There’s something special about Key West. Located at the southernmost tip of Florida, it’s the last stop before Cuba—and the international influence makes a trip to Key West feel like a vacation abroad.
Key West isn’t a place where you’ll find a lot of mega-hotels or big chains. Instead, there is a plethora of charming locally-owned bed and breakfasts, intimate resorts, and unique accommodations for travelers to choose from.
These are the 11 best Key West hotels for every type of trip.
The Best Old Town Key West Hotel: Southernmost Beach Resort
Just a short walk away from the famed nightlife of Duval Street, the Southernmost Beach Resort is the best hotel to book if you plan on spending a lot of time in Key West’s historic Old Town.
The property was fully renovated in late 2021, and everything looks brand new. When you’re not out experiencing Old Town, enjoy the hotel’s three heated pools, catch some rays on the private tanning pier, or lounge on nearby South Beach. For a VIP experience, rent one of the hotel’s private poolside cabanas.
The Best Key West Hotel Rooms With Balconies: DoubleTree Resort by Hilton Grand Key Key West
Enjoy the tropical scenery from your private balcony at The DoubleTree Resort by Hilton Grand Key West. The majority of the hotel’s spacious rooms feature a private balcony, some with pool views and others that overlook the property. Make a complimentary cup of coffee with the in-room coffee makers and watch the sunrise from your balcony each morning.
The Key West Hotel With the Best Pool: Havana Cabana at Key West
The Havana Cabana Resort is the closest you’ll get to Cuba without leaving Florida. From the classic cars parked out front (which can also take guests into town) to the authentic mojitos and music poolside, the Havana Cabana really feels like Havana.
The resort is centered around a sprawling pool (the largest in Key West), around which guests will find games (including giant Jenga, foosball, and ping pong), hammocks, lounger chairs, and private cabanas.
The Best Key West Hotel for Destination Weddings: The Reach Key West Curio Collection by Key West
Key West is a popular location for destination weddings, and it’s easy to see why, especially at The Reach Key West. The hotel has a stunning ceremony location, a covered gazebo perched over the Atlantic Ocean that will work in any weather. Receptions can be held outside on the beach or lushly landscaped lawn, or indoors in a modern and light-filled space.
Couples can add on unique amenities for an unforgettable wedding, including a custom sand sculpture or sunset sail.
The Best Key West Hotel for Groups: Parrot Key Hotel & Villas
Families and friends who need a lot of space for their group trip will find it at the Parrot Key Hotel & Villas. Choose from standard guest rooms, one-bedroom suites, two-bedroom suites, or three-bedroom villas to have the perfect mix of privacy and shared space.
Families will also love the activities offered at this hotel, which include kid-friendly scavenger hunts and beach games like Yahtzee, paddleball, and bocce.
The Best Key West Hotel on the Beach: Casa Marina Key West
Key West (a coral island) isn’t known for its sandy beaches—but that doesn’t mean there aren’t any here. One of Key West’s best beaches is the 1,000 foot private one at Casa Marina that’s reserved for hotel guests. For days when the ocean is too cold or too rough, the property also has two outdoor tropical pools for swimming.
For the easiest beach access, book one of the Ocean View Suites with Lanai, which offer walk-out access that will put you just steps away from the sand.
The Best Adults-Only Key West Hotel: The Cabana Inn Key West Adults Only
Guests must be 18 or older to stay at The Cabana Inn Key West, making this the perfect hotel to book if you’re looking for an adults-only Key West vacation. The resort offers amenities tailored to adults as well, including a daily wine and cheese happy hour and Starbucks coffee/tea available 24/7. There’s also free breakfast, WiFI, and daily bottled water included in the rate.
The hotel offers a number of off-site excursions that can be booked for an extra fee, including sunset sails, snorkeling, parasailing, fishing, and more.
The Best Cheap Key West Hotel: 24 North Hotel Key West
Looking for the best budget hotel in Key West? 24 North Hotel is a great affordable choice that still feels luxurious with lots of unique amenities included in the rate. Check out a book from the hotel’s Underwater Library, which stocks waterproof books that you can take in the pool or ocean without damage.
Or, get active with 24 North’s Bootcamp in a Box (a self-guided 30-minute workout), running maps, or free yoga sessions.
When you’re ready to head into Old Town, the hotel offers a free air-conditioned shuttle to and from town.
The Best Key West Resort for Couples: The Gardens Hotel
For the most romantic Key West vacation, book a couples trip to The Gardens Hotel. You and your sweetheart can sip champagne from the hotel’s award-winning Wine Gallery while listening to live jazz, relax with a couple’s massage, and then enjoy a sunset sail to end the evening.
Surprise your significant other by adding on the Romance Package to your room, which includes a dozen roses, chocolate-covered strawberries, and Tattinger Champagne.
For extra privacy, book one of the four brand-new cottages that feature their own pool.
The Best Luxury Key West Hotel: Ocean Key Resort A Noble House Resort
Splurge on a stay at the most prestigious address in Key West—Zero Duval Street, which is home to the Ocean Key Resort. The hotel’s prime location offers incredible views of the Gulf of Mexico, along with easy access to historic Old Town.
The resort features luxurious amenities including welcome cocktails and chilled towels at the pool. There’s fine dining on-site as well—the waterfront Hot Tin Roof Restaurant is reported to have the best sunsets in town.
The Best Key West Hotels for Families: Ella’s Cottages Kimpton Key West
Families will have plenty of space at Kimpton Ella’s Cottages. This boutique collection of 22 rooms offers unique and historic accommodations that have been converted from a beauty salon, butcher shop, and casino into family-friendly cottages.
Kids will love the hotel’s outdoor pool, complimentary custom-designed loaner bikes, and free snorkel kit.
Key West FAQ
Where is Key West?
Key West is the southernmost island in the Florida Keys. It’s actually closer to Cuba than it is to Miami.
How Far is Key West from Miami?
Key West is 159 miles from Miami. The drive from Key West to Miami usually takes an average of 4 hours.
What Airlines Fly to Key West?
Key West has its own international airport, which is serviced by American Airlines, Delta, Silver Airways, United Airlines, JetBlue, and Allegiant Air.
Can You See Cuba From Key West?
Unfortunately, the 90 miles between Cuba and Key West means that it is too far to see Cuba from Key West.
Does Southwest Fly to Key West?
Southwest no longer flies to Key West.
Can You Drive to Key West?
Yes, you can drive to Key West—a number of bridges connect the Florida Keys to the mainland. A drive to Key West makes for a very scenic road trip!
When is Fantasy Fest in Key West?
The famous Fantasy Fest is an annual 10-day party that is usually held in late October.
You Might Also Like:• Can You Bring Batteries on Planes?
• The 14 Best Vacation Rental Sites for Travelers in 2024
• Where to Find Premium Airfare Deals on First Class and Business Class
• The 15 Most Walkable Cities in the US, Ranked
• Mexico Passport Requirements: Do I Need a Passport to Go to Mexico?
We hand-pick everything we recommend and select items through testing and reviews. Some products are sent to us free of charge with no incentive to offer a favorable review. We offer our unbiased opinions and do not accept compensation to review products. All items are in stock and prices are accurate at the time of publication. If you buy something through our links, we may earn a commission.