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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 The Perry Hotel & Marina Key West

Havana Cabana at Key West is a Cuban-inspired, family-friendly resort on North Roosevelt Boulevard with Key West’s largest pool and lively poolside bars; read this if you want a social, budget-conscious stay near Smathers Beach and a shuttle to Old Town. The Perry Hotel & Marina Key West is a marina-focused boutique resort on Stock Island with waterfront dining and on-site marina services; read this if you’re after a boat-friendly stay outside Old Town with a quieter, marina lifestyle.

Updated · about 3.5 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-centric stays and families who want a lively, Cuban-flavored scene with free shuttle access to Old Town.

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The Perry Hotel & Marina Key West, Key West, Florida

The Perry Hotel & Marina Key West

Marina-focused · Boutique resort · Waterfront dining

Best for travelers who want a quieter, marina-side boutique stay with dock access and on-site seafood dining.

Quick Verdict: Havana Cabana at Key West vs The Perry Hotel & Marina Key West

When Havana Cabana at Key West wins: choose Havana Cabana if you prioritize a big resort pool, poolside bars and nightly lounge vibes, easy shuttle access to Duval Street, free self-parking, and a property designed for families and groups.

When The Perry Hotel & Marina Key West wins: choose The Perry if you want a refined marina setting, on-site marina and boating activities, two outdoor pools with fitness and rental options nearby, and a quieter base outside Old Town with on-site seafood dining.

Bottom line: pick Havana Cabana for a social, Cuban-themed, family-friendly stay focused on pool time and convenience to Smathers Beach; pick The Perry for a marina-oriented, boutique experience with stronger boating and waterfront-dining options farther from Duval Street.

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Havana Cabana at Key West vs The Perry Hotel & Marina Key West – At a Glance

Side-by-side facts for Havana Cabana at Key West and The Perry Hotel & Marina Key West
CategoryHavana Cabana at Key WestThe Perry Hotel & Marina Key West
Overall vibeLively, Cuban-themed resort with a focus on poolside fun and eventsMarina-focused boutique resort with a relaxed waterfront atmosphere
LocationNorth Roosevelt Blvd (New Town), about 2.9 miles / 11-minute drive to Duval StreetStock Island waterfront, outside Old Town with marina access
Size (rooms)106 rooms100 guestrooms (supplier listing)
Who can stayAll ages welcomed (primary guest must be 21+ to check in)
PoolsKey West’s largest single pool; heated; open 10 AM–11 PMTwo outdoor pools; pool hours published (access 8 AM–10 PM noted for the property)
Restaurants & barsFloridita Food Truck (Cuban), Mojitos Pool Bar, Flama Cabana loungeTwo restaurants including Matt’s Stock Island (seafood); 2 bars and 2 poolside bars
Spa & wellnessNo on-site spa; complimentary shuttle to off-site fitness facilityNot published
Known forCuban-inspired design, largest pool in Key West, active poolside nightlifeMarina on site, docking/boat services, waterfront seafood restaurant
Parking & transportFree self-parking, complimentary shuttle to Downtown Key West and airport pickup by requestSelf parking (surcharge), close to Key West Intl. Airport
Pet policyPet-friendly (dogs up to 50 lbs, up to 2 per room) with feePet fee noted in supplier listing (pet fee policies published)

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 pool hub vs Stock Island marina

Havana Cabana at Key West – Location

Havana Cabana sits on North Roosevelt Boulevard in New Town, closer to Smathers Beach and about a 10–15 minute drive to Old Town.

  • Address: 3420 N. Roosevelt Blvd, Key West, FL 33040
  • About 2.9 miles / an 11-minute drive to Duval Street; complimentary shuttle to downtown stops
  • Near Smathers Beach (roughly 0.8 miles) and Searstown shopping

Better if you want beach access, easy parking, and shuttle access to Old Town.

The Perry Hotel & Marina Key West – Location

The Perry sits on Stock Island with direct marina access and a quieter, waterfront setting outside Old Town.

  • Address: 7001 Shrimp Road, Key West, FL 33040
  • On-site marina and boat services; near Robbie’s and local waterfront attractions
  • About a short drive from Old Town attractions; not within Old Town walking distance

Better if you’re arriving by boat or want a quieter, waterfront base with marina services.

Rooms: Cuban style and practical layouts vs boutique marina rooms

Havana Cabana at Key West – Rooms

Rooms at Havana Cabana are Cuban-inspired, with hand-painted murals and family-friendly layouts.

  • 106 rooms across 8 room types (examples: Premium Room (Lola), Room, Poolside (Havana))
  • Options include King, Queen, sofa-bed and family-size setups; standard Havana Room ~275 sq ft
  • Complimentary Wi‑Fi, in-room coffee, safe, and resort-fee inclusions

Choose Havana Cabana for themed rooms and family-friendly configurations near the pool.

The Perry Hotel & Marina Key West – Rooms

The Perry’s guestrooms lean toward boutique styling with many room-type names tied to the property’s Perry/Mangrove/Stock Island room categories.

