If you’ve ever driven into Key West, you know that moment when the overseas highway finally ends and you’re forced to make a choice. You either veer left toward the chaotic, cruise-ship-clogged streets of Duval, or you stay right on North Roosevelt. Most tourists make a beeline for the historical center. They want the gingerbread houses. They want the ghost tours. But honestly, staying at Havana Cabana Key West North Roosevelt Boulevard Key West FL offers a completely different vibe that most people overlook until they’re actually standing poolside with a mojito in hand.
It's a waterfront hotel, but not in the "sand between your toes" kind of way. It’s located on the Gulf side of the island, perched right on the edge of the salt ponds and the bay. This isn't the beach. It’s the Atlantic-meets-Gulf periphery where the mangroves grow thick.
The property used to be an Inn at Key West, but after a massive renovation a few years back, it leaned hard into the Cuban heritage of the island. It’s loud. It’s colorful. There are vintage cars parked out front that look like they crawled straight out of a 1950s postcard from Malecón. You’ll see a 1957 Chevy Bel Air or a bright pink Ford Fairlane sitting under the palms. It’s a mood.
The Reality of Staying on North Roosevelt Boulevard
Let’s get the geography straight because people get confused. Key West is tiny, but it’s not that tiny. If you stay at Havana Cabana Key West North Roosevelt Boulevard Key West FL, you are about three miles away from the Southernmost Point. You aren't walking to Duval Street. Don't even try it unless you want to spend forty minutes sweating through your shirt on a narrow sidewalk next to traffic.
But here is the thing: that distance is actually a feature, not a bug.
The "Old Town" area is loud. It smells like stale beer and exhaust. By staying on North Roosevelt, you get a buffer. The hotel runs a shuttle—a big, bright bus—that drops you off right near the action and picks you up every hour. It’s basically a free Uber that lets you drink all the Hemingway Daiquiris you want without worrying about parking a rental car, which, by the way, costs a fortune in the city center.
Parking at Havana Cabana is actually included or significantly cheaper than the garages downtown. That matters.
That Pool is the Center of the Universe
Usually, hotel pools are an afterthought. A concrete rectangle with some lukewarm water. Not here. The pool at Havana Cabana is arguably the largest on the island. It’s a massive, lagoon-style setup surrounded by lush greenery that makes you forget you’re essentially across the street from a shopping center with a Publix and a Staples.
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It’s the social hub.
You’ve got the Mojito Bar right there. They claim to have over 25 different versions of the drink. Honestly? Some are better than others. The classic is unbeatable, but the watermelon one hits different when the humidity is at 90%. They play Latin music—Salsa, Reggaeton, Son Cubano—pretty much all day. It’s vibrant. If you’re looking for a silent, meditative retreat where you can hear a pin drop, this isn't your spot. Go find a B&B on a side street for that. This is where people come to feel like they’re actually in the Caribbean.
The "Cabana" part of the name isn't just marketing fluff. There are actual cabanas you can rent, and they’re tucked into the foliage. It feels private even though you’re thirty feet away from a hundred other people.
What the Rooms are Actually Like
Rooms in Key West are notoriously small. It’s an island; space is at a premium. The rooms at 3420 North Roosevelt Blvd are surprisingly decent in size, mostly because the building was originally constructed when they weren't trying to cram humans into shoe boxes.
The decor is "Tropical Chic." Think dark woods, floral prints that don't look like your grandma’s curtains, and plenty of art that nods to Havana.
- The View Factor: If you book a "Pool View," you’re going to hear the music. If you’re a light sleeper or you like to nap at 2:00 PM, ask for a room facing the exterior or the higher floors.
- The Amenities: They do the standard stuff well—high-speed Wi-Fi that actually works (rare in the Keys), decent coffee, and walk-in showers.
- The Vibe: It feels like a boutique hotel despite having over 100 rooms.
Eating at Floridita
You can’t talk about Havana Cabana Key West North Roosevelt Boulevard Key West FL without mentioning the food truck. Yes, a food truck. Instead of a stuffy, white-linen dining room, they have Floridita.
It’s a permanent fixture on the patio.
