Casa Marina, A Waldorf Astoria Resort

At any moment, you expect the landed gentry to walk across the oceanfront lawn of this luxurious resort, just as they did when this 13-acre resort was built back in the 1920s. This property is on the largest private beach in Key West and it has the same richly appointed lobby with beamed ceilings, polished pine floor, and original art as it did when it was built.

The 311 rooms of the Casa Marina Resort have a light, sophisticated, but still island-y feel, with neutral tones, sheer curtains, and sleek hardwood or tiled floors. The resort also offers great in-room amenities, including free Wi-Fi, flat-screen TVs, and espresso machines.

This pedigreed grande dame resort was conceived by Henry Flagler, the magnate whose railroad first opened up the island (and much else in Florida) to unprecedented commerce and well-heeled tourism, but finished only after his death. Its fortunes have waxed and waned since the doors first opened in 1920, but in 2007 the property underwent an overhaul that, beyond the cosmetic, also put in place many eco-friendly improvements such as recycling systems and more efficient energy use.

Since opening its doors on New Year's Eve in 1920, the Waldorf Astoria-owned Casa Marina has served as a beachfront hideaway for Hollywood's elite (Rita Hayworth and Gregory Peck have both rested their heads here) and everyday travelers. Situated on a private beach (Key West's biggest), the landmark hotel underwent a major $43 million renovation back in 2007, which brought state-of-the-art amenities and a breezy, tropical style to the Art Deco grande dame's 311 rooms and suites – all of it just a short walk to bustling Duval Street.

Part of this hotel was built in 1921 by Henry Flagler, the other building wings were built in the 1980s. Guest rooms and suites are available with ocean views, many with balconies or patios.