Which Key to Stay On in the Florida Keys? A Local’s Guide to Finding Your Perfect Island

With more than 40 inhabited islands stretching from Key Largo to Key West, the Florida Keys offer a tropical escape unlike anywhere else in the U.S. But when it comes to planning your trip, one question comes up again and again — which Key should you stay on?

I’ve lived in the Florida keys for over a decade and have found that each island has a distinct feel — from laid-back fisherman towns to luxury beach resorts and lively nightlife. When choosing a place to stay it can look like a blur of crystal blue water and swaying palm trees, so I’m here to highlight the differences.

Choosing the right key can be integral to your vacation, so you don’t spend it driving around or wondering what to do. Whether you’re chasing sunsets, snorkeling adventures, or pure relaxation, this guide will help you choose the best Key to stay on for your travel style.

This article is part of my complete Florida Keys travel guide, where I share itineraries, island guides, and essential tips for planning your Keys vacation.

Key Largo: Best for First-Timers & Snorkelers

Vibe: Gateway to the Keys, laid-back, nature-focused
Drive time from Miami: ~1.5 hours

Key Largo is the first island you’ll reach when driving down the Overseas Highway — and it’s perfect for travelers who want a taste of the Keys without venturing too far south. I’ve lived here for many years and would way it’s the perfect way to escape the hustle and bustle of Miami without a long drive.

It’s easy to get out on the water here by boating or kayaking. There are lots of mangrove forests to paddle through and spot manatees. Those who love fishing can also find their paradise here, venturing into the mangroves or out on the open water.

Key Largo is home to John Pennekamp Coral Reef State Park, the country’s first underwater park. There you can take a glass bottom boat tour, a snorkel tour to see the famous Christ of the Abyss statue underwater, or a dive tour in the ‘diving capital of the world.’

Stay here if you love:

• Easy access from the mainland
• Snorkeling and diving adventures
• A quiet, nature-driven getaway

Top Resorts & Hotels in Key Largo

• Luxury Resorts:
  • Bungalows Key Largo (Adults Only): All-inclusive tropical escape for honeymooners and couples who appreciate privacy and not having to leave the resort for meals and watersports.
  • Playa Largo Resort & Spa: Luxury beachfront with amazing sunsets. A Marriott property with every amenity you could want and one of the best beaches in Key Largo. My family and I often eat at the on-site restaurant for the view and visit the waters near the beach by boat since it is clear, calm, and has good depth.
• Mid-Range Hotels:
  • Baker’s Cay Resort: A renovated Hilton property with a little bit of everything, a small beach, tucked away pool with waterfall, and modern design throughout.
• Budget Hotels:
  • Bay Harbor Lodge & Coconut Bay Resort: A cute boutique hotel made up of bungalows spread throughout a beachfront property. Perfect for those who prefer an intimate retreat over a sprawling resort. Their fresh homemade scones are to die for in the morning, and the free use of their kayaks and paddle boards are a great bonus.

→ See more things to do in my Key Largo Guide and Key Largo 3 Day Itinerary.

Islamorada: Best for Couples & Fishing Enthusiasts

Vibe: Upscale island charm with an adventurous twist
Drive time from Miami: ~2 hours

Known as the “Sportfishing Capital of the World,” Islamorada blends luxury resorts with small-town island life. With great gourmet dining, fun dive bars, luxury resorts, and fishing charters everywhere, Islamorada is the perfect balance of island life, without the long drive to Key West.

I love visiting the boutiques, art studios, and breweries that give Islamorada a bohemian feel. If you visit on the Third Thursday of the month, don’t miss the Art Walk, when all the shops stay open late and craft vendors come to set up their pop-up shops.

Islamorada also keeps things interesting on the water, with a famous sandbar which is a hotspot for boaters on the weekend to play music, mix drinks, and float around the shallow, clear waters. You can even see them congregated on the water from one of the bridges! There are also boating sandbar tours that will take you out there to join the locals, which is a classic Keys experience.

There are also a few museums centered around scuba diving and Florida Keys history which are worth checking out on a cloudy day. Other on-land activities include the beach at Founder’s Park, exploring Windley Key Fossil Reef Geological State Park, and kayaking in Long Key State Park.

