Location suggestions in Florida

[Nathan Gesner]

Help me out, folks!

I'm in the market for a vacation rental in Florida. Our winters get pretty cold so we intend to use it for shorter vacations right now but will eventually use it for working vacations (30 - 90 days at a time). This will be a shared home for us and our good friends, either taking turns or even vacationing together. I am looking for towns/areas to consider, not specific homes. We plan to purchase in the next 3-6 months.

• WARM: It has to be a warm place in the winter. I've spent a lot of time in the Pensacola/Destin area and the winters are too cold. We need a place that will chill our Wyoming bones in the winter months (most likely December - March).
• WATER: it could be a beach house (sunsets are a favorite) but would consider lakes, canals, or other bodies of water for canoes, paddle boards, swimming, sunsets, etc.
  WALK: It must be good for long walks with our dogs and friends. That can be in a quiet residential area, on the beach, or in a nearby park.
  WINE: We enjoy good eateries, drink, and live entertainment. We know how to enjoy life without the hustle-and-bustle of the big city so something more rural is preferred.
  WINGS: Within 1-2 hours of a good airport but we'll consider anything. 
  WEEKEND GETAWAY: The home will be rented out when we're not using it. Zoning must allow for vacation rentals, the location should be attractive to potential renters, and we'll need a property manager.
  WEALTH: Low on the priority list. We want something that pays for itself and our travel out there. A net of $10,000 is sufficient; anything above that would be icing on the cake.

I hope you enjoy the effort put into my "W" list! If you know of an area or specific town for me to consider, I would love the recommendations. We're hoping to take a trip this winter to check out specific spots and start shopping.