This island town is abundant with history and possesses a unique charm you can’t find anywhere else.
The chain of islands are actually remnants of an ancient coral reef system that was there thousands of years ago and sits just off the southern coast of Florida. Key West is the southernmost point in the United States and resides just 94 miles from Cuba, and the relationship with its close neighbor is celebrated all over the island through art, history, and cuisine.
The island, once called “Cayo Hueso” meaning “bone cay” served as a communal graveyard for the indigenous people at the time which is how it got its name.
Spanish culture and architecture are everywhere since the first European settlers arrived from Spain in 1571. While most know and love Key West for its serene beaches, immaculate sunsets, and water sports this island offers that and so much more.
Throughout pre-colonial times, the island was inhabited by the Calusa people. Juan Ponce de León was the first European to visit the island and it quickly came under Spanish rule before Great Britain gained control in 1763. Throughout the island, history is celebrated and homage is paid to the island’s roots.
Today, the old island is a hotspot for tourists who visit from around the world. Many cruise ships port into Key West weekly. The island is relatively small with a hometown feel and tight-knit communities. You may hear some call it the “Conch Republic” which is a term applied to the entire Florida Keys.
While you have several hotels and resorts to choose from, we’ve found two of the best hotels in Key West.
24 North Hotel
24 North hotel is newer and is only a 4-minute Uber ride from Key West International Airport.
It provides modern upscale amenities, great proximity to beaches, drink specials at the Toasted Coconut, breakfast and lunch options, a Starbucks, gym, and swimming pool making it an all-encompassing place to relax on the island.
Because of its great location, everything is within driving distance or an Uber ride. Shuttles, event space, bicycles, and games are all available on the property. It’s a truly laid back environment which reflects the carefree attitude of the island.
On any given day, you may find a sponsored party equipped with a DJ and complimentary beverages taking place by the pool.
The Gates Hotel
This cozy hotel is the sister property to 24 North Hotel and is within walking distance. For those who enjoy a more relaxed environment, this is one property you’ll love.
The interior decor is tasteful and stylish. The moment you walk in, you’re greeted with rum punch, natural sunlight beaming through the giant windows, and art reflecting the island’s beauty.
It’s modern, chic, and stylish all wrapped into one. On the property, you will find a beautifully landscaped interior, a stage for live music, a cigar deck, cigars for purchase, a full-service bar, bicycles for rent, and a lunch/breakfast spot called the Blind Pig.
The rooms come with all your standard amenities including a mini fridge, Keurig, blow dryer, hygiene products, a phone, and cable TV.
The rooms are stylish mirroring the chic, beachy furniture in the hotel lobby
Another great feature to both properties is the shuttle service to Mallory Square.
If you’re going to spend time in Key West, watching the sunset at Mallory Square on the pier should be at the top of your list.
The Gates Hotel and 24 North Hotel have great shuttle drivers that bus people back and forth every 30 minutes. From Mallory Square, shops and Duval Street are all within walking distance. Of all the things to do in Key West, this is definitely the most memorable.
Restaurants and vendors line the pier, and you can have a nightcap on Duval Street which is similar to Bourbon Street in New Orleans.
Walkways are landscaped with native trees and plants and the weather is extremely humid and hot. The nights cool down nicely, but the afternoons are definitely sizzling.
Rodriguez Cigar Lounge
Key West offers several beaches including Smathers Beach, Fort Zachary Tayor Historic State Park, and Higgs Beach Dog Park.
All the beaches are near the hotel and Uber is the cheapest way to go although taxi drivers are likely natives of the island so they offer more backstory during the drive to the destination.
The public beach that serves beer and offers a bit of a history lesson is Fort Zachary. This is a historic park with several beach spots and picnic tables to lounge around.
This beach is only $5 a car and it really serves as a donation to fund the park.
New event lawn called the Sunset Green
If you’re looking for places to get married in Key West, 24 North Hotel and the Gates Hotel are great options. The property will soon feature beautiful event space this December.
The new area known as the Sunset Green will be able to host a variety of events. The 12,105 sq.ft lawn is nestled between both properties so guests can stay at both hotels. The newest addition will be able to host as many as 1,200-standing guests or 800 seated guests on its evergreen lawn making it the perfect venue for weddings and social events.
- Hotel shuttles (free to Mallory Square and back)
- Mallory Square
- Dinner at Sunset Pier
- Drinks on Duval Street
- Fort Zachary Historic State Park and Beach
- Hemmingway Home
- Rodriguez Cigar Factory (The Gates Hotel has a nice selection of Rodriguez cigars as well)