Stay here if you love:

• Boutique resorts and waterfront dining
• Fishing, kayaking, and boating
• Romantic sunsets and art galleries

Top Resorts & Hotels in Islamorada

• Luxury Resorts:
  • Cheeca Lodge & Spa: Classic Keys luxury. Three restaurants, oceanfront pools, and even a golf course!
  • The Moorings Village: Private villas set in a palm tree grove. A low-key, family-run, oceanfront oasis.
  • The Islands of Islamorada: Multi-bedroom villas and tons of on-site activities make it perfect for families.
• Mid-Range Hotels:
  • Three Waters Resort: Recently given a multi million dollar facelift, this ocean front property has a tiki bar, rooftop bar, Italian restaurant, and a Starbucks, not to mention stunning views all around.
• Budget Hotels:
  • Islander Resort: Laid-back retro vibes with a sandy beach, two pools, and a variety of watersports available.

→ For more things to do and where to eat, check out the full Islamorada Guide.

 Marathon: Best for Families & Central Location

Vibe: Family-friendly, relaxed, local
Drive time from Miami: ~2.5 hours

Located right in the heart of the Florida Keys, Marathon is the perfect home base for exploring up and down the island chain. It’s one of the few areas with real sandy beaches — Sombrero Beach, Coco Plum Beach, and Curry Hammock State Park — and has plenty of attractions for families and nature lovers.

These beaches are actually where loggerhead turtles come annually to nest. That’s why you’ll notice that many lights are red around here, so baby turtles don’t confuse them for the moon when heading out to sea for the first time.

Marathon is really made up of several islands, but since they are smaller and in close proximity they are often grouped together when referencing. There is a low key, local vibe and like the rest of the Keys it has great snorkeling, boating, and dive bars. Be sure to stop in at The Turtle Hospital for a look behind the scenes at the rehabilitation efforts for injured and sick sea turtles.

Stay here if you love:

• Easy access to beaches
• Central location for day trips
• A quieter, less touristy vibe

Skip the hassle of looking for flights! Use my Award Booking Concierge Service. I’ll find the flights on points and let you know exactly how to book. As an experienced traveler, I also build out custom itineraries (with or without points) that let you enjoy the trip without the planning.

Top Resorts & Hotels in Marathon

• Luxury Resorts:
  • Isla Bella Beach Resort: Luxury meets tropical style with multiple swimming pools and mediterranean inspired architecture.
• Mid Range Accommodations:
  • Marlin Bay Resort: Boater’s paradise with dockage and resort style amenities (shower, sauna, pool). Multi-bedroom townhomes are also available for rent. We’ve stayed here multiple times while sleeping on the boat and absolutely love the beautiful grounds and perfect location near restaurants and snorkel spots.
  • Hawk’s Cay Resort: Family-friendly resort with a daily schedule of activities, a pirate ship pool, and lagoon perfect for swimming. It’s also a Preferred Hotel & Resort, making it a great use of Citi ThankYou Points.
• Budget Bungalows:
  • Tranquility Bay Beachfront Resort: Townhome-style cottages with access to three pools, an onsite cafe, and a private sandy beach.

→ Best restaurants and things to do in the Marathon Travel Guide

Big Pine Key & The Lower Keys: Best for Nature & Peace

Vibe: Quiet, wild, and naturally beautiful
Drive time from Miami: ~3 hours

If you’re craving serenity and scenery, the Lower Keys are where the wild side of the islands begins. Big Pine Key is home to the endangered Key deer and Bahia Honda State Park, one of the best beaches in the Keys and best spot for sunset.

Spot the Key deer outside of No-Name Pub or at the one of the trails encompassed by the National Key Deer Refuge Nature Center, like the Blue Hole Observation Platform.

This area is very popular with campers and RV travel, so you’ll see numerous oceanfront campgrounds. You can even camp right in Bahia Honda State Park, but be sure to book your reservation way ahead of time.

Staying in Big Pine is great if you are generally doing your own activities with your family while camping, looking for budget friendly accommodations, or want the whole other side of the spectrum by enjoying one of the Key’s finest resorts, Little Palm Island.

