Here at The Cottages on the Key vacation rentals we understand what makes a luxury vacation home right for you. We make it our business to find a vacation rental that meets all of your needs and goes above and beyond your expectations. By providing the finest in vacation rentals we can ensure that your vacation is a success no matter where you decide to stay.


When you are staying in The Cottages on the Key Vacation Homes it is impossible to be bored. You will find activities and attractions for you and your significant other to your entire family. There will also be many restaurants that will tempt your taste buds. So what are you waiting for, book online today and get out and enjoy a Siesta Key Vacation!

Property Management

We know what it takes to run a successful vacation rental management company. Providing quality homes, cleaned by quality employees, and providing quality customer and concierge service is what sets us apart from the rest. Whether you are renting with us or putting your rental in our hands as an owner you can be sure that you working with the best.

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Planning your next escape but need some assistance...
Our Accommodation Specialists will gather properties that fit your needs and provide insights during a time that works best for you! Schedule A Call provides you with a 3-Step form that provides us with directional information and you the ability to select a day and time* that is best to call you! We live here and are excited to have your come visit! *ALL TIMES ARE IN US EASTERN STANDARD TIME
Visit our Frequently Ask Questions section for answers to many questions our guest have!