Havana Cabana at Key West

A Cuban Idea, Committed To

Ninety miles of water separate Key West from Havana, and a good deal of the island’s character comes from that proximity. Most hotels nod at it. This one builds the whole property around it, from the colour palette to the food truck to the name of the pool bar. Havana Cabana sits on North Roosevelt Boulevard on the Gulf side of the island, a low resort of a hundred-odd rooms arranged around a very large pool, with a lounge that opens in the evening and music that carries across the deck most of the day. It is unashamedly a resort rather than an inn, and it is good at being one.

Why It Works

Space is the argument. Old Town charms and then runs out of room: small pools, tight lots, no parking. Out here the property has the acreage to put in a pool worth spending a day beside, cabanas around it, and somewhere to leave the car, then runs a shuttle so the town is still available when you want it. The second reason is that the theme is carried through rather than painted on, which shows up in the food, the drinks and the way the staff work the deck. Guests come for a week of daylight, not for a base.

Why This Location

North Roosevelt Boulevard is the working edge of Key West, the road everyone takes into town, facing the Gulf rather than the Atlantic. That means sunsets from this side of the island and calm water, and it means you are a short drive rather than a walk from Old Town. The hotel shuttle drops near Duval, which removes the parking question entirely. The Historic Seaport and its charter docks, Smathers Beach on the Atlantic shore and the island’s airport are all a few minutes away in their respective directions. Choose this address if you want the town in the evening and the pool in the daytime, in that order.

Fast Facts

• Price: €€€

• Vibe: Cuban, colourful, sociable, poolside

• Rooms: Just over a hundred, laid out low around the pool deck

• Best For: Groups of friends, couples who want a pool day, travellers with a dog, anyone who would rather not park in Old Town

• Our Favorite Thing About the Hotel: Floridita, the Cuban food truck parked permanently on the property, open from breakfast to late

• Dining: Floridita Food Truck for Cuban plates, Mojitos Pool Bar for drinks and light food through the day, Flama Cabana for tapas and rum cocktails in the evening

• Amenities: The largest hotel pool on the island by the property’s own count, private cabanas, complimentary Old Town shuttle, bicycle rentals through the concierge, dogs welcome up to fifty pounds, two per room

• Attractions: Duval Street via the hotel shuttle, Key West Historic Seaport, Smathers Beach, Key West International Airport

The Pool Is the Property

Book here and the pool is what you are booking. It runs long rather than deep, ringed with chaises and private cabanas, and it stays busy from late morning until the light goes. Mojitos Pool Bar opens at mid-morning and closes near midnight, which tells you most of what you need to know about the rhythm of the place. Take a cabana if you intend to stay put for the day; take a room set back from the deck if you intend to nap. Both are reasonable choices here, and they are not the same holiday.

Floridita, Mojitos and Flama Cabana

The food operation is split three ways and it works better than a single restaurant would. Floridita, the Cuban food truck, handles the long day from breakfast through to late, which is the right format for a pool property. Mojitos Pool Bar covers drinks and light plates without anyone leaving their lounger. Flama Cabana opens in the evening, Wednesday through Sunday, with tapas and rum cocktails and a different register altogether, dimmer and slower. Old Town restaurants are a shuttle ride away when you want a proper table.

Before You Book

This is not a walk-to-Duval address and pretending otherwise leads to disappointment. The shuttle solves it, but check the running hours if you plan late evenings. Dogs are welcome within a weight limit and a two-per-room cap, worth confirming when you reserve. Bicycles rent through the concierge and are the pleasant way to reach the seaport. And if quiet is the priority, ask for a room away from the pool deck: the music is part of the concept, not an accident.