This one is for the architectural adventurists: an experimental structure designed in 1950 by Paul Rudolph and Ralph Twitchell, on Siesta Key near Sarasota, FL. Small (800 sq. ft.) and strange(but very cool!)-looking, the Cocoon/Healy Guest House (click link for slide show) has a curved roof made of steel straps, and glass walls with wood jalousies. Two bedrooms, one bath; boat dock; fully wired. Available for year-round rental at $1,250/month, unfurnished (you wouldn’t need much). For further details, contact Martie Lieberman, 941/724 1118, modernsarasota.com.
Could this be your warm-weather pied a terre?
casaCARA: Old Houses for Fun & Profit 