking for in a retirement destination. The entire community is built around living a better, healthier lifestyle.

That means that residents here can enjoy an impressive amount of preserved green space, pools in every neighborhood, endless miles of trails, and some of the fastest internet speeds you will find anywhere in the world. On top of that, Lake Nona offers a plethora of educational options and outstanding healthcare facilities.

Read: Retirement Spotlight: Lake Nona

24. Jupiter

Jupiter is a great place for people who like to golf, hit the beach or peer at the ocean and relax. There are many fun activities and destinations in Jupiter, such as the Jupiter Inlet Lighthouse and Roger Dean Stadium, and plenty of places to eat overlooking the ICW (Intracoastal Waterway) or ocean.

Read: Retirement Spotlight: Jupiter

25. Palm Coast

Located along the Atlantic Coast about halfway between St. Augustine and Daytona Beach, Palm Coast offers the perfect combination of nature and golf for anyone who likes to enjoy both at the same time. Whether you choose to focus more on golf or nature, you will be happy to have both right at your fingertips here in one of Florida’s best kept secrets!

Read: Retirement Spotlight: Palm Coast

There you have it, the top 25 best places to retire in Florida today. Be sure to bookmark this page and check back often because we are constantly updating this page. Better yet, sign up for our Florida retirement newsletter and we’ll let you know when we update this list.