Where to Stay in the Florida Keys: Best Islands & Hotels

Martina Rosado
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Map of the Florida Keys

Key Largo – large island 25 miles off the coast of Key West. It has a variety of accommodations from beachside to large bayside villas to the more rustic.

Key West – Smaller island, home to Hemingway and Duval St.

North Key Largo – Beautiful Island with a Slew of Bungalow-Style Beachfront Accommodations

Crawl Key – A smaller island, similar to Key Largo with a range of rentals.

Best Hotels

Scoma’s – one of Key West’s finest lodging options. Features an open-air lobby and some of the friendliest staff on the island.

Dona Paula – Classy hotel in Key Largo. Perfect for an upscale getaway

Melrose Hotel – By far the best location in Key West with rooms with an amazing view. An established favorite in Key West.

Key West -Home of Hemingway, Duval Street and best choice for when you want to feel like a local.

Key Largo – Near Miami and popular with Miami crowd. You feel like you are on the edge of a metropolitan city instead of a tiny fishing village

North Key Largo – Another great choice on the Florida Keys with large, bayfront homes to rent.

Key West

If you truly want to live on an island experience, Key West is the place to go. “The Conch Republic” is what many call the main city of Key West. It is the ground zero of the Florida Keys, with a population of about 8,000 year-round residents and almost a few times that during the summer months. An island chain of 20 islands and keys are all that form the Florida Keys. .

There are plenty of attractions and natural sights around Key West. A couple highlights:

  • an artificial reef, for snorkeling and scuba diving
  • a butterfly garden
  • wildlife refuge, for some of the last remaining natural white mangrove trees of the world
  • works of art like a giant concrete sculpture of a cigar store Indian

The Best Hotel for Key West

For a great resort the The White and Orange Sand Castles just a two-minute walk from Duval Street, both of the castle-like hotels are in the heart of Key West. Great for walking around the town to get from one island to another, these two buildings are exactly what you want in Key West.

They are not fancy or luxurious, but they are very clean, staff is very friendly, great food, and a comfortable place to stay.

Best Places to Stay in Key West

With its endless beaches and laid-back atmosphere, Key West feels a little like New Orleans. There certainly isn’t anything like it in the rest of America.

You can spend the day at Mallory Square, taking in the street performers and enjoying a drink on the steps of the courthouse. The best part about Key West, though, is its glamorous history. If you visit between the months of March and November, you’ll see the annual Fantasy Fest, featuring the arrival of pirates, mermaids, and many other famous characters from the island’s history.

You can also end the night at either of the famous bars, Sloppy Joe’s or Duval Street, hearing live music every night of the week.

However, the best part about staying in Key West is the “Plantation Days” (and nights) atmosphere you’ll find while exploring the island. Sprawled out across almost 100 beautifully manicured acres, the grounds of Mallory Square hotel are the perfect setting for reconnecting with nature and finding yourself through meditation and yoga.

It’s a unique way to both relax and enjoy yourself.

Key Largo

Now that you’ve made it to the island that this guide is named for, it’s time to check in.

Restaurants: Three Palms – The best restaurant on Key Largo. It has a wonderful view of the ocean and the best fish tacos in the world. They also have a bar and a swinging porch that has the best sunset cocktail on the island.

Sugarloaf Key

The Two STORY house has WIFI and was the movie set for the home from Home Alone. It’s beautiful inside and has a view of the ocean as well.

Horseshoe Bay – A friends beach house. You’ll sleep like a king in the king sized bed. There is a nice patio that overlooks the beach with plenty of seating, if you’re out there during the day. It also has a screened in porch that is also on the beach. It’s the perfect place to read a novel on the porch at night.

Best Places to Stay in Key Largo


The Keys are full of great places to stay. They could be considered a form of nature—n’splash․ vacation destination. Whether you’re looking for a budget-friendly place or a luxury resort, the Keys will not disappoint.

Intrigue Key Resort

Intrigue Key Resort is a breathtaking property situated right on the ocean and is the only oceanfront resort in Southwest Florida.

This resort is nestled right at the base of the stunning Seven Mile Bridge. You’ll love the gem-like views of the turquoise water and white sand beaches that come with the stay as well as the self-contained resort…all in a breathtaking setting.

A night here will not be complete without indulging in one of the beautiful sunset dinners. Intrvue key could not be more romantic.

A post shared by Intrvue Key Resort (@intrvuekey) on Feb 8, 2016 at 4:02pm PST

The Intrvue Key Resort is a short walk from the shops and restaurants of Key West, Florida. This Southern and seaside getaway has everything you need, including a relaxing pool surrounded by tropical plants and soothing waterfalls.


Redfish, Islamorada & Key Largo.

At the southern end of the Florida Keys is Marathon, Redfish, Islamorada and Key Largo. This area is best known for its swimming and fishing, staying at the Sunset Key Condominium.


Known as the “Key to the World” this island is home to a historic lighthouse as well as a revitalization of the historic Marine Corps base.


Redfish is considered a community in the middle of the Florida Keys. It has some of the best beaches of the area and is a great place to stay for the adventure of it all. Redfish also has some great restaurants and fun places to just chill out at.


The Florida Keys located on Islamorada is a great place to stay while you fi sh or just cruise the beaches and soak up the sun.

