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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 DoubleTree Resort

Havana Cabana at Key West is a Cuban-inspired, all-ages 4-star resort on North Roosevelt Boulevard centered on Key West’s largest pool and poolside Cuban dining. DoubleTree Resort by Hilton Grand Key - Key West is a branded, full-service 4-star resort near Smathers Beach and the airport; read this if you want a comparison between a pool-and-culture boutique stay and a recognizable Hilton-style resort with meeting space.

Updated · about 1.2 miles (1.9 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 guests who want a lively pool scene, Cuban-flavored food and drink, and easy shuttle access to Old Town.

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DoubleTree Resort, Key West, Florida

DoubleTree Resort

Branded full-service · conference center · near Smathers Beach

Best for travelers who want a full-service Hilton experience with meeting space, an airport shuttle, and straightforward access to Smathers Beach.

Quick Verdict: Havana Cabana at Key West vs DoubleTree Resort

When Havana Cabana at Key West wins: choose Havana Cabana if you care most about a big, heated resort pool with active poolside bars, Cuban-themed dining and evening live-music vibes — it’s the better pick for pool-focused stays, informal events, and guests seeking a distinct Cuban atmosphere.

When DoubleTree Resort wins: pick DoubleTree if you need larger meeting and event facilities, a branded full-service experience (Hilton-family benefits), complimentary airport shuttle service, and on-property business amenities — it’s stronger for conferences, larger groups, and travelers prioritizing beach shuttle access.

Bottom line: Havana Cabana is the choice for a compact, characterful, pool-centric Key West stay; DoubleTree is the practical, full-service resort option if you want meeting space, standard Hilton-style services, and easy airport/beach connections.

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Havana Cabana at Key West vs DoubleTree Resort – At a Glance

Side-by-side facts for Havana Cabana at Key West and DoubleTree Resort
CategoryHavana Cabana at Key WestDoubleTree Resort
Overall vibeCuban-themed, playful, pool-forwardBranded resort, business- and family-friendly
LocationNorth Roosevelt Blvd, New Town; shuttle to Downtown/Old TownSouth Roosevelt Blvd / Grand Key area; near Smathers Beach and close to the airport
Size (guest rooms)106 rooms216 guestrooms
Audience / age policyAll ages welcome (primary guest must be 21+ to check in)All ages welcome (not adults-only)
PoolsHome to the largest pool in Key West; heated; poolside bar and food serviceOne outdoor pool, poolside bar and pool cabanas (surcharge)
Restaurants & barsFloridita Food Truck (Cuban), Mojitos Pool Bar, Flama Cabana waterfront loungePalm Haven restaurant (American cuisine), 1 bar/lounge, 1 poolside bar
Spa & fitnessNo on-site spa; complimentary transport to an off-site fitness facility (no on-site gym)24-hour fitness center on site; spa: Not published
Business & eventsTiki Hut waterfront venue, Tiki Hut & meeting spaces (~1,820 sq ft total); small-group and wedding focusConference center with ~7,000 sq ft (meeting rooms, ballroom) for larger meetings and events
Airport accessAbout 1.1 miles from Key West International Airport; airport pick-up can be arranged
Parking & transportFree self-parking, complimentary shuttle to downtownSelf parking (surcharge), complimentary airport shuttle and free beach shuttle

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
See all photos →

Location: New Town Cuban character vs Grand Key full-service

Havana Cabana at Key West – Location

Havana Cabana sits on North Roosevelt Boulevard in New Town, a short drive from Old Town.

  • About 1.1 miles (roughly a five-minute drive) from Key West International Airport.
  • Complimentary shuttle to Downtown Key West, Mallory Square and the harbor.
  • Near Searstown shopping and a short drive to Duval Street (about 2.9 miles).

Choose Havana Cabana for a New Town base with regular shuttle service into Old Town and a quieter street-side location.

DoubleTree Resort – Location

DoubleTree Resort is on South Roosevelt Boulevard/Grand Key, close to Smathers Beach and the airport.

  • By the ocean and a quick drive to Smathers Beach (about 4-minute drive to the beach).
  • Complimentary roundtrip airport shuttle available on request and free beach shuttle.
  • Easier walk/drive access to beachside recreation and some local marinas.

Choose DoubleTree when proximity to Smathers Beach and airport shuttle convenience matter most.

Rooms: boutique Cuban rooms vs larger branded rooms

Havana Cabana at Key West – Rooms

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

  • Room types include Premium Rooms (Lola, Luis), Havana Rooms, and Superior Studios; many options for families (some rooms sleep up to 4).
  • Complimentary Wi‑Fi, in-room coffeemakers and safes included via resort fee benefits.
  • No elevator — upper floors reached by stairs; property emphasizes compact, characterful rooms.

Havana Cabana’s rooms emphasize local style and are sized for families and groups; check accessibility needs because there’s no elevator.

DoubleTree Resort – Rooms

DoubleTree has 216 guestrooms with standard Hilton-style amenities and premium bedding.

