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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 Southernmost Beach Resort & Guesthouses

Havana Cabana at Key West is a Cuban-inspired, family-friendly resort on North Roosevelt Boulevard centered on Key West’s largest pool; read this if you want poolside vibes, free parking and a shuttle into Old Town. Southernmost Beach Resort & Guesthouses is a larger Southernmost-area beach resort and guesthouse complex; read this if you prefer beachfront access and staying inside Old Town near Duval Street.

Updated · about 3.0 miles 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 families and groups who want Cuban food and cocktails on site and easy parking.

See rooms & suites
Southernmost Beach Resort & Guesthouses, Key West (FL), Florida

Southernmost Beach Resort & Guesthouses

Southernmost location · Beachfront · Spa & full resort services

Best for travelers who want to stay in Old Town with direct beach access and resort-scale services.

Quick Verdict: Havana Cabana at Key West vs Southernmost Beach Resort & Guesthouses

When Havana Cabana wins: Choose Havana Cabana if you want a lively, family-friendly resort with Key West’s largest single pool, on-site Cuban dining and drinks, free self-parking, and a shuttle to Downtown — it’s the better pick for guests driving in or who plan to spend most time at the pool and nearby Smathers Beach.

When Southernmost Beach Resort & Guesthouses wins: Pick Southernmost Beach Resort & Guesthouses if being in the Southernmost/Old Town neighborhood and staying steps from beach access and Old Town attractions is your priority; the resort scale, on-site spa and multiple guest services suit travelers who want to be central to Duval Street and waterfront sights.

Bottom line: Havana Cabana is a northside, pool-and-parking focused property that works well for families, drivers, and guests who want large outdoor pool time and Cuban-themed dining; Southernmost Beach Resort & Guesthouses is the better option for visitors who want beachfront location and Old Town proximity, with more traditional resort amenities.

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Havana Cabana at Key West vs Southernmost Beach Resort & Guesthouses – At a Glance

Side-by-side facts for Havana Cabana at Key West and Southernmost Beach Resort & Guesthouses
CategoryHavana Cabana at Key WestSouthernmost Beach Resort & Guesthouses
Overall vibeCuban-inspired, casual resort with a big pool and family-friendly programmingLarge Old Town beachfront resort and guesthouse complex with full-service amenities
LocationNorth Roosevelt Boulevard (New Town); shuttle to DowntownSouthernmost / Old Town on/near Duval Street and immediate beach access
Size106 roomsNot published
AgesAll ages welcome (primary guest must be 21+ to check in)All ages welcome (check-in min age 18 listed in supplier policy)
Pools / beachOne very large heated resort pool (hotel says largest in Key West) plus hot tub; day passes availableOutdoor swimming pool(s) and direct beach access
Restaurants & barsFloridita Food Truck, Mojitos Pool Bar, Flama Cabana (waterfront lounge)On-site restaurants and bar(s) (names not published in supplier listing)
Wellness & servicesNo on-site gym (complimentary transport to off-site fitness), no spa on siteSpa services listed, fitness and tour/ticket services available
Parking & transportFree self-parking, complimentary shuttle to Downtown and airport pickup on requestOn-site parking (charges may apply) and concierge/tour desk; shuttle/transport options not specified
Accessibility & policiesWheelchair accessible parking and paths; no elevator (stairs to upper floors)Wheelchair accessible and accessible rooms listed
Known forLargest pool in Key West, Cuban food and mojitos by the poolSouthernmost location and beachfront access

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 base vs Southernmost / Old Town beach access

Havana Cabana at Key West – Location

Havana Cabana sits on North Roosevelt Boulevard in New Town, roughly a 10–15 minute drive to Old Town and Duval Street.

  • About 2.9 miles from Duval Street; complimentary shuttle to Downtown and Mallory Square.
  • Close to Key West International Airport (around a five-minute drive reported).
  • Near Smathers Beach and Searstown Shopping Center; convenient if you’re driving.

Good for guests who value easy parking, quick airport access and shuttle service into Old Town.

Southernmost Beach Resort & Guesthouses – Location

Southernmost Beach Resort & Guesthouses is positioned in the Southernmost area/Old Town, putting you within walking distance of many waterfront sights and Duval Street attractions.

  • Immediate proximity to Southernmost Point, nearby museums and Old Town attractions listed within a few blocks.
  • Public transportation and Key West Bus Station are accessible; airport about 4.2 km away.
  • Resort is on/near the beach, so you won’t need a car to reach sand and water.

Choose Southernmost if you want to be inside Old Town with beach access and short walks to Duval Street.

Rooms: Cuban motifs and poolside options vs multiple guesthouse/resort room types

Havana Cabana at Key West – Rooms

Havana Cabana has 106 Cuban-inspired rooms, many named by room type and several with balconies or sofa beds.

  • Room types include Premium Room (Luis/Lola), Room (Havana), Room with Sofa bed, Superior Studio and Poolside options.
  • Family- and group-friendly layouts (some rooms sleep up to 4; studios with bunks available).
  • Complimentary Wi‑Fi, in-room coffee, and standard room amenities; primary guest must be 21+ to check in.

Rooms are themed and aimed at families or groups who want pool access and flexible bedding.

