The minute I landed in the Florida Keys, I knew I was in trouble. Now I spend way too much time browsing real estate listings instead of packing my bags to leave. Life down here just hits different, especially in spots like Marathon, where boat captains tell stories at fish shacks and everyone seems to be living their best life, or Key West, where sunset celebrations are basically a religion.
These are the best places in the Florida Keys to call home, and each one has its own magic. From quiet islands where manatees visit your dock to spots where everyone knows their favorite bartender’s life story, I’m sharing 12 places that’ll make you want to trade your regular life for permanent island time.
Most Livable Places in Florida Keys
Looking for the best places in the Florida Keys? Explore the vibrant island life in Key West, known for its lively Duval Street, historic landmarks, and stunning sunsets. Relax in Key Largo, a paradise for divers and snorkelers with its crystal-clear waters and marine sanctuaries. Enjoy the tranquility of Duck Key, offering luxury resorts and breathtaking ocean views. Experience world-class fishing and waterfront dining in Islamorada, the sportfishing capital of the world. Whether you’re seeking adventure, relaxation, or scenic beauty, these are some of the top places to visit in the Florida Keys.
- Best for cultural richness: Key West
- Best for underwater adventures: Key Largo
- Best for serene retreats: Duck Key
- Best for upscale living: Islamorada
- Best for nature enthusiasts: Big Pine Key
- Best for community living: Tavernier
- Best for balanced lifestyle: Marathon
- Best for family-friendly living: Key Colony Beach
- Best for tranquil island life: Cudjoe Key
- Best for authentic Keys experience: Stock Island
- Best for peaceful living: Long Key
- Best for secluded charm: Big Coppitt Key
1. Key West
- 💰 Average Monthly Cost: $4,000 – $6,500
- 🌟 Unique Features: Historic architecture, vibrant nightlife, and beautiful beaches.
- 📅 Best Time to Live There: Winter for mild weather; summer for fewer tourists.
- 🏆 Perfect For: Artists, retirees, and beach lovers.
Key West isn’t just a place—it’s a state of mind. At the southernmost point of the U.S., this lively island is where history, culture, and laid-back island vibes collide. Streets lined with pastel-hued conch houses, a thriving arts scene, and the famous Sunset Celebration at Mallory Square make every day feel like a festival.
It’s a paradise for boaters, snorkelers, and history buffs. Explore Ernest Hemingway’s house, sip a cocktail on Duval Street, or take a sunset sail in turquoise waters. The food scene is unbeatable, from fresh seafood to legendary Key lime pie.
But the best part? Key West is all about community. Whether you’re diving into the nightlife or enjoying the slow island pace, this place welcomes everyone with open arms. If you want a life where every sunset is an event, Key West is the place to be.
2. Key Largo
- 💰 Average Monthly Cost: $3,200 – $5,000
- 🌟 Unique Features: Famous for diving, state parks, and laid-back island life.
- 📅 Best Time to Live There: Fall to spring for ideal weather.
- 🏆 Perfect For: Divers, nature lovers, and families.
Love underwater adventures and laid-back island living? Key Largo might be for you. Known as the “Diving Capital of the World”, it’s home to John Pennekamp Coral Reef State Park, where crystal-clear waters reveal vibrant marine life, sunken ships, and endless snorkeling spots.
Beyond the reefs, life here is relaxed and community-driven. Local markets, seafood shacks, and marinas set the tone for a casual, ocean-loving lifestyle. Whether you’re kayaking through mangroves, paddleboarding at sunset, or grabbing a beer at a waterfront tiki bar, life moves at a slower, more enjoyable pace.
With proximity to Miami but a world away from the chaos, Key Largo is perfect for nature lovers and water sports enthusiasts. If you’re after a place where the ocean is your playground and every day feels like a vacation, this is it.
3. Duck Key
- 💰 Average Monthly Cost: $3,500 – $5,500
- 🌟 Unique Features: Exclusive, quiet community with resort-style living.
- 📅 Best Time to Live There: Year-round.
- 🏆 Perfect For: Luxury seekers and second-home buyers.
Tucked between the Atlantic Ocean and the Gulf of Mexico, Duck Key is a hidden gem for those craving peace, privacy, and waterfront luxury. This small, upscale island is known for its charming canals, scenic bridges, and postcard-perfect views.
Here, the outdoor lifestyle reigns supreme. Spend your days boating, kayaking, or snorkeling in pristine waters. Fishing is world-class, and the island’s marina makes it easy to set sail anytime you want. If you prefer relaxation, beachfront hammocks and sunset cocktails are the norm.
The tight-knit community feel is part of Duck Key’s charm. Homes range from cozy waterfront cottages to multimillion-dollar estates, all offering breathtaking ocean vistas. With quiet streets, clear waters, and a stress-free pace, Duck Key is perfect for those looking to escape the noise and embrace island serenity.
