Where to stay in the Florida Keys – Best 5 islands

Did you know that this coral cay archipelago is 120 miles (almost 200km) long? No wonder you find it hard to understand where to stay in the Florida Keys.

Let me add also that there are over 800 islands in the archipelago. So, how easy is it to find the right location for the holiday?

In this guide, I have grouped the best places to stay in the Florida Keys in 5 areas, including of course the world-famous Key West and other 4 unique groups of islands, all interconnected by the Overseas Highway.

Every area has its unique character, which may cater more to couples or families, beach lovers, or action travelers. Everyone with their own budget.

And you know the best? It’s all updated, with no old stuff, closed restaurants, or hotels in need of attention.

If you are coming from 2 or 3 days in Miami and you want to be up to date with the Keys news, have a look at the KeysNews website, very informative. 

Where to stay in the Florida Keys – In a nutshell

This is one of the best places to stay in Florida, if not the best. If you have just 1 minute to read, this is a quick summary in an easy-to-read table. But there is so much more info below about every single island

And let me expand the table

• 👨‍❤️‍👨 Where to stay in the Florida Keys for couples: in Key Largo for the adventure couple (check out the Coconut Bay Resort), in Key West for a laid-back and boutique hotel (check out Kimpton Winslow’s Bungalows resort) and Big Pine Key for a romantic and isolated breakaway (Barnacle B&B is the perfect spot). Read more below about a stay for couples.
• 👪 Where to stay in the Keys for families: in Marathon Island with small kids (check out the Courtyard by Marriott) and Islamorada with grown-up kids (Islander Resort). Read more below for a family stay
• 🏊 Best place to stay in the Florida Keys on the beach: Key West for beach and lifestyle (check out the Hyatt Residence Club for a room with a hot tub) and Marathon Island for beach and easy life (Tranquility Bay Beachfront)
• ☀️ Where to stay in Key West: The Artist House in Upper Duval, the district to be, is my favorite choice. You should check out my full guide to where to stay in Key West.
• 🚶 Top experiences in Florida Keys and Key West that you should not miss (free cancellation up to 24 hours in advance):
  • A Sunset sail on a dreamy 105-foot schooner
  • A Sunset Party Cruise by Catamaran, including food and drinks, alcoholic too, a real bargain
  • The unmissable snorkeling trip at the local reef, for the amazing colors. Or this combined eco-tour including also dolphins watching
  • For a fun family day, you should not miss out on the Hop-On/Off island tour on the Old Town Trolley
  • For some real fun check out the Ultimate Watersports Adventure Tour
• 😄 Still unsure about the Keys attractions? I wrote a guide with 35 things to do in the Florida Keys that you should not miss. You will be surprised by a few hidden
• If you are debating on where to stay in Florida, and what to visit, besides the keys, I highly suggest these are 3 destinations: Siesta Key, Marco Island, and Panama City Beach.

Best islands to stay in Florida Keys

Yes, I said “800 islands” but this is more of a fact number because, in reality, most of them have really tiny sizes and no inhabitants.

In this guide, I focus on the best islands to stay in the Florida Keys for a holiday.

In the list below, you will find the top 5 areas. These are where you will find hotels, accommodations with full kitchens, activities, restaurants, cafes, and tourism infrastructure.

From your island, you can explore other inhabited islands by boat, or just drive your car through the 42 bridges to explore the hidden beaches, awesome snorkeling points, and family-oriented attractions of the Florida Keys.

All around is the magical Atlantic Ocean.

Key West (the most famous of all)

If you watch movies, follow the news, or generally exist in the 21st century, then you have most likely heard of Key West.

This popular little island is the cultural hub of the whole Florida Keys.

Despite its notorious status as a party island, it has managed to preserve a welcoming small hometown vibe.

In addition to this, Key West promises a fun-packed trip with the likes of The Mel Fisher Maritime Heritage Museum and the urban wonders of Mallory Square to keep you busy.

• 📖 Keep reading on my dedicated Guide to the best areas and accommodations in Key West
• 🏩 Best accommodations in the area: The Artist House, boutique style or DoubleTree by Hilton, value for money with access to tennis courts
• 🚶 More things to do in Key West: check out the Key West section on the things to do in Florida Keys

Key Largo (scuba diving and water sports)

We all have our list of dream water activities to try out.

Maybe you want to take a snorkeling adventure. Or it could be that you want the adrenaline-filled fun of a water skiing session.

Whatever the case, when in the Florida Keys then Key Largo is the place to visit for all these.

This island is located on the northernmost end of the Florida Keys and happens to be one of the longest in the archipelago.

It is also home to iconic marine state parks including the John Pennekamp Coral Reef State Park.

