Something special happens the moment you begin the scenic drive down the Overseas Highway into 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 and adventure envelops you, no matter how many times you make that journey. Known not only for world-class 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. Summer ushers in a special energy with the best of what The Keys has to offer on full display. In Flamingo’s Summer 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 pack up the convertible and head south.

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

SKIPJACK RESORT SUITES & MARINA

Opened: 1975

Bring the kids and the boat and settle into Skipjack’s laid-back vibe at our resort hotel and private, 54-slip marina in Marathon Key. Steps away from Boot Key Harbor and ideal for families, each of Skipjack’s 60 well-appointed suites features easy access to the resort’s casual restaurant serving the Keys’ freshest seafood, classic tiki bar, sunny pool deck, gym, tennis courts, beach bicycles and more. Experience Gulfside, bay or sea fishing with a fishing charter. Or explore local waters with your own vessel by using the ramp at our marina with space for boats up to 60 feet, electric power, fresh water, and boat rentals.

Marathon // (305) 289-7662
skipjackresort.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  // (305) 664-3333
islandvilla.com

HAWKS CAY RESORT

Opened: 1984
Owner: Carey Watermark Investors

Hawks Cay Resort, situated on the scenic and secluded isle of Duck Key, is where guests come to enjoy a piece of the Caribbean in the Florida Keys. The resort’s key features are its intimate location, glorious sunsets and aquamarine waters. Home to gourmet restaurants, watersports and award-winning spa, Hawks Cay is recognized as the premier Florida Keys resort destination.

Duck Key, Florida // 305-289-5100
www.Hawkscay.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, two oceanfront swimming pools, a hot tub, shuffleboard, volleyball, a 200-foot fishing pier with amazing views and 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

THE PERRY HOTEL

Opened: May 1, 2017

Named one of the best-designed hotels by Architectural Digest, the 100-room Perry Hotel offers an upscale twist on Stock Island’s iconic maritime heritage. From the idyllic marina that surrounds us to the award-winning American coastal comfort food from our fantastic onsite restaurants, The Perry Hotel is a one-of-a-kind Key West getaway.

7001 Shrimp Road, Key West, FL. 33040 // (305) 296-1717
perrykeywest.com

SUNSET GREEN

Opened: December 2017
Management: Highgate

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
Management: Highgate

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
Management: Highgate

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