29034 Rose Dr

This property stands out as a well-updated, canal-front home in Big Pine Key, positioned to attract STR guests seeking boating and waterfront experiences. The recent renovations, new furnishings, and move-in-ready condition reduce near-term capex risk and support premium nightly rates. Underwriting metrics suggest strong cash flow and a high cash-on-cash return, assuming occupancy and ADR targets are met. The primary caveat is that the investment thesis depends on continued demand for STRs in the Florida Keys and the ability to maintain high occupancy in a competitive market.

Big Pine Key, FL is a sought-after destination in the Lower Florida Keys, known for boating, fishing, and relaxed island living. The STR market here is driven by vacationers seeking waterfront access and proximity to both the ocean and bay. While demand for STRs remains strong, the market is competitive and subject to regulatory oversight, making ongoing compliance and market monitoring essential. The property’s size and amenities align with typical guest preferences for the area.

Eden Pines is a quiet, residential neighborhood characterized by canal-front homes and natural surroundings, including the presence of Key Deer. The area appeals to guests seeking a tranquil, authentic Keys experience with easy boating access. While detailed location-specific demand signals are limited, the property’s waterfront setting and updated condition should support guest appeal at a medium-to-high confidence level.

At a $785,000 purchase price, underwriting metrics project a monthly expected income of $9,222 and cash flow of $2,988, with a 22.8% cash-on-cash return based on a 20% down payment, 6.4% interest rate, and 25% expense ratio. These projections assume a $489 ADR and 62% occupancy, both of which are achievable but require effective management and sustained guest demand. The high-confidence underwriting reflects strong income potential, but performance is sensitive to occupancy and nightly rate assumptions.