• 📖 Keep reading below about Key Largo in the Adventure Couple Section
• 🏩 Best accommodations in the area: Coconut Bay Resort, right on the sandy beach
• 🚶 Best things to do in Key Largo: check out the Key Largo section on the things to do in Florida Keys

Marathon (family friendly)

Marathon is a collection of mini islands jam-packed with adventure-worthy attractions waiting to be explored. For small and big kids too.

This includes everything from water sports and numerous gorgeous beaches to quaint restaurants and shops to check out after a fun day in the calm water.

With all this to offer, it is without a doubt the best option when traveling as a family.

• 📖 Keep reading below about Marathon in the Family Section or Best Place for Beaches Section.
• 🏩 Best accommodations in the area: Courtyard by Marriott (for families, within walking distance from tennis courts) and Tranquility Bay Beachfront for the amazing private beach
• 🚶 Best things to do in Marathon: check out the Marathon section on the things to do in Florida Keys

Islamorada (adventure galore)

If you have an adventurous spirit drawn to the unbeaten path, then Islamorada is the perfect island for your trip.

Most of the attractions here are natural wonders, including underwater marine kingdoms and beautiful nature trails for walks and biking, some of them facing the Gulf of Mexico.

It also offers you a chance to truly enjoy the beauty of sports fishing. After all, it is the Sports Fishing Capital of the world.

And in the late afternoon, head to the Tiki Bar for a few drinks in a relaxed vibe environment.

• 📖 Keep reading below about Islamorada in the Family & Adventure Section
• 🏩 Best accommodations in the area: Islander Resort, a real tropical paradise
• 🚶 More things to do in Islamorada: check out the Islamorada section on the things to do in Florida Keys

Big Pine Key (relax and isolation)

Sometimes when you are on holiday, all you want to do is relax.

You don’t want to go exploring or plan an itinerary of attractions to visit.

You just want to sit on a beach, possibly under the palm trees, and take in the breathtaking ocean views around you.

Well, that’s what Big Pine Key exists for, connected by the Seven Mile Bridge to Marathon Island.

This isolated little southern Florida Key has a nice, calm and relaxed vibe.

You will get all the peace, quiet and privacy you need to truly unwind.

• 📖 Keep reading below about Big Pine Key in the Romantic and Relaxed Stay
• 🏩 Best accommodations in the area: Barnacle B&B, adults only
• 🚶 More things to do in Big Pine Key: check out the Big Pine Key section on the things to do in Florida Keys

On your third or fourth trip, you may also want to explore other more isolated areas. Just keep in mind that you may have to stock up before reaching your destination as in most cases it will be a Robinson Crouse kind of holiday.

In saying that, if you have a car, I really suggest setting apart one or two days for the exploration of the Florida Keys. A magical part of the world.

It’s a real adventure and the 42 bridges you will drive through are an experience by itself.

Best place to stay in the Florida Keys for couples

• 🥇 Key Largo is the best are for the adventures couples, with diving and snorkeling being the top highlight
• 🥈 Key West is the ultimate destination if you are looking for a laid-back and boutique stay
• 🥉 Big Pine Key is all you need for a secluded and romantic breakaway

All the Florida Keys are a couple’s getaway destination dream come true.

I mean, who wouldn’t want to take romantic strolls on the beach or immerse themselves in the rich regional culture with their significant other?

There are, however, some islands in the archipelago that are better suited for the romantic needs of a couple than others.

Here are two of them and what you can expect from each.

Key Largo (for the adventure couple)

This is perfect for couples that love adventure and the outdoors.

Key Largo is in the northern part of the archipelago, the first key of any Florida Keys road trip

The island is particularly famous for the numerous water-related activities for you to try out.

You could go for a once-in-a-lifetime exploration of the Florida Reef in the iconic marine park.

You could also go scuba diving at one of the many diving centers.

One of the best in the region is the Rainbow Reef Dive Center. The center is best known for having the top diving instructors and facilities on the island.

And if you are up for some exercise, you can always find a fitness center on the island.

Key West (laid-back and boutique stay)

If you and your partner are looking for a more laid-back and relaxation-centered trip then Key West should be your top option.

The best part is the access to numerous boutique accommodation options. These range from ritzy resorts to lower-budget resorts.

I wrote a dedicated post for the best areas to stay in Key West that will answer all your questions.

The island is also perfect for its lively night scene, with many restaurants for those romantic dinner dates out while on your trip.

A great option to try out for a romantic dinner is Latitudes.

This swanky seaside restaurant serves amazing American cuisine which you get to enjoy on their luxuriously decorated premises. You will also get a breathtaking view of the ocean.

For late-night drinks and a more casual night out, try 801 Bourbon Bar. Located in a beautiful pastel pink building, this cocktail bar hosts numerous live performance artists to make the night more interesting.

Finally, you can go all touristy and have a fun photoshoot session at the monumental Southernmost Point of the Continental USA.

Big Pine Key (romantic and isolated)

This is a little secret.