Stay here if you love:

• Camping, kayaking, or RV travel
• Wildlife and outdoor adventures
• Escaping the crowds

Top Resorts & Hotels in Big Pine Key

• Luxury Resorts:
  • Little Palm Island Resort & Spa: One of Florida’s most exclusive private island resorts
• Budget Accommodations:
  • Parmer’s Resort: Budget friendly rooms with good customer service, breakfast, and the Keys essentials – a pool and beach.
  • Sugarloaf Key Hotel: Pull up your RV, or rent a room, either way you’ll get a relaxing retreat and pool to cool off in.

 Key West: Best for Nightlife, History & Iconic Vibes

Vibe: Historic, lively, colorful
Drive time from Miami: ~4 hours

At the end of the road lies Key West — a vibrant mix of Caribbean flair, historic architecture, and endless entertainment. It’s where sunsets at Mallory Square turn into nights on Duval Street and mornings spent sipping Cuban coffee at Blue Heaven.

Key West is a well known cruise ship stop, treasure-hunting capital, and nightlife central. Its most popular street, Duval Street, is what other places like Nashville’s Broadway and New Orlean’s Bourbon Street wish they were.

The area surrounding Duval street is called Old Town and is made up of a cluster of victorian homes, historic attractions, and fabulous restaurants. This is where everyone wants to be, and where you should stay despite the pricier accommodations.

If your budget is guiding your trip, then you may end up staying in New Town, the eastern side of the island where US1 wraps around the edge and strip malls offer the essentials to local residents.

Things to do are practically endless in Key West. There’s beaches like Fort Zachary Taylor State Park, historical homes like the Ernest Hemingway Home and the Truman Little White House, family-friendly places like the Key West Butterfly Conservatory, and the famous Mallory Square Sunset Celebration.

Stay here if you love:

• Walkable neighborhoods and nightlife
• Boutique hotels and historic charm
• A lively, social atmosphere

For more help planning your trip, visit my Florida Keys travel guide to explore island comparisons and sample itineraries.

Top Resorts & Hotels in Key West

• Luxury Resorts:
  • Pier House Resort & Spa: Iconic waterfront stay with private beach right on Duval Street. We had a great stay here, it’s so conveniently located, and yet tucked away from the sometimes chaotic Duval Street.
• Mid-Range Hotels:
  • Southernmost House: I’ve always loved looking at this grand old mansion, colorfully painted, against the ocean waves. It’s as dramatic looking as it sounds, and has amenities and service to match. Perfect for couples looking for an oceanview stay.
  • Ella’s Cottages: Get to experience life in old Key West while immersed in this gorgeous historic home that feels light and tropical. Only a block away from Duval, making it perfect for couples that want to have easy access to nightlife.
  • Andrew’s Inn & Garden Cottages: Great location with an old Florida feel, this boutique property has outstanding hospitality and a daily happy hour.
• Budget Hotels:
  • Doubletree Resort by Hilton Hotel Grand Key: If you are going to be in New Town, then make sure that there is a hotel shuttle like the Doubletree has. The free shuttle takes you to downtown, the airport, and the beach. There is nothing better than not having to deal with Key West parking and having a large pool to come back to relax in.

→Save my favorite food spots and cover the best things to do- all in the Key West Travel Guide

How to Choose the Best Key for You

Travel Style	Stay On	Highlights
First-Timers	Key Largo	Easy access, snorkeling
Couples	Islamorada	Romantic, upscale resorts
Families	Marathon	Central, beaches, affordable
Nature Lovers	Lower Keys	Quiet, wildlife, camping
Nightlife Seekers	Key West	Historic charm, entertainment

Local Tip: Don’t Limit Yourself to One Key

One of the best parts of visiting the Florida Keys is that each island is just a short drive from the next. You can easily stay in one spot and take day trips — or split your trip between two Keys to experience both relaxation and excitement.

Each Key in the Florida Keys offers its own version of paradise — it all depends on the experience you’re looking for. From the coral reefs of Key Largo to the energy of Key West, there’s no wrong choice — just a new island adventure waiting around every turn of the Overseas Highway.

Example: Spend 2 nights in Islamorada for kayaking and sunsets, then 2 nights in Key West for nightlife and culture.

→ 10 Essential tips for Visiting the Florida Keys

→ Ultimate 7 Day Florida Keys Road Trip

Ready to plan your full itinerary? Explore my complete Florida Keys travel guide for everything you need to know before you go.

Staying in the Florida Keys FAQ