by The Editors | December 5, 2018

Winter Travel Spotlight: The Florida Keys and Key West

Our favorite places to stay throughout the Keys

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A spirit of freedom envelops you, no matter how many times you make the journey South to the Florida Keys and Key West. Something special happens while spending time with loved ones under those bright winter stars. Known not only for world-class sailing, snorkeling, diving, fishing and outdoor pursuits, but also for fine art galleries, museums and cultural festivals in constant rotation, The Florida Keys and Key West are beloved treasures of our state. Winter ushers in a festive astmosphere with the best of what The Keys has to offer on full display. In Flamingo’s Winter Travel Spotlight 2018, we highlight some of our favorite places to stay, from high-style five-star resorts to chic boutique hotels and laid-back luxury villas. 

CASA MARINA, A WALDORF ASTORIA RESORT

Opened: New Year’s Eve 1920

The Casa Marina is an iconic beachfront property located on Key West’s largest private beach, the perfect destination for water sports and recreation. Enjoy toes-in-the-sand dining at Sun Sun Beach Bar & Grill, plus two dazzling pools, a rejuvenating spa, a fitness center and 11,000 square feet of meeting and event space.

Key West // (305) 296-3535
casamarinaresort.com

THE REACH, A WALDORF ASTORIA RESORT

Opened: 1984

The Reach, a Waldorf Astoria Resort, is situated on Key West’s only private natural white sand beach,  just steps away from world-famous Duval Street. Enjoy spectacular amenities like an oceanfront pool, water sports rentals, a fitness center, oceanfront dining at Spencer’s by the Sea and meeting and event space.

Location: Key West // (305) 296-5000
reachresort.com

ISLANDER RESORT

REOPENING: dec. 2018

Islander Resort has unveiled a reimagined luxury experience steeped in casual elegance and inspiring oceanfront surroundings, making us a premier destination in the Florida Keys. Our beautiful property features a private beach with complete water sports offerings, two oceanfront swimming pools, Tides Beachside Bar & Grill, and Elements Lounge & Restaurant.

Mile Marker 82, Islamorada  // (305) 664-2031
islanderfloridakeys.com

KONA KAI RESORT, GALLERY & BOTANIC GARDENS

OPENed: 1991

A Key Largo gem, Kona Kai gets everything just right. The magical, intimate adults-only property is a two-acre hideaway with private botanic gardens, art gallery, tennis courts, bay-side beach, pool, jacuzzi and sunset pier. There’s 13 cottage-style rooms and suites with fully appointed kitchens and original art. Hope to see you soon!

Key Largo //  (305) 852-7200
KonaKaiResort.com

OCEAN KEY RESORT

Opened: 1988

An illusory setting that vacation dreams are made of.  Towering palms, colorful flora and unexpected touches await in one of the country’s most sought-after locales.  Where Duval Street begins in Historic Key West, the Ocean Key Resort & Spa invites their guests to indulge in the playfulness of the island.  Take in the luxurious surroundings – whimsical and true to the energy of the Florida Keys.  Relax at LIQUID, the resort’s pool bar and lounge, dine at acclaimed Hot Tin Roof, decompress at SpaTerre, or let go on the world famous Sunset Pier.

Key West  // (800) 328-9815
oceankey.com