Aerial view of Naples, Florida.

The 9 Best Small Towns To Retire In Florida

Welcome to Florida, the Sunshine State—a land where palm trees sway lazily in warm breezes, and the orange sun dips below the Gulf of Mexico horizon, filling the sky with layers of twilight. Many think of bustling Miami or the magical kingdom in Orlando when Florida crosses their minds. Yet, for those looking to step off life's fast track and into the flip-flops of retirement and relaxation, there are quieter pockets of paradise waiting. Choices include daily fishing excursions on cerulean lakes, flea markets that feel like treasure hunts, and decades-old diners where everybody knows your name—and your order. Welcome to a world where the grass truly is greener, the skies bluer, and the fresh-squeezed orange juice sweeter. If you're dreaming of a peaceful escape for your golden years, you're in the right place. It's time to explore some cozy, lesser-known corners of the Sunshine State.

On a national scale, the Sunshine State ranks high in terms of attractions and weather. Experts agree that retiring in one of the small towns is a smart move in Florida, which placed a close second in 2021 according to Bankrate's list of the best states to retire. Retirees receive a high quality of life with decent healthcare resources and no state income tax. The state also ranks highly in racial diversity and the LGBTQ population.

Florida is teeming with a happy active-adult community that is staying healthy along the beaches and willing to share them with more senior friends. Although the costs of retiring are rising across the nation, the Sunshine State remains one of the more affordable places to endeavor to live out your golden years' dreams, where small towns will meet all your amenities and service demands.

Gulf Breeze

You can see the whole town of Gulf Breeze in the view with a bridge in the far off distance
Gulf Breeze, Florida.

With a population of 7,000, Gulf Breeze is a popular place to retire, where 25% of residents are over the age of 65. The town has a humid subtropical climate with little weather variation and 63 inches of annual rainfall. The median home value of $436,900 is worth the easy access to various medical facilities across the bridge in Pensacola and in nearby Milton. There is also great public transit around town and the surrounding areas, as well as scrollable streets for daily venturing. Enjoy a small-town atmosphere with a detached feel while being a hand's reach away from all the attractions, dining scenes, entertainment, and cultural activities in Pensacola.

This western Florida Panhandle town, hemmed in by water on three sides and the Naval Live Oaks Preserve on the east side, is set idyllically along the end of the Fairpoint Peninsula. Gulf Breeze is a tax-friendly community with a lower crime rate than the national average, a public library, and the Gulf Breeze Zoo with over 1,000 animals. It is also close to Santa Rosa Sound via the Pensacola Bay Bridge. Seek the feel of old Florida along the white sand beaches and azure waters at the preserve, along the Gulf Islands National Seashore, and on Pensacola Beach across the water.

Key West

Aerial view of Key West in Florida
Key West in Florida.

Key West is part of a small coral island chain located just southwest of the Florida peninsula. This lively, small town feels remote yet inviting, thanks to its pleasant climate, numerous beaches, and retiree-friendly features. With only 26,000 residents, Key West offers fine dining restaurants, banks, grocery stores, and top-rated medical facilities, such as the 24-hour hospital at Lower Keys Medical Center right in Key West. Despite a high cost of living and a median home value of $728,500, you can live in a community that is largely crime-free and has been home to notable figures like Harry Truman, John James Audubon, Tennessee Williams, and Ernest Hemingway.

Key West appeals to retirees as a dream spot for enjoying their golden years. Wealthy residents thrive with easy beach access and a relaxed, yet vibrant, lifestyle. Walk along Duval Street, filled with restaurants, shops, bars, and cafes, or explore the Old Town to watch stunning sunsets. Many choose to live modestly in condos or apartments rather than private homes or gated communities, riding bikes like locals to stay active. The tropical climate fuels all these activities, offering warm temperatures year-round, hot and humid summers, and a welcoming community of residents.

Lakewood Ranch

A senior man jogs along a lakeside path in the light of the rising sun in Lakewood Ranch, Florida
Lakewood Ranch, Florida. Image credit Ken Schulze via Shutterstock

Over the past few years, Lakewood Ranch has been growing in demand among retirees, and named one of the hottest places to retire in 2023. The small town of around 35,000 residents, 30% of which are in the 65+ bracket, along the envied central west coast, is near the big cities of Sarasota and Bradenton, both home to beautiful, vast beaches. Buy a home at the median home value of $474,600 and invite friends over. Choose from a variety of 55+ neighborhoods, such as Cresswind at Lakewood Ranch and Del Webb at Lakewood Ranch.

