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- Best Overall: Hyatt Centric Key West Resort and Spa – See Rates at TripAdvisor "Arrival at the 120-room, pet-friendly property begins with a glass of champagne — just a taste of the indulgences to come."
- Best Budget: Oceans Edge Key West – See Rates at TripAdvisor "From there, throw down your bags and grab a tropical cocktail to enjoy by one of six pools."
- Best Boutique: The Gates Hotel – See Rates at TripAdvisor "The boutique is adept at mixing contemporary design with retro Floridian flair."
- Best for Families: Sunset Key Cottages – See Rates at TripAdvisor "When you're not admiring the view from your cottage, make time for an on-site bite at award-winning Latitudes Restaurant."
- Best for Romance: H2O Suites – See Rates at TripAdvisor "Prepare for complimentary champagne and Chambord as a greeting upon arrival."
- Best for Luxury: Casa Marina Resort – See Rates at TripAdvisor "Outside, the glorious grounds are lined with palm trees and rich foliage, you can even follow a path down to a swimmable beach."
- Best for Singles: Little Palm Island Resort & Spa – See Rates at TripAdvisor "No stay at the intimate retreat is complete without making a stop by the spa or dining in the restaurant which serves up French and Pan-Latin cuisine."
- Best for Business: Pier House Resort & Spa – See Rates at TripAdvisor "Get your fill of Key West history at Chart Room, a cocktail lounge known as one of the island’s greatest hidden gems."
- Best Center City: Chelsea House Pool and Gardens – See Rates at TripAdvisor "The centrally-located property is a short walk from the center of Key West's activity, just two blocks from Duval Street."
Best Overall: Hyatt Centric Key West Resort and Spa
Hyatt Centric is located in Old Town Key West — an area locals call the "oasis off Duval." Here, visitors are located conveniently close to the action on Duval Street but still removed enough from the hustle and bustle that they can enjoy some waterfront R&R. Arrival at the 120-room, pet-friendly property begins with a glass of champagne — just a taste of the indulgences to come. The Hyatt Centric Key West has a private marina with options for jet skiing and scuba diving excursions, or if you're looking for pampering (as opposed to adrenaline-pumping activity), the onsite Jala Spa offers pre- and post-tanning treatments, wraps, facials, and deep tissue massages. Looking to dine onsite? The hotel offers two restaurants: SHOR, which serves up catch-of-the-day shellfish, grass-fed meats, and a lauded Key Lime pie; and Blue Mojito, where live entertainment meets craft cocktails, fish tacos, and Cuban paninis. We suggest ending the day there as it's an ideal place to watch sailboats drift by as the sun begins to set.
Best Budget: Oceans Edge Key West
This Key West property is as traditional as oceanfront boardwalk resorts come with three-story buildings done up in white clapboards and walkways that skirt the water's edge. Oceans Edge Key West may be a budget stay, but it offers 175 spacious suites and even more standard rooms, each of which range from 382 to 575 square feet. But before you even enter your room, you'll be enamored by the entrance: a dense thicket of tropical flora and fauna where overlapping palm fronds waft scents of coconut, key lime, and orchids. From there, throw down your bags and grab a tropical cocktail to enjoy by one of six pools, because when you're on vacation, unpacking can wait. That said, if you do want to explore your accommodations before you step out, suites offer private living rooms, wet bars, flat-screen TVs, local art and custom furnishings. An on-site marina has 111 wet and 52 dry slips, and guests can immediately take advantage of activities in the Gulf and Atlantic — including kayaking and paddleboarding trips to the world's third largest barrier reef. Best of all? Your first hour is totally complimentary!
Best Boutique: The Gates Hotel
Having opened in the late fall of 2014, the independent Gates Hotel is a relative newcomer to the scene, offering 100 minimalist rooms whose motifs nod to old school Key West. The boutique — positioned at the start of Key West, on North Roosevelt Boulevard (hence its name) — quickly proved it was adept at mixing contemporary design with retro Floridian flair, offering guests a comfortable, casual atmosphere in which to relax. One specific place in which to do just that? Rum Row, an onsite bar where you'll find signature cocktails and tapas as well as nightly entertainment. There’s also a pool with cabanas and daybeds available if you're looking to soak up some southern sun. For fans of art, the common areas of the resort, as well as the guest rooms, feature photography by award-winning local photographer Jorge de la Torriente of De La Gallery.
Best for Families: Sunset Key Cottages
Sunset Key Cottages is (unsurprisingly) located on Sunset Key, a secluded 27-acre island in Key West Harbor. Though it's situated just 500 yards off the coast of Key West proper, this island sanctuary feels worlds away. A great spot that offers a bit of a respite from all the activity of downtown, the tropical-themed property features one-, two-, three-, and four-bedroom cottages, each with traditional Key West architectural elements like pastel-hued wood and authentic Victorian-style tin roofs. Inside, there's no escaping the fact that you're at the beach: ocean and garden-view guestrooms are done up with white cottage-style furnishings, tasteful seashell accents, and blue hues.