  • 100 guestrooms with a wide set of named room types (e.g., Room, 1 King Bed (Perry); Mangrove King; Studio Suite, 1 King Bed, Poolside (Lanai))
  • Rooms offer private furnished balconies or patios per supplier listing and premium bedding
  • Complimentary Wi‑Fi and designer toiletries in private bathrooms

Choose The Perry for varied boutique room types and more balcony/patio options near the marina.

Dining & drinks: Cuban casual and pool bars vs marina seafood and multiple bars

Havana Cabana at Key West – Dining & drinks

Havana Cabana focuses on Cuban flavors across casual, poolside, and waterfront lounge venues.

  • Floridita Food Truck: all-day Cuban food (8:00 AM–10:00 PM), walk-up service
  • Mojitos Pool Bar: more than 15 mojito varieties; open 10:00 AM–11:00 PM with poolside service
  • Flama Cabana: Cuban cocktail lounge with tapas, live music, sunset views (Tue–Sun, 5 PM–midnight)

Best for guests seeking Cuban food, a lively pool bar scene, and evening lounge music.

The Perry Hotel & Marina Key West – Dining & drinks

The Perry pairs marina views with seafood-forward dining and multiple bar options on site.

  • Number of restaurants: 2 — includes Matt’s Stock Island (seafood) listed in supplier highlights
  • Two bars/lounges and two poolside bars for daytime and evening drinks
  • Cooked-to-order breakfast available for a surcharge (hours noted 8:00 AM–11:30 AM)

Best for guests who want waterfront seafood dining and several on-site bar options.

Pools & signature amenity: biggest single pool vs marina and dual pools

Havana Cabana at Key West – Pools & signature amenity

Havana Cabana is built around its large courtyard and what the property calls Key West’s largest pool.

  • Largest pool in Key West; heated and open 10 AM–11 PM
  • Poolside loungers and dedicated Mojitos Pool Bar with service starting at 11 AM
  • Day passes are offered to non-guests for pool access

Pick Havana Cabana if a large, active pool is the primary draw for your stay.

The Perry Hotel & Marina Key West – Pools & signature amenity

The Perry emphasizes its marina and offers two outdoor pools alongside marina amenities.

  • Two outdoor pools noted in supplier listing
  • Marina on site with dock and boating activities; boat tours and fish cleaning table available
  • 24-hour fitness facilities and bicycle rentals complement pool offerings

Pick The Perry if you want pool time plus direct marina access and boating services.

Wellness & nightlife: poolside music and shuttle access vs fitness and quieter evenings

Havana Cabana at Key West – Wellness & nightlife

Havana Cabana’s wellness offering centers on poolside activity rather than a spa.

  • No on-site spa; hotel provides complimentary transport to an off-site fitness facility
  • Lively evening options at Flama Cabana with live music and sunset views
  • Pool events and late-night bar service keep the property social after dark

Good for travelers who want activity-focused wellness (pool, shuttle to gym) and on-site nightlife.

The Perry Hotel & Marina Key West – Wellness & nightlife

The Perry combines fitness, pools, and a calmer waterfront evening scene.

  • 24-hour fitness facilities on site and fitness classes available
  • Two poolside bars and evening dining at on-site restaurants
  • Fewer late-night party options than Old Town; more low-key waterfront dining

Better for guests who want a hotel gym and quieter waterfront evenings rather than loud pool parties.

Who Wins? Best Pick by Travel Style

Best for families and groups
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 — family-friendly room setups, largest pool in Key West, and shuttle service to Old Town.

Best for boaters and marina access
The Perry Hotel & Marina Key West, Key West, Florida

The Perry Hotel & Marina Key West

The Perry — on-site marina, dock services, and boating activities make arrivals by sea and boating days easy.

Best for pool parties and daytime social scene
Guest reading in wicker chair in a sunny lounge at Havana Cabana at Key West

Havana Cabana at Key West

Havana Cabana — Mojitos Pool Bar, large heated pool, and poolside service create a lively daytime environment.

Best for a quieter, upscale waterfront stay
The Perry Hotel & Marina Key West, Key West, Florida

The Perry Hotel & Marina Key West

The Perry — boutique marina setting, waterfront restaurants, and dual pools for a more relaxed stay outside Old Town.

Frequently asked questions

Havana Cabana at Key West vs The Perry Hotel & Marina Key West: FAQs

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Which hotel is closer to Duval Street and Old Town?

Havana Cabana is closer to Old Town by road (about 2.9 miles / an 11-minute drive) and offers a complimentary shuttle to downtown; The Perry is on Stock Island and requires a short drive into Old Town.

Which property is better for bringing a dog?

Havana Cabana is explicitly pet-friendly for dogs up to 50 lbs (max two per room) with a pet fee; The Perry lists a pet fee in its supplier notes but check directly for current pet policies and fees.

Do either hotel provide marina or boating services?

The Perry has a marina on site, docking and boat tours available; Havana Cabana does not offer marina services.

Which hotel has a spa?

Havana Cabana does not have an on-site spa. The Perry’s supplier listing does not publish a spa — not published.

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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