Mixed-age neighborhoods provide an ideal downtown experience along Main Street, featuring an eclectic mix of boutiques and restaurants. Enjoy modern entertainment options such as Lakewood Ranch Cinemas, along with concerts and festivals held annually on Main. Opt for waterside apartments at Waterside Place for scenic views right from your window. This multi-generational community is a popular retirement spot, praised for its vibrant small-town charm and affordable living, set amidst contemporary amenities.

Naples

Naples coastline, Florida aerial view.
Naples coastline, Florida.

The southern waterfront city of Naples is a desirable place in the US to retire because of its historical center, architectural wonders, lively vibe, and attractions for all ages. Join one happy, go-lucky small community of just 19,000 people, with over 50% of the population 65+. You will have great access to superb medical care, foodie heaven downtown, and activities like golf, fishing, and kayaking in the mangroves. You can spend days exploring the Old Town of Naples and never get tired of the scenic sights. Get all the sun, sand, and sea you desire at the beach and head shopping along Fifth Avenue, Third Street South, and the Trail of Treasures, an area with vintage finds. Hit the renowned Naples Zoo with your grandkids or head on a getaway to the Everglades.

Naples combines Florida's finest offerings, including shopping, recreation, and beautiful beaches, all within a charming small-town atmosphere. It features historic downtown Naples, luxury shops and boutiques, and numerous championship-level golf courses along the Gulf Coast, known for some of the nation's most breathtaking beaches. With so much packed into a small area, it's understandable that home prices, once affordable, are gradually rising. The "Naples Valencia Trails" is an impressive 42,000-square-foot clubhouse providing resort-style living, complete with daily events, clubs, entertainment, a pool, and a restaurant. Residents can enjoy performances at the social hall or take a leisurely walk or jog along the community’s renowned trails.

Ocala

Photo of the gazebo of the historical downtown square in Ocala Florida on a beautiful sunny day
Ocala, Florida.

The smaller town, in 2020 recently ranked 6th among the nation's 10 best places to retire, according to a US News & World Report. Ocala scored highest for housing affordability and had a high healthcare score. The unique and quickly growing town today, with new attractive services and amenities geared to all, remains a highly desirable destination for the best gold years. Ocala is popular among retirees for its history, horses, and culture, amid some of the nation's most beautiful landscapes. Enjoy a vibrant downtown scene with shops and restaurants on a morning coffee run, mingle and people watch, and spend the evening in good company.

Ocala is a fantastic destination for retirement, offering endless activities and a range of affordable housing options or exclusive 55+ communities. Residents can join various clubs, such as the Ocala Palms Golf & Country Club, leagues, and hobby groups. The On Top of the World community features excellent leisure facilities, including cultural venues, golf courses, sports courts, swimming pools, a fitness center, a health club, and a spa. Alternatively, consider Del Webb Stone Creek, a highly rated, budget-friendly community with many amenities like golf courses.

St. Augustine

Aerial view of Castillo de San Marcos along the stunning turquoise waters in St Augustine, Florida
Castillo de San Marcos in St Augustine, Florida.

St. Augustine is the deeply historic and endlessly romantic "Oldest City" in the nation. This small city is a highly sought-after retirement destination and perfect for history and architecture fans. With a population of almost 15,000 residents living along the east coast, you will have uncrowded views from the renowned waterfront, the best beach strolls, unique culture along the streets, and even an entertainment scene. It is also only 40 miles south of Jacksonville and 60 miles north of Daytona Beach.

The variety of shopping options and unique dining experiences cater to all tastes and will keep you busy. The city takes great care of its residents aged 65 and older, who make up 26% of the population, with new establishments constantly emerging. You can choose from excellent retirement communities such as the gated St. Augustine Parkland Preserve at World Golf Village, ideal for active adults, or the Reverie at Trailmark, a 55+ community situated between St. John's River and the Atlantic Ocean. The first community is well known for its amenities, including a pool and a lifestyle director who helps neighbors connect and stay active.

