Laid-back family resorts are generally the standard in Islamorada in the Middle Keys. These upscale picks are exceptions.

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Casa Morada

Islamorada, Florida, United States

Originally opened in the 1950s, the 16-room Casa Morada is an intimate boutique hotel designed to be a relaxing retreat from the outside world. The elegant suite-style rooms, gorgeous tropical garden grounds, hammocks hanging between the trees, waterfront pool deck and