Easygoing, Caribbean feels prevail in Key West, one of Florida’s most popular vacation destinations. Although tourism has definitely taken center stage here over the years, it’s still a pleasantly distinct place with a refreshing, freedom-loving, sunset-worshipping personality. From the raucous nightlife of Duval Strip to the heritage architecture of Old Town, from magnificent seafood of conch fame to unlimited outdoor escapades, Key West is always there for life’s enjoyment. Edgy at times and true to its hippie spirit, it is still a wildly interesting place to visit in Florida, and staying somewhere upscale is ideal for exploring it properly. So, here are the top luxury hotels in Key West that are sure to take your Caribbean vacation to new heights.
H2O Suites
Three things define the upscale H2O Suites resort. First, it’s an all-suite hotel, so you get brilliantly-furnished rooms with fully-equipped kitchens. Secondly, it’s an adults-only accommodation with 25 as the minimum age, meaning a more refined experience. And finally, it’s literally steps away from the bar-filled frenzy of Duval Street, the epicenter of what’s happening in Key West. Add a superb rooftop pool with panoramic views of the picturesque surroundings, a fitness center, awesome landscaping, and you’re getting one of the best luxury hotels in Key West. The icing on the cake is the private plunge pool in every suite – a fantastic amenity rarely encountered in Key West.
The Gardens Hotel
There are many hotels with “garden” in their name, but The Gardens Hotel gives them all a run for their money. You won’t want to leave the green grandeur of the courtyard, as it is truly spectacular. Previous guests have been charmed by the outdoor spaces here and loved the landscaping. The rooms are highly praised, too, with reviewers describing the experience of staying here as “serene,” and they’ve called The Gardens Hotel “your own little secluded paradise.” Vintage furniture in the suites combined with modern amenities gives the hotel that special Key West allure. Its central location in the middle of the historic neighborhood, one of the best places to stay in Key West, puts you right into the heart of the city with unlimited exploration possibilities.
Ocean Key Resort & Spa
Imagine staying in a room that gives you a daily front-row seat to the endless beauty of Key West’s sunsets. Ocean Key Resort & Spa is that accommodation. Set right on the city’s edge, it features the stunning Gulf of Mexico beautifully. The interiors are custom-designed, taking into account Key West traditions and employing local art in the decor. The on-site restaurant may very well be the most scenic in the city, boasting an extended terrace deck above the water with all-encompassing views and high-quality Florida cuisine. There’s also an exclusive oceanfront outdoor swimming pool with a swanky bar and a 24-hour fitness center. For total relaxation, you have access to the brilliant SpaTerre with its various luxury treatments. If you’re celebrating something special or simply just prefer an all-inclusive style of travel, Ocean Key Resort & Spa offers some of the best all-inclusive packages in Florida.
Hyatt Residence Club Key West, Beach House
It is very homey and cozy at Hyatt Residence Club Key West, Beach House. The accommodation offers suites with fully-equipped kitchens that will have you feeling like you’re staying in your own tropical beach house. Still, it’s a luxury resort in Key West, so you’ll have a lagoon-shaped swimming pool and access to the sandy beach of the Gulf of Mexico, quite a rarity for Key West lodgings. While not that far from the Duval Strip action, Hyatt Residence is more of an “unapologetic place to unwind” kind of accommodation with a tranquil atmosphere and quiet surroundings, so keep that in mind. Order some drinks at the tiki bar, choose a sunbed, and enjoy Key West’s nightly sunset displays – some of the best sunsets in the world.
The Capitana
A luxury boutique resort in Key West with direct access to the water? Count us in. One of the best-reviewed properties in the city, The Capitana blends style with its stunning Gulf of Mexico setting and with impressive results. Apart from the sunny rooms, you also have the chance to book a cottage for an even more private holiday. You’ll be greeted by airy designs that emphasize white aesthetics, beautiful views, and contemporary amenities. The Capitana has the soul of a typical Florida resort but the execution of an intimate home-away-from-home kind of boutique hotel. McKee’s Tiki Bar, with a spectacular terrace right next to the water, is perfect for scenic dining and trying the local seafood. Guests have raved about the hotel’s cleanliness, value for money, and fantastic location near one of the best beaches in the Florida Keys – Fort Jefferson in Dry Tortugas National Park.
