man diving into a pool

Key West’s Largest Pool

The pool at Havana Cabana is the heart of our resort. It’s the largest pool in Key West – a destination unto itself, and a place that manages to be both a tranquil oasis and a hub of activity. Take a dip, play games, or simply relax at Key West’s largest and most happening pool!

Complimentary Perks:

  • Chaise lounges with service
  • Poolside smoothies served at 12pm
  • Poolside Popsicles served at 2pm

Seasonal Resort activities

If there’s a holiday, we’re celebrating it! We’ll take any excuse to put on a pool party, but can you blame us when we have the best pool in Key West? From big national holidays to more locally known events, we’ve got events for everyone!

Daily Resort activities

Our tiki and pool are always hopping with activities! Whether you want to leave it all behind and be a mermaid for the day, or just want to enjoy some poolside music, we’ve got you covered.

What To Do In Key West

There’s always something exciting happening in Key West – no matter what time of year you visit. The city’s event calendar is packed with festivals, celebrations, tournaments and other one-of-a-kind occasions. Our concierge staff can make recommendations or help you plan your activities.

Havana Cabana living room decor and setup

Barbary Beach House Key West

2001 South Roosevelt Boulevard, Key West, Florida 33040 USA

Somewhere between the southern edge of the Continental U.S. and ordinary, that’s where you’ll find our stunning Key West Resort. On an island whose story unfolds like the greatest adventure ever written.

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Key West Golf Club

6450 College Rd, Key West, FL 33040, United States

Spanning 200 acres and designed by famed architect Rees Jones, this 18-hole golf course provides challenging and rewarding play for golfers of every skill and experience level. Tee off among breathtaking views of tropical mangroves here at the “Gateway to the Caribbean”.

Smathers Beach

2601 S Roosevelt Blvd, Key West, FL 33040, United States

Framed by coconut trees and located just a short bike ride away from Havana Cabana, Smathers Beach embodies the tropical splendor of Key West. Enjoy a picnic with your family and take a leisurely swim here on Key West’s largest public beach.

Southernmost Point

Whitehead St &, South St, Key West, FL 33040, United States

The legendary Southernmost Point buoy is one of the most visited landmarks in Key West. Be sure to have your photograph taken next to it!

Ernest Hemingway House

907 Whitehead St, Key West, FL 33040, United States

Arguably one of Key West’s most renowned residents, Ernest Hemingway resided at 907 Whitehead Street throughout most of the 1930s. Today, his house is a U.S. National Historic Landmark, and is listed on the U.S. Register of Historic Places; take a guided tour and catch a glimpse of the dozens of cats that live on the property.

Rodriguez Cigars

113 Fitzpatrick St, Key West, FL 33040, United States

​In 1947, the Rodriguez Family began the masterful art of cultivating tobacco on their private plantation in the town of Siguaney. The tobacco plantation was called La Finca de Carmencita. Located in the Las Villas province of Cuba, La Finca de Carmencita specialized in growing, aging, and curing filler tobacco leaves for numerous manufacturers throughout Cuba.

Key West Butterfly and Nature Conservatory

1316 Duval St, Key West, FL 33040, United States

Witness the beauty of over 50 different species of butterflies at this glass-enclosed observatory, which also features several species of birds and an on-site learning center.


​Mallory Square

400 Wall St, Key West, FL 33040, United States

There’s no better place to catch the sunset in Key West than at this waterfront plaza; indeed, Mallory Square’s “Sunset Celebration” is one of the city’s most beloved tourist attractions. The square also includes a sculpture garden, live performers and plenty of great shopping and dining.

KINO Sandals

107 Fitzpatrick St, Key West, FL 33040, United States

​Kino sandals are made on location in Key West, Florida. Being only 90 miles from Cuba keeps them close to their ancestors homeland where they have been worn for decades. Kino’s Plaza is located in the heart of old town on the corner of Green Street and Fitzpatrick Street, where traditional methods are used to make these unique sandals to this day! Stop by and check us out and see how our Kino’s sandals are made and why they are so popular. We bet you won’t leave without a pair!

Papa’s Pilar Rum Distillery

201 Simonton St, Key West, FL 33040, United States

​Inspired by Ernest Hemingway’s spirit of adventure, Papa’s Pilar is crafted for those with a restless spirit who seek exploits of epic proportions, much like Papa himself. Papa was a man of many things – an author, storyteller, sportsman, adventurer – but one thing he was not was a spectator. Papa’s Pilar is an homage to Hemingway’s adventures, and an inspiration for yours.

Santiago’s Bodega

7305, 207 Petronia St #101, Key West, FL 33040, United States

La Trattoria Venezia

524 Duval St, Key West, FL 33040, United States

​Prime Steakhouse

951 Caroline St, Key West, FL 33040, United States

7 Fish

921 Truman Ave, Key West, FL 33040, United States

Cuban Coffee Queen

284 Margaret St, Key West, FL 33040, United States

El Meson De Pepe

Mallory Square, 410 Wall St, Key West, FL 33040, United States

Origami Sushi Bar

1075 Duval St STE C3, Key West, FL 33040, United States

El Siboney

900 Catherine St, Key West, FL 33040, United States

Decorative Illustration

​From The Blog

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