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Havana Cabana at Key West Key West, Florida
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Hotel comparison guide

Havana Cabana at Key West vs Hilton Garden Inn Key West / The Keys Collection

Havana Cabana at Key West is a Cuban-inspired, family-friendly resort on North Roosevelt Boulevard known for the largest pool in Key West and poolside Cuban food and drinks. Hilton Garden Inn Key West / The Keys Collection is a New Town Hilton-branded hotel with standard Hilton services and a larger room count — read this if you’re choosing between a lively, themed pool resort and a familiar midscale brand in New Town.

Updated · about 0.8 km apart

Resort pool surrounded by palm trees and lounge chairs at Havana Cabana at Key West

Havana Cabana at Key West

Cuban-inspired · Largest pool in Key West · Free self-parking & shuttle

Best for pool-focused stays, Cuban-flavored dining, and guests who want a resort-style vibe near Smathers Beach.

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Hilton Garden Inn Key West / The Keys Collection, Key West, Florida

Hilton Garden Inn Key West / The Keys Collection

Hilton brand · 141 rooms · Free area shuttle & business facilities

Best for travelers who prefer a familiar Hilton property with on-site business amenities, a fitness option, and a straightforward New Town location.

Quick Verdict: Havana Cabana at Key West vs Hilton Garden Inn Key West / The Keys Collection

When Havana Cabana wins: choose Havana Cabana if you want a resort feel, the largest pool in Key West, poolside mojitos and Cuban food, or if you’re traveling with family or a group that will use the pool and on-site dining.

When Hilton Garden Inn wins: choose the Hilton Garden Inn / The Keys Collection if you want Hilton-brand predictability, more room types and accessible business/meeting facilities, or if proximity to the airport and a standard midscale hotel fit your plans.

Bottom line: Havana Cabana is the place for a themed, social pool-and-dining experience; Hilton Garden Inn is the pragmatic pick for travelers who value a known-brand stay, more room variety, and business-friendly amenities.

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Havana Cabana at Key West vs Hilton Garden Inn Key West / The Keys Collection – At a Glance

Side-by-side facts for Havana Cabana at Key West and Hilton Garden Inn Key West / The Keys Collection
CategoryHavana Cabana at Key WestHilton Garden Inn Key West / The Keys Collection
Overall vibeCuban-inspired, resort-style, social pool sceneHilton-branded, midscale hotel with business-friendly features
Location (Key West / neighborhood)North Roosevelt Blvd (New Town); shuttle to DowntownIn Key West (New Town); near Key West Tropical Forest & Botanical Garden
Size (rooms)106 rooms141 rooms
Ages / audienceAll-ages; family-friendly (primary guest must be 21+ to check in)
Pools & hot tubsLargest pool in Key West; heated; poolside bar and service; day passes soldOutdoor pool and hot tub; pool cabanas available (surcharge)
Restaurants & barsMojitos Pool Bar, Floridita Food Truck, Flama Cabana (waterfront lounge)Two on-site restaurants including The Garden Grille and a bar/lounge; continental breakfast available for a fee
Spa & fitnessNo on-site spa; no on-site gym — complimentary transport to off-site fitness facilityFitness facilities on site; no published on-site spa in supplier listing
Known forPool (largest in Key West), Cuban dining and cocktails, waterfront lounge eventsHilton brand reliability, meeting spaces, proximity to botanical garden and airport
Parking & transportFree self-parking; complimentary shuttle to downtown and to a fitness facilityUncovered/self parking (surcharge applies); complimentary area shuttle
Accessibility & family servicesWelcomes families, pet-friendly (dogs up to 50 lbs), wheelchair-accessible path and parking but no elevatorWheelchair accessible (may have limitations); accessible pool and business spaces; pet policy not published in supplier listing

A Look Inside Havana Cabana at Key West

Havana Cabana at Key West: rooms & suitesRooms & suitesHavana Cabana at Key West: pools & beachPools & beachHavana Cabana at Key West: diningDiningHavana Cabana at Key West: spa & wellnessSpa & wellness
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Location: New Town access vs. New Town convenience

Havana Cabana at Key West – Location

Havana Cabana sits on North Roosevelt Boulevard in New Town with a complimentary shuttle to Downtown Key West and Smathers Beach nearby.

