Where to Live in the Florida Keys: The Best Islands & Neighborhoods for Every Lifestyle

Where to Live in the Florida Keys: The Best Islands & Neighborhoods for Every Lifestyle

Thinking about moving to the Florida Keys? You’re not alone. This tropical stretch of paradise — known for its turquoise water, boating lifestyle, and laid-back culture — draws people from all over the world. Each part of the Keys offers something unique and each key is quite different. Whether you’re looking for luxury, tranquility, investment potential, or a community-oriented vibe, there’s an island (or two) that fits your goals.

Let’s break down the Florida Keys by region — Upper, Middle, and Lower Keys — and explore what makes each area ideal for different lifestyles, budgets, and long-term plans.

Upper Keys: The Gateway to the Islands

The Upper Keys are closest to the mainland and offer the most convenience for full-time residents who still want access to Miami or Fort Lauderdale. This area includes Key Largo, Tavernier, and Islamorada — all known for their strong sense of community and easygoing tropical lifestyle.

Key Largo

Best for: Commuters, full-time residents, families, divers

Vibe: Accessible, family-friendly, and full of local charm

Why People Love It:

• Proximity to Miami (just 1.5 hours away)
• Home to John Pennekamp Coral Reef State Park — the first underwater park in the U.S.
• Known as the “Dive Capital of the World”
• Strong public school system, family-friendly neighborhoods, and waterfront properties with canal access
• Median home prices: $650K–$950K, with both condos and single-family homes available

Popular neighborhoods: Port Largo, Largo Sound Village, Ocean Shores, Anglers Park

Tavernier

Best for: Budget-conscious buyers, those seeking a quieter atmosphere

Vibe: Underrated, community-driven, peaceful, historical charm

Why People Love It:

• Situated between Key Largo and Islamorada
• Slightly lower home prices and less tourist traffic
• Home to Old Settler’s Park and access to bayside sunsets
• Mix of charming bungalows, newer builds, and mobile home communities

Median home prices: $550K–$800K

Islamorada

Best for: Luxury buyers, second homeowners, fishing and boating enthusiasts

Vibe: Upscale island living with a vibrant arts and culinary scene

Why People Love It:

• Known as the “Sport Fishing Capital of the World”
• Incredible waterfront estates, resort-style living, and boutique marinas
• Rich in local history, culture, art galleries, and dining (don’t miss Morada Bay or Lazy Days)
• Weekly farmers markets, monthly art walks, and frequent live music
• Home to high-end communities like Port Antigua, Plantation Point, and Venetian Shores

Median home prices: $950K–$1.5M+

Middle Keys: The Heart of the Island Chain

If you’re looking for balance between work, lifestyle, and access to the water, the Middle Keys are ideal. This area includes Marathon, Duck Key, and Key Colony Beach — all offering some of the best deep-water access and boating amenities in the Keys.

Marathon

Best for: Boat owners, retirees, full-time residents, investment rental properties

Vibe: Nautical, laid-back, and practical

Why People Love It:

• Central location — equidistant from Key West and Key Largo
• Sombrero Beach, Curry Hammock State Park, and the Seven Mile Bridge
• Ample dockage, marinas, and boat services
• Family-friendly, with parks, schools, and a hospital (Fishermen’s Community Hospital)
• Great for vacation rentals — offer many short term (7 day rental) opportunities
• Key communities include Sombrero Beach, Coco Plum, and Ocean Isles Fishing Village

Median home prices: $600K–$950K

Duck Key

Best for: Luxury buyers, part-time residents, resort-style living

Vibe: Exclusive and scenic, fantastic boating, active community for runners/bikers

Why People Love It:

• Home to Hawks Cay Resort
• Quiet, private island feel with high-end homes and resort amenities
• Community includes canal homes, villas, and upscale waterfront estates
• Well-kept landscaping and a pristine atmosphere

Median home prices: $1M+

Key Colony Beach

Best for: Investors, retirees, and boaters

Vibe: Peaceful, walkable, well-kept

Why People Love It:

• Self-contained city with its own police department and post office
• Gorgeous canals with quick ocean or bay access
• Golf course, restaurants, marina, and beach access
• Allows weekly vacation rentals, making it ideal for second homeowners seeking income

Median home prices: $900K–$1.3M

Lower Keys: Tranquility Meets Culture

The Lower Keys offer the most remote feel, ideal for those seeking peace and natural beauty — with Key West bringing back the excitement. This area includes Big Pine Key, Cudjoe Key, Sugarloaf Key, and Key West.

Big Pine Key

Best for: Nature lovers, full-time residents, off-the-grid living

Vibe: Quiet, rustic, eco-friendly

Why People Love It:

• Home to the Key Deer Refuge and Bahia Honda State Park
• More affordable properties, often with large lots
• Ideal for RVers, hobby farmers, or buyers looking for affordable land
• Limited commercial development, more residential than touristy

Median home prices: $500K–$700K

Cudjoe & Summerland Key

Best for: Boaters, canal homeowners, retirees

Vibe: Upscale but peaceful

Why People Love It:

• Quick access to both open water and Key West
• Canal-front homes with direct boating access to the Gulf or Atlantic
• Less tourism, more full-time residents
• Summerland Key is known for deep-water lots and private airstrips

Median home prices: $750K–$1.2M+

Key West

Best for: Artists, investors, entertainment seekers, vacation home buyers

Vibe: Colorful, historic, lively

Why People Love It:

• A destination in itself — full of culture, music, nightlife, and art
• Historic Old Town offers Conch-style homes, walkability, and charm
• Excellent vacation rental income potential — but zoning is tight, and transient licenses are required
• A small-town feel with vibrant festivals, from Fantasy Fest to Hemingway Days
• Neighborhoods to explore: Old Town, Truman Annex, Casa Marina, New Town

Median home prices: $950K–$1.5M+

Which Key Is Right for You?

• For luxury + leisure: Islamorada or Duck Key
• For boaters: Marathon, Summerland, or Key Colony Beach
• For culture and rentals: Key West
• For peace and nature: Big Pine Key or Cudjoe
• For full-time/ easily accessible vacation home + Fishing/ boating: Key Largo or Tavernier

Still not sure where you belong in the Keys? Let’s talk about your lifestyle, priorities, and budget — and I’ll help you find your perfect piece of paradise.