Exploring the 15 Best Places to Retire in Florida

As many retirees know, Florida is famous not just for its 55+ communities and incredible weather, but for a lifestyle that provides the perfect retirement balance. Because of this, we often get asked one very important question: ‘Where is the best place to retire in Florida?’ The answer obviously depends on a variety of factors, making it hard to narrow down where to start exploring.

That’s why we decided to delve into Travel + Leisure’s ranking of the top 15 places to retire in Florida. The difference between our list and theirs? Ours re-ranks each area based on firsthand experiences and feedback from actual Explore55Plus buyers and sellers. In this article, we aim to shed some light on the diverse cities throughout Florida, and dive into what makes each location appealing, to help you find the ideal city to retire in!

1. Sarasota – Lakewood Ranch

To start off our list, we have Sarasota. This area is incredible when it comes to walkability through downtown, stunning homes, and premier master-planned communities like Lakewood Ranch. Our favorite thing about Sarasota is its proximity to both St. Pete and Naples, where you can enjoy activities like boating, dolphin watching, or the arts. We also love the Old Florida, boutiquey feel that Sarasota has. The real estate market here is diverse, with properties ranging from luxurious waterfront condos (which can be pricey) to more affordable options, making it a sought-after location for retirees. (Travel + Leisure’s #2)

Interested in exploring this area? Connect with one of our Sarasota Experts!

2. Mount Dora

Mount Dora has consistently held a top spot on our list of top retirement destinations. So, you can imagine our shock when we discovered it was placed at the very bottom of Travel + Leisure’s! If you’re not looking for a 55+ community, but want the Florida retirement lifestyle, Mount Dora has you covered. This is a phenomenal area to buy an affordable home. If you do want a 55+ community, it might be pricier, but it is worth it! Mount Dora has a charming and walkable downtown area, excellent dining, and reasonably priced living options. When you’re not relaxing at home, you can sail on the Harris Chain of Lakes or spend the day sitting by calming Lake Dora. (Travel + Leisure’s #15)

Interested in exploring this area? Take a look at Lakes of Mount Dora!

3. Orlando

Between the theme parks and the cities located within the greater Orlando area like Clermont, Leesburg, and Kissimmee, we feel like Orlando has some of the top retirement communities in Florida. We absolutely love this area for its easy access to either coast, tons of entertainment, proximity to Disney World and Universal Studios, the beautiful chains of lakes and the peace of mind of being away from hurricanes. There is a diverse range of 55+ communities in all price ranges that make Orlando a top contender in our eyes, proving Florida’s central cities can be just as enticing and exciting as its coastal counterparts. (Travel + Leisure’s #6)

Interested in exploring this area? Take a look at Trilogy Orlando and Del Webb Sunbridge!

4. St. Petersburg

Our exploration wouldn’t be complete without St. Petersburg. We even considered putting this higher on our own list. This city has a fun, walkable downtown, sailing and water activities, the pier overlooking the gorgeous bay, and the St. Pete-Clearwater International Airport that makes getting in and out of the area a breeze. You can also take the Sunshine Skyway Bridge to Sarasota to enjoy the city life and entertainment there. Pricing in this city is all over the board, so there is a good chance you’ll find something within your budget. If you’re dreaming of retiring in a condo close to the water, this area is a gem worth considering. (Travel + Leisure #8)

Interested in exploring this area? Connect with one of our St. Petersburg Experts!

5. Ocala

Ocala is hugely popular with many buyers who contact us looking for a retirement home. Number 5 on our list and number 14 on Travel + Leisure, this low-key area is affordable, accessible, and surrounded by natural beauty. If you don’t want to spend an arm and a leg on a house and prefer a lifestyle away from the big-city hustle and bustle, Ocala is a prime choice. Notably, the area is home to the World Equestrian Center, offering state-of-the-art facilities for equestrian enthusiasts and adding to the charm of living in this tranquil part of Florida. Ocala continues to grow with new 55+ communities being developed and a very reasonable price point for homes in the area. (Travel + Leisure #14)

Interested in exploring this area? Take a look at On Top Of The World and Oak Run!

6. Tampa

Tampa Bay took the top spot on Travel + Leisure’s list, but number 6 on ours. A choice that sparked our curiosity. Known for its sports teams – the Lightning, the Rays, and the Buccaneers – Tampa is a prime location for sports fans. Beyond the sports, the area offers easy access to some of our favorite places, like Clearwater, and a variety of activities including cruises, boating, and fishing. You also have easy access to Crystal River where you can take part in scalloping and kayaking, not to mention plenty to explore within Tampa itself. While there are certainly more pros than cons to living here, we must point out that traffic might be a consideration and the distance to or from 55+ communities in the area. Most are situated farther inland along the outskirts of Tampa. (Travel + Leisure #1)

Interested in exploring this area? Take a look at Sun City Center and Del Webb Southshore Falls!

7. Ponte Vedra Beach

The Ponte Vedra area, along with the surrounding cities of Jacksonville and St. Augustine, is up and coming in the 55+ community landscape. With the development of many new master-planned communities, you’ll have plenty of options to choose from here. These communities focus on modern clubhouses, walking trails, and catering to an active lifestyle so retirees can enjoy all that the natural area has to offer. This sought-after location does tend to be on the pricier side compared to other areas on our list. (Travel + Leisure #12)

Interested in exploring this area? Take a look at Del Webb Ponte Vedra!