Venice

Welcome to historic old town of Italian city district in Florida with 124 sidewalk restaurant with outdoor sitting area with empty chairs and tables, Venice Florida
The historic district of Venice, Florida. Image credit Andriy Blokhin via Shutterstock

One of the nation's most picturesque and romantic towns is also among the top for the best retirement lifestyles, with over 60% of the population in the 65+ age group. Venice offers a high quality of life and a variety of affordable healthcare options. There is also entertainment for all tastes and ages, along with outdoor activities like kayaking and paddleboarding along the Intracoastal Waterway through the heart of the city. With a population of around 26,000, you can enjoy all services within a small-town atmosphere, along with sun, sea, and sand on the beaches with no crowds. This coastal town, offering all the perks of a major city but with a laid-back, beachy vibe, is a dream destination for a peaceful retirement.

Buy your own place at the median home value of $290,600 and feel safe with minimal crime to enjoy daily strolls alone or with friends. Enjoy the beaches and find parks every few blocks, where only the quiet swooshing of palm trees and the chirping of birds will disturb your tranquility. Downtown Venice is replete with local establishments and fine dining venues where you can enjoy live music and idyllic sunset views. You can also take up golf or tennis, or take a day trip to nearby cities like Sarasota, Manasota Key, and Nokomis Beach for more entertainment.

Vero Beach

Aerial shot Vero Beach hotels and condominium buildings
Vero Beach, Florida.

The peaceful, quiet, and always sunny town of Vero Beach is your ideal retirement spot, especially if you're interested in WWII history. Own your own home at affordable prices, with an average value of $287,500, and enjoy a slower pace of life amid friendly locals. You can explore two shopping malls and a historic downtown area that once served as a US Naval Station. Lead a stress-free life on the beautiful beaches where you can relax daily by the ocean. This small beach town in Southeast Florida, situated between Melbourne and Port St. Lucie, offers plenty of coastal activities to stay active or simply relax while sunbathing.

There is surfing, swimming, fishing, boating, and snorkeling that attract tourists, along with Disney’s Vero Beach Resort, a major employer in the area. Vero Beach is not a tourist trap but a community-centric town with many planned vacation and retirement communities that offer private beaches, pools, restaurants, tennis, golf, and social events. Downtown Vero is full of boutique shopping and dining options, breweries, and local favorites like The Tides, The Citrus Grillhouse, and The Lemon Tree. You will also have access to two hospitals in the event of need.

Winter Park

Retail stores on South Park Avenue in downtown Winter Park
Downtown Winter Park, Florida.

The small city in central Florida that is Orlando's suburb is a great place to retire with excellent health care, ranking ninth according to WalletHub. Winter Park is less than 30 miles from Disney World for a unique outing to reminisce on your childhood or when the grandkids finally get to visit you and Mickey Mouse together. Winter Park is a great landlocked place to retire on a budget, with small-town charm, brick streets, and oak trees for atmospheric strolls.

You will not even miss the beach with a gorgeous chain of lakes at your fingertips. Winter Park is a quiet city known for its worth in the booming culinary and arts scene, with notable favorites like concerts and shows at the Dr. Phillips Center for the Performing Arts. Catch a classic movie at the Enzian Theater with your sweetheart or friend, and dine al fresco at sunset on Park Avenue. Enjoy open-air cafes in the morning for a coffee over a newspaper while watching locals grab a drink before work.

Florida ranked first in 2022 according to Bankrate’s culture and diversity ranking, with a high share of residents over 65, racial diversity, and different ethnicities. The Sunshine State's pleasant winter weather continues to draw retirees from big cities and small towns for all budgets and preferences of "lively." Choose to retire along any coast, and you will live vacation-style golden years with prime access to the beaches and healthcare facilities.

If you are tired of the long winters and enjoy the beach in your daily pursuits, you can stay active through swimming and keep your mind healthy through relaxation. These small towns all offer a variety of lifestyles, as well as the typical Florida weather and friendly residents. Retire in your own place on a budget or choose community-style living with clubs and hobbies to enjoy with your friends and neighbors.

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