I don't know about houses on the beach in North America because I avoid those areas, but here are a couple excellent choices for international destinations that I recommend:
Any of the islands in the Maldives, especially the northern and central islands during this time of year (lots of afternoon showers in the late afternoon in the southern areas), but good weather year-round basically, sun every day. Great people, VERY tourist friendly. Expensive, but very worth it. Vacation place would actually be one of those houses that you see are actually IN the water (Google Maldives vacation and you should find some examples) and the water is probably the best in the world I have ever seen. Lots of tropical fish, easy swimming right outside of your door if you wish, great water sports, including surfing, speed boats, snorkeling and of course swimming. Good bars and decent nightlife as well if you are into that type of thing.
Koh Samui off of the coast of Thailand is another favorite of mine. Very nice island, and VERY cheap as well. I would say about 5 times cheaper than going to the Maldives. If your only staying a week there you could get the hotel or even a bungalow right on the beach for $25-150 USD per night, a pretty good price compared to the Maldives. Drinks and food are very cheap, and there is lots to do. Animals, safaris, kite boarding, snorkeling, you name any water sport this place has got it. If you were on a budget, I would say you could stay for a week for around $1000 maybe even less, including room and first rate restaurants and going out each night. There are a few great sports bars on the island as well. Only bad thing about this is that you would have to shell out the $1000+ for the plane ticket to BKK and then take a speed boat ride to the island, there is an airport there but no flights from the U.S. generally.
Anyways, those are just a few international destinations I can recommend you when it comes to staying on the beach somewhere nice. If you are looking to buy in the two areas I listed, expect to pay a lot to live in the Maldives and way less in Koh Samui. The benefit you would have is I believe they have no laws about sports betting and/or gambling in these areas (I heard somewhere that gambling and huge mega-casinos are expanding throughout Asia), is you could place any sports wagers you wanted with whatever book you wanted to. Overall, two great places to vacation/live during the fall/winter months.