Southernmost Beach Resort
Key West, Florida
Coastal Classic, $$ (From $199)
When the time is right for all things lively and joyous in Key West, head straight to the Southernmost Beach Resort, the iconic oceanfront property located at the quiet end of Duval Street with a private beach and tanning pier that juts into the Atlantic. The property has welcomed island-life seekers for over 70 years (since 1948) with a collection of nine pastel-colored buildings and guesthouses that are as easy on the eyes as the calm Florida Straits. Conch fritters and Caribbean-inspired bites are easily washed down with key lime coladas that flow freely from the cabana-flanked pool bar.
At a Glance
The Vibe: Oceanside oasis steps from the party.
Standout Detail: The friendly, multi-lingual staff who share local tips and island tales.
This Place Is Perfect For: Couples who love to be pampered poolside, Key West first-timers who want to be close to the action of Old Town.
Rooms: 262 rooms spread out in nine pastel-colored buildings with six deluxe and superior room categories, four oceanfront options, and one three-bedroom suite. Crisp white linens and simple contemporary coastal design keeps your view on the ocean, as the majority have private balconies. Cuisinart coffee makers, mini fridges, and USB plugs comfort the hi-tech traveler. The La Mer & Dewey Houses are also part of the Southernmost property, with two apartment-style Victorian-era guest houses with their own entry and private courtyard, concierge, daily breakfast, and afternoon canapes.
On Site: Days at Southernmost are centered around chilling oceanside and imbibing poolside. Choose your pick from the tanning pier, three pools (one oceanfront and another adults-only), private beach, or adjacent South Beach (guests have priority access with loungers). There's also a fitness center and spa with a large menu of treatments and private cabanas for al fresco massages. The generous lawns have hammocks, sun-loungers, and Adirondack chairs, highlighting the island-living vibe.
Food + Drink: Three bars (one sandy, two poolside) and the lively Southernmost Café make up the dining scene here. At the oceanside restaurant, chef Kevin Lundry serves a coastal menu with Asian-Caribbean flair (drunken scallops, ahi tuna-stuffed avocado, local catch fish fry, conch chowder). The Pineapple Bar (adjacent to the Pineapple Pool) has live music every Wednesday afternoon, where the signature caipirinha cocktail muddled with Florida pineapple keeps the bar tabs open.
What to Do Nearby
The hotel has several island excursions available to guests including an eco tour of the island's backcountry and remote sanctuaries with lush mangrove islands, crystal-clear sand bars, and calm turquoise waters perfect for snorkeling. Private seaplanes to Dry Tortugas National Park can also be arranged, as can sunset helicopter tours of the island and big game fishing trips. If you'd prefer to explore the island on foot, Duval Street and its near two-mile stretch of bars, cafés, gift shops, and open-air nightclubs are within a sandal's reach of the hotel.