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They serve Cuban sandwiches that are actually authentic—pressed bread, pickles, mustard, the whole deal. The breakfast is where they really shine, though. You can get a Cuban coffee (a Cafecito or a Colada if you’re feeling brave and want to vibrate for the next six hours) and some guava pastries.
Is it the cheapest food on the island? No. But it’s convenient, and it tastes better than half the "tourist trap" spots on the main drag. For dinner, most guests end up wandering across the street or taking the shuttle, but for a quick bite between pool dips, the truck is solid.
Dealing With the "Resort Fee" Reality
Let’s be real for a second. Every hotel in Key West hits you with a resort fee. It’s annoying. At Havana Cabana, that fee covers the shuttle, the parking, the pool towels, and the "amenities."
Some people complain about it because they feel like they’re being nickeled and dimed. I get it. But when you factor in that a Lyft from North Roosevelt to Duval Street is $15 to $25 each way, the shuttle pays for itself in two trips. Plus, they have bicycles.
Key West is one of the most bike-friendly cities in America. Grab one of the hotel cruisers. Pedal down the Promenade, feel the salt air, and look at the houseboats. It’s the best way to see the "real" Key West without the stress of driving.
The Cultural Connection
The hotel leans into the history of the Cuban refugees and the connection between Key West and Havana, which are only 90 miles apart. There’s a lot of respect for that history here. You’ll see murals and photos that tell the story of the "Conch Republic."
It’s not just a theme; it’s the soul of the island.
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Many of the staff members have deep roots in the community. If you take a second to talk to the bartenders or the front desk folks, they’ll tell you where to find the best secret spots. They’ll point you toward Chico's Cantina for Mexican food (a local favorite nearby) or tell you which reef is currently best for snorkeling.
Practical Tips for Your Stay
If you’ve decided to book a stay at Havana Cabana Key West North Roosevelt Boulevard Key West FL, don't just wing it.
First, check the cruise ship schedule. Seriously. When three ships are in port, Duval Street is a nightmare. That’s the day you stay at the hotel pool. When the ships leave in the evening, that is when you take the shuttle downtown for dinner.
Second, utilize the concierge. They can book the Fury water adventures or the Yankee Freedom (the ferry to the Dry Tortugas) right from the lobby. The Dry Tortugas trip is expensive and takes a full day, but it’s a bucket-list item.
Third, don't expect a beach. I’ll say it again for the people in the back: Havana Cabana is on the water, but there is no swimmable beach on North Roosevelt. For that, you’ll need to head to Smathers Beach or Fort Zachary Taylor. Both are a quick bike ride or drive away.
Is It Right For You?
This place is for the traveler who wants the "Florida Keys" aesthetic without the "Old Town" price tag or noise. It’s for the family who needs a big pool to keep the kids busy. It’s for the couple who wants a cool, Instagrammable backdrop but also wants a reliable shuttle to the bars.
It’s not for the person who wants absolute silence or the person who wants to be able to stumble from a bar directly into their hotel room bed.
Actionable Next Steps
- Check the Shuttle Schedule Immediately: As soon as you check in, snap a photo of the shuttle times on your phone. It usually runs late into the evening, but you don't want to miss the last one and pay $30 for a taxi.
- Join the Loyalty Program: Even if you only stay once, Noble House Hotels (the parent company) often offers perks like late check-out or drink vouchers for members.
- Book the Dry Tortugas in Advance: If you're staying here to see the national park, book the ferry months ahead. It sells out faster than anything else on the island.
- Explore the "New Town" Side: Don't ignore the neighborhood. Some of the best, most affordable seafood is on this side of the island. Check out Roostica on Stock Island (just a bridge away) for incredible pizza and atmosphere.
- Use the Bikes Early: The bike fleet is popular. If you want to spend the day on two wheels, get to the rental desk by 9:00 AM before the good ones are taken.
The beauty of the Havana Cabana location is that it gives you a base of operations. You can go as hard as you want in the tourist zones, then retreat back to a place that feels like a tropical compound. It's a strategic choice for a Key West vacation that balances the party vibe with actual relaxation.