The Cottages On The Key
July 1, 2023
Siesta Key, Florida
Job Type
$50,000 - $60,000



The Cottages on The Key is a vacation rental property management company based in Siesta Key, Florida. With a commitment to the art of hospitality, we are passionate about sharing experiences in the area with guests worldwide.

Additionally, vacation rental owners benefit from our full property management services. As a company, we consider each homeowner's goals, creating customized white glove services that match their financial goals and the uniqueness of their property. It's that same individualized approach that has made us successful and has contributed to our growth.

At The Cottages on The Key, culture is extremely important. We strive to create a supportive and inclusive environment where everyone feels valued. When working with us, you'll find that our Team functions as a unified and collaborative unit, which enables us to maintain an excellent work-life balance.


Looking for an exciting position where your creativity and career collide? We need a talented Photographer/Videographer with drone experience to help us show off our stunning properties and create stand-out travel and social content. In this role, you'll be taking property photos and videos and creating virtual tours, with the flexibility to manage your schedule as long as you’re meeting your deadlines. Plus, you'll get to explore Sarasota and her Islands, meet awesome people, and even have the chance to travel as we grow nationally. Day-to-day responsibilities will include but are not limited to taking internal and external photographs, recording videos and drone shots for new listings, facilitating listing updates, and showcasing lifestyle experiences at properties and throughout Sarasota for social media. As The Cottages on the Key grows, national travel will be necessary to perform job roles for properties outside of Sarasota.

This is an exciting opportunity for an experienced professional photographer. Please provide a link to your updated portfolio in your resume or cover letter.


  • Take internal/external photographs/videos and drone shots for new listings and listing updates
  • Shoot lifestyle/experience images at properties and throughout Sarasota and her Islands and create dynamic social content.
  • Plan and execute photo and video shoots, edit and retouch images, and create virtual tours.
  • Manage your own schedule and ensure that all deliverables are completed on time and to the highest possible standard.
  • Assistance with new client onboarding
    • Staging newly onboarded homes and performing all necessary photoshoots to advertise on the rental market
  • Making a note of all relevant information and ensuring cross-departmental communication when necessary for new clients
  • Practice excellent creative and communication skills
  • Utilize time management to ensure responsibilities such as videographing/editing/submitting content are completed in a timely manner
  • Organizational coordination with all department heads


  • Proven professional experience as a photographer and videographer is required. Please include a link to your updated portfolio on your resume or in a cover letter. 
  • Experience in real estate or vacation rental photography is preferred.
  • Skilled in photo and video editing software and able to deliver polished, ready-to-use visuals.
  • Familiarity with the area and local drone regulations is a benefit
  • Excellent communication and customer service skills, with the ability to represent the company's brand and maintain a professional demeanor at all times.
  • Able to work collaboratively and creatively with our marketing and sales departments.
  • Must live in the Siesta Key, FL area.


Salary: $50,000 - $60,000


  • Paid time off such as PTO, sick days, and vacation days
  • Health insurance
  • Employee recognition programs
  • Workplace perks such as recreation activities, food and coffee, and flexible work schedules