25 Best Places to Retire in Florida – Updated for 2020

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 hope this list can help you.

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

1. Sarasota

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 town of Sarasota. This city combines the historic Old Florida feel with vibrant cultural districts to create one of the most perfect atmospheres anywhere.

Where to Retire in Sarasota:

Lakewood Ranch is the #2 selling community in the country behind The Villages, and it owes a large part of its success to its location in Sarasota.

Though Lakewood Ranch is considered a multi-generational community, there are certain neighborhoods that are 55+, such as Del Webb at Lakewood Ranch.

2. New Smyrna Beach

Located just 15 miles south of Daytona Beach is where you will find New Smyrna Beach. This quaint little beach town offers the atmosphere that many Boomers are looking for, but also brings quite a few unique amenities to the table.

New Smyrna is only about 20 minutes away from where I used to live in Daytona Beach Shores, and we often found ourselves down in New Smyrna for one reason or another (usually food or drink related…haha!) a few times per week.

Where to Retire in New Smyrna Beach:

Perfectly situated in Central Florida’s favorite beach town, Venetian Bay (A Geosam Capital development) offers World Class Resort-Style amenities to its residents.

Play a round of golf on their 18-Hole Championship golf course, spend a day with your family at the Beach and Swim Club, enjoy a relaxing day at their World Class Spa, stay active by joining the on-site fitness center or walking and biking on the miles of beautiful trails.

Residents also enjoy dining at the onsite restaurants. Residents sense a feeling of belonging. Variety is well defined at Venetian Bay with wide spread appeal.  You’ll discover luxury estates in gated private communities; semi-custom homes; mid-sized single family homes and duplexes; maintenance free luxury townhomes and apartment homes. 

With prices ranging from the $200k’s to over $1 million, there really is something for everyone at Venetian Bay.

Get more information about Venetian Bay 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. It’s no wonder why you’ll find so many 55+ communities there.

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.

Where to Retire in Fort Myers:

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.

4. The Villages

Located about an hour north of Orlando, The Villages was not even called “The Villages” when it first began. It actually 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 2,429 new homes sold here in 2019.

Interested in learning more about The Villages? Well I wrote an entire book on the place:

5. 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.

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.

Where to Retire in Naples

Valencia Trails in Naples, FL offers the best resort lifestyle with a magnificent 42,000 sq. ft. Clubhouse where every day new events, clubs, and entertainment abound. Relax by the pool, grab a bite at the restaurant, catch a show in the social hall, or take a relaxing stroll or jog along the community’s iconic trails. The options are endless!

Designed for 55+ living, the gorgeous contemporary style single-family homes at Valencia Trails offer the ultimate in style, convenience, and luxury with spacious living areas, impressive gourmet kitchens, and screened and covered patios to make the most of Florida’s beautiful weather year-round. Come home to luxurious standard features including tile roof, brick pavers, stainless steel and gas appliances, designer tile flooring throughout main areas, rich stone exterior finishes and so much more.

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.

Where to Retire in Kissimmee:

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.

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!

Where to Retire in St. Augustine:

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.

9. Port Orange

Located just 15 minutes south of famous Daytona Beach, Port Orange is known for its small town feel, but also for its close proximity to the big city amenities that residents can enjoy up in Daytona Beach, as well as in nearby Orlando.

Longtime Florida for Boomers readers know that I used to live in Port Orange, and even though I live on the beachside now, we spend the majority of our time, do most of our shopping, and eat most of our meals in Port Orange.

We love it because Port Orange is laid back and quiet, while still providing all the amenities one could possibly want.

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.

Where to Retire in Tampa:

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.

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.

Where to Retire Near Jacksonville:

Just south of Jacksonville is where you’ll find Parkland Preserve at World Golf Village, an active adult neighborhood offered by Freedom Homes, a D.R. Horton company.

Community features include a gated entrance, amenity center with pool and Lifestyle Director to help residents meet their neighbors, stay active and make new friends! Homes start in the $200k’s and are single-story, thoughtfully designed and feature covered lanais to enhance your Florida lifestyle.

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.

