Considering Florida vacation / rental condo again

[Kenneth LaVoie]

My wife and I are fully aware that just "renting" vs. buying a second home (and VRBO'ing it when we're not using it) is almost always going to be the better financial decision...however...here we are, about every 3 years, considering it again! there's just something about being able to go at a moment's notice and having a locked up closet where we keep our own supplies & some clothes, so we don't have to pack much. 

We would like to purchase a condo as close to the water as possible in a location that is not completely overrun with people but also somewhat desirable. It doesn't have to be the perfect place we would like to retire because we probably will never spend more than 2-3 months a year there as we plan to travel worldwide in just a few years. But it should be decent enough. We've stayed in Cocoa Beach and liked it but didn't love it. We've heard NOTHING but good about the Venice area and a little north and south of that. We would of course like a place that doesn't restrict rentals. Heard halfway decent things about Cape Coral. 

I haven't made our wishes 100% clear I know, but based on what I've said, what areas might make sense? 

[Villy Ellinger]

I'm in Fort Walton Beach, FL. Have three units here and yes, I self-manage (I agree with @Marc Jackson) and do have a profit for sure. Destin is more expensive and rather saturated, but places like Ft Walton Beach, Panama City Beach and Navarre Beach on the Emerald Coast still offer some reasonable beach deals. If you want to make a profit you probably cannot afford to give 20-30% or more of your gross to a management company. You will need to either self-manage completely or possibly self manage mostly and get some lower-cost (usually flat fee) admin/booking assistance with to deal with responding to guests right away, track inquiries, dispatch the cleaning crew, etc, but you'll still need to budget on putting in some hours managing your place.

I can't speak to other areas but the Florida Panhandle is definitely an option to consider. Good luck!