Tips for Finding the Best Vacation Rentals in the Florida Keys

By Lora Keleher , last updated November 12, 2011

If you’re dreaming of sipping an ice-cold beverage on the beach, as you relax in the Florida Keys, you should consider these tips for finding the best vacation rentals. Whether you’re looking to travel to the famous Key West, Key Largo, Islamorada, Marathon, or the lower keys, you can make the most of your trip by learning about the activities and attractions for which each destination is known, and then booking your trip accordingly.

Select Your Florida Keys Destination

Each of the areas in the Florida Keys can be the perfect vacation destination, depending on your interests and lifestyle. Key West is one of the best-known destinations in the keys, featuring a bustling nightlife, lavish restaurants, cosmopolitan shops, and historical attractions like Earnest Hemingway’s home and the Audubon House. Although families do vacation in Key West, keep in mind that the island is a hotspot for partygoers, rebels, and the gay and lesbian community, and many bed and breakfasts don’t allow children under 12.

Scuba divers interested in visiting the nations first underwater park, hikers who wish to explore the state parks, and anyone looking for a relaxing, but not overly lavish vacation spot should investigate Key Largo. This northernmost spot in the keys gives you a taste of everything the keys has to offer without appealing to specifically to a particular group, making it a nice spot for groups who have varying interests.

Famous for sport fishing and upscale accommodations, the six islands that make up the Islamorada area of the keys are home to many different fishing spots, diving spots, and upscale hotels and restaurants. The area is also known for being an ideal honeymoon spot, and couples can enjoy the glorious sunsets, hiking trails, diving spots, and romantic beaches. The family-friendly area of Marathon boasts a friendly island atmosphere, and includes parts of Vaca Key, Grassy Key, and Fat Deer. You can swim with dolphins, scuba dive amongst wrecks and participate in water sports during the day, then enjoy a taste of island cuisine and nightlife after a long day in the sun.

If you’re looking to break away from the hustle and bustle of modern life, consider venturing to the Lower Keys, where you can fish, snorkel, sail, and explore the wilderness, away from shops, nightlife and the majority of other vacationers. Though not for people looking to shop, party, or visit well-known attractions, the lower keys are ideal for independent travelers who enjoy solitude and water sports.

Plan Ahead

Most people start planning summer vacations immediately after the winter holidays, and if you start looking before the holidays, or even a year prior, then you’ll have much better chance of finding the perfect rental. If you’re concerned about booking so far in advance, consider purchasing trip cancellation insurance, which provides reimbursement for prepaid expenses if you have to cancel your trip. One great place to start looking for accommodations is the official tourism site for the Florida Keys. The site lists popular attractions, as well as hotels, motels, cottages, and other rental types by area. You can also scour the web for Key West specific rentals or use booking sites like Expedia. Another option is to contact a Florida Keys based real estate agent, and see if they can provide recommendations based on your desired accommodations and amenities.

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