9 of our favorite points hotels in the Florida Keys

Mar 5, 2021

This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. Terms apply to the offers listed on this page. For an explanation of our Advertising Policy, visit this page.

Editor’s note: This is a recurring post, regularly updated with new information and offers.


The Florida Keys have always enjoyed a tropical allure, with a convenient location to boot. Visitors have flocked here for decades to enjoy the easy lifestyle, gorgeous aquamarine water and cooling trade winds.

Several years ago, the area was hit by the devastating Hurricane Irma, but hotels, restaurants and other local businesses have worked tirelessly to repair the damage and reopen — and some places have returned better than ever before.

Get the latest points, miles and travel news by signing up for TPG’s free daily newsletter.

Key West Duval Street
Duval Street in Key West. (Photo by romrodinka / Getty Images)

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 homes and, of course, Key West’s famous Duval Street with its restaurants, shops and colorful sights.

Aerial image of the Overseas Highway Florida Keys. (Photo by felixmizioznikov / Getty Images)
Aerial image of the Overseas Highway. (Photo by felixmizioznikov / Getty Images)

When booking Florida Keys hotels, there are a variety of funky options, historic properties and traditional resort hotels that can fit any style of traveler.

And luckily, there are plenty of options for those looking to use points for an island escape. Let’s take a look at some of our favorite options:

The Saint Hotel Key West, Autograph Collection

The Saint Hotel Key West, Autograph Collection. (Photo courtesy of Marriott)

In the middle of Old Key West, The Saint Hotel provides a boutique experience (it has just 36 guest rooms, some of them loft-style with balconies and multiple beds) with the benefits of a large chain property status recognition and the ability to earn and redeem points. The hotel boasts a convenient location on Eaton Street, just a block away from the buzzing bars and restaurants of Duval Street. And on property, you’ll find a small but chic pool area and a lobby bar to enjoy a cocktail before heading out for the evening.

How to book: This is a Category 7 Marriott Bonvoy property, meaning free nights will cost between 50,000 and 70,000 points per night depending on your travel dates. If your Bonvoy account needs a boost, consider opening the Marriott Bonvoy Brilliant™ American Express® Card, which is currently offering a welcome offer of 125,000 bonus Marriott Bonvoy points after you use your new card to make $5,000 in purchases within the first three months. Plus, earn up to $200 in statement credits for eligible purchases at U.S. restaurants within the first six months of card membership. Offer Expires 5/12/2021.

Playa Largo Resort and Spa, Autograph Collection

Playa Largo Resort and Spa, Autograph Collection. (Photo courtesy of Marriott)

Set on almost 15 acres of beachfront, Playa Largo Resort and Spa in Key Largo features 177 guest rooms, suites and bungalows and even a standalone beach house. The resort also offers several restaurants and dedicated activities for kids. Don’t miss feeding the schools of giant tarpon while you are here.

How to book: This is a Category 7 Marriott Bonvoy property, meaning free nights will cost between 50,000 and 70,000 points per night depending on your travel dates.

Casa Marina, A Waldorf Astoria Resort

Casa Marina Key West. (Photo courtesy of Facebook)

This iconic beachfront hotel in Key West is filled with the grandeur and elegance of the 1920s. The Casa Marina was brought to life 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.

How to book: You can book rooms starting from 62,000 Hilton Honors points per night, with rates generally topping out at 90,000 points per night. If you wish to top up your Honors-point balance, consider the Hilton Honors American Express Aspire Card, which is currently offering a welcome bonus of 150,000 Hilton Honors points after you spend $4,000 on purchases in the first three months of account opening. The information for the Hilton Aspire Card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.          

The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton. (Photo courtesy of Facebook)

Formerly a Waldorf Astoria property, the newly renovated Reach is now part of the Curio Collection by Hilton, but it’s still one of the best beachfront hotels on the island of Key West. There are tons of watersports available to guests and even a private pier from which you can often spot dolphins. It’s an intimate, elegant destination for those seeking a casual retreat with a high level of service.

How to book: Award nights usually start from 124,000 Honors points apiece, but can soar to much more than that, depending on the nights of your travel. This property could also be a great candidate for the free-night certificates that come with the Hilton Aspire card.

Baker’s Cay Resort, Curio Collection by Hilton

Baker’s Cay Resort, Curio Collection by Hilton. (Photo courtesy of Facebook)

Formerly the Hilton Key Largo, the recently opened Baker’s Cay Resort, Curio Collection by Hilton, features nearly 14 acres of waterfront to explore, two waterfall pools, hammocks on its private beach and 200 guest rooms. It’s also pet-friendly, meaning you can travel worry-free with your furry family members.

