Are you looking for the best places to stay in the Florida Keys? You’ve come to the right place. Whether you’re trying to plan where you should base your Florida Keys vacation or just plotting your stops on a Florida Keys road trip, whether you’re searching for luxury resorts or cozy cottages surrounded by tropical gardens, we’ve rounded up some of the best places to stay in Florida Keys that will make your vacation unforgettable.
And let’s start all of this by saying, welcome to the land of sun, sand, and sea – the Florida Keys! From the colorful architecture of Key West to the serene beaches of Islamorada, there’s something for everyone in this tropical paradise. Get ready for an adventure-packed getaway filled with stunning scenery, delicious cuisine, and endless fun at one of America’s best road trip locations and one of the best warm winter vacation spots in the United States!
We have multiple options for where to stay in the Florida Keys for every type of traveler, cozy B&Bs, luxury beachfront resorts, and historic inns, to quiet hotels.
Our guide to the best places to stay in the Florida Keys also highlights the best activities nearby at each location starting at the north area of the Florida Keys at Key Largo and making our way down south to Key West including hotel selections for where to stay including information on the rooms and amenities available.
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Happy travels!
Where to Stay in the Florida Keys
Table of Contents (Jump to Any Area To Stay in the Florida Keys Using this Shortcut)
Key Largo
Welcome to Key Largo, the first and largest of the Florida Keys known for being laid back and that famous lyric in that Beach Boys song. This tropical paradise is known for its crystal-clear waters, abundant marine life, stunning coral reefs, and a great spot for snorkelers and divers.
Plus Key Largo has fun, quirky roadside attractions to delicious seafood restaurants, Key Largo has a lot to offer visitors looking for a unique vacation experience and is one of the best places to stay in the Florida Keys not to mention it’s one of the most scenic drives in Florida.
There are plenty of restaurants and bars nearby if you’re planning on staying in this area a few days including some incredible seafood.
Key Largo Attractions
Key Largo has plenty of activities that could keep you here for an entire vacation, which is totally an option! This is why this is such an ideal place to stay in the Florida Keys whether you stay for one night or an entire week.
The most popular attractions include outdoor spaces and preserves like John Pennekamp Coral Reef State Park which protects the only living coral reef in the United States, there are plenty of water activities to enjoy here from snorkeling to kayaking.
Crocodile Lake National Wildlife Refuge and Butterfly Garden is another great stop that preserves and protects the American crocodile habitat as well as the Dagny Johnson Key Largo Hammock Botanical State Park.
And another one of our favorite sustainable activities in the Florida Keys in Key Largo is the Florida Keys Wild Bird Rehabilitation Center in Tavernier.
Being in Key Largo also means you have easy access to explore Everglades National Park as well.
Places to Stay in Key Largo
Kona Kai Resort Gallery & Botanic Gardens
Kona Kai Resort Gallery and Botanic Gardens is a gorgeous boutique property is the perfect place to stay in the Keys if you’re looking for a charming, quiet spot with an incredible waterfront location. This resort offers 13 individual charming, beachy cottages for its guests located in one of the two only frost-free tropical botanic gardens in the United States.
With your stay, you get free access to kayaks, stand-up paddle boards, and paddle boats. There’s also a pool and hot tub for swimming. Along the water, you can find a dock for sunbathing, sunset watching, and hammocks under the swaying palm trees to relax.
Each of the cottages comes with a fully equipped kitchen, so if you do like to cook on vacation you have this option but there are plenty of incredible seafood restaurants nearby. Breakfast is included.
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Baker’s Cay Resort Key Largo
Baker’s Cay Resort Key Largo is an incredible 4-star hotel is another perfect place to stay in the Florida Keys in Key Largo. The airy and cozy rooms come with balconies overlooking its waterfront location. You can easily upgrade to a 1-2 bedroom suite with separate living rooms and fully equipped kitchens.
There are two restaurants on-site, two pools, a spa, and a gym all on-site. You can rent water activity equipment here as well.
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Islamorada
Islamorada is another fantastic place to stay in the Florida Keys whether you’re on a road trip making your way down to Key West or looking for a relaxing place to spend your entire vacation at. Islamorada is a very quiet and peaceful place popular for watersports and fishing.
Dubbed the “Sportfishing Capital of the World,” Islamorada is home to some of the best fishing grounds in Florida. But fishing isn’t the only thing this little slice of heaven is famous for. From world-class dining experiences to breathtaking sunsets, there’s something for everyone on this charming island. So buckle up and let’s dive into what makes Islamorada a must-visit destination!
There are plenty of seafood restaurants and bars nearby for your stay. This area is perfect for a relaxing vacation or for water adventurers!
Islamorada Attractions
Some of the best things to do in Islamorada are all of the water activities from sport fishing, snorkeling, kiteboarding, wakeboarding, boat tour, kayaking, and stand up paddleboarding.
There’s also the Indian Key Historic State Park where you can find shipwreck remains from the 1800s, Windley Key Fossil Reef Geological State Park, and Long Key State Park.
There are also three different breweries here including the Florida Keys Brewing Co., Islamorada Beer Company, and Heartbreakers Brewhouse.
