Most lenders see "Monroe County" on the address and panic. I see opportunity. Jumbo, DSCR, STR, second home, conventional, structured around the actual realities of flood zones, wind, and insurance pricing in the Florida Keys.
Insurance availability, flood zone classification, condo questionnaire fights, non-warrantable buildings, and FEMA remap timing all conspire to break deals that look fine on paper. I run the deal the way an experienced Keys broker actually has to.
Key Largo · Tavernier · Plantation Key · Islamorada. Mostly accessible to mainland insurance carriers. Best for second-home jumbos and STR DSCR.
Marathon · Duck Key · Grassy Key · Crawl Key. Hardest market for insurance, Citizens-heavy. STR is regulated; vacation rental income must be documented carefully.
Big Pine · No Name · Cudjoe · Summerland · Sugarloaf · Key West. Strong DSCR and second-home territory. Many properties stilted/elevated, VE zone strategy required.
Pre-1972 builds in Key West and the Lower Keys carry their own quirks, grandfathered flood, ICC payouts, elevation strategies. We've structured these.
Boat slip valuations, pier financing, hatchet marina condo questions, Marina Vale's specialty.
Monroe County STR ordinances are strict. We navigate occupancy proof, T-12 vs projected income, and DSCR lender preferences for vacation rental loans.
If a lender hasn't done a deal in Monroe County in the last 90 days, they don't actually know how to structure one. I do them weekly.
HOI quote came in at $14k? Citizens-only? Surplus lines? I have a network of FL coastal carriers and re-shoppers. Often we get the binder down 30 to 50% just by re-quoting properly.
Property landed in VE/AE after FIRM remap. Elevation certificate, NFIP vs private flood, Risk Rating 2.0 strategies, all part of the playbook.
HOA litigation, <50% owner-occupied, single-entity ownership over 10%, most lenders walk away. Portfolio jumbo and non-QM carry these.
Need to use STR income to qualify? DSCR with projected income works. Some lenders take T-12 AirDNA. We pick the right one for the property.
Fannie's second-home rules (rate hits, occupancy intent) make Keys second homes tricky. Sometimes investment financing is actually cheaper after rate adjustment.
Old flood policy assumed by buyer = thousands in annual savings. We close pre-FIRM transactions before any rate change is triggered.
Monroe County 2026 conforming limit is $990,150, anything above is jumbo. I write jumbo deals from $990K to $5M+ in the Keys regularly.
Jumbo details →No-tax-return investor loans. Qualifying off the rental income, projected or actual. The right product for Airbnb/VRBO operators.
DSCR details →Up to 89.99% LTV with the right structure. Keys second-home buyers, primary in another state, weekend home in the Keys. We do this constantly.
All programs →Self-employed buyers who don't show income on tax returns. 12 or 24 months of business statements, or CPA-prepared P&L.
Non-QM →$0 down, no PMI. Less common than mainland, but I close them. VA appraisal scrutiny on coastal properties demands a broker who knows what to flag.
VA details →Retirees with $$$ in brokerage but limited W-2 income. Asset-based qualification gets the loan done, we use 60-70% of liquid assets / 360 months.
More →Whether you're under contract, pre-shopping, or just exploring, a 30-minute strategy call will save you weeks of back-and-forth with national lenders who don't actually understand the Keys.
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