Southernmost Beach Resort & Guesthouses – Rooms

Southernmost lists many room types from economy doubles to ocean-view king rooms and suites across its resort and guesthouse offerings.

  • Room names include Double deluxe, Partial ocean view king, Ocean View King, Deluxe Balcony King, and multiple 'La Mer' and Avalon options.
  • Selected rooms have balconies or terraces; wheelchair-accessible rooms are available.
  • Complimentary Wi‑Fi in all rooms and a mix of pool- and ocean-view accommodations.

More varied room inventory across a resort/guesthouse complex, with options that put you closer to Old Town and the beach.

Dining & drinks: Cuban-focused poolside options vs multiple on-site outlets

Havana Cabana at Key West – Dining & drinks

Havana Cabana centers dining around Cuban flavors and poolside cocktails.

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

Best if you want Cuban food and a strong, pool-to-evening drink program without leaving property.

Southernmost Beach Resort & Guesthouses – Dining & drinks

Southernmost lists restaurants and bars among its amenities; exact signature outlet names aren’t published in the supplier listing.

  • Supplier listing confirms on-site restaurants and bar(s) and food service for guests.
  • Daily housekeeping and bar service are part of resort amenities.
  • Concierge and ticket services can help arrange off-site dining or reservations in Old Town.

Expect full-service dining and bar options on site and easy access to Old Town restaurants.

Pools, beach & signature amenity: large resort pool vs beachfront access

Havana Cabana at Key West – Pools, beach & signature amenity

Havana Cabana’s headline amenity is its very large, heated resort pool with poolside bar and day passes.

  • Hotel advertises the largest pool in Key West, open 10:00 AM–11:00 PM and heated.
  • Poolside Mojitos Bar and pool service, plus cabanas/chaise lounges covered by the resort fee.
  • Non-guests can buy a day pass for pool access.

Pick Havana Cabana for pool-focused days, pool parties and easy poolside dining and drinks.

Southernmost Beach Resort & Guesthouses – Pools, beach & signature amenity

Southernmost provides outdoor pool(s) and direct access to the nearby beach as part of its resort experience.

  • Supplier listing includes outdoor swimming pool(s) and a beach for guest use.
  • On-site poolside bar and massage/spa services complement beach time.
  • Ticket/tour desk and concierge help arrange water activities and excursions.

If your priority is beach time and staying in Old Town, Southernmost’s beachfront location is the advantage.

Wellness & nightlife: spa and full-service resort amenities vs live-music lounge and off-site fitness

Havana Cabana at Key West – Wellness & nightlife

Havana Cabana focuses nightlife and evening energy in its Flama Cabana lounge and offers off-site fitness access.

  • Flama Cabana hosts live music and a sunset lounge atmosphere several evenings a week.
  • Property does not operate an on-site fitness center; complimentary transport to an off-site fitness facility is provided.
  • No full-service spa on site; spa services listed as not available in third-party sources.

Good fit for guests who want a lively evening scene on property and don’t need an on-site gym or spa.

Southernmost Beach Resort & Guesthouses – Wellness & nightlife

Southernmost lists a spa and fitness offerings among its amenities and provides a more traditional resort-service mix.

  • Spa/sauna and a fitness center are included in the supplier amenities list.
  • Daily housekeeping, concierge, ticket services and banquet/meeting facilities support longer stays or events.
  • Nightlife options include easy walks to Duval Street bars and restaurants given the Old Town location.

Better for guests who want a full-service resort experience with an on-site spa and immediate access to Old Town nightlife.

Who Wins? Best Pick by Travel Style

Best for pool days and pool parties
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 — home to the largest pool in Key West with poolside bar service and easy day-pass access.

Best for staying inside Old Town and on the beach
Southernmost Beach Resort & Guesthouses, Key West (FL), Florida

Southernmost Beach Resort & Guesthouses

Southernmost Beach Resort & Guesthouses — immediate proximity to Southernmost Point and beach access in Old Town.

Best for Cuban dining and rum-forward cocktails without leaving property
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 a focused Cuban food-and-drink program.

Best for on-site spa and multiple resort services
Southernmost Beach Resort & Guesthouses, Key West (FL), Florida

Southernmost Beach Resort & Guesthouses

Southernmost Beach Resort & Guesthouses — spa, concierge, tours, and a broader set of resort facilities are listed.

Frequently asked questions

Havana Cabana at Key West vs Southernmost Beach Resort & Guesthouses: FAQs

See all FAQs →
Which property is closer to Duval Street?

Southernmost Beach Resort & Guesthouses is located in Old Town and is closer to Duval Street; Havana Cabana is in New Town and relies on a shuttle for Downtown access.

Which hotel is better for families with kids?

Havana Cabana is family-friendly with a very large heated pool and family-sized rooms; Southernmost is also family-friendly but is more focused on beach and Old Town access.

Is parking available at either property?

Havana Cabana offers free self-parking; Southernmost lists car park with charges applying per the supplier listing.

Do both hotels have spas and fitness centers?

Southernmost lists a spa and fitness center among its amenities. Havana Cabana does not operate an on-site gym (it provides complimentary transport to an off-site fitness facility) and third-party sources indicate it does not have a spa.

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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