13. Clermont

Sitting right in the heart of Central Florida, just 20 miles west of Orlando, is where you will find the impressive little city of Clermont. It has been ranked as one of the Top 25 Best Places to Retire by Forbes and Money Magazines and was also voted the #1 Florida Bicycle-Friendly Community.

As if that wasn’t enough already, Clermont is also home to 18 athletes that competed in the 2016 Olympics, it is considered the center point of the impressive Coast-to-Coast Trail, and the city is still growing and developing at an incredible rate.

Where to Retire in Clermont:

Carefree living, quality Taylor Morrison construction and lots of choices – that’s what you’ll find at Esplanade at Highland Ranch in Clermont. Whether you’re ready to live the Florida lifestyle year-round or ease into it with a vacation home, the time of your life is waiting at this resort style 55+ community.

Esplanade at Highland Ranch is outfitted with an extraordinary level of amenities including a stunning clubhouse with fitness room and multipurpose room for yoga and exercise classes, a card room, pickle ball, bocce ball, tennis courts and billiards. Swim laps or just soak in the large resort-style pool or hot tub. Large conservation areas supply opportunities for strolls on elevated boardwalks and nature trails.

Select from a variety of distinctive floor plans designed for the way you live, play and entertain. Twelve beautifully designed floor plans ranging from 1,700-3,000 square feet showcase the most popular standard features inspired by homeowners to add convenience, style and value.

Get more information about Esplanade at Highland Ranch here.

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.

15. St. Cloud

Located along the southern banks of East Lake Tohopekaliga near Kissimmee and just south of Orlando, St. Cloud is a quiet city that was originally known as a retirement destination for Civil War veterans. 

In addition to having a rich history, the area also offers a type of small-town living that is getting harder and harder to find here in Florida. Combining that small town atmosphere with access to all of the amazing amenities located just to the north in Orlando makes St. Cloud a perfect mixture of old and new Florida living.

Where to Retire in St. Cloud

The Lakes at Harmony is an active adult community located in the master-planned community of Harmony in St. Cloud. These two and three bedroom homes are built for the way you live today, with space where you need it most. Among the spacious outdoor living space, many of which include water or conservation views, residents also enjoy a private recreation center and pool.

From the miles of walking and biking trails, to the community garden, parks and fitness center, Harmony has something for everyone. Gather at the Town Square which includes a spa, market, physician office, restaurants and more or play a round of golf on the only Johnny Miller Signature course in Central Florida without ever leaving your community.

Get more information about The Lakes at Harmony here.

The water is calling you to Twin Lakes, one of the most desirable active lifestyle communities in Central Florida. It’s time to live less crowded on the tranquil shores of Live Oak Lake where residents enjoy lakeside living with boating, fishing, kayaking and many other amenities usually reserved for fine resorts. With a clubhouse, pool, patio areas, newly opened fitness center and a full time activities director, there is something for every- one in this outstanding community. Twin Lakes, by Jones Homes USA, is now selling new homes with luxury features and advanced home technology, from the low $200k’s in the “convenient to everything,” Orlando Area.

Get more information about Twin Lakes here.

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.

Where to Retire in Daytona Beach

The community that everyone is talking about in Florida right now is Latitude Margaritaville in Daytona Beach. The Jimmy Buffett inspired 55+ community is the first of several communities being developed in partnership between Minto Communities and the Margaritaville brand.

17. Winter Garden

Located about 25 minutes west of downtown Orlando, Winter Garden offers residents the perfect combination of an Old Florida feel and plenty of modern amenities. 

You’ll love strolling through the historic downtown district but will also enjoy the lake lifestyle, the thriving cultural scene, shopping at the weekly farmers’ market, and dining at the impressive collection of modern restaurants. 

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.

Where to Retire in Boynton Beach:

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.

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.

Where to Retire in Ocala:

There are a handful of 55+ communities in Ocala, but one in particular stands out among the crowd.

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 private 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 23 floor plans available with prices ranging to suit every budget starting from the $170k’s.

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.

Where to Retire in Port St. Lucie:

Valencia Grove at Riverland is the newest 55+ community on Florida’s East Coast. Located in Port St. Lucie, Valencia Grove 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.

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.

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.

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.

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!

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 whenever we update this list.

Over to you…

Know a great place in Florida that we should consider adding to the list in the future?

Let us know in the comments section below!