$55,000/month

Wake up in Port Royal, pour a coffee on the loggia, and walk to the Gulf while the morning is still yours. This turnkey furnished Mediterranean residence on Gordon Drive was built for exactly this kind of season — arrive with a suitcase and start living. Step through the arched mahogany doors into a two-story great room where light pours down from clerestory windows and a carved stone fireplace anchors the room. Beyond it, a walled courtyard opens like a private retreat: a heated pool and raised spa glowing against mosaic tile and wrought-iron niches, a covered lanai with gas grill and lounge seating, and nothing but palms and sky overhead. Dinners come easy here. The chef's kitchen has double ovens, gas cooktop, an island built for gathering, and a wet bar with wine cooler for the pre-dinner pour. Everyone spreads out afterward — the family room's media wall, the paneled study, the upstairs terraces. With 4 bedrooms plus a den, 5 full and 1 half baths, and 4,669 square feet across two floors served by a private elevator, guests come and go without ever crowding each other. The main-level primary suite opens straight to the pool and retreats to a spa bath with soaking tub and stained-glass light. Third Street South and Fifth Avenue are minutes away; the sand is closer than that.