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The Florida Keys have always enjoyed a tropical allure, with a pretty convenient domestic location. Visitors have flocked here for decades to enjoy the easy lifestyle, gorgeous aquamarine water and cooling trade winds. While this area was hit by Hurricane Irma in 2017, most of the hotels and restaurants have now had time to repair and reopen — in some cases, making themselves better than ever.
Connected via bridges and waterways, the Florida Keys number some 1,700 islands in all, but most are not accessible or inhabited. They begin with Key Largo, which is closest to mainland Florida. From there, highlights include Islamorada, Duck Key, Marathon Key, the Seven Mile Bridge, Big Pine Key, Ramrod Key and, ultimately, Key West, which is just 90 miles north of Cuba and the southernmost spot in the United States.
Thankfully, you can access the Keys from mainland Florida thanks to the picturesque Overseas Highway. Visitors come for diving, Easter egg-colored houses and, of course, Key West’s famous Duval Street with its restaurants, shops and colorful sights.
When booking Florida Keys luxury hotels, there are a variety of funky options, historic properties and traditional resort hotels that can fit any style of traveler. Make any of these eight accommodations your home base for a tropical escape:
This landmark Hilton-owned beachfront hotel in Key West is filled with the grandeur and elegance of the 1920s. It was conceived by railroad tycoon Henry Flagler, and the who’s who of society and industry have called this a vacation destination for nearly 100 years. This beachside resort has two stunning pools and a lobby that has recently been refurbished in grand style. Plus, it’s only steps from Duval Street.
Rates: Starting at $203, or around 77,000 Hilton Honors points per night (also bookable at the Chase Travel portal and Hotels.com/Venture).
With 118 rooms, this boutique hotel in Key West resembles a plantation-style home that features an open-air piazza overlooking the magnificent Gulf of Mexico. Guests have access to boat docks and other watersports, as well as a heated outdoor pool that overlooks the waterfront. Guests will enjoy the relaxed vibe of this modern hotel and the short stroll to Duval Street or Old Town.
Rates: Starting at about $265, or 25,000 World of Hyatt points per night
Tip: Build your points balance with the World of Hyatt Credit Card. Or, transfer your Chase Ultimate Rewards points to your Hyatt account on a 1:1 basis. (Earn Ultimate Rewards points with the Chase Sapphire Preferred Card or Chase Sapphire Reserve.)
Where the Hilton Key Largo was severely damaged by Hurricane Irma, the Baker’s Cay Resort in the Curio Collection was later reborn. Just opened in 2019 and located on 14 acres, this pet-friendly resort has 200 rooms and a private beach.
Rates: Standard rooms with one king or two queen beds are often bookable for 60,000 Hilton points per night. Like at many Keys hotels, there is a $38 per night resort fee, but remember, those staying purely on Hilton points can avoid that.
Playa Largo Resort & Spa in Key Largo offers a day camp for the kids and tons of activities for the adults. There are several restaurants, upscale accommodations and some impressive high-tech gadgets everywhere you turn. Be sure to feed the schools of giant tarpon. Playa Largo is part of Marriott’s Autograph collection, so you can use all those Marriott Bonvoy points you’ve been stacking up.
Rates: Starting at $171, or 60,000 Marriott points per night
Tip: Earn Marriott points with the Marriott Bonvoy Boundless Credit Card or Marriott Bonvoy Brilliant™ American Express® Card. You can also transfer Chase Ultimate Rewards points to your Marriott account on a 1:1 basis.
If your idea of luxury includes someplace eclectic, Pier House is a great Key West option. This is the place where Jimmy Buffett played his first gig in Key West in the 1960s. Located at 1 Duval Street, you can’t be more in the middle of the action here. Visit this legendary hotel to embrace both your romantic and adventurous sides while enjoying the private white sand beach.
Rates: Starting at $220 (or book through American Express Travel or the Chase Travel portal using those points as shown below with Chase Sapphire Reserve)
Use your IHG Rewards Club points at this Key West icon that dates back to 1926. You can luxuriate in stunning ocean views from the rooftop deck, which is the highest point anywhere on the island. Lounge poolside and let your inner Tennessee Williams come out.
Rates: Starting at $189, or 40,000 IHG Rewards Club points per night.
Tip: Your fourth reward night is free if you hold the IHG Rewards Club Premier Credit Card.
The sister property to Casa Marina, this is one of the best beachfront hotels on the island of Key West. There are tons of watersports and a private pier from which dolphins are often spotted. This is an intimate, elegant destination for those seeking a casual retreat with a high level of service. Note that this property is undergoing an extensive renovation and will transition to a Curio, Collection by Hilton property. It will be closed from Aug. 1–Nov. 30, 2019.
Rates: Starting at $203, or 80,000 Hilton Honors points per night. This is a great place to use the weekend anniversary night that is available with several of the Hilton credit cards, such as the Hilton Honors American Express Surpass® Card (currently awarding 130k bonus points and a weekend award night with $4,000 in spending in the first four months).
Located on Duck Key, this massive complex is a haven for families and large groups. Hawks Cay Resort underwent a massive renovation after Hurricane Irma and offers dozens of on-site activities, including supervised kids camp, world-class tennis instruction and more. We stayed here on a recent trip and our family loved the array of amenities offered as well as our waterfront townhouse accommodations.
Rates: Starting at $239, use points from a card such as the Capital One Venture Rewards Credit Card to offset the charge on your statement.
Despite the many boutique properties located through the Florida Keys, it is also possible to book many excellent hotels using points to pay the bill — either via traditional hotel points or flexible points. Have you been to the Keys recently? What’s your favorite points-friendly hotel in the area?
Featured image courtesy of Hawks Cay Resort
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