Siesta Key Property Management Services

White Glove Property Management Focused On Exceptional Guest Experiences + Revenue Optimization

As a property owner the “Cottage Crew“ will build a relationship with you based on trust, transparency, and superior service. We find the right guests and pair them with the right house from our exclusive collection of vacation homes, located in one of the most desirable beach destinations in the world. Our well-defined homes and outstanding concierge service create lasting impressions with every guest and maximum investment results for every owner.

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The Cottage Difference: How We Work (For You)

We approach the return on investment of your home like it’s ours. managing the business enterprise of your vacation rental on your behalf, while you passively earn income from our endeavors. Simply put, we won’t make money unless you do. Our history of proven results and extensive marketing channels, which also include Airbnb and VRBO, ensure that your property reaches the largest national market.

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Caring For You (And Your Home)

Creating an amazing and fulfilling experience for guests and owners is at the heart of what we do. Success for our owners comes by adhering strictly to our brand standards across the portfolio. We focus on the homes that will stand out from other available rentals in the area resulting in higher rental income. That means more revenue with lower usage for your home. We also ensure that your home is consistently maintained to the highest standards.

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What's Next

What's Next (Steps)

It doesn’t matter if you have a home yet or not. Contacting The Cottages on the Key is the next step. If you are ready to invest in us, we are ready to invest in you. Our company ethos is to build a trusting, collaborative partnership that results in positive outcomes. We’ll walk through each step in the process with you. We want to help make your dreams a reality.

Our Partners

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What Our Owners Are Saying

5 out of 5

I have been an owner of a vacation rental property on Siesta Key for about 8 years. During that time I have been through five different rental agencies attempting to find that one agency that has lived up to everything they promised in their “sales pitch” to me prior to signing with them. I found that agency in The Cottages on the Key, they have proven to be the best rental agency I have ever been associated with - hands down!

- VJ

5 out of 5

We are very thankful to The Cottages on the Key. Everyone is so informative and responsive. They gave us an opportunity to get rental income and we’ll use it once in a while to vacation with friends and family. Thanks again!

- Tom & Amy M.

5 out of 5

Anybody can promise results, but The Cottages on the Key have more than lived up to the promises made in their sales presentation. They are quick to respond to any need. We wanted our guests to feel special when renting our place and they worked with my wife to set the house perfectly for guests. We travel the world and stay in rental properties and we know what we look for. The Cottages delivered and goes beyond in all dimensions. The timely communications and transparency are also greatly appreciated. We loved our experience with the Cottages this first year and look forward to many more.

- Dave & Joyce S.

5 out of 5

Would definitely recommend your rental home being managed by The Cottages on the Key! Can't say enough about The Cottages! Incredible staff that truly treats our home like it's theirs. And when a looming natural disaster is at the doorstep, the professionalism, care, commitment, and communication only increase. Thank you all and hope your homes and family are safe!

- Chris C.

5 out of 5

The Cottages on the Key took over management of 10 of our seasonal rental properties. They have exceeded their projected revenue every year with the exception of 2020 when Covid hit and seasonal rentals were not allowed for over 2 months. They still came within 5% of meeting their projected revenue, even though we weren’t able to rent the last week in March and pretty much all of April and May. This is very commendable in my opinion.

- Sam P.