Discover the Best Places to Stay in the Keys

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The Florida Keys attract visitors from all over the world and for good reason! But what many people don’t know is that there’s so much more to the Florida Keys outside of Key West. I’m going to share with you some of my favorite places to stay in the Keys, including an option in Key West for those of you who have your heart set on that specific destination.

If you’re unfamiliar with the area, the Florida Keys are a string of tropical islands stretching about 120 miles between the Atlantic Ocean and the Gulf of Mexico. They are known for their laid-back vibe, stunning coral reefs, and exceptional watersports, making them a perfect escape for both adventure and relaxation. The Keys are divided into three main sections: the Upper Keys, the Middle Keys, and the Lower Keys, and each area has its unique charm, attractions, and reasons to visit.

Getting to the Florida Keys

Many tourists get to the Florida Keys by flying into either Miami International Airport or Ft. Lauderdale International Airport and renting a car from there. The drive from Miami to the Upper Keys typically takes about an hour depending on traffic conditions and the drive from Ft. Lauderdale to the Upper Keys takes about two hours. The road that you’ll drive on is a two-lane highway with beautiful views of the ocean, but if there is an accident then you’ll experience heavy delays so give yourself plenty of time.

If you’re in Southwest Florida, you can easily get to Key West without driving at all by taking the Key West Express ferry from Fort Myers or Marco Island. This 3.5-hour ferry takes you directly from Fort Myers Beach to Key West without any hassle at all. I took this route when I lived in Fort Myers and it was fantastic!

The Upper Keys

The Upper Keys is the gateway to the Florida Keys with the two major towns being Key Largo and Islamorada.

Key Largo is known as the “Diving Capital of the World,” and is home to the John Pennekamp Coral Reef State Park, the first undersea park in the U.S. Here, you can dive or snorkel to explore the vibrant coral formations and the famous Christ of the Abyss statue. For those who prefer to stay dry, glass-bottom boat tours offer a glimpse into the underwater world without getting wet.

Islamorada, or “Purple Isle,” is about 40 minutes further south and is famous for its sport fishing, claiming the title of the “Sportfishing Capital of the World.” With more recreational fishing boats per square mile than anywhere else, anglers can chase after sailfish, tarpon, and bonefish in these waters. Islamorada is also home to Theater of the Sea, a marine mammal park where visitors can swim with dolphins, sea lions, and rays in natural salt-water lagoons.

Places to Stay in the Upper Keys

Amara Cay Resort

Amara Cay Resort is located in Islamorada and minutes from The Marine Mammal Center and the History of Diving Museum. Their ground floor was renovated a couple of years ago and it is truly beautiful! Past the check-in desk and concierge, you can find a lounge area with inviting swinging chairs and a bar area where you can get breakfast in the mornings. Down the hallway that leads to the beach and pool, you’ll find games like Scrabble built into the wall which gives off a playful vibe and is perfect for families. Outside, you’ll find a pier, lounge chairs on the beach, a beautiful pool, and kayaks and paddle boards available to rent. The rooms at this hotel have a clean, coastal feel making your dreamy beach vacation a reality. Most rooms also have either balconies or lanais with some having floor-to-ceiling windows with water views!

Cheeca Lodge & Spa

This Islamorada resort has been around since 1946, known then as the Olney Inn which hosted VIP guests from presidents to movie stars. Today, Cheeca Lodge has grown over the years but still maintains its’ status of “the” place to stay in the Florida Keys. This property is well hidden off Highway 1 and you’ll probably pass it if you’re not careful. Once you step inside, the Cheeca Lodge engulfs you with coastal glitz and glamour. Many hotels in the Keys have a lighter, airy vibe, but the décor at Cheeca Lodge plays into the darker wood tones and incorporates different beachy textures like rattan, coral, and iridescent shells, making it feel more luxe. There’s a bar located just across from the check-in desk in the lobby with great cocktails. There’s also a small boutique outside in the courtyard where you can pick up anything from resort wear to toiletries that you forgot to pack. Past the lobby, you’ll find two pools to your right, a long pier, and a cute little tiki hut area where you can relax in the sun. The hotel offers many on-site activities such as paddle boarding, beach volleyball, beach bikes, and kayaking. They even have multiple tennis courts and a 9-hole golf course! Their room options range from oceanfront suites to lagoon or golf course views depending on your budget and interests. They also offer private one or two-bedroom casitas complete with kitchens that are perfect for families and small groups.