  • Address: 3420 N. Roosevelt Blvd; about 1.1 miles from Key West International Airport (per hotel materials).
  • Complimentary shuttle service to Downtown Key West, Mallory Square and the harbor; not within easy walking distance of Duval Street.
  • Nearby: Regal Key West (walkable), botanical garden and beaches reachable by short drive.

Choose Havana Cabana if you want resort access to downtown without staying in Old Town.

Hilton Garden Inn Key West / The Keys Collection – Location

Hilton Garden Inn is also in New Town, close to Key West Tropical Forest & Botanical Garden and a short drive from beaches and Old Town.

  • Address: 3850 N Roosevelt Blvd; highlighted as in Key West (New Town).
  • About 2.7 km / 1.7 mi from Key West Intl. Airport (preferred airport listed).
  • Short drives to attractions: Smathers Beach, Key West Golf Club, and the botanical garden.

Choose the Hilton for a New Town location with easy airport access and nearby green spaces.

Rooms: playful Cuban design vs. Hilton-standard options

Havana Cabana at Key West – Rooms

Havana Cabana offers 106 Cuban-inspired rooms with hand-painted murals and a compact set of room types.

  • 106 rooms; standard Havana Room ~275 sq ft and can sleep up to 4 guests.
  • Room types include Premium Room (Patio), Room (Havana), Superior Studio, and Premium Balcony rooms.
  • Rooms include complimentary Wi‑Fi, in-room safe at front desk, and 24-hour front desk service.

Havana Cabana’s rooms emphasize themed design and a resort feel in a smaller-property footprint.

Hilton Garden Inn Key West / The Keys Collection – Rooms

Hilton Garden Inn has 141 individually decorated guestrooms with a broad list of room type names and configurations.

  • 141 guestrooms; supplier listing shows many room types (2 Queen Beds, King Bed, suites, and accessible rooms).
  • Microwaves, LCD TVs, laptop-compatible safes, and complimentary wired internet in rooms (per listing).
  • Options include pool-view, garden-view, balcony, and suite configurations listed by supplier.

The Hilton offers more room variety and predictable in-room amenities for business and leisure travelers.

Dining & drinks: Cuban-themed, pool-to-waterfront vs. hotel grille

Havana Cabana at Key West – Dining & drinks

Havana Cabana centers dining on Cuban flavors across a food truck, pool bar, and a waterfront lounge.

  • Floridita Food Truck: Cuban fare open 8:00 am–10:00 pm (walk-up, all-day menu).
  • Mojitos Pool Bar: over 15 mojito varieties; open 10:00 am–11:00 pm with poolside service.
  • Flama Cabana: waterfront Cuban cocktail lounge with tapas, live music and a humidor; open Tue–Sun evenings.

Pick Havana Cabana if Cuban food, pool cocktails and a lively waterfront lounge are priorities.

Hilton Garden Inn Key West / The Keys Collection – Dining & drinks

Hilton Garden Inn features mainstream American cuisine at on-site venues and a hotel bar/lounge.

  • Two on-site restaurants including The Garden Grille offering American cuisine.
  • Bar/lounge and poolside bar available; continental breakfasts available for a fee.
  • Concierge and lobby services support dining reservations and local recommendations.

The Hilton is a safe choice for familiar American dining and a standard hotel bar experience.

Pools & signature amenity: largest pool in Key West vs. standard hotel pool

Havana Cabana at Key West – Pools & signature amenity

Havana Cabana promotes the largest pool in Key West as its signature amenity with poolside service and events.

