
Havana Cabana at Key West
Best for travelers who want a lively, family-friendly pool scene with Cuban food and drinks and a complimentary shuttle to Downtown Key West.
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Havana Cabana at Key West is a Cuban‑inspired, family-friendly resort on North Roosevelt Boulevard known for Key West’s largest pool and shuttle to Old Town. The Gates Hotel Key West is a modern lifestyle hotel at the entrance to Key West (New Town) aimed at travelers who prioritize a contemporary pool scene, value, and shuttle access over Old Town walkability.
Updated · about 0.3 miles apart

Best for travelers who want a lively, family-friendly pool scene with Cuban food and drinks and a complimentary shuttle to Downtown Key West.

Best for travelers who want a contemporary, value-oriented hotel in New Town with a convenient location near the airport and a smaller outdoor pool and shuttle options.
When Havana Cabana at Key West wins: Choose Havana Cabana if a large heated pool, daily poolside cocktails and Cuban-themed dining are central to your trip, or if you want a complimentary shuttle to Old Town and free self-parking.
When The Gates Hotel Key West wins: Choose The Gates if you prefer a more modern, lifestyle hotel at the New Town/airport entrance with straightforward amenities, a recently renovated property, and on-site business services.
Bottom line: Both hotels sit in New Town and serve as practical bases for exploring Key West, but Havana Cabana leans heavily on a distinctive Cuban theme and a large resort pool (better for social pool time and families), while The Gates is a cleaner, modern alternative for travelers who prioritize a contemporary hotel experience and proximity to the airport.
| Category | Havana Cabana at Key West | The Gates Hotel Key West |
|---|---|---|
| Overall vibe | Cuban‑themed, lively resort atmosphere focused on poolside activity and social dining | Modern lifestyle hotel with a clean, contemporary feel |
| Location (neighborhood) | North Roosevelt Blvd (New Town), not within walkable distance to Duval Street | |
| Size (rooms) | 106 rooms | 100 rooms |
| Ages / policy | All ages welcome; primary guest must be 21+ to check in | All ages welcome; primary guest minimum age 21 |
| Pools | Largest pool in Key West (heated), poolside bar, day passes available | Outdoor pool with poolside bar and cabanas (surcharge); pool access hours published |
| Restaurants & bars | Floridita Food Truck (Cuban), Mojitos Pool Bar, Flama Cabana lounge | 2 restaurants and a coffee shop/cafe; a bar/lounge and poolside bar |
| Spa & wellness | No on-site spa; complimentary transport to an off-site fitness facility | No on-site spa (health/beauty spa listed as nearby) |
| Accessibility & parking | Free self-parking including accessible spaces and EV charging; no elevator | Self parking (surcharge), uncovered parking, EV charging station, wheelchair-accessible features |
| Shuttle / transfers | Complimentary shuttle to Downtown Key West and airport pick-up available on request | Area shuttle available (surcharge) that operates within 4 miles |
| Known for | Largest pool in Key West and Cuban-inspired food/drinks | New Town/entrance location and newly renovated modern rooms |
Havana Cabana sits on North Roosevelt Boulevard in New Town, a short drive from Old Town and the airport.
Good pick if you want easy airport access plus a shuttle into Old Town without staying inside the Old Town walkable core.
The Gates sits at the entrance to Key West in New Town, close to the airport and local New Town attractions.
Convenient for arrivals and departures and for travelers who want a modern hotel base outside Old Town.
Havana Cabana’s rooms are Cuban‑inspired with murals and a variety of room types for families and groups.
Room mix and themed design cater to families, groups, and travelers who want character and flexible bedding.
The Gates offers modern, newly renovated room options such as Double Room and ADA King.
Choose The Gates for straightforward, contemporary rooms and accessible room options.
Havana Cabana focuses on Cuban‑inspired dining and a lively pool bar program.
Stronger choice if you want a Cuban food-and-drink focus and poolside cocktail culture without leaving the hotel.
The Gates has a small selection of on‑site dining options and a pool bar for casual meals and drinks.
Good if you want basic on‑site dining and café options in a modern setting; for more variety you’ll head into Old Town.
Havana Cabana is built around its large heated resort pool and poolside programming.
Pick Havana Cabana when the pool is the main focus of your stay.
The Gates offers an outdoor pool and poolside bar with cabana options (usually for a surcharge).
The Gates suits travelers who want a quieter pool experience with modern surroundings rather than a resort pool scene.
Havana Cabana does not operate an on‑site fitness center but provides transport to a nearby gym; nightlife centers on on‑site bars and shuttle trips to Old Town.
Good for guests who want on‑site evening socializing and don’t need a hotel gym on site.
The Gates lists fitness and business amenities via on‑site facilities or nearby services, and some evening entertainment is available.
Choose The Gates if you prefer a modern hotel with basic wellness options and on‑site evening lounge space.

Havana Cabana — Key West’s largest heated pool with an active pool bar and poolside programming.

The Gates — newly renovated, contemporary rooms and a straightforward lifestyle-hotel experience.

Havana Cabana — on-site Floridita Food Truck, Mojitos Pool Bar, and Flama Cabana lounge focused on Cuban flavors.

The Gates — positioned at the island entrance near Key West International Airport for fast arrivals and departures.
Both are in New Town and require a drive to Duval Street; Havana Cabana offers a complimentary shuttle to Downtown Key West while The Gates' shuttle typically runs for a surcharge.
Havana Cabana has the larger, heated resort pool and promotes it as the largest pool in Key West; The Gates has a smaller outdoor pool.
Yes. Both properties welcome guests of all ages; the primary guest checking in must be at least 21.
Havana Cabana does not have an on-site spa; The Gates lists a health/beauty spa as nearby rather than on-site.
Explore how Havana Cabana at Key West stacks up against other hotels nearby:
vs. sites like Expedia, Hotels.com and other OTAs ·