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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 Key West Resort & Marina

Havana Cabana at Key West is a Cuban-inspired, family-friendly resort on North Roosevelt Boulevard with Key West’s largest pool and poolside Cuban dining. Hilton Key West Resort & Marina is a full-service Hilton property with a marina and multiple outdoor pools — read this if you’re choosing between a lively, mid-sized Cuban-flavored resort and a larger, brand-name marina resort.

Updated · about 3.6 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 · Family-friendly

Best for pool-focused stays, Cuban-flavored food and drinks, and easy access to Smathers Beach and a shuttle to Old Town.

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Hilton Key West Resort & Marina, Key West, Florida

Hilton Key West Resort & Marina

Marina setting · 6 outdoor pools · Full-service Hilton

Best for travelers who want a recognizable full-service brand, on-site marina and more pool options and meeting space.

Quick Verdict: Havana Cabana at Key West vs Hilton Key West Resort & Marina

When Havana Cabana at Key West wins: Choose Havana Cabana if you want a smaller, personality-driven property with the largest pool in Key West, Cuban-themed bars and restaurants, free parking, pet-friendly rooms, and a complimentary shuttle to downtown.

When Hilton Key West Resort & Marina wins: Choose the Hilton for larger property scale, a marina on site, multiple outdoor pools, more suite and accessible-room options, and the amenities and services associated with a major hotel brand.

Bottom line: Pick Havana Cabana for a lively, Cuban-style, pool-and-bar focused stay close to Smathers Beach and family groups; pick the Hilton for a more conventional full-service resort experience with marina access and more pool variety.

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Havana Cabana at Key West vs Hilton Key West Resort & Marina – At a Glance

Side-by-side facts for Havana Cabana at Key West and Hilton Key West Resort & Marina
CategoryHavana Cabana at Key WestHilton Key West Resort & Marina
Overall vibeCasual, Cuban-inspired, colorful midscale resortFull-service Hilton with marina and conventional resort facilities
LocationNorth Roosevelt Blvd, New Town; about 1.1 miles from Key West Intl. Airport and ~2.9 miles from Duval StreetStock Island area; near Stock Island Yacht Club & Marina and several Key West attractions (Hilton is ~3.6 mi from Southernmost Point per supplier highlights)
Size (rooms)106 rooms175 guestrooms
Audience / age policyAll ages welcome; primary guest must be 21+ to check in
PoolsHome to Key West’s largest pool; heated, open 10 AM–11 PMSix outdoor pools, pool umbrellas and poolside bar service
Restaurants & barsFloridita Food Truck (Cuban fare), Mojitos Pool Bar, Flama Cabana waterfront loungeRestaurant and poolside bar; coffee shop/cafe listed but supplier does not publish signature restaurant name
Spa / wellnessNo on-site spa; complimentary transport to off-site fitness facilityNot published
Signature featureCuban theme, largest pool in Key West, poolside mojitosOn-site marina and six outdoor pools; brand-name full-service hotel
Pet policyPet-friendly (dogs up to 50 lbs; max two per room; pet fee applies)Pet fee applies (supplier listing mentions a pet fee will be charged; service animals exempt)
Parking & transportFree self-parking; complimentary shuttle to Downtown Key West and arranged airport pick-upSelf parking (surcharge); complimentary shuttle/concierge services noted

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 Cuban style vs. Stock Island marina

Havana Cabana at Key West – Location

Havana Cabana sits on North Roosevelt Boulevard in New Town, a short drive from Smathers Beach and a shuttle ride to Old Town.

  • About 1.1 miles from Key West International Airport (roughly a 5-minute drive).
  • Shuttle service to downtown, Mallory Square, and the harbor is complimentary (part of resort-fee inclusions).
  • Not within easy walking distance of Duval Street; car, shuttle, or taxi recommended.

Better if you want proximity to Smathers Beach, free parking, and a shuttle into Old Town.

Hilton Key West Resort & Marina – Location

Hilton Key West Resort & Marina occupies a Stock Island location next to a yacht club and marina, with water-access activities nearby.

  • Near Stock Island Yacht Club & Marina (0.4 mi) and Key West Golf Club (1.6 km).
  • Within a 15-minute drive of Duval Street and Smathers Beach per supplier highlights.
  • On-site marina and easy access to boat tours and water sports.

Better for travelers who want a marina setting and easy boating access while still being a short drive from Old Town.

Rooms: Size and choices

Havana Cabana at Key West – Rooms

Havana Cabana offers 106 Cuban-styled rooms and a handful of premium/balcony options with compact, colorful layouts.

  • Room types include Premium Room, Patio (Lola); Room, Poolside (Havana); Superior Studio, Multiple Beds; and several Premium Room options with balconies.
  • Standard Havana Rooms are roughly 275 sq ft and can sleep up to four guests.
  • No elevator on property — upper floors accessed by stairs; some wheelchair-accessible rooms are available but check limitations.

Good choice for couples and families who want themed rooms and several balcony options in a smaller property.

Hilton Key West Resort & Marina – Rooms

Hilton Key West Resort & Marina offers 175 guestrooms with a broad lineup of ocean-view, partial-ocean-view and accessible suites.

