1 . Cheeca Lodge & Spa

Islamorada, Florida

CALL DIRECT: +1 (866) 264 - 0820


You'll never forget the enchanting oceanfront luxury of the Cheeca Lodge & Spa!

Considered the premier luxury resort of Florida Keys, Cheeca Lodge & Spa offers exceptional accommodations, world-class fishing, and much more! Rooms feature West Indies- inspired designs tucked away in lush gardens behind cascading waterfalls and glistening pools. Indulge in delicious oceanfront dining at one of the three restaurants, or spend your days on the beautiful blue waters of the Keys, scuba diving, snorkeling, or fishing! Discover the legacy!

2 . Sunset Key Guest Cottages, A Westin Resort

Key West, Florida

CALL DIRECT: +1 (877) 564 - 1273


Located on a gorgeous 24-acre private Florida island, discover Sunset Key Guest Cottages!

Looking for a luxurious resort that takes you out of the ordinary and puts you in the extraordinary? Rent a one, two, three or even four-bedroom cottage with Sunset Key Guest Cottages and get just that! The cottages each include spacious wrap-around verandas, with Adirondack chairs and tables. Relax in ultimate tranquility as you take in the gorgeous sunrise and eat your complimentary breakfast before starting on your daily adventure. Get swept away with luxury at Sunset Key Guest Cottages!

3 . Little Palm Island Resort & Spa

Little Torch Key, Florida

CALL DIRECT: +1 (800) 343 - 8567


This is the perfect Florida Keys paradise, fit for a president, celebrities, and you!

Take your vacation to another level and spend your days basking in the sun on a private island so secluded you have to take a boat or plane to get there! Sound too good to be true? Little Palm Island Resort & Spa is not a figment of your imagination but instead is the answer to your vacation prayers. White-sand beaches, crystal-blue waters, glistening pools, beautiful accommodations, and a stunning marina make up just the start to your perfect retreat at Little Palm Island!

4 . Ocean Key Resort & Spa

Key West, Florida

CALL DIRECT: +1 (800) 328 - 9815


The perfect balance of relaxation and play make Ocean Key Resort & Spa the perfect destination for your Florida Keys vacation!

Don't force yourself to choose between a time of utter relaxation and complete adventure of play; instead, get the best of both worlds! Ocean Key Resort & Spa sits in a perfect central location with an endless list of activities and entertainment options. In the same breath, relax on the white-sand beaches or unwind at the Spa to rejuvenate mind, body, and spirit. Choose from one of the bright and vibrant rooms or suites and experience a stay unlike any other!

5 . Chesapeake Beach Resort

Islamorada, Florida

CALL DIRECT: +1 (866) 588 - 0250


Halfway between Key West and Miami is a tropical escape unlike any other: Chesapeake Beach Resort!

Known for spacious, comfortable, and luxurious villas, Chesapeake Beach Resort offers much more than average rooms. Here, you can enjoy two heated pools, water sports, tennis courts, and one of the best fishing areas in the world! Of course, the rooms themselves aren't bad either. Guests enjoy 37” TVs, Stereo radio/CD/alarm with MP3 docking capabilities and WIFI. Remodeled rooms that include kitchens and bathrooms are a nice touch as well. Okay, it's more than 'not bad' - it's a dream come true!

6 . The Reach Resort A Waldorf Astoria Resort

Key West, Florida

CALL DIRECT: +1 (866) 537 - 5241


A beachfront playground for the child inside everyone at The Reach Resort!

Located near the heart of Old Town, Key West is a charming yet intimate The Reach Resort. Hosting Key West's only natural beach, this resort is a Caribbean hideaway with gracious hospitality and classic luxury you won't find anywhere else. Snorkeling, scuba diving, swimming pools, and more are guest favorites. Best of all, each room has a private balcony that gives stunning views. Dive into luxury and seclusion at The Reach Resort - you won't be disappointed.

7 . Casa Marina

Key West, Florida

CALL DIRECT: +1 (866) 397 - 6342


Experience the timeless luxury of the Florida Keys at Casa Marina!

Nestled on the largest private beach in Key West is the classic Casa Marina. Since the 1920s, this resort has attracted visitors from all over the world and is even listed on the National Register for Historic Places. Guests of the Casa Marina enjoy access to world-class water sports, deep-sea fishing, wind surfing, and diving in America's only living barrier reef! Come and discover a tradition that has won the hearts of thousands before - Casa Marina!

8 . Hawks Cay Resort

Duck Key, Florida

CALL DIRECT: +1 (866) 525 - 5709


Small and secluded yet central to Miami and Key West, come see what makes guests fall in love with Hawks Cay Resort!

With so much going on, it'll be hard to limit your time at Hawks Cay Resort! Fishing, kiteboarding, diving, swimming with dolphins, and kayaking are just the start to the seemingly endless list of activities going on. After a long day of action, pull up a beach chair, open some wine, and watch the glorious sunset on the peaceful waves of the Atlantic. Villas and rentals in various sizes meet your every need, and make vacationing easier than ever!

9 . Tranquility Bay

Marathon, Florida

CALL DIRECT: +1 (866) 452 - 5369


As the name suggests, Tranquility Bay Beachhouse Resort offers nothing but peace and relaxation for a truly awe-inspiring trip!

Kick the standard hotel rooms out the window and vacation in a luxurious two- or three-bedroom beach house instead! Tranquility Bay Beachhouse Resort offers unique homes featuring flat-screen TVs, homemade furniture, and a view that can't be beat. Overlooking the Gulf of Mexico, enjoy award winning dining, two beaches, world-class fishing, snorkeling, two swimming pools, and a beachfront TJ's tiki bar! Come and find your slice of paradise at Tranquility Bay!

10 . Islander Resort

Islamorada, Florida

CALL DIRECT: +1 (305) 664 - 2031


The best kept secret in the Florida Keys is the Islander Resort!

Ideal for weddings, family vacations, or romantic trips for two, Islander Resort offers a deluxe array of accommodations, activities, and amenities. Designed with its guests in mind, kick back and relax with a full kitchen, patio furniture, outdoor grills, and - of course - the beautiful ocean at your finger tips. Test your luck at deep-sea fishing, take a party boat fishing with family and friends, or take a unique sunset cruise!