Investing in Key West, FL — Market Analysis
Key West is a land-scarce island market with extraordinary STR yields — permitted vacation rental properties routinely gross $100,000+ annually, justifying the ultra-premium acquisition cost. With a median home price of $895,000, acquiring a rental property in Key West requires a minimum $179,000 down payment for a DSCR loan (20% of purchase price) or $224,000 for a conventional investment property loan (25%). At current DSCR investor rates around 7.5%, your estimated monthly payment on a $716,000 DSCR loan is approximately $5,006 in principal and interest, with a total PITIA (including taxes and insurance) of approximately $6,870/month.
For a long-term rental strategy, Key West properties at the median price point generate an estimated $5,200/month in gross rent — a gross rent multiplier of approximately 14.3x. After accounting for all operating expenses including vacancy, property management, maintenance, capital reserves, taxes, and insurance (typically 35% of gross), estimated net operating income runs around $3,380/month. This produces an estimated cap rate of 4.5% and an estimated monthly cash flow of $-1,630 after P&I on a DSCR loan. The LTR DSCR ratio of 0.76x reflects the premium pricing in Key West relative to rents — common in appreciation-driven markets. Most investors here pursue STR income, portfolio/blanket lending, or no-ratio DSCR products that don't require a minimum DSCR.
Short-term rental is an active strategy in Key West. Based on typical occupancy and nightly rates for this market, a well-managed STR property could generate approximately $12,200/month in gross revenue. This produces an estimated STR DSCR ratio of 1.78x — well above the 1.0 threshold and qualifying for best-tier DSCR pricing at most lenders. Note: DSCR lenders that accept STR income typically require 12-24 months of AirDNA or VRBO data, or a signed lease agreement from a property management company projecting annual revenue. Estimates above are for illustration only — actual performance depends on property location, amenities, and management quality.
Monroe County's high-balance conforming limit of $990,150 means DSCR loans up to $990,150 at 80% LTV qualify for Fannie Mae/Freddie Mac-eligible investor pricing — typically 0.5-0.75% lower than true jumbo DSCR rates. For Key West investors acquiring properties in the $1M+ range, confirming whether the transaction stays within the conforming limit significantly impacts the rate and investor pricing tier.
Tayton Capital finances investment properties in Key West across all major product types — DSCR, conventional investor, jumbo, and portfolio — with no limit on the number of properties financed. We close investment transactions remotely, including LLC vesting and title coordination.

