Luxury Property Advisor
About the Company
The Cottages on the Key (TCOK) is the premier luxury vacation rental management company on Siesta Key, Florida, specializing in high-end, boutique vacation homes designed for unforgettable getaways and exceptional guest experiences.
For over 12 years, we have built a reputation for five-star hospitality, personalized service, and meticulous property care, earning a 4.8 out of 5-star rating on Google and becoming the trusted leader in Southwest Florida's luxury rental market.
Our mission is to expand our portfolio with industry-leading luxury properties, strengthen our presence within the local community, and deliver our five-star hospitality to even more guests in the coming years. We are actively growing our collection of premier vacation homes, working with discerning homeowners who share our vision of providing guests with an unparalleled luxury experience.
At TCOK, we don’t just manage properties—we create exceptional stays that turn first-time visitors into lifelong guests. Our commitment to service, excellence, and innovation drives everything we do, making us the preferred choice for homeowners, travelers, and partners alike.
About the Role
You’re the first handshake, the first impression, the spark that turns interest into action. As a Luxury Property Advisor, your mission is simple: connect luxury rental homeowners with our expert team and help them see why The Cottages on the Key is the best choice for maximizing their rental potential. This is a fully remote, part-time opportunity with industry-leading performance pay, perfect for motivated professionals who want flexibility, autonomy, and high earning potential. You craft your own schedule, focus on warm leads (no cold calling!), and get rewarded for results. You’ll leverage top-tier communication and marketing strategies to increase homeowner response rates, build excitement, and set them up for success with our Luxury Property Consultants. Every call, every conversation, and every connection brings us closer to growing our footprint in the luxury rental space. This role reports to the Director of Sales and works closely with our sales and marketing teams to drive high-impact prospecting campaigns. If you’re a social, driven, and persuasive communicator with a knack for building relationships, this is your chance to thrive in a high-energy, results-driven environment—all while enjoying the freedom of remote, part-time work.
Responsibilities
• Be a Great Teammate – Contribute to a strong, supportive, and success-driven team culture while working together to advance TCOK’s mission of expanding our luxury portfolio while delivering five-star hospitality.
• Engage Luxury Vacation Homeowners – Use state-of-the-art communication and marketing techniques to drive homeowner engagement and spark interest in TCOK’s luxury rental program.
• Work a High Value Sales Pipeline – Manage a structured sales process, nurturing warm leads, tracking progress, and ensuring a seamless transition from initial interest to consultant.
• Collaborate with Luxury Property Consultants – Work closely with our experts to ensure homeowners receive the best possible guidance and support in joining our program.
• Expand TCOK’s Market Presence – Help grow our footprint in Siesta Key and Southwest Florida by strategically positioning our brand within the luxury vacation rental space.
• Educate & Guide Homeowners – Communicate the benefits of professional property management and revenue optimization through highly personalized, value-driven conversations.
Hospitality
Sales and Management
Part-time