  • Room types include Room, 1 King Bed, Balcony, Ocean View; Room, 2 Queen Beds, Ocean View; multiple suite configurations and accessible rooms.
  • Rooms feature refrigerators, LCD TVs, Egyptian cotton sheets and private furnished balconies per supplier listing.
  • Many accessible-room options listed (roll-in showers, mobility/hearing-accessible rooms and bathtubs).

Better if you want a wider selection of ocean-view rooms, suites, and accessible-room choices at a larger property.

Dining & drinks: Cuban casual vs. Hilton’s cafe and bar

Havana Cabana at Key West – Dining & drinks

Havana Cabana focuses on Cuban-inspired casual dining across a food truck, lively pool bar and a waterfront lounge.

  • Floridita Food Truck serves breakfast through dinner (8:00 AM–10:00 PM) with Cuban staples and casual fare.
  • Mojitos Pool Bar offers over 15 mojitos and operates daily 10:00 AM–11:00 PM with poolside service.
  • Flama Cabana is a waterfront lounge serving tapas, rum-focused cocktails, live music and a humidor (Tue–Sun evenings).

Choose Havana Cabana for Cuban-focused, casual all-day dining and lively poolside drinks.

Hilton Key West Resort & Marina – Dining & drinks

Hilton lists a restaurant, a poolside bar and a coffee shop/cafe on-site; supplier listing does not publish a signature restaurant name.

  • Dining includes at least one restaurant, one poolside bar and one coffee shop/cafe per supplier listing.
  • Cooked-to-order breakfast is available for a surcharge (approx. USD 5–32).
  • Room service is available during limited hours and there’s a 24-hour front desk/concierge to assist with dining options.

Better if you want standard full-service hotel dining options and 24-hour front-desk support for reservations.

Pools & waterfront: Largest single pool vs. multiple pools and marina

Havana Cabana at Key West – Pools & waterfront

Havana Cabana is built around Key West’s largest single pool, with heated water, loungers and poolside service.

  • Largest pool in Key West; heated and open 10 AM–11 PM.
  • Poolside extras include chaise lounges with service, specialty pool drinks and a heated hot tub nearby.
  • Day passes are available for non-guests.

Pick Havana Cabana if a single large, feature-rich pool and lively pool bar are your priority.

Hilton Key West Resort & Marina – Pools & waterfront

Hilton Key West Resort & Marina offers six outdoor pools plus a marina and a range of water activities on site.

  • Six outdoor pools with pool umbrellas and poolside bar service.
  • Marina on site with on-property boat tours, motor boating, kayaking and fishing available nearby.
  • Water-sport options and rental services (bicycles, scooters, mopeds) are offered on site.

Pick the Hilton if you prefer more pool variety and direct marina access for boating and water activities.

Wellness & nightlife: fitness access and evening options

Havana Cabana at Key West – Wellness & nightlife

Havana Cabana does not operate an on-site gym but supplies complimentary transport to a local fitness facility and offers an evening lounge scene.

  • No on-site fitness center; free shuttle to a nearby fitness facility is provided.
  • Live music and a cigar humidor at Flama Cabana for evening entertainment (Tue–Sun).
  • Concierge can help arrange local tours, sunset sails and snorkel trips.

Good for travelers who prioritize poolside nightlife and are comfortable using an off-site gym.

Hilton Key West Resort & Marina – Wellness & nightlife

Hilton lists a 24-hour fitness facility and multilingual concierge services for local activities and tours.

  • 24-hour fitness facilities on site per supplier listing.
  • Concierge and tours/ticket assistance available; multilingual staff and 24-hour front desk.
  • Evening options include bar/lounge and poolside bar activity; specific evening entertainment varies and is not published in supplier listing.

Better if you want on-site 24-hour gym access and full-service concierge support for activities and dining.

Who Wins? Best Pick by Travel Style

Best for a big pool party
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 — Key West’s largest pool with a lively Mojitos Pool Bar and poolside service.

Best for marina access and boating
Hilton Key West Resort & Marina, Key West, Florida

Hilton Key West Resort & Marina

Hilton Key West Resort & Marina — on-site marina and a range of water-based activities.

Best for Cuban food and evening rum 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 provide continuous Cuban-themed dining and drinks.

Best for more room types and accessible options
Hilton Key West Resort & Marina, Key West, Florida

Hilton Key West Resort & Marina

Hilton Key West Resort & Marina — larger room roster with many ocean-view suites and accessible-room configurations.

Frequently asked questions

Havana Cabana at Key West vs Hilton Key West Resort & Marina: FAQs

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Which is better located for Old Town and Duval Street?

Both require a short drive: Havana Cabana is farther from Duval Street (about 2.9 miles) but offers a complimentary shuttle to downtown; the Hilton is a short drive as well and sits on Stock Island near marina activities.

Which hotel has the better pool scene?

Havana Cabana centers on the largest single pool in Key West with a dedicated pool bar and a party vibe; the Hilton offers more pool options across six outdoor pools and quieter pool variety.

Are either property adults-only?

No. Neither Havana Cabana nor Hilton Key West Resort & Marina are adults-only; both welcome families and guests of all ages, though the primary guest must be at least 21 to check in.

Can I bring my dog?

Havana Cabana welcomes dogs up to 50 lbs (max two per room) with a pet fee; Hilton’s supplier listing notes a pet fee is charged and service animals are exempt — check the Hilton for current size and fee limits.

More Havana Cabana at Key West Comparison Guides

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