8. St. Augustine

If we could, we’d combine St. Augustine, Ponte Vedra Beach, and Jacksonville into one area on this list. Retirees searching in one of those cities can easily open their search up to consider all three. Why limit your search when you can have the best of all three? Here, you’re close to historic St. Augustine, beautiful beaches, great restaurants, easy access to downtown Jacksonville, Palm Beach, and Space Coast. The best part? The diverse pricing means finding a home within your budget is a definite possibility. (Travel + Leisure #11)

Interested in exploring this area? Take a look at Parkland Preserve!

9. Jacksonville

Jacksonville made it to number 9 on both our list, and Travel + Leisure’s list. This is another community we would have put a little bit higher on our list if there weren’t so many other great options. Jacksonville is quickly becoming a 55+ magnet with new communities popping up in and around the area. You’ll never be wondering what to do with downtown Jacksonville and St. Augustine nearby offering a plethora of dining, shopping, and entertainment options. Prices here don’t range as widely as some of the other areas, but you are still able to find a moderately priced home in a new 55+ community here. (Travel + Leisure #9)

Interested in exploring this area? Take a look at Del Webb eTown and WaterSong at RiverTown!

10. Fort Myers

Number 10 on our list, but number 5 on Travel + Leisure’s, we are big fans of Fort Myers! This city has easy access to Naples and Sarasota, along with plenty of boating, fishing, and water activities. They are still a recovering community post-hurricane, but are a testament to Florida’s resilience and the appeal of its beach towns. There aren’t a lot of dedicated 55+ communities here, and the traffic is seasonally dependent, but it is a great option to consider. (Travel + Leisure #5)

Interested in exploring this area? Take a look at Pelican Preserve!

11. Vero Beach

North of Port St. Lucie, Vero Beach has world renowned golf courses, scuba diving, and beautiful beaches, making it a nice option for retirees who are looking for natural surroundings and waterfront living. This coastal city is between Daytona Beach and Miami, offering accessibility to big-city amenities, but keeping the charm of a small coastal town. There aren’t a lot of 55+ communities in the city itself, but Vero Beach is known for its tight-knit community with plenty of events and activities for a fulfilling social lifestyle. (Travel + Leisure #13)

Interested in exploring this area? Connect with one of our Vero Beach experts!

12. Fort Lauderdale

Fort Lauderdale was among the surprising entries on the list. This city stands out for its proximity to other incredible cities in Florida. The infrastructure, including the Brightline train, promotes this connectivity, offering easy access to Miami, Boynton Beach, and Vero Beach. You’ll also find world-class golf, nightlife, and a budding art scene. With the right budget, a love for an active lifestyle, and the desire to shop and explore, this could be a great place to retire. The real estate market in the area caters to a range of budgets for a retirement home amidst the buzz of city life. (Travel + Leisure #4)

Interested in exploring this area? Connect with one of our Fort Lauderdale experts!

13. Key West

Key West is an awesome city to vacation in, but we hesitate to consider it as one of the top retirement destinations in the state. It reminds us of The Villages if it weren’t a 55+ community. The main drag is full of bars and shops, but it is on the smaller side when compared with cities on this list. We feel it might be a better location for snowbirds to retire. Key West is great for avid boaters and those who don’t mind driving far to get to larger cities. (Travel + Leisure #10)

Interested in exploring this area? Connect with one of our Key West experts!

14. Gainesville

It truly came as a shock to us when Gainesville came in at number 3 for Travel + Leisure. When we think of Gainesville, we think of it as more of a college town than an optimal place for retirees. That doesn’t mean that Gainesville has nothing to offer those who are 55 and over. Here, you will find great healthcare and plenty of natural beauty. It does lack in 55+ communities which makes it a less obvious choice for retirees, but it is filled with gorgeous springs and natural parks which could be the perfect place for nature loving retirees. (Travel + Leisure #3)

Interested in exploring this area? Connect with one of our Gainesville experts!

15. Gulf Breeze

Last on our list is Gulf Breeze. This city was number 7 for Travel + Leisure, which was the biggest surprise to us – mostly because we had never heard of it. After doing some research of our own, the small peninsula of Gulf Breeze is near Pensacola. This location gives you access to Pensacola and Pensacola beach. It also puts you close to Florida’s Panhandle where you can explore Destin and other states. There is not a 55+ community market in Gulf Breeze, but it could be a great opportunity to find a retirement home if you aren’t looking for the traditional retirement community experience. (Travel + Leisure #7)

Interested in exploring this area? Connect with on of our Gulf Breeze experts!

Take the Next Steps with Explore55Plus

Florida's diverse landscape offers a multitude of options for retirees, from bustling cityscapes to serene beach towns and everything in between. Our journey through the state's top retirement destinations reveals that the best choice depends on individual preferences, from lifestyle and activities to community vibes and accessibility.

At Explore55Plus, we are committed to helping you navigate these choices, connecting you with knowledgeable agents who specialize in retirement communities across Florida. Whether you're years away from retirement or looking to make your move soon, our team is here to guide you towards your dream retirement home. Connect with an Explore55Plus expert today!

Click here for the full Travel + Leisure article on their 15 Best Places to Retire in Florida.