Key Largo

With the Keys’ largest auction, Key Largo is an old-fashioned town with a lot of history and events going on. Check out Buddy Holly’s grave at the Bahia Honda State Park.

Best Places to Stay in Marathon

Key, Florida.

The Barefoot Resort is the oldest resort in Marathon.

We recommend staying here if you’re visiting the area or staying the night in Marathon.

You’ll be able to sleep in the middle of a nature preserve, and breakfast is included in your rate.


Islamorada is a popular area for vacationers because it’s convenient to both the mainland and the Florida Keys. It’s the third-largest and third-most populous island in the Florida Keys.

It is a favorite tourist destination for many reasons, but it also features many high-end resorts and a wide range of accommodations.

The area also offers a nice variety of things to do, including snorkeling, scuba diving, fishing, biking, and deep-sea fishing.

It’s also known for several stunningly beautiful white-sand beaches. It’s also a great place to enjoy a slower pace and explore nature.

There are many areas to explore and enjoy in Islamorada, including Captain Gary’s Corner, Dry Rocks Natural Area, Windley Key State Park, and the Stock Island Key Historic District.

There are plenty of things to do and plenty of gorgeous beaches and waters to enjoy. Islamorada is a perfect place to relax and reconnect with nature.

Best Places to Stay in Islamorada

You have seen the movie Jaws. The area is named after the Portuguese word for “shark.” You are going to love it, too. The surprising thing about Islamorada is the amount of stuff you can do and the amount of time you can spend on the water without having to get in the water! The beautiful white sand beaches are great for a late afternoon nap and the glassy blue Gulf…well it just seems to go on for infinity.

If the name Islamorada sounds better as the name of a burger than the name of an island town, you can satisfy that craving at Lay’d ” a fabulous little burger joint that has become a local favorite. Everyone knows where to find it, and it’s a great place to hang out.

Areas to Stay in Key Largo

The island of Key Largo was once home to a bustling community of military air base. The long-term visitors to this area knew this and soon began calling it “Little Havana.” Over the past few years, a number of new bed-and-breakfasts have taken advantage of the close proximity to George Washington’s historic home, Grancy’s Island, and the water.

Big Pine Key

One of the most tragic stories to emerge from the current recession is the plight of the artisans that live on the Big Pine Key on the Florida’s lower keys. The artists primarily create fine wood turned artworks, and they have been left to struggle through the recession to finish their products. The majority of the inhabitants of Big Pine Key are artists, musicians, and other creative professionals.

When you stay on Big Pine Key, you get a unique look at the real Florida Keys. Spend your day at the beach and explore the island at night. There are many art galleries to enjoy and a fantastic place for a home cooked meal.

If you happen to be on Big Pine Key when the weather is nice, check out the art festival in the old town of Key Colony.

The only thing bigger than the art festival is the prices at the art festival. Everyone was scouring the little shops trying to buy the perfect sculptures for their own garden. It is a great place to browse arts and crafts.

Choose which island is best for you and your family, and then choose from the below list of hotels to get a great deal.

Where to Stay in Big Pine Key

There are two main choices for accommodations, the pricier ones in Islamorada and the more affordable ones in Big Pine Key, which is closest to Key Largo. Which one is better for you depends on how much you value beach privacy and access to the nightlife.

If you like to be where there’s a lot of action, Islamorada is your best bet.

But if you’re more for the quiet beach and all the resale stores, then you should go with Big Pine Key.

Each of them has their own pros and cons.

Big Pine Key is located in the southern part of the Keys, approximately two hours by car from Miami. It’s the closest place to Key Largo on the Florida mainland.

The capital of the region is Islamorada, a seven-mile-long island with a good climate for people who enjoy beaches and nightlife. It has everything you could ask for in a vacation spot, being close to Key Largo and having its own exciting nightlife, several bars and restaurants, and just about all the amenities a person could ask for in a resort.

Hotels in Islamorada:

  • One & Only Ocean Club
  • � (Big Pine Key)
  • at Wyndham Vacation Rentals

Little Torch Key

Key West,Islamorada, & Upper Keys.

Little Torch Key is the best island in The Florida Keys for fishing, sunsets, and dolphins.

Key West, the hometown of Ernest Hemingway, is the entertainment capital of the South. “Parrot” Island is a likely spot to see these bright green parrots.

Upper Keys are home to a unique sandbar that is part of the world’s largest estuary, the Northwest Ranges…a perfect spot to snorkel or explore.

Islamorada, one of the Live-Aboards…islands with no residents, is also the home of the famous underwater observatory, the Big Pineapple coral reef.

The rest of the Islands are better for the lazy person. They run along the coast on freeways and have highrise condos for larger, older people. There are a lot of retiree specials…and they are for the most part cheap, just so you know.

Where to Stay in Little Torch Key

There are many choices to stay in Little Torch Key. The two most popular choices are:

Sandpiper Club: This club is on the smaller side but offers the convenience of everything on one island. The Sandpiper offers a fitness center, swimming pool, dining area, and bars. Of course, you can also rent golf carts or bikes to get around.

Casa Marina: This is a little larger than the Sandpiper and offers a little more for kids. The pool area is kept by the hotel’s staff and you can easily find a lounge chair to lay out on.