The 106-room, Cuban-themed, pet-friendly waterfront Havana Cabana Key West is the closest travelers can get to Cuba without actually crossing the ocean. It’s located just a few minutes’ drive from Key West’s historic Old Town and is brimming with a sense of old-world charm and authentic character.
Stepping inside this resort feels like stepping into a local family’s own immaculate mansion, offering a warm sense of invitation mixed with a playful air of rebellion. Immediately upon walking in the front doors and standing in the grand atrium to gaze up at the two grand curved staircases, guests know they’re in for an eventful stay.
We hope you love the Havana Cabana Key West! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.
Havana Cabana Key West combines classic and contemporary accommodation
The feeling of old-fashioned glamor is combined with the luxury of modern amenities. Havana Cabana boasts the title of being home to Key West’s largest (and therefore, most fun) pool. Guests can visit this lagoon-style oasis’ legendary Mojitos Pool Bar, which concocts more than a dozen unique varieties of the classic rum-based cocktail adjacent to the action.
The pool is considered the “heart of the resort” and is surrounded by loungers, day beds, and private cabanas, which creates a tropical sanctuary for resting and recovering after a night out on the town (or just for soaking up the Florida sunshine). There are regular poolside events, including live entertainment and weekend pool parties with DJs every Saturday and Sunday. Adjacent to the pool, the tiki pavilion harbors a collection of games like giant Jenga, foosball, and corn hole, among other nostalgic favorites.
The walls of the entire property are decorated in vibrant, floor-to-ceiling Cuban-inspired outdoor murals painted by local artists, which add positive energy to the public spaces on-site and pay homage to the cultural influence that makes this property a special place to spend time.
Rooms at the Havana Cabana Key West carry forth the island vibes
Inside this Key West boutique hotel, guests will enjoy spacious rooms with a modern, eclectic Cuban touch. Rooms feature private balconies with views of the pool, ocean, or “standard” (the exterior of the resort). There are a variety of types of airy rooms, all decorated to feel like an authentic trip abroad to a boutique Cuban inn. The beds’ headboards are outfitted with the same sturdy, rich wood as the desks, the nightstands, and the floors.
These darker, caramel wooden tones playfully contrast against a bright palette of tropical aquamarine, whites, and natural tones. Everything in the hotel is equally playful, from the bulk toiletry bottles in the bathrooms, which feature puckish phrases and pictures on the shampoo and conditioner bottles, to the goodies sold down below in the on-site gift shop, which offers guests the opportunity to bring a piece of Cuba (by way of Key West) home, with them.
One of the standout elements of the property is the festive and bold outdoor murals, which stand as a proud representation of the property’s Cuban influence. The collection of original, hand-painted murals adorn the walls of Havana Cabana and depict the stories of the country. In these brushstrokes, visitors can get a sense of the history, romance, and beauty of the Caribbean island set less than 100 miles from Key West, and feel the strong emotions each of the three renowned South Florida artists inflicted on their masterpieces.
Those who seek authentic Cuban fare will rejoice at the hotel’s on-site Floridita Food Truck, which serves a Cuban-inspired menu from a chic, renovated Airstream. Diners can choose between classic options like Cuban cheese toast, freshly made Pan Con Lechon, or the hearty “Havana Burger.” On the ground just adjacent to the food truck under the tiki hut, get a glimpse of one of the hotel’s colorful murals — this one depicting Havana Cabana’s designated mascot, “Maiden” – the goddess of the sea, inspired by the water spirit Yemaya. The painting honors the mermaids of the Florida Keys and is meant to welcome hotel guests in a community-centric area.
Traveling to Florida? Check out Matador’s Florida accommodations guides:
- 15 beautiful Florida Airbnbs for every type of traveler
- The best 11 Airbnbs near Universal Studios
- The 12 best Miami Airbnbs from South Beach to Little Havana
- 8 of the coolest Airbnbs near Disney World, Florida
- 15 beautiful Florida Airbnbs for every type of traveler
- 6 Kissimmee Airbnbs for a multi-generational family Disney trip
- 11 Key West Airbnbs to experience the best of the island
- 11 gorgeous Florida Keys Airbnbs to catch the ‘Keys Disease’
- These New Smyrna Beach Airbnbs showcase the best of Florida’s central coast
The resort offers ample onsite entertainment and easy access to the best of Key West
As for daily resort activities, visitors won’t ever be bored whether they’re spending time at the hotel or exploring the island. On-site, there’s a 24-hour Fitness Center with a smattering of cardio machines and weights, complete with a view of the ocean directly across the street.
Since Havana Cabana doesn’t believe Happy Hour has to be limited to the afternoon — the hotel actually hosts a daily, morning “Rise and Unwind Happy Hour” at Mojito’s Pool Bar from 10 a.m. — 12 p.m. serving $9 specials on cocktails and beer.
Those who’ve dreamed of living life “under the sea” can experience swimming with a real Key West Mermaid from 10-11:30 a.m. during “Fintastic Fridays.” Those who love a good, old-fashioned pool party can cannonball into an unmatched bash every Saturday and Sunday from 12 p.m — 4 p.m. when the hotel hosts epic pool events known to make a serious splash.
To enjoy spending time on the island off-site, visitors can use the free, dedicated shuttle service to quickly and easily get downtown and raise some raucousness on the notoriously naughty Duval Street. Or, rent bicycles or vintage Vespas to spend time outside on the island exploring with a new set of wheels.
Sign up for excursions and guided tours at the hotel’s dedicated concierge desk to embark on one of the many signature adventures of the Florida Keys. From backwater kayaking and deep-sea fishing to reef snorkeling and deep-wreck dives — there are dozens of outdoor opportunities to get outside and enjoy the sun-soaked weather.
The hotel also hosts 1,820 square feet of space for meetings and events. The dedicated on-site event planning team can arrange for experiences like mojito mixing competitions, cigar rolling classes, or Cuban sandwich making.
When it’s time to leave, Havana Cabana lessens the blow by offering free shuttle rides to Key West International Airport. From the upbeat spirit of everyone encountered on-site to the boisterous events and activities available to attend, included in each stay — a trip to Havana Cabana Key West is a memory that will shine bright for years to come.