Opal Key Resort & Marina
An upscale resort is the right way to enjoy Key West’s delights. At Opal Key Resort & Marina, you’ll find an oceanfront location, exquisite rooms, flawless service, and a marina. Despite being steps away from the lively Duval Street, Mallory Square, Aquarium, and Key West Museum of Art & History at the Custom House, the hotel still delivers a very private and elevated experience. Whether you book one of the rooms or the suites, you’ve got beautiful interiors, lots of sunlight, and gorgeous water views. The outdoor swimming pool area and three waterfront restaurants are highly Instagrammable, too.
Simonton Court Hotel
At Simonton Court Hotel, wake up to the birds chirping, enjoy breakfast under the leaves of the palm trees, and take a morning dip in the swimming pool next to your cottage. While you’re indeed on a tropical island, you’re also in the heart of busy Downtown Key West. But at Simonton Court, it’s easy to exit the touristy chaos. It offers an escape in private and chic cottages, a Key West specialty. Set in a repurposed tobacco factory, Simonton Court Hotel is a fantastic lodging if you’d like to feel the quirkiness of Florida’s far out tropical outpost yet never be far away from the center of the action. It’s an adults-only resort with four swimming pools, a variety of cottages, and decor that mixes authenticity with modernity. Step outside and find yourself in the middle of the historic neighborhood filled with typical conch houses, lush greenery, and hip galleries.
Santa Maria Suites
An oasis of luxury awaits at the Santa Maria Suites. By the pretty pool area surrounded by the lush greenery of the Florida Keys, you will find a peaceful retreat. The ambiance is enhanced by the elegant room options. You can choose between the villas and the suites. Both options have slick modern aesthetics, are filled with Key West sun rays, and feature spacious equipped kitchens for extra comfort. The location has consistently been a hit among reviewers who have noted the proximity to both the sea and the Duval Strip. Be sure to explore the outdoor attractions of the neighborhood, such as The Key West Butterfly and Nature Conservatory and Higgs Memorial Beach Park. And definitely don’t miss a chance to snap a picture at the Southernmost Point of the Continental U.S. – one of the top things to do in Key West.
Oceans Edge Resort & Marina
Water is everywhere you look at Oceans Edge Resort & Marina. As one of the best resort options in Key West and on Stock Island, it’s the perfect accommodation for a retreat. The balconies with ocean views delight guests, the sumptuous rooms provide a sophisticated stay, and six swimming pools can fully satisfy any craving for the water. Those who prefer to go sailing will be glad to find an excellent marina in front of the hotel. Also, you’re never too far from the vibrant Key West city center, as a shuttle connects Oceans Edge to the Old Town. When you venture out, be sure to dive into the island wilderness at Key West Tropical Forest & Botanical Garden, also situated on Stock Island. The hotel also offers free bike rentals, so you can explore your surroundings even easier.
The Conch House Heritage Inn
Key West had one particularly famous resident, the celebrated literary genius and ultimate traveler Ernest Hemingway, putting Key West on the map as one of the best vacation destinations for literary nerds. Just a block away from Hemingway’s former French Colonial-style home on Whitehead Street (now a novelist’s museum), you’ll find The Conch House Heritage Inn, the perfect accommodation to feel the Old World atmosphere in the preserved historic architecture of a typical Key West Bahamas-inspired home. It sports a pretty wooden facade, an obligatory front porch, and a variety of authentically chic rooms (one of which is named after Hemingway). The outdoor swimming pool is a wonderful addition, and the hotel’s central location makes discovering Key West effortless.
Andrew's Inn & Garden Cottages
A personalized and tranquil choice for a luxurious Downtown Key West stay is Andrew’s Inn & Garden Cottages. It’s one of the best-reviewed boutique hotels in the city and a truly tropical escape in the middle of the center with its outdoor swimming pool, cocktail service by the water, elegantly furnished cottages, and delightful landscaping full of Caribbean plants. There are many cool perks, too, like free on-site parking, free bike rentals, fast WiFi throughout the property, and a complimentary Happy Hour.
Perry Hotel Key West
A luxury hideaway on Stock Island, Perry Hotel Key West has a casual feel, industrial looks, and top-notch service. Their deep-water marina is among the largest around, so you won’t have any problems if you happen to be arriving in your own vessel. Rooms are spacious and feature balconies that open up to ocean panoramas. Two swimming pools, among the best hotel pools in Florida, guarantee relaxing plunge time, the modern fitness center with an F45 training gym adds that active fix to your leisure and the fire pits provide some precious outdoor time in the evenings. Also, when in Key West, you must try the local seafood. The on-site waterfront Matt’s Stock Island Kitchen & Bar is among the best spots on Stock Island for just that.