The Bungalows Key Largo

This is for all you luxury hotel lovers! I’ve had my eye on this hotel since it opened in 2019 where it received tons of press and for good reason. This hotel is one of the best adults-only, all-inclusive resorts in the entire state of Florida! The property sits on the shoreline in the middle of a huge botanical garden making you feel like you’ve stepped into a completely different world after checking in. Bungalows go above and beyond in every way and seem to have thought of every small detail to ensure your stay is absolutely magical.

When you arrive for check-in, you’ll receive welcome drinks and sit with a staff member to go over every detail of your all-inclusive package. They’ll help you set up any on-site activities and reservations at the fine dining restaurant or spa. All watersports and yoga classes are included in your stay and you have optional add-ons such as a sunset cruise, scuba diving or snorkeling excursions, or a ride on their very own catamaran that departs daily. Once checked in, you’ll be off to your private bungalow (hence the name of this resort)! With private, individual bungalows, you don’t have to worry about having a loud neighbor in the next room over and you’ll have complete privacy. Multiple on-site dining options are included with your stay, all with décor to die for. The Hemingway Bar is my personal favorite with its’ vibrant, fun atmosphere. One incredible amenity is the Key Largo Spa; services here do cost extra, but it’s completely worth it. Right after the locker room, there’s a side-by-side Himalayan salt room and an eucalyptus steam room. Stepping out of the salt room, you’ll see a lounge area where you can relax while gazing out into their black bamboo zen garden. From the zen garden, you’ll follow the path to your private treatment room. If you haven’t figured it out yet, Bungalows specializes in privacy and seclusion and they really know how to give you the most relaxing beach vacation of your life.

The Middle Keys

Marathon and Duck Key are popular areas within the Middle Keys. Marathon sits in the middle of the Florida Keys and is a great family-friendly destination. Marathon offers beautiful beaches, such as Sombrero Beach, and the opportunity to encounter local wildlife at the Turtle Hospital, where injured sea turtles are rehabilitated and released. Marathon is also the last stop before the Seven Mile Bridge, one of the longest bridges in the world, offering panoramic ocean views—a must-see at sunset! Key Colony Beach is a peaceful residential community in the Middle Keys and offers a tranquil escape with all the amenities needed for a relaxed vacation. Its well-maintained beaches, golf course, and close proximity to Marathon’s attractions make it a perfect base for families and couples alike. You can find lots of vacation home rentals in this area if you’re traveling with a larger group and looking to rent an entire house.

Places to Stay in the Middle Keys

Isla Bella

Isla Bella Resort is located in Marathon and is huge. This secluded property sits on 24 acres with over a mile of it located on the water. The rooms are impeccably decorated and all have ocean views so you can’t go wrong with staying here. The entire property gives off a very luxurious, unique vibe that made me feel like I was stepping into an upscale beach club or hotel somewhere in the Mediterranean. The buildings are a crisp white and make a great contrast against the lush, tropical grounds. There’s a private dock off the beach which is the perfect place to catch some rays in a chair with a great book or you can opt for a hammock under a palm tree. If you’re feeling adventurous, you can rent a kayak on-site or even sign up for boat tours at the activities counter in the Isla Bella Marketplace which also serves as an eating hall and amazing gift shop. If you pop in, be sure to pick up my favorite little cookies from Kristi’s Key Lime Cookies! The main on-site restaurant is Il Postino and just walking by and getting a whiff of their food is enough to make you want to go inside. The interior of the restaurant is gorgeous and they have an outdoor patio overlooking the water. This restaurant is surprisingly open to the public but be sure to make a reservation if you’re not a guest!

Hawk’s Cay

If fishing is your main priority on your Florida Keys vacation then Hawks Cay Resort on Duck Key is for you! They have an 85-slip marina on-site and fishing charters that guests can sign up for, along with many other water activities. This resort has multiple pools and beaches encouraging you to find your perfect relaxation spot, and one thing that makes Hawks Cay unique is that they even have a dolphin encounter experience that kids love! The room options at Hawks Cay range from typical resort rooms to two-bedroom suites and private villas complete with a kitchen. This resort is one of the top options for families, not only because they have a plethora of water activities, multiple pools, and the dolphin encounter, but also because some of the room options include a king-size bed and bunk beds making it an all-around kid-friendly experience!

