While new travel bans recently implemented included tighter restrictions for Cubans coming to the U.S., American citizens have long dealt with strict regulations for travel to Cuba. Visiting Cuba is not as easy as hopping on a flight with your swim trunks packed — there are very specific categories of travel allowed, and general tourism is not one of them. However, if you want to get a taste of Cuba on U.S. soil, Havana Cabana Key West is a resort entirely inspired by the island nation and just a couple miles away from Key West’s lively Old Town.
Havana Cabana Key West channels vintage Cuban flair — from classic Chevys in the courtyard to colorful hand-painted murals and flamenco music echoing throughout the property. Rooms balance that Cuban aesthetic with comfort, including amenities like mini-fridges, microwaves, blackout drapes, Wi-Fi, and Cuban coffee — some even include balconies or poolside access. Spend quiet mornings around the largest pool in Key West until the vibes shift into energetic fun by midday — complete with live entertainment, day cabanas for rental, and poolside service offering a plethora of mojitos and Cuban-inspired bites from the on-site Floridita Food Truck.
While it used to be adults-only, the resort has now opened up to welcome all ages, adding it to the must-visit family vacation destinations list. Inside tip: If you’re traveling with your “fur-kids,” you’re also in luck with this pet-friendly resort. In fact, four-legged guests are allowed everywhere in the resort except the pool and hot tub area (the resort even hands out pet goodie bags when you check in!).
Planning your Cuban-esque getaway at Havana Cabana
Room prices range from $175 to $300+ a night, but visitors can also find package deals and various discounts offered through the resort’s website. If you’re visiting Key West on a budget, Havana Cabana offers an appealing assortment of perks with the daily resort fee of $55. This includes complimentary shuttle service running hourly (9 a.m. to 10:30 p.m.) to Duval Street, so you can easily ditch your rental car and enjoy downtown nightlife, dining, and sunset-viewing spots stress-free. Airport pick-up and drop-off is free for visitors coming from Key West International — but you must schedule it a day in advance. The fee also gets guests one free drink, free poolside churros and infused water from 4 p.m. to 6 p.m., and a 24-hour concierge service.
For an additional charge, take advantage of the resort’s bicycle and scooter rentals, or order a classic car ride through the concierge for an iconic Cuban cruise. If you’re nostalgic about the classic Keys, ask the concierge about rum tastings or cigar evenings. Travelers with pets will want to check out Key West’s pet-friendly beaches and parks, like Key West Dog Beach and Higgs Beach Dog Park. Pets are allowed on the shuttle, and there are a handful of pet-welcoming dining options in the area as well, such as Blue Heaven, Salute!, and Half Shell Raw Bar.
Havana Cabana’s location on Roosevelt Boulevard places you a quick ride from attractions like Smathers Beach, the Ernest Hemingway House, the Key West Butterfly and Nature Conservatory, and the Southernmost Point. If you’re looking for a playful, laid-back Keys retreat with good music and Cuban vibes, Havana Cabana puts you right in the mix.
