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10 Questions to Ask Before Hiring a Vacation Rental Manager
Interviewing vacation rental managers? These 10 questions on fees, licensing, taxes, and guest care reveal the right fit before you sign.

Ryan Osborne
7 hours ago4 min read
Where to Eat on Anna Maria Island: A Local's Guide
Where to eat on Anna Maria Island in 2026: toes-in-the-sand seafood, Old Florida burger shacks, and the comeback of a beloved fine-dining icon.

Ryan Osborne
Oct 164 min read
Security Deposits vs Damage Protection for Vacation Rentals
Security deposit, damage waiver, or platform protection? What actually covers guest damage at your vacation rental — and what each costs you in bookings.

Ryan Osborne
Oct 144 min read
Largo, FL: Renting Out Your Home Near the Gulf Beaches
Nightly rentals are legal in Largo's residential zones, and a new $600 registration program starts January 2027. What Largo, FL rental owners must know.

Ryan Osborne
Oct 125 min read
Best Restaurants in St. Petersburg, FL: A Local's Guide
Where to eat in St. Petersburg, FL: Michelin-recommended spots, Central Avenue favorites, Old Florida smoked fish, and waterfront dining on Beach Drive.

Ryan Osborne
Oct 94 min read
Vacation Rental Guest Screening That Doesn't Kill Bookings
How to screen vacation rental guests without losing bookings: what Airbnb and Vrbo already check, red flags worth a question, and tools that work.

Ryan Osborne
Oct 75 min read
Tampa Airbnb Management: What City Owners Need to Know
No city STR ordinance, a new county registry in 2027, and a 13.5% tax stack — what Tampa Airbnb owners need to know, from a local management team.

Ryan Osborne
Oct 54 min read
Tampa with Kids: Busch Gardens, ZooTampa & More
Planning a family trip to Tampa? A local's guide to Busch Gardens, ZooTampa, the Florida Aquarium, and free fun along the 2.6-mile Riverwalk.

Ryan Osborne
Oct 24 min read
Heated Pools in Florida Rentals: Cost vs Booking Lift
What pool heating really costs Florida rental owners — gas vs heat pump vs solar — and why a heated pool books more winter nights on the Gulf Coast.

Ryan Osborne
Sep 304 min read
St Pete Beach Short-Term Rental Management: Owner's Guide
Where short-term rentals are legal in St Pete Beach, the licenses and taxes owners need, and why monthly rentals are the play in residential zones.

Ryan Osborne
Sep 284 min read
St Pete Beach & Pass-a-Grille: A Visitor's Guide
Plan your St Pete Beach trip: Pass-a-Grille's historic streets, Shell Key, the Don CeSar, the Corey Avenue Sunday Market, and how to get around.

Ryan Osborne
Sep 254 min read
Should Your Vacation Rental Allow Dogs? The ROI Case
Allowing dogs can widen your booking pool and add fee revenue. The honest ROI math for Gulf Coast vacation rental owners — plus how to limit the risk.

Ryan Osborne
Sep 234 min read
Vacation Rental Management in Sarasota, FL: What to Expect
What Sarasota vacation rental owners should expect: city registration, county 30-day rules, taxes, seasonality, and what good management handles.

Ryan Osborne
Sep 214 min read
Gulfport, FL: Art Walks, Dining & Old-Florida Charm
Gulfport, FL packs art walks, a Tuesday market, waterfront dining, and Old-Florida charm into a few walkable blocks on Boca Ciega Bay. A local's guide.

Ryan Osborne
Sep 184 min read
Furnishing a Vacation Rental That Books: Room-by-Room
A room-by-room furnishing checklist for vacation rental owners: what earns bookings and five-star reviews on the Gulf Coast — and where to save.

Ryan Osborne
Sep 164 min read
Siesta Key Vacation Rental Management: An Owner's Guide
Zoning decides everything on Siesta Key. What rental owners need to know about the 30-day rule, weekly-rental condos, taxes, and local management.

Ryan Osborne
Sep 144 min read
A Weekend in Bradenton: Riverwalk & Old Florida Charm
Plan a weekend in Bradenton, FL: the Riverwalk, Village of the Arts, Robinson Preserve, Cortez fishing village, and where Old Florida still lives.

Ryan Osborne
Sep 114 min read
Direct Bookings vs Airbnb & Vrbo: Cutting Platform Fees
Airbnb's 15.5% host-only fee is here. What direct bookings really cost Gulf Coast rental owners — and when cutting platform fees actually pays off.

Ryan Osborne
Sep 94 min read
Anna Maria Island Vacation Rental Management: Owner Guide
Own a rental on Anna Maria Island? Holmes Beach certificates, Bradenton Beach rules, the 13% Manatee tax stack, and what local management should handle.

Ryan Osborne
Sep 74 min read
Things to Do in Sarasota: Arts, Beaches & the Bayfront
From the Ringling and the new Mote SEA aquarium to Siesta Key sand and free bayfront events, a local's guide to filling a Sarasota vacation.

Ryan Osborne
Sep 44 min read
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