  • Rooms include refrigerators and LED televisions; down comforters and premium bedding are noted.
  • Complimentary wired and wireless internet access throughout the property.
  • Large property scale with more rooms and standard full-service hotel facilities.

DoubleTree is the more conventional, larger-property option if you want standard branded room amenities and more room inventory.

Dining & drinks: Cuban-focused casual options vs single American restaurant

Havana Cabana at Key West – Dining & drinks

Havana Cabana centers its food and drink around Cuban flavors in casual formats.

  • Floridita Food Truck serves Cuban breakfast, lunch and dinner (walk-up service).
  • Mojitos Pool Bar offers 15+ mojitos and poolside service daily; Flama Cabana is a waterfront lounge with tapas and live music.
  • Non-hotel guests are welcome at the food and drink venues; evening live music and a cigar humidor at Flama Cabana.

Pick Havana Cabana for a casual, Cuban-flavored dining and nightlife experience concentrated around the pool and waterfront lounge.

DoubleTree Resort – Dining & drinks

DoubleTree’s on-site dining is centered on Palm Haven with pool and bar service.

  • Palm Haven offers American cuisine with pool views and alfresco dining; buffet breakfast is available for a fee.
  • There is a bar/lounge and a poolside bar for drinks and casual service.
  • Room service is available during limited hours.

DoubleTree provides conventional, full-service dining suitable for families and business guests, with fewer on-site specialty culinary venues.

Pools & beach access: largest pool vs resort pool + beach shuttle

Havana Cabana at Key West – Pools & beach access

Havana Cabana promotes the largest pool in Key West with active poolside service.

  • Largest pool in Key West, heated, open daily 10:00 AM–11:00 PM with chaise lounges and poolside service.
  • Mojitos Pool Bar and poolside food options keep the pool area lively; day passes available to non-guests.
  • Poolside Tiki Hut event space for small weddings and gatherings.

If pool time is the priority, Havana Cabana’s pool scene is the main draw.

DoubleTree Resort – Pools & beach access

DoubleTree has an outdoor pool, poolside bar, and provides complimentary beach shuttle service to Smathers Beach.

  • One outdoor pool with pool cabanas available (surcharge) and poolside bar service.
  • Free beach shuttle simplifies getting to Smathers Beach without driving.
  • Pool hours and cabana availability may be subject to property schedules and extra fees.

DoubleTree balances pool and beach access; use the beach shuttle if you plan significant beach time.

Wellness, nightlife & events: fitness and meetings vs meeting-heavy full service

Havana Cabana at Key West – Wellness, nightlife & events

Havana Cabana focuses on poolside nightlife and small-to-medium events rather than on-site fitness or spa services.

  • Flama Cabana hosts evening live music and a small-bites menu; a cigar humidor is available.
  • Event spaces are geared to weddings and small meetings (Tiki Hut and ~1,820 sq ft of meeting space).
  • No on-site spa; complimentary transport to a nearby fitness facility is provided.

Choose Havana Cabana for social evenings, weddings, and small-group gatherings with Cuban flavor rather than big corporate meetings.

DoubleTree Resort – Wellness, nightlife & events

DoubleTree supports larger meetings and provides a 24-hour fitness center on site.

  • About 7,000 sq ft of conference/meeting space including a ballroom; suitable for larger events and business gatherings.
  • 24-hour fitness facilities are available on property for guests.
  • Concierge and full-service hotel offerings support event logistics and business travel needs.

DoubleTree is stronger for meetings, business travelers and guests who want on-property fitness options.

Who Wins? Best Pick by Travel Style

Best for pool-centered 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 heated pool in Key West with lively pool bars and poolside service.

Best for meetings and events
DoubleTree Resort, Key West, Florida

DoubleTree Resort

DoubleTree — roughly 7,000 sq ft of conference space, ballroom and meeting rooms for larger groups.

Best for Cuban-themed dining and nightlife
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 with live music and cigars.

Best for airport/ beach logistics
DoubleTree Resort, Key West, Florida

DoubleTree Resort

DoubleTree — complimentary roundtrip airport shuttle on request and a free beach shuttle to Smathers Beach.

Frequently asked questions

Havana Cabana at Key West vs DoubleTree Resort: FAQs

See all FAQs →
Which hotel is better if I want to spend most of my time at the pool?

Havana Cabana — it advertises the largest pool in Key West, heated with active poolside service and a dedicated pool bar.

Which property is better for a business meeting or conference?

DoubleTree — it offers about 7,000 sq ft of conference/meeting space including a ballroom and dedicated business-center services.

Are either of these hotels adults-only?

No. Both properties welcome guests of all ages; the primary guest must be at least 21 years old to check in at Havana Cabana.

Which hotel is closer to Smathers Beach?

DoubleTree is nearer to Smathers Beach and offers a free beach shuttle; Havana Cabana is a short drive away and provides shuttle service to downtown and can arrange beach access.

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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