@Louis Zameryka
The houses that I own for STR are all in the 220-245k range, 3-4br in no or low HOA communities. But, I also manage them myself.
Regarding a 250k no-HOA house vs a large 5 to 9 bedroom resort house/community, it just depends on your market view. There are 2 schools of thoughts when it comes to STR in FL:
1. Low or no HOA houses - these are usually 3-4br houses in communities with few to no amenities. They are cheap to maintain, fixed costs are low and hence give you a lot of flexibility when it comes to pricing. The disadvantages are that since they are smaller and "cheaper", you have more competition (including hotels at that point), hard to find a property manager that will manage them (they are higher maintenance, you have to take out trash and recycles, etc), and there is a limit to how much you can charge since there is so much competition. With that being said, since most people now prefer Airbnb houses to hotel, they tend to do well as long as your place is well remodeled, unique, and well managed.
2. Large houses in rental communities - these are usually the 5+ bedrooms. I see them as a levered play on the STR market. They usually start in the mid 300s and can go as high as 500k as you well noticed. The monthly HOA fees can be substantial, but you can charge more. On the other hand, your competition is just those other resort houses. Big families and groups will usually prefer these, and can seem more attractive to the "resort" style traveler.
They both have pros and cons, that's why it will depend on your view. Want a starter house that you can manage yourself? Go with a no-HOA one. Want to go "big" on the STR market theme and have a professional property manager? Go with the resort-style house.
Serena