If you are looking for the best place to stay in the Keys for couples next to the beach, isolated, where you can have a romantic and relaxed time, then look no further than Big Pine Key and more specifically the Southeast Point.

This beach is beautiful but even more, is the sense of separation from the busy world.

You may think that you are suddenly in paradise, far from everything and everyone.

And for a funny night head to the nearby Little Torch Key for the Kiki’s Sandbar

There is only one accommodation option on this beach and that is why you will be more likely on your own, a great choice if you are after a romantic stay.

Where to stay in the Keys for families

• 🥇 Marathon is the best island to stay in the Florida Keys if you are traveling with small kids
• 🥈 Islamorada is instead the top location if you are going on vacation with grown-up kids

Considering the Florida Keys for your next family vacation?

Well, you are in luck because these islands are just overflowing with fun family activities and attractions to make memories with.

For the most part, the islands are relatively close to each other.

This means commuting from one to the next to enjoy different activities should not be too hard, especially if you have a car.

However, when it comes to deciding where exactly to stay and operate from, two options stand out as great for families.

Marathon (small kids)

Located between Islamorada and Big Pine Key, Marathon is the best suited for family-friendly fun.

There is so much to do and see here with kids of any age.

With just a short drive, you could take them to play with dolphins at the Dolphin Research Center or visit Dolphins Connect in Duck Key

You could enjoy a nice day of waterside fun at Coco Plum Beach or Sombrero Beach.

Finally, you can go on a food adventure as a family with Fish Tales Market and Eatery. This seafood restaurant is popular among locals and with good reason. They serve amazing and fresh dishes that even the pickiest of the children wouldn’t help but enjoy.

Islamorada (grown-up kids)

Islamorada is perfect if you have grown-up kids looking for a more active adventure.

You could go biking on the trails, trekking, or even fishing.

For parents and older children, fishing is a must-try on this island famous for the trade.

You could also include your children in this activity by taking one of the many fishing charters including Bamboo Charters.

Kayaking in the ocean is also another option very popular, especially with boys.

Best place to stay in the Florida Keys on the beach

• 🥇 Key West is the best island to stay in Florida Key for beaches and lifestyle, with so many restaurants and bars to enjoy the night as well.
• 🥈 Marathon is the best area to stay for beaches in a laid-back environment

If you are planning a trip to the Florida Keys then beach bumming should be very high on your list of things to do.

Below are 2 islands in particular with the most to offer in terms of beach access and related activities.

Key West (beach and lifestyle)

Key West is perfect for beach lovers looking for a bit of excitement in addition to the beauty and relaxation of any other island.

Some of the island’s best beaches include Higgs Beach, Fort Zachary Beach and Smathers Beach.

Fort Zachary Beach, in particular, is an absolute dream with its beautiful white beaches and clear calm waters.

Read more on my post about the best beaches and accommodations nearby in Key West

In addition to the breathtaking beaches, Key West has a vibrant night scene with numerous high-end restaurants contributing a great deal to this.

One such eatery is Blue Heaven. This fusion cuisine restaurant serves the best American and Caribbean dishes. It also happens to have a bar and a pool if you really want to turn your night out into a party.

After your hearty meal, pay for a trip to the aptly named Better Than Sex Dessert Restaurant. Their tasty treats will definitely provide the perfect end to your dun day.

The Hyatt Residence Club is ideal for beach lovers with its quick access to a scenic private beach (see photos here). The hotel offers a slew of awesome amenities including a spa, a pool, an on-site bar as well as air conditioning and Wi-Fi. It is also next to several popular eateries and watering holes, including Tavern and Town for those fun nights out.

Marathon (beach and easy life)

The best beaches on this island are Sombrero Beach, which is a public beach, and Inch beach, which is members-only.

The beautiful island is also every foodie’s dream with its eclectic array of restaurants and cafes for you to explore.

One of these is Frank’s Grill. This Italian gem has the best pasta and pizza in the area and is a spot you definitely must visit.

Another must-visit eater is Sweet Savannah’s of the Florida Keys. This is a bakery and ice cream café all wrapped into one. You definitely have to try their signature cupcakes while on the island.

Where to stay in Key West

Key West is the most popular of all the islands, and for a good reason, it’s absolutely gorgeous.

This is also where you can find the southernmost point of the continental USA.

I started writing here more about the best places to stay in Key West and I soon realized there was too much to say for just a little section on this post.

I then decided to write a full guide dedicated to Where to stay in Key West with all the best areas, the most romantic places, the gorgeous beaches, the lovely old town and so much more

It’s an extensive post to all the cool areas in Key West to spend a fantastic holiday.

Frequently Asked Questions about Where to stay in Florida Keys

About the Author

Stefano is a seasoned travel expert and the visionary founder of MEL365.com, a leading travel website with traffic across 6 continents. With a rich background in the travel industry, Stefano spent four pivotal years at Amadeus Travel Distribution System, gaining invaluable insights into travel technologies and distribution.