Something special happens the moment you set sail for an adventure in The Florida Keys. The air shifts and your mood lifts when surrounded by the vibrant water, warm sunshine and blue skies. The Florida Keys’ spirit of freedom envelops you, no matter how many times you make the journey by road or by boat. 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. Fall ushers in a special energy with the best of what The Keys has to offer on full display. In Flamingo’s Fall 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. All that’s left to do is raise the main and head south.

KEY LARGO BAY MARIOTT BEACH RESORT

Opened: 1994

Discover the key to paradise with the resort’s endless possibilities. Book a massage, sip a tropical drink by the pool or dive into some water sport activities. Seventeen waterfront acres, private balconies and three on-site restaurants with spectacular views invite you to taste the Florida Keys in style.

Key Largo // (305) 453-0000
keylargomarriott.com

MARRIOTT KEY WEST BEACHSIDE

Opened: Dec 15, 2008

This Marriott property features exceptional suites, upscale amenities, complimentary transportation on the island, a marina with charter boats and water sports rentals, and one of the finest restaurants beloved by locals.

3841 N Roosevelt Blvd, Key West // (305) 296-8100
www.Marriottkeywest.com

SHERATON SUITES KEY WEST

Opened: 1993

Find your paradise at this all-suite hotel adjacent to Smather’s Beach and 1.5 miles from Key West International Airport. Thrill-seekers enjoy a variety of water activities just steps from your room, while sun seekers relax by the large outdoor resort pool. Discover rich history, flavorful cuisine and unique shops exploring our quaint, colorful island.

Key West // (305) 292-9800
sheratonsuiteskeywest.com

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, two dazzling pools, a rejuvenating spa, a fitness center and 11,000 square feet of meeting and event space.

1500 Reynolds St., 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 and just steps away from world-famous Duval Street. Enjoy spectacular amenities such as an oceanfront pool, water sports rentals, a fitness center, oceanfront dining at Spencer’s by the Sea and functional meeting/event space.

1435 Simonton St., Key West // (305) 296-5000
reachresort.com

ISLANDER RESORT

REOPENING: Fall 2018

The Islander Resort offers the perfect accommodations for spending a long weekend or a long winter. Our beautiful oceanfront property features a state-of-the-art conference center, a pristine private beach with complete water sports offerings, a splash pad, two oceanfront swimming pools, a hot tub, shuffleboard, volleyball, a 200-foot fishing pier and Tides Beachside Bar & Grill. Introducing our new culinary experience, Elements, featuring an elegant indoor bar and fine dining. All Islander accommodations offer complimentary wireless internet. We never charge resort fees!

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

SUNSET GREEN

Opened: December 2017

A new 12,105-square-foot shared multipurpose event lawn serves as the focal point for award-winning boutique lifestyle hotels 24° North and The Gates. The lawn, complete with food truck, provides entertainment for up to 800 seated guests or 1,200 standing and can be used to host weddings, yoga, concerts, movie nights or lawn games.

Key West // (305) 928-1095
thekeyscollection.com

24° NORTH HOTEL

Opened: November 2015

24° North Hotel ties the historical roots of Cuba and Key West together. With its authentic island ambience, Cuban theme and splashy pool deck scene, the 145-room boutique lifestyle hotel invites guests to explore what makes the Southernmost City incomparable. Historically minded adventurers are greeted with vibrant Cuban culture, bits of history and hospitality.

Key West // (305) 320-0940
24northhotel.com

THE GATES HOTEL

Opened: March 2015

The soul of Key West is captured in our 100-room lifestyle boutique property. Discover an authentic Key West experience, that highlights the diversity of cultures that makes this southernmost island so unique. A main attraction is Rum Row, a chic pool, bar, and lounge scene. Be inspired by the selection of rums and experience a modern twist on the Cuban cigar.

Key West // (305) 320-0930
gateshotelkeywest.com

ISLAND VILLA RENTALS

Opened:   1998

Island Villa is your connection to finding inviting FL Keys vacation properties from Key Largo to Tavernier to Islamorada and beyond.  Whether you’re planning a vacation or destination wedding, we can help you find your ideal Florida Keys vacation rental.

Islamorada, Florida Keys // (305) 664-3333
islandvilla.com