Also, be sure to check out Anne’s Beach or Library Beach for a white sandy place to cool off in the water and Robbie’s of Islamorada for the famous tarpon fish feeding!
Places to Stay in Islamorada
Amara Cay Resort
Another great place to stay in the Florida Keys in Islamorada is the Amara Cay Resort. This upscale 3.5-star resort has a gorgeous waterfront location with gorgeous rooms with chic decor. Many rooms have balconies with ocean views, sitting rooms, and kitchenettes.
Relax at the poolside rum bar, hang out in a hammock or swim at the private beach, or relax in the heated outdoor pool that looks out at the ocean or play bocce ball.
There is also an American restaurant on site with a tiki bar and a fitness center.
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Postcard Inn Beach Resort and Marina at Holiday Isle
The Postcard Inn is a gorgeous 3-star property is located on its own private white sand beach. The casual rooms have nautical-inspired decor and upgraded rooms offer ocean-view balconies and whirlpool tubs, separate living areas, and kitchenettes.
There are plenty of places to eat and drink here including 4 different bars and restaurants. One of them being a tiki cocktail bar. There are also two pools on the property and boat rentals available here.
This is a great place to stay in the Florida Keys if you’re looking to soak up some time by the pool or beach.
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Moorings Village
If you’re a fan of the Netflix series Bloodline then you will recognize this property! Moorings Village is a luxury 4-star hotel is an iconic place to stay in the Florida Keys. This gorgeous property is set on an 18-acre former coconut plantation right on the water, talk about a perfect paradise setting.
The upscale beach cottages offer anything from 1 to 3 bedrooms with full kitchens and furnished porches for the perfect place to hang out while you’re on vacation. Some cottages even have full laundry appliances and beach views.
There’s a heated outdoor pool, tennis court, fitness center, spa, hammocks, and watersport equipment included in guest amenities during their stay. The watersport equipment includes paddleboards and kayaks as well as bicycles so you can ride around to restaurants and other Islamorada activities nearby.
We also dined here at the Morada Bay Beach Cafe which was delicious and the perfect place for a sunset meal.
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Marathon
Another lovely place to stay in the Florida Keys is the city of Marathon, located on a set of 13 islands in the Florida Keys. This is where you can find some of the best sport fishing, boating activities, and beautiful sandy beaches in all of the Florida Keys (and the world) with tons of waterfront restaurants to choose from and other watersports like jet skiing, kayaking, and paddleboarding.
Marathon Activities
Marathon has tons of great options for activities to enjoy including one of the best beaches in the Florida Keys, Sombrero Beach. This is where you can also witness marine life responsibly at the Turtle Hospital.
This is where you can also enjoy some nature at Crane Point Hammock, Curry Hammock State Park, and Bahia Honda State Park.
You’ll be just before the famous Seven Mile Bridge that’s completely surrounded by water and you can learn about the history on Pigeon Key Island.
Places to Stay in Marathon
Isla Bella Resort
Isla Bella Resort is a gorgeous 4-star resort is the perfect place to stay in the Florida Keys if you’re looking for a relaxing vacation. Located right on the water there is a beach bar and restaurant on the property, as well as several pools and beach cabanas, perfectly located under the shade of swaying palm trees.
The rooms are spacious and luxe with their own private balcony and seating areas facing the water, we loved our stay here and would always recommend this for where to stay in the Florida Keys for couples looking for a romantic getaway!
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Tranquility Bay Beachfront Hotel & Resort
Tranquility Bay Beachfront Hotel & Resort is another incredible place to stay in the Florida Keys in Marathon. This beautiful 4-star property offers brightly decorated rooms as well as 2 to 3-bedroom beach houses that have fully equipped kitchens, living spaces, and private porches with waterfront views.
There is enough here to entertain the whole family including 3 pools, a putting green and a beachside bar. There is also a Mediterranean restaurant on site. There’s beach access as well as a fitness center and spa here too making it where to stay in the Florida Keys for the ultimate relaxing vacation with exciting entertainment options.
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Lower Keys
Closer to Key West down the Overseas Highway is another fantastic place to stay in the Florida Keys Lower Keys. Compared to the other places to stay in the Keys the Lower Keys are much quieter and laid back before getting to the party central in Key West.
Connected to Marathon by the Seven Mile Bridge, there are multiple Keys to explore here including Big Pine Key.
This is also where you will find the famous endangered Key Deer. We had a hard time believing there was enough room for the deer to live, but there is a whole population who lives here and they’re adorably small!
This is also a great place for water activities like kayaking, fishing, diving, and swimming.
Lower Keys Attractions
You’re now on the other side of the famous overwater Seven Mile Bridge as well as other outdoor areas to explore. Connect with nature at the National Key Deer Refuge and Bahia Honda State Park.
This is also where you can find the freshwater Blue Hole and great kayaking at No Name Key.
And by being just on the other side of the bridge from Marathon you have all their activities to explore as well as everything nearby in Key West.
Places to Stay in the Lower Keys
Hawk’s Cay Resort
A great place to stay in the Florida Keys in the Lower Keys is Hawk’s Cay Resort on the island of Duck Key. This gorgeous oceanfront resort is located on a marina and one of the most famous adults-only resorts and places to stay in the Florida Keys making it a great escape for couples.
