
Sell or Keep Your Pinellas Vacation Rental? A Decision Guide
Should you sell your Pinellas vacation rental or keep it? When keeping works, the property tax reset at sale, depreciation recapture, 1031 timing and what to gather first.
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Broker · Airbnb Superhost · Pinellas Native
Broker of Mangrove Bay Realty
✓Florida Licensed Broker · #BK3436609· Active through 09/30/2028VerifyTroy Nowak is broker of Mangrove Bay Realty (FL license BK3436609), an Airbnb Superhost, and a short-term rental specialist realtor in Tampa Bay and Pinellas County. He helps people buy and sell short-term rentals, furnished rentals, and investment properties in St. Petersburg, Clearwater, Largo, Indian Rocks Beach, Treasure Island, St. Pete Beach, Madeira Beach, Clearwater Beach, and Tampa. Before real estate, Troy spent over a decade as a Pinellas County math teacher and the head boys’ varsity basketball coach at Dunedin High School, so when he talks about neighborhoods, schools, and what makes Pinellas tick, he’s lived it. Since launching his real estate career in 2019, he has closed 325+ sales with an average price of $523K, ranging from first-time buyers at $117K to luxury waterfront at $1.9M. He is also a property manager who owns and manages short-term and furnished rentals in Pinellas County, and he brings former institutional acquisition experience to investor guidance.
Public review profiles
Origin
Troy taught Algebra II and Geometry at Pinellas County schools for nearly a decade before he ever sat for the real estate exam. The last four years of that run, he was the head varsity boys' basketball coach at Dunedin High — the same high school that zones half the neighborhoods buyers ask him about today.
Two things carried over from coaching: people remember how you treated them long after the score gets forgotten, and the best players are the ones who see the play developing two steps ahead. Same applies to a transaction.
The big-box brokerage model wasn't built for the kind of client work he actually wanted to do: short-term-rental underwrites, institutional-style acquisition screens, downtown condo plays, and waterfront comps that require eyes on the ground. Today he is the broker of Mangrove Bay Realty, manages the Dunedin Duo STR, and answers his own phone.
What I've done
325+
Career sales
Since 2019 · $117K-$1.9M
6
Rental properties owned & managed
STR · midterm · furnished rentals
BK3436609
Broker
Mangrove Bay Realty
Where I add value
Find Troy elsewhere
Most of the market commentary lives on the journal here, but you'll also find Troy on these platforms.
From the journal
Market reads, neighborhood guides, STR underwrites — published when there's something real to say.

Should you sell your Pinellas vacation rental or keep it? When keeping works, the property tax reset at sale, depreciation recapture, 1031 timing and what to gather first.
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Can you run an Airbnb in Tarpon Springs, FL? Only in listed zones, most by conditional use. The 6 week line, the 1,200 foot rule, owner occupancy, condos and taxes.
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Can you Airbnb a condo in Indian Shores, FL? The town says it has no rental restrictions, so condo documents decide. State license, 13% taxes and the new beach rule.
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Can you Airbnb in Treasure Island, FL? Tourist dwellings are allowed only in CG, RFM-30, RFH-50 and PR-MU zones, not in RU-75 or RM-15. Zone table, taxes and licenses.
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Step-by-step Pinellas County buyer due diligence checklist: flood zones, property lines via GIS, inspection flags, insurance, and when to survey before you make an offer.
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Can you Airbnb in St. Pete Beach? Stays under 30 days are allowed only in RM zoning and the Pass-A-Grille Overlay, up to 3 times per 12 months. Monthly rentals are allowed.
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Before you write an offer, Troy checks the exact address against the city or county STR rules (for example St. Petersburg allows 3 stays per 365 days in residential zones, and unincorporated Pinellas Certificates of Use do not transfer, so a new owner applies within 30 days under Ord. 25-15), plus zoning, flood zone, insurance, and the numbers. As an Airbnb Superhost who owns and manages his own Pinellas rentals, he also tells you what operating the property will really take.
Troy prices an operating rental on what a buyer can legally do with it, then gets the records ready: permits and registrations, booking history, the furnishings list, and how future reservations hand off at closing. He markets it to buyers who understand STRs.
Yes. Troy Nowak is broker of Mangrove Bay Realty, Florida license BK3436609. He has 325+ closings since 2019 with a $523K average sale price, 45 Zillow reviews, and 56 Google reviews.
Pinellas County (St. Petersburg, Clearwater, Clearwater Beach, Largo, Indian Rocks Beach, Treasure Island, St. Pete Beach, and Madeira Beach) and Tampa. Call or text (727) 404-5530.
Drop your info — Troy texts back personally, usually within the hour.