How to book: Standard rooms can be had for as few as 51,000 Honors points per night but can be much higher depending on the dates of your travel.

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort & Spa. (Photo courtesy of Hyatt)

With 118 rooms, the Hyatt Centric Key West resembles a plantation-style home with an open-air courtyard overlooking the magnificent Gulf of Mexico. Guests will enjoy the relaxed vibe of this modern hotel and the short stroll to Duval Street or Old Town. You’ll also have access to boat docks and watersports when you stay here, as well as a heated outdoor pool that overlooks the waterfront.

How to book: This is a Category 6 World of Hyatt property, requiring 25,000 points per night for award stays. And, remember it’s relatively easy to accrue World of Hyatt points since the program is a transfer partner of Chase Ultimate Rewards. Points earned from cards like the Chase Sapphire Preferred® Card, which is currently offering a welcome bonus of 80,000 points after spending $4,000 on purchases in the first three months of account opening, can be transferred into Hyatt at a 1:1 ratio allowing you to quickly build up your points balance.

Hyatt Residence Club Key West, Beach House

Hyatt Residence Club Key West, Beach House. (Photo courtesy of Facebook)

For those traveling on points with a larger group or a family, look no further than the Hyatt Residence Club Key West, Beach House. This property features large, villa-style guest rooms with master and guest suites, screened-in porches, fully equipped kitchens and more. Elsewhere on the resort you’ll find grills for guest use, pools, jacuzzis and a beach area with a private dock. There are also two additional Hyatt Residence Club options on Key West if the Beach House isn’t quite what you’re looking for.

How to book: Award nights require 25,000 World of Hyatt points apiece.

Crowne Plaza La Concha Hotel and Spa

Crowne Plaza La Concha Hotel and Spa. (Photo courtesy of Facebook)

The Crowne Plaza La Concha is a Key West icon dating back to 1926. Take in stunning ocean views from the rooftop deck, the highest point anywhere on the island, lounge by the pool or take advantage of the resort’s perfect spot right on Duval Street.

How to book: Standard rooms typically go for 60,000 points per night. If you’re looking to add to your stash of Rewards Club points, consider The IHG® Rewards Club Premier Credit Card, which is currently offering a sign-up bonus of 140,000 points after spending $3,000 within the first three months of account opening.

Kimpton Winslow’s Bungalows

Kimpton Winslow’s Bungalows. (Photo courtesy of IHG)

Kimpton actually has a total of five properties on Key West. All of them are great options, but the largest of the group, Winslow’s Bungalows, named after painter Winslow Homer who spent his winters in Key West in the early 19th century, really stands out. The property is made up of several unique and historic homes, meaning that no two rooms are designed the same. Located in Old Key West, this beautiful property is an ideal destination for all types of travelers.

How to book: Standard rooms typically go for 60,000 points per night.

Bottom Line

Despite the myriad boutique properties located throughout the Florida Keys, it is also possible to book many excellent hotels using points to pay for your accommodations. And thanks to the relaxed, low-slung atmosphere in the Keys, many of these points hotels have an intimate boutique feel, making it a true best-of-both-worlds destination.

Additional reporting by Jon Bailey.

Featured photo by Stanley Chen Xi, landscape and architecture photographer/Getty Images.

The All-New United Quest℠ Card

WELCOME OFFER: Up to 100,000 bonus miles

TPG'S BONUS VALUATION*: $1,040

CARD HIGHLIGHTS: 3X miles on United® purchases

*Bonus value is an estimated value calculated by TPG and not the card issuer. View our latest valuations here.

Apply Now
More Things to Know
  • Earn 80K bonus miles after you spend $5,000 on purchases in the first 3 months your account is open. Plus, an additional 20K bonus miles after you spend $10,000 in the first 6 months
  • $250 Annual Fee
  • Earn 3X miles on United® purchases, 2X miles at restaurants, on select streaming services & all other travel, 1X on all other purchases
  • Earn 3X miles on United Airlines purchases
  • Earn 2X miles at restaurants and on select streaming services
  • Earn 2X miles on all other travel
  • Earn 1X mile on all other purchases
  • Each year, receive a $125 credit on United® purchases and two 5k-mile anniversary award flight credits. Terms apply.
Regular APR
16.49% to 23.49% Variable
Annual Fee
$250
Balance Transfer Fee
Either $5 or 5% of the amount of each transfer, whichever is greater.
Recommended Credit
Excellent, Good

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.