The rooms are laid back, many of which have private balconies and you can ask for one with ocean views. There are also villas available that have 2-3 rooms with fully equipped kitchens and some even with their own private pools.
Don’t miss out on the 5 outdoor pools, fitness center, tennis courts, putting green, and spa facilities.
There are also restaurants on-site as well as access to book watersport activities like fishing and diving.
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Key West
Key West is undeniably the most popular of places to stay in the Florida Keys. This southernmost part of Florida and the US, only 90 miles away from Cuba, is where you can find the nightlife and all the action when it comes to entertainment in the Keys.
Key West has no shortage of history and culture either. With tons of historic homes to tour that were the homes of famous figures, maritime history, and of course prohibition-era history! Not to mention great food and key lime pie, free-roaming chickens, and fun sunset celebrations!
Key West also has some great diving and water activities to enjoy as well as a few great beaches like Smathers Beach or Fort Zachary Taylor Historic State Park making it an all-over well-rounded pick for places to stay in the Florida Keys.
Key West Attractions
There’s so much to do in the concentrated area of downtown Key West that you can easily pack a lot in one day or over several days depending on how long you’re staying.
Some of the most famous things to do in Key West include walking down the shops and bars that line Duval Street, enjoy the sunset celebration at Mallory Square with street performers, party all night at any of the many clubs and bars, check out museums in historical homes like the Hemingway Home and Truman Little White House to museums like the Key West Shipwreck Museum.
Don’t miss checking out famous stops for photos like the Mile 0 Marker and the Southernmost Point of the continental US.
You also don’t want to miss trying the famous key lime pie here in Key West, if you fall in love like we did then you may want to learn how to make a Florida key lime pie recipe at home too!
Be sure to read this post if you only plan on doing a one day trip to Key West.
Places to Stay in Key West
Courtney’s Place
Courtney’s Place is a great place to stay in the Keys if you find yourself wanting to have a B&B style accommodation in the heart of Key West. This charming cottage property is a family run B&B with a relaxed atmosphere just one street away from Duval Street, where all the action is.
There are various options for accommodation style here from individual rooms to renting an entire cottage. Cottages come with kitchens or kitchenettes depending on which one you rent as well as porches.
There is a pool on site, free breakfast, tropical garden, barbeque area, and bike rentals available.
Perry Hotel Key West
Located about a 10-minute drive away from all the action in the heart of Key West, this is an ideal place to stay in the Florida Keys party central if you’re looking to remove yourself from the party when you sleep. This quiet location is located right in the Stock Island Marina.
The rooms at Perry Hotel Key West are cozy and modern with balconies or terraces overlooking the water or outdoor pool area.
There are scooters available for rent on the property to take down to Key West or you can use their free shuttle service. There’s a great restaurant and bar on-site as well.
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Southernmost Beach Resort
Another one of the most beautiful places to stay in the Keys if you’re in Key West is in the heart of all the action one block off of Duval Street. This gorgeous colonial-style hotel is right on the water with a prime location next to the Southernmost point of the continental US!
Most of the airy, cozy rooms at Southernmost Beach Resort have views of the water and some even offer waterfront balconies.
There are 4 bars on the property, full spa services, 3 pools, croquet, bocce ball, beach chairs, fitness center, and parking. There’s also access to a private pier and beach for guests.
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The Marker Key West
Another gorgeous property in Key West and a fantastic place to stay in the Florida Keys is the Marker Key West. Located in the heart of downtown Key West, this upscale hotel is situated right on the water.
The modern rooms include private balconies with either a pool or harbor view. There is an exercise room, 3 pools, restaurant, bar, and bike rentals available on-site making it one of the best places to stay in the Florida Keys in Key West if you want to be on the water and easy access to exploring around.
The setting here makes for an absolute tranquil getaway close to all the nightlife and entertainment.
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Which island you should stay at in the Florida Keys depends on what you want to do. If you’re looking for nightlife and entertainment options stay in Key West, if you’re looking for a laid-back vacation with outdoor activities stay in Key Largo, if you’re looking to be in a quiet place but close to exploring other areas of the Keys stay in Marathon or Islamorada.
The prettiest Key in Florida is debatable as they are all beautiful, but if we had to pick the prettiest of the Florida Keys we’d say Key Largo because of the beaches, marine life, and scenic views.
The prettiest water in the Florida Keys can be found around Key West at Smathers Beach and Fort Zachary Taylor Historic State Park Beach. Also, the prettiest water can be found at Dry Tortugas National Park which is a day trip from Key West.
Key West is the most walkable destination in the Florida Keys with a vibrant downtown, you actually don’t want a car to explore the best of Key West unless you’re looking to explore beyond downtown.
The best months to visit the Florida Keys are in the dry season which is from November through April, the busiest and most comfortable time of year to visit. March through May is a great time to visit too after all the winter visitors before hurricane season starts.
The cheapest time to visit the Florida Keys and score deals on hotels is in the fall from September through November, although this is rainy season and there are chances of hurricanes this time of year.
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