General Notice On Pricing and Availability...


Arriving late, or with a group, we can help minimize stress by leaving the essentials in your kitchen prior to your arrival!


Unlike many places on Siesta Key, all of our properties feature well maintained bikes and locks.

Heated Pool(s)

During the winter months from mid-November to mid- April, all of our pools are heated for continued use and your enjoyment.

Americas #1 Beach

Siesta Key Beach is consistently rated as America's #1 beach by various sources, it's the reason finding a place to stay can be as challenging as finding enough time in a day!

On-Site Laundry

All of our cottages have on-site laundry and starter clean kit for 13+ loads, enjoy and stay 'clean' with peace of mind!


All of our cottages have high speed wireless internet, with more then enough bandwidth to stream, video chat and surf all at the same time... So #CottageOn and share your memories while you re-energize from the Siesta Sun!

Here at The Cottages on the Key, 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. What better place in the world to find one than right here on Siesta Key in Sarasota, Florida, ranked #1 Beach in the United States and #5 in the world. By providing the finest in vacation rentals in Siesta Key, we can ensure that your vacation is a success no matter which home is right for you.​


Siesta Key Beach, on Florida’s Siesta Key, has sand that is almost pure quartz, so it’s no wonder the beach has been recognized for having some of the whitest and finest sand in the world…

Boats, Charters, and Tours

Here is a list of our tried and true adventure partners, we will help you make arrangements and facilitate special requests! It’s another way we #CottageOn!

Top places to Eat

With so much to experience during your visit and seasonal menus, we have listed some of our favorite places to eat in the Siesta Key area…

Looking for answers?

Take a moment to look through our Guest Handbooks: Frequently Asked Questions or call us! We are here to provide you with the best possible options and services. If you have a question or request that isn’t addressed we look forward to hearing your voice, after all it is a toll-free call!

Proud Chamber Member
We are proud to support local businesses along with Siesta Key Chamber of Commerce, as we continually strive to provide our guests and locals with the best possible experiences!