4. Islamorada
- 💰 Average Monthly Cost: $3,800 – $6,000
- 🌟 Unique Features: Sportfishing capital with upscale waterfront living.
- 📅 Best Time to Live There: Winter and spring.
- 🏆 Perfect For: Fishermen, boaters, and water sports enthusiasts.
Known as the “Sport Fishing Capital of the World,” Islamorada is a paradise for anglers, adventurers, and anyone who loves life on the water. Stretching across six stunning islands, this spot is equal parts luxury and laid-back charm.
Fishing isn’t the only draw—Islamorada has a bustling arts scene, waterfront dining, and stunning nature parks. Snorkel in Alligator Reef, sip cocktails at a beachfront tiki bar, or check out the local galleries and live music spots. Sunsets here are legendary, best enjoyed from the deck of a boat or a beachside hammock.
The community is welcoming yet exclusive, with high-end homes, luxury resorts, and plenty of oceanfront properties. Whether you’re after thrill-seeking adventure or tranquil island vibes, Islamorada delivers. It’s a place where life is as exciting—or as relaxed—as you want it to be.
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5. Big Pine Key
- 💰 Average Monthly Cost: $2,800 – $4,500
- 🌟 Unique Features: Home to the endangered Key deer and scenic nature trails.
- 📅 Best Time to Live There: Winter for mild weather.
- 🏆 Perfect For: Nature lovers and retirees.
If your idea of paradise includes untouched nature, quiet streets, and friendly neighbors, Big Pine Key is calling. Known for its wildlife and relaxed vibe, this island is a haven for nature lovers and those looking to escape the crowds.
Big Pine is famous for the adorable Key deer, which roam freely through backyards and nature trails. The waters are perfect for kayaking, paddleboarding, and snorkeling, while the National Key Deer Refuge offers endless hiking opportunities. It’s also just a short drive from the livelier scene in Key West, giving you the best of both worlds.
The housing market ranges from affordable bungalows to waterfront homes, all offering a laid-back, community-focused lifestyle. If you want to swap traffic noise for the sound of palm trees swaying in the breeze, Big Pine Key is your perfect escape.
6. Tavernier
- 💰 Average Monthly Cost: $3,000 – $4,800
- 🌟 Unique Features: Peaceful residential area with easy access to Key Largo and Islamorada.
- 📅 Best Time to Live There: Fall to spring.
- 🏆 Perfect For: Families and retirees.
Just south of Key Largo, Tavernier offers a small-town feel with big ocean views. It’s a tight-knit community where locals know each other by name, and life revolves around the water, local markets, and sunset strolls.
Tavernier’s secluded beaches, calm waters, and historic charm make it a hidden gem for those looking for a peaceful, slower pace. Outdoor enthusiasts love fishing, kayaking through mangroves, and spotting manatees in the canals. The seafood here is as fresh as it gets, with dock-to-table restaurants serving up the best catch of the day.
With affordable homes, strong community ties, and easy access to both Key Largo and Islamorada, Tavernier is a great pick for anyone looking to enjoy island life without the tourist crowds. If you want a low-key, coastal lifestyle with a touch of Old Florida charm, this is the place to be.
7. Marathon
- 💰 Average Monthly Cost: $3,200 – $5,200
- 🌟 Unique Features: Centrally located, great for boating, and home to the famous Seven Mile Bridge.
- 📅 Best Time to Live There: Year-round.
- 🏆 Perfect For: Boaters and active families.
If you want the best of both worlds—small-town charm with big-time amenities—Marathon is the place to be. Spanning 13 islands, this vibrant city is a hub for boating, fishing, and laid-back island living, offering something for everyone.
Marathon’s beaches and barrier reefs make it a paradise for divers and snorkelers, while spots like Sombrero Beach and the Turtle Hospital add to its local charm and family-friendly appeal. It also boasts one of the best school systems in the Keys, making it ideal for families looking to settle down in paradise.
The housing options range from affordable bungalows to waterfront estates, and the tight-knit community makes it easy to feel at home. Whether you’re spending your day fishing on the Gulf, enjoying fresh seafood, kayaking through mangroves, or catching a sunset cruise, Marathon balances relaxation and adventure perfectly.
8. Key Colony Beach
- 💰 Average Monthly Cost: $3,500 – $5,800
- 🌟 Unique Features: Private island-style living with canals and a yacht club.
- 📅 Best Time to Live There: Winter and spring.
- 🏆 Perfect For: Boating enthusiasts and retirees.
Luxury meets small-town charm in Key Colony Beach, one of the most desirable places to live in the Florida Keys. This pristine island city is known for its canal-front homes, white sandy beaches, and private marinas, offering a resort-style atmosphere without the crowds.
