Annual vs Seasonal Condo Rental

[Kyle Smaagard]

Hey folks,

I have an opportunity to purchase a 2 bedroom 2 bath condo down in Naples FL from a friend. Listed for 180k currently, I haven't asked specifically on a price but am estimating around 150k for planning purposes. I currently own three properties (VA, NM, and MS) that are all annual rentals (I'm in the military and purchase wherever I go).

I'm trying to figure out if it would be better to hold as a seasonal rental or annual rental. My plan (right now) is to contact a property management company and ask them some questions since they know the local area but I was wondering if anyone on BiggerPockets had any advice.