  • Largest pool in Key West; heated and open daily (pool hours published as 10 AM–11 PM).
  • Poolside Mojitos bar and chaise lounges with service; day passes available for non-guests.
  • Tiki Hut and waterfront event venues tie pool and waterfront activities into events and weddings.

If the pool is the centerpiece of your trip, Havana Cabana is tailored around that experience.

Hilton Garden Inn Key West / The Keys Collection – Pools & signature amenity

Hilton Garden Inn offers an outdoor pool and a hot tub along with poolside amenities and cabanas (surcharge).

  • One outdoor pool and one hot tub; pool cabanas may be available for a surcharge.
  • Pool is accessible and included among the hotel’s recreational amenities with loungers.
  • Hotel lists sailing, snorkeling, and other water activities nearby rather than a private beach.

The Hilton provides a conventional hotel pool setup rather than a resort-scale pool scene.

Wellness & nightlife: off-site fitness transport vs. on-site gym

Havana Cabana at Key West – Wellness & nightlife

Havana Cabana does not have an on-site gym or spa; guests get complimentary transport to a nearby fitness facility.

  • No on-site fitness center per the hotel's FAQ; complimentary shuttle to a partner fitness facility is provided.
  • No on-site spa published in hotel materials.
  • Nightlife centers on Flama Cabana’s live music and downtown Old Town (shuttle provided).

Expect to travel off-property for gym or spa services; on-site nightlife is themed and pool/waterfront-focused.

Hilton Garden Inn Key West / The Keys Collection – Wellness & nightlife

Hilton Garden Inn lists fitness facilities on site and provides business and meeting amenities.

  • Fitness facilities on site (wheelchair-accessible fitness center listed).
  • Business center, meeting rooms, and multilingual staff support work-focused stays.
  • Hotel lists nearby ecotours, sailing, and other outdoor activities rather than in-house nightlife.

The Hilton is better suited for travelers who want an on-site gym and business services.

Who Wins? Best Pick by Travel Style

Best for pool-focused vacations
Lobby entry with large floor-to-ceiling windows and vintage car outside at Havana Cabana at Key West

Havana Cabana at Key West

Havana Cabana: largest pool in Key West, poolside mojitos, and a social pool atmosphere.

Best for predictable brand comforts
Hilton Garden Inn Key West / The Keys Collection, Key West, Florida

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn: Hilton-standard rooms, on-site fitness, and business center/meeting spaces.

Best for Cuban food & cocktails
Guest reading in wicker chair in a sunny lounge at Havana Cabana at Key West

Havana Cabana at Key West

Havana Cabana: Floridita Food Truck, Mojitos Pool Bar and Flama Cabana waterfront lounge.

Best for airport convenience & nearby green space
Hilton Garden Inn Key West / The Keys Collection, Key West, Florida

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn: short drive to Key West Intl and close to the Key West Tropical Forest & Botanical Garden.

Frequently asked questions

Havana Cabana at Key West vs Hilton Garden Inn Key West / The Keys Collection: FAQs

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Which hotel is closer to Duval Street and Old Town?

Both are in New Town and require a short drive to Old Town; Havana Cabana offers a complimentary shuttle to Downtown, which can be convenient for visiting Duval Street.

Which property has a better pool experience?

Havana Cabana is built around a large, heated resort pool with a dedicated pool bar and poolside service; Hilton Garden Inn has a standard outdoor pool and hot tub.

Do either hotels include breakfast?

Breakfast is available for a surcharge at both properties; the Hilton lists continental breakfast for a fee, and Havana Cabana offers cooked-to-order breakfast for a fee.

Are these hotels family-friendly?

Yes. Both properties welcome families; the primary guest checking in must be at least 21 years old at each hotel.

More Havana Cabana at Key West Comparison Guides

Explore how Havana Cabana at Key West stacks up against other hotels nearby:

Sun loungers around circular pool under palm trees at Havana Cabana at Key West
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