The Hemingway House in Key West, Florida on a sunny day — The Hemingway House in Key West, Florida

The Lower Keys

The Lower Keys are probably the most visited section of the Florida Keys due to the ever-so-popular Key West. Big Pine Key and Key West are the top places to stay in the Lower Keys. The National Key Deer Refuge, home to the endangered Key deer, offers hiking trails and chances to spot these unique, diminutive deer. The Lower Keys are also ideal for eco-tours, kayaking through mangrove forests, and exploring remote beaches.

At the end of the Overseas Highway lies Key West, the southernmost point of the continental U.S. This colorful, lively island boasts a rich history, vibrant nightlife, and a mix of cultures. From the Ernest Hemingway Home and Museum to the sunset celebrations at Mallory Square, Key West pulses with energy and creativity. Don’t miss a visit to Duval Street, where you can sample the island’s famous Key lime pie, or take a photo at the iconic buoy marking the southernmost point.

Places to Stay in the Lower Keys

Ella's Cottages

Located in the heart of Old Town, Key West, Ella's Cottages offers a uniquely bohemian retreat inspired by the vibrant energy and eclectic vibe of this iconic island. The boutique property caters to guests seeking a more personalized, intimate lodging experience. There are six rooms at Ella’s Cottages and they range from one-bedroom to two-bedroom rooms. There’s an outdoor pool on the property that is perfect for those lazy days. This hotel offers welcome drinks upon arrival, a concierge service that can help plan activities for you, and a complimentary continental breakfast. They even allow pets for an additional fee per night! Ella’s Cottages is part of the Key West Historic Inns hotel group and they have other amazing properties nearby such as Ridley House, Winslow’s Bungalows, Lighthouse Hotel, and Fitch Lodge. All properties are historic buildings so if you’re looking for a unique place to stay, then this is for you!

Little Palm Island Resort & Spa

Little Palm Island Resort & Spa is the only private island resort in the U.S. and stands as an epitome of luxury and exclusivity, a hidden gem located off the Florida Keys coastline. This adults-only paradise is accessible via seaplane or a private boat, ensuring your arrival starts the unforgettable journey with a touch of style and excitement. The resort offers a remarkable blend of luxury, privacy, and natural beauty, making it an ideal escape from your regular daily life. The dining options at Little Palm Island serve culinary masterpieces, with menus crafted using local seafood, produce, and spices, all inspired by the islands themselves. They even offer a Culinary Indulgence package which is similar to an all-inclusive resort. The resort offers a range of activities, from exclusive experiences and sandbar sessions to sailing and scuba excursions, ensuring that there's never a dull moment. Little Palm prides itself on their recently redesigned thatched roof private bungalows all complete with ocean views. Their standard bungalow is 550 square feet with an outdoor deck and an outdoor shower - who doesn’t love an outdoor shower when you’re in paradise? From there, they offer Romance Suites, Grand Suites, and Premier Suites which the latter two are almost double the size of the standard suite and Romantic Suite.

No matter which area in the Florida Keys you’re vacationing in, these are some of the best places to stay in the Keys. This tropical paradise offers a diverse range of accommodations to suit every traveler. Whether you seek luxury resorts with stunning ocean views, family-friendly resorts, or charming boutique hotels tucked away in secluded corners of the islands, the Florida Keys have something for everyone. From Key Largo to Key West, each key offers its own unique charm and attractions. Whichever place you choose to stay, one thing is certain - you will be greeted by warm hospitality and unforgettable memories! So pack your bags, pick your favorite spot, and let the magic of the Florida Keys enchant you.

Happy travels!

-Tess

Tess Arnold

Hi! I’m Tess, founder of TravelingTessie.com, and not only do I love to travel, but I love immersing myself in new places and finding off the beaten path experiences wherever I go! I’ve lived in 4 different states & traveled to 13 countries and counting. I believe that tourism is meant to benefit both visitors and locals alike—and I want to bring that idea back into the travel industry by highlighting companies run by locals such as tours, hotels, restaurants, and more. On Traveling Tessie you can find hidden gems in top destinations around the world, travel tips, detailed city guides, and tons of inspiration for your next trip! If you love travel as much as I do, then please join me on this journey! I hope you enjoy my content as much as I enjoy providing it for you!

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