Navigating the 30-day barrier.
Most of Naples blocks short-term rentals. We specialize in the pockets that don't — high-yield 7-day rentals in Unincorporated Collier County, underwritten by a broker + licensed appraiser, with full DBPR and tax compliance handled for you.
The Jurisdiction Map
Same zip code. Different rulebook.
Naples STR investing is a legal exercise first, a real-estate exercise second. Buy in the wrong jurisdiction and your business model is illegal on day one.
City of Naples
Old Naples · Aqualane Shores · Port Royal
Grandfathered code generally prohibits rentals under 30 days for single-family homes. Beautiful real estate — wrong vehicle for STR cash flow.
Unincorporated Collier County
Naples Park · Vanderbilt Beach · select pockets
Daily and weekly rentals are legal with county registration and a Florida DBPR vacation-rental license. This is where every viable Naples STR strategy lives.
Where we hunt
Three pockets do most of the work.
Naples Park
Walk-to-beach grid, no HOA, weekly rentals fully legal. The flagship 3BR pool-home play.
Vanderbilt Beach Condos
Vanderbilt Towers and The Dunes — buildings with built-in rental programs and proven occupancy.
Lely Resort
Rare purpose-built subdivisions zoned for high-turnover vacation use — a niche, but a clean one.
Financial Spotlight
The Naples Park 3/2 pool-home play.
The flagship STR asset class in 2026: a 3-bedroom, 2-bath pool home in Naples Park, walking distance to Vanderbilt Beach, no HOA, fully county-compliant.
Seasonality
March is the Super Bowl.
Average monthly gross revenue, representative Naples Park 3BR pool home (2026 benchmarks).
The 360° Service
Turnkey DBPR + tax compliance — done for you.
The paperwork is what scares novice STR investors out of the market. We handle the Collier County registration, the Florida DBPR vacation-rental license, and the monthly 11% combined tax setup so your asset is producing legally from day one.
- 01
Collier County STR Registration
Annual filing, property safety affidavit, responsible-party designation.
- 02
Florida DBPR Vacation Rental License
State-level transient lodging license — required before guest #1.
- 03
Tax Setup
6% FL Sales Tax + 5% Collier Tourist Development Tax — registered, collected, remitted monthly.
- 04
Insurance Re-Rating
Owner-occupied policies don't cover STR. We coordinate the rewrite + flood/wind.
Underwriting Discipline
The risks we model — before you wire the deposit.
City of Naples 30-day rule
Single-family in Old Naples, Aqualane Shores, etc. cannot do <30 day stays. We don't write offers there for STR clients.
HOA rental restrictions
Even county-legal buildings can have private rental minimums in their docs. We screen the docs before contract.
Insurance shock
Post-Ian wind/flood premiums materially affect NOI. We model real quotes — not desktop estimates.
Hurricane revenue gap
Aug–Sep can lose weeks. Reserves and seasonally-weighted underwriting are non-negotiable.
Ready to own a legal, cash-flowing Naples STR?
One 30-minute call. We'll map jurisdiction, target the right pocket, model the deal with real numbers, and walk you through compliance end-to-end.
Consult Before You Commit
Schedule a Real Estate Strategy Consultation
A 60-minute private session to evaluate land value, renovation feasibility, build comparison, market ceiling pricing, and risk—before you sign anything.