Residents enjoy golfing, waterfront dining, and year-round boating, with the Atlantic Ocean just minutes away. The area is perfect for snorkeling, paddleboarding, and fishing, while its beachfront parks and walking trails make it easy to soak in the island’s beauty. Evenings are best spent watching the sunset from a dockside restaurant or enjoying a quiet stroll along the palm-lined streets.
With well-maintained neighborhoods, a strong sense of community, and a reputation for safety, Key Colony Beach is perfect for families, retirees, and vacation homeowners alike. If you dream of a peaceful retreat with all the perks of island life, this postcard-perfect paradise is hard to beat.
9. Cudjoe Key
- 💰 Average Monthly Cost: $2,900 – $4,600
- 🌟 Unique Features: Quiet residential area close to Key West.
- 📅 Best Time to Live There: Fall to spring.
- 🏆 Perfect For: Retirees and remote workers.
For those who want quiet island living without being too far from Key West, Cudjoe Key should be on your radar. Known for its laid-back vibe, scenic canals, and excellent boating access, this spot is perfect for those who love life on the water and appreciate nature’s tranquility.
Fishing, kayaking, and paddleboarding are part of everyday life, with beautiful mangrove trails, coral reefs, and open ocean access right at your doorstep. It’s also a prime spot for stargazing, with some of the clearest night skies in the Keys, making nighttime here just as magical as the days.
Cudjoe Key’s housing market is diverse, offering cozy waterfront cottages, modern homes, and private estates with panoramic ocean views. While it’s peaceful and secluded, it’s just a 20-minute drive to Key West, making it a great option for those who want a quiet retreat with easy access to the action.
10. Stock Island
- 💰 Average Monthly Cost: $3,000 – $5,000
- 🌟 Unique Features: Up-and-coming area near Key West with a growing arts scene.
- 📅 Best Time to Live There: Winter for ideal temperatures.
- 🏆 Perfect For: Artists and young professionals.
Once known as Key West’s working-class neighbor, Stock Island is now one of the coolest up-and-coming places to live in the Florida Keys. With a bohemian spirit, thriving art scene, and marina-front seafood joints, it’s got an authentic Old Florida feel—without the tourist chaos of Key West.
Life here revolves around the water. Whether you’re a fisherman, boater, or diver, Stock Island is home to some of the best marinas and fresh seafood markets in the Keys. The local restaurants serve up dock-to-table meals, and the artist community is thriving, with galleries and studios popping up all over.
The housing options range from affordable homes to stylish waterfront properties, making it one of the best Keys for young professionals and creatives. If you want Key West energy with a more relaxed, local vibe, Stock Island is the perfect place to drop anchor.
11. Long Key
- 💰 Average Monthly Cost: $2,700 – $4,300
- 🌟 Unique Features: Serene environment with excellent fishing and kayaking.
- 📅 Best Time to Live There: Year-round.
- 🏆 Perfect For: Outdoor enthusiasts and retirees.
If peace, privacy, and nature are at the top of your list, Long Key is a dream destination. This island is home to Long Key State Park, where pristine beaches, crystal-clear waters, and endless outdoor adventures await. Whether you’re into hiking, fishing, or simply relaxing by the shore, this spot offers an unspoiled slice of paradise.
Long Key is perfect for nature lovers, kayakers, and birdwatchers. The calm waters make it a fantastic spot for fishing and paddleboarding, while the scenic trails offer unmatched views of the ocean. It’s one of the most secluded and quiet islands in the Keys, ideal for those looking to escape the hustle and bustle of everyday life.
Housing here is limited but incredibly scenic, with waterfront homes offering breathtaking sunrises and sunsets. If you want to disconnect from the fast-paced world and embrace a simple, nature-filled lifestyle, Long Key is the ultimate paradise.
12. Big Coppitt Key
- 💰 Average Monthly Cost: $2,800 – $4,500
- 🌟 Unique Features: Affordable alternative to Key West with a relaxed vibe.
- 📅 Best Time to Live There: Winter and spring.
- 🏆 Perfect For: Budget-conscious island dwellers.
Just a 10-minute drive from Key West, Big Coppitt Key is the perfect mix of quiet island life and city convenience. If you want affordable waterfront living near Key West’s energy but without the constant crowds, this is your spot.
The tight-knit community here enjoys canal-front homes, beautiful sunrises, and easy access to the Lower Keys’ best boating and fishing. Locals spend their days kayaking through mangroves, casting a line from their backyard docks, or simply enjoying the laid-back island lifestyle. It’s also one of the more budget-friendly places in the Keys, making it a great pick for locals, retirees, and young families looking to settle in paradise.
Big Coppitt Key offers a relaxed, low-key vibe, but when you crave excitement, Key West is just down the road. If you’re after a peaceful escape that keeps you close to the action, Big Coppitt Key is for you.
