1 . Keys Holiday Rentals, Inc.

Islamorada, Florida

CALL DIRECT: +1 (305) 664 - 8808


Whether you're interested in renting a condo or a single family home, Keys Holiday Rentals, Inc will be more than happy to assist you!

Keys represents properties throughout the Upper Keys, from Key Largo to Islamorada. Their condos are ideal for smaller groups who want a community type of living. You'll love the multitude of amenities like swimming pools, hot tubs, and tiki picnic areas. Meanwhile, rental homes are perfect for family vacation, with most featuring private dockage on canals leading to the ocean! Get out and experience the crystal clear waters, spectacular snorkeling, and fishing the Keys are known for!

2 . Key West Vacation Rentals

Key West, Florida

CALL DIRECT: +1 (866) 588 - 8139


The largest and most acclaimed vacation spot in Key West, Key West Vacation Rentals is the picture of opulence and tropical comfort.

KWVR takes pride in sowing the seeds of relaxation upon your arrival. Besides the always incredible beachfront property and views, you'll be enjoying fully stocked kitchens, private pools and hot tubs in some of the best weather in the country. Grab a drink and kick back as the dedicated staff work tirelessly to make sure that your stay in one that you'll never forget. It's simply the the best value in paradise!

3 . Hawks Cay

Duck Key, Florida

CALL DIRECT: +1 (866) 525 - 5709


Snorkel into a secluded lagoon of luxury at Duck Key's Hawks Cay Island Resort.

Island life is calling you to the Duck Key's Hawks Cay Island Resort. Sparkling aquamarine water surrounds this silent isle with a snorkeler's paradise. Fish the Gulf Stream within reach of a reef, join a shipwreck or night dive, or swim with Atlantic Bottlenose Dolphins at Dolphin Connection, the onsite dolphin research facility. All flavors of aquatic adventure await you outside the charming island decor of your waterfront or island view villa at Hawks Cay Island Resort & Calm Waters Spa.

4 . Englewood Beach & Yacht Club

Englewood, Florida

CALL DIRECT: +1 (888) 712 - 6148

From $105

Discover a peaceful Florida vacation at the Englewood Beach & Yacht Club. This charming destination is located between the Gulf of Mexico and Lemon Bay, offering you a prime setting to soak up the sun and indulge in a variety of exciting beach activities. Their luxury one, two, and three-bedroom accommodations come equipped with kitchens, cozy living rooms, balconies and much more! It's everything you need for a memorable vacation!