When you're not admiring the view from your cottage, make time for an on-site bite at award-winning Latitudes Restaurant, go for a dip in the tropical pool, lay out on the white sand beach, or indulge in a treatment or two at the Spa on Sunset Key. Sports-minded guests can also get in a game of tennis at the onsite courts. If you're around in the afternoon, listen for the bell which announces “Sweets Served Daily,” a beloved ritual on the island — and one kiddos will particularly enjoy — where desserts are served from a colorful “conch cruiser” by the ice cream man.
Best for Romance: H2O Suites
If you're escaping to the Keys on a romantic rendezvous, the 22-room adults-only H2O Suites is an ideal base. Here, half of the hotel's suites come with private pools and all offer 24-hour concierge service as well as balconies, patios, spacious living areas, wet bars, spa-inspired baths with rainfall showers and Italian marble, and sumptuous king-size beds. There’s also complimentary champagne and Chambord as a greeting upon arrival — certainly the way we'd like to be received. Post welcome drink, you can head up to the resort’s rooftop pool where mimosas, Bloody Marys, and wine meet assorted tapas. A nightly turndown service also reveals frozen Dove ice cream bars, muffins, and chocolates, but don't worry — you can work it all off (or not, no judgment) at the onsite fitness center which features state-of-the-art cardio and resistance equipment as well as free weights.
Best for Luxury: Casa Marina Resort
As a Waldorf Astoria property, the Casa Marina Resort is prepped to impress with 300 rooms that meld modern, tropical decor and an elegant yet relaxed atmosphere. Rooms are all about neutral tones and slick hardwood floors, but don't be mistaken — there's a lot of luxury to be found in the little details, including top-of-the-line espresso machines. Outside, the glorious grounds are lined with palm trees and rich foliage, you can even follow a path down to a swimmable beach — a 1,100-foot stretch of private sand that's just steps from Duval Street. And if that's not enough for you, there are also two tropical pools, plush cabanas, plenty of water activities, spa services, a restaurant, and a bar right at your feet. In fact, there's so much to see and do onsite that you may forget you're in town to explore Key West, not just the resort.
Best for Singles: Little Palm Island Resort & Spa
For singles hoping to happen upon a love connection, Little Palm Island Resort & Spa is your best bet. The secluded island resort is reachable only by boat or seaplane and has 30 luxe suites with private oceanfront verandas and idyllic views. Bungalow Suites are the way to go here: the sensual guestrooms are housed in thatched-roof bungalows that feature authentic West Indies decor, refreshing outdoor bamboo showers, and custom-made king-size beds enveloped in butterfly canopies. No stay at the intimate retreat is complete without making a stop by the spa or dining in the restaurant which serves up French and Pan-Latin cuisine. But, if the goal of your trip is to look for nightlife and maybe, just maybe meet that special someone, drop by the tropical Tiki Bar. If things work out, and you find someone to share the rest of your trip with, the chef is known to pack picnic lunches for guests to take on sea-planing or sailing excursions. Before you book just be forewarned — there are no telephones or televisions, and guests under the age of 16 are not permitted.
Best for Business: Pier House Resort & Spa
Pier House Resort & Spa has been welcoming guests in the Florida Keys for more than 50 years. Here, you'll find 119 guest rooms and 23 suites, each with beautiful views either of the ocean or nearby dock. Get your fill of Key West history at Chart Room, a cocktail lounge known as one of the island’s greatest hidden gems. In fact, it was also known as the unofficial headquarters of American businessman and treasure hunter Mel Fisher.
While the hotel's hospitality is legendary — at the end of a working day you'll want to indulge in some pampering at the Spa at Pier House — it's also home a host of business-savvy amenities. If you're organizing an event, conference, or seminar you can make use of multiple venues including a 2,600 square-foot meeting room, sunset terrace, beach and garden spaces, and intimate conference rooms where audiovisual equipment and full-service catering are also available. Of course, throughout the resort, you'll find high-speed complimentary Wi-Fi, and should you be taking a working lunch, there are three onsite restaurant ideal for a casual business meal.
Best Center City: Chelsea House Pool and Gardens
In Old Town Key West, Chelsea House Pool and Gardens offers intimate accommodations with just 48 guestrooms — split between three buildings, two of which are century-old Victorian-style mansions. The vibe here is contemporary casual, and each room is individually decorated. The centrally-located property is a short walk from the center of Key West's activity, just two blocks from Duval Street, where all the classic restaurants, nightlife, and iconic attractions can be found. When you're not exploring downtown, it's worth taking a walk around the resort's acres of tropical gardens, lounging poolside, or reading a book and enjoying a cold drink in the comfortable lounge area. Stay in budget by taking advantage of free continental breakfasts served by the pool each morning, and if you want to watch Netflix, don't worry about overdoing it with cellphone data — high-speed Wi-Fi is complimentary.