ISLAND
Where to stay in the FLORIDA KEYS
The Florida Keys offer a unique coastal escape, stretching from Key Largo to Key West in a chain of islands connected by one of the most scenic drives in the country. We spend a lot of time guiding clients through the best hotels in the Florida Keys, helping them choose between private island resorts, boutique waterfront stays, and lively properties in the heart of Key West. For those looking for more space and privacy, there are also several standout options featured in our private villas and retreats collection. It’s a destination that captures that easygoing, nostalgic energy often associated with Jimmy Buffett, where life slows down and time is best spent on the water. Unlike more traditional beach destinations, the Keys are less about long stretches of sand and more about the overall experience, from boating and snorkeling to simply enjoying the rhythm of island life.
Each key has its own personality. The Upper Keys, including Key Largo and Islamorada, are known for their relaxed pace, excellent fishing, and a more residential feel. As you move further south, the energy gradually shifts, culminating in Key West, where historic charm, colorful streets, and a lively dining scene create a completely different atmosphere. The journey between the islands is part of the appeal, with sweeping ocean views and countless places to stop along the way.
Days in the Keys are often spent on the water, followed by evenings that center around fresh seafood, sunset views, and a laid-back social scene. The experience is easy to tailor depending on how active or relaxed you want your time to be.
We’ll help you map out the right route, choose the best places to stay, and bring the entire trip together in a way that feels seamless from start to finish.
FLORIDA KEYS
Luxury Hotels
Start with the Florida Keys Travel Tips & Insider Insight below, and we’ll help you shape a trip that brings together the best of each island.
CHEECA LODGE & SPA
VIBE
iconic, active, full-service resort
PERFECT FOR
families, adventure seekers, fishing enthusiasts
WHY WE LOVE IT
Cheeca Lodge captures that classic Florida Keys lifestyle, where barefoot luxury meets a fun, activity-driven atmosphere set across 27 acres of oceanfront. It’s one of those rare resorts that truly offers something for everyone, with a private beach, fishing pier, golf, watersports, and great dining, all wrapped in a relaxed, easygoing setting that still feels polished and iconic.
WELLNESS
Located within the picturesque Cheeca Spa at Cheeca Lodge in Islamorada, Florida Keys, and tucked behind vivid flora and cascading waterfalls, is 5,700 square feet of space designed to surround you with tranquility. The spa features opulent amenities such as a heated lap pool with butler service, a fully equipped fitness center, and more, creating an experience that is designed to exceed expectations.
VIBE
classic, full-service resort, total relaxation
PERFECT FOR
active families, small social groups, fishing enthusiasts
WHY WE LOVE IT
Hawks Cay feels like a true Florida Keys playground, set on its own private island with a mix of villas and resort amenities that make it incredibly easy for families and groups. With everything from a saltwater lagoon and multiple pools to a marina, watersports, and endless activities, it’s one of those rare places where you can be as active or as relaxed as you want without ever leaving the property.
WELLNESS
Calm Waters Spa offers traditional and locally-influenced spa treatments and therapies that utilize the natural ingredients and aromas of the islands. Choose from one of the signature Florida Keys spa packages or customize your own unique Florida spa experience.
VIBE
stylish, full-service resort, total relaxation
PERFECT FOR
adventurous families, girlfriend getaways, hopeless romantics
WHY WE LOVE IT
Isla Bella feels like a true oceanfront retreat in the Florida Keys, with a rare stretch of private waterfront and sweeping views from every room that keep you constantly connected to the sea. Set across expansive grounds with multiple pools, dining options, and space to spread out, it strikes that perfect balance between laid back island living and a more polished, full resort experience
WELLNESS
You’re in one of the most beautiful locations in the Florida Keys, steps away from the sand and the sea, a world away from the every day. At the Spa at Isla Bella, it’s easy to find calm, serenity, tranquility. It’s all around you. Here you are pampered and waited on, your spirit is refreshed, your mind, rejuvenated.
LITTLE PALM ISLAND IN FLORIDA KEYS
VIBE
adults only, laid back luxury, once in a lifetime getaway
PERFECT FOR
romantic beachfront resorts, total relaxation, wellness weekends
WHY WE LOVE IT
Little Palm Island is one of the most unique escapes in the U.S., a true private island experience where you arrive by boat or seaplane and instantly feel worlds away. With thatched roof bungalows, no TVs or distractions, and a completely adults-only atmosphere, it’s all about slowing down, disconnecting, and sinking into a level of seclusion and barefoot luxury that’s incredibly rare this close to home.
WELLNESS
There is a Florida Keys spa resort that exists solely to promote health and well-being for mind, body and soul. It is SpaTerre, the signature spa of Noble House Hotels & Resorts. Here, exotic Four Hands Massage, CBD treatments using luxurious macadamia nut oil and organic vanilla, and body rituals using sustainably sourced seaweed are custom-designed to replace the weight of the world with the feeling of utter relaxation.
VIBE
classic, stylish, full-service resort
PERFECT FOR
friends & families, exploring locally, views for days
WHY WE LOVE IT
Tranquility Bay feels like your own slice of the Florida Keys, with spacious beachfront villas, a wide stretch of private white sand, and a relaxed, residential feel that makes it easy to truly settle in. It’s peaceful and uncrowded, with just enough amenities, from multiple pools to watersports, to let you do as much or as little as you want, all in a setting that lives up to its name.
WELLNESS
Rediscover inner peace and harmony with our in-room spa services. Custom-made herbal scrubs, facials, and body masks will transport you to wherever you want to be, all from the comfort of your guest room or beach house. Switch off and turn on your senses as you enjoy a range of therapies – including massages and body treatments – on the private spa menu, all designed to encourage peace, harmony, and balance.
Florida Keys Travel Tips & Insider Insight
The Florida Keys are best experienced as a journey rather than a single destination. Each key offers a slightly different feel, and understanding how to pace your time between them will shape the overall experience.
- Key Largo and Islamorada are ideal for a quieter start, known for their laid-back atmosphere, easy water access, and smaller, more intimate resorts.
- For a memorable dinner, Pierre’s in Islamorada is a standout, known for its elegant setting and sunset views over the water.
- A drive along the Overseas Highway is a must-visit experience. The stretch between Islamorada and Key West offers some of the most scenic views in the region, with open water on both sides and plenty of places to stop along the way.
- Key West brings a different energy, with more activity, nightlife, and a walkable historic center. It’s worth spending at least a night or two here to round out the experience.
We keep a curated, up-to-date list of the best places to stay, dine, and explore throughout the Florida Keys, and will guide you to the right options and handle the booking process from start to finish.
