Cyndee Haydon

Expertise / Specialties

Vacation Rentals, Second Homes

About Me

Cyndee Haydon is a short-term rental and waterfront real estate specialist with expertise in vacation rental properties along Florida’s Pinellas Gulf Beaches, including Indian Shores, Indian Rocks Beach, Madeira Beach, and Clearwater Beach.

She has more than 20 years of experience in Pinellas County real estate and has completed 435+ residential transactions totaling more than $230 million in closed sales.

Her career includes 150+ vacation rental property transactions, helping investors evaluate and purchase income-producing and waterfront beach properties.

Over the past five years alone, Cyndee has closed 139 transactions totaling more than $107 million in sales, including 62 short-term-rental-friendly properties and 28 sales above $1 million.

Cyndee is widely consulted by investors for her expertise in vacation rental property performance, coastal property risks, waterfront buyer and seller negotiations, and short-term rental investment strategy.

Cyndee evaluates every vacation rental purchase using the Haydon SHORE™ STR Investment Framework, a proprietary five-factor methodology covering Supply and Demand, Hosting Rules, Operating Economics, Risk and Resilience, and Experience and Earnings Potential.

Her work includes advising clients on flood insurance considerations, FEMA rebuilding rules, and the FEMA substantial improvement rule (commonly known as the 50% rule) that can affect renovation and rebuilding options for coastal properties.

Many buyers seek Cyndee’s guidance when evaluating which condominium buildings allow weekly rentals and which beach properties consistently perform well as vacation rentals.

Her approach focuses on helping investors identify properties with the strongest potential for rental income, guest satisfaction, and long-term property value.

In many cases, Cyndee advises investors not to purchase properties when coastal risks or structural issues could negatively affect long-term investment performance.

Cyndee holds the CRS, ABR, SRS, RENE, RSPS, CLHMS, CIPS, and SRES professional designations and certifications.

The Sandbars To Sunsets Team at Future Home Realty advantage:
1. FastExpert Top 2 in Indian Rocks Beach and Indian Shores (2026)
2. Homelight "Sells Homes Fast Florida"
3. 2026 Treasurer, Florida Realtors
4. 2026 Chair, NAR Regulatory Issues Forum
5. 2023 Chair, NAR Insurance Committee
6. 2022 Florida Realtors Associate Realtor of the Year