OUR New Web Experience

We are rolling out new updates and resolutions to our NEW website experience over the next few weeks. As we move from exact dates to desired property and adventure searches, our CottageCrew is evolving with the ever changing needs of our fellow travelers... You asked to sort by property, sleep count, type, location, bedrooms and more, we delivered! We look forward to this continued roll-out, keep sending us your ideas! #CottageON


CEO | Founding Partner


...we the experience seekers!

As many of you know there can be difficulty in locating a property that suits your needs. You may be a yearly Siesta Socialite or a first-time traveler, no matter the situation, we are here to help provide you with the best possible experiences, information, and accommodations.

Our CottageCrew is curating information from the surrounding areas based on first-hand experiences. With seasonally-focused information updates, new property insights and sorting features, you can take advantage of spending your time planning your adventures and less time looking through options!

Our growing partnership provides our travelers (and ourselves) with internally reviewed and tested adventures. We provide the additional offerings to you as options to consider when visiting. Our partner’s reliability, values, and family-oriented mentality, gives us peace of mind in recommending them to you. And by becoming part of The Cottages on the Key Family, we can extend to you best rates and values!

During this period of evolution, I would like to extend my appreciation for your understanding and patience as we release these updates. We admit we also have a hard time waiting to share our experiences, maybe its Key Life, but we are committed to providing you the most amazing experience in vacation planning!


  • At the top every page you will notice a ‘grey bar’ with a link that can take you back to ‘Visit Original Website’ if you prefer
  • All of your reservations, holds, and invoices remain intact
  • Partnership information is restricted to confirmed guests only and access is exclusive to our travelers through our various programs
  • It’s always 5 o’clock somewhere, but on Siesta Key you are free to indulge and experience at your leisure, just please do so responsibly (we are not “clock watchers” but your safety means everything to us.)


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...we are to help!



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New Guests


Down Payment

Partially Refundable^

Payment Plan

General Cancellation

PatioPartner Services

#GetSandy Access

Past Guests

$ 99.♥♥

Down Payment

Fully Refundable^

Payment 60 Before check-in

5% - 18 Month Loyalty^^

PatioPartner Services

#GetSandy Access

...we the travelers!

As a locally family owned and run business, we know that great experiences are worth repeating, and booking directly provides the opportunity to build lasting relationships while maximizing the use of our hard earned time off! Call us for more information and START YOUR JOURNEY TODAY!


There are few constants in life, however we can all agree that time does seem to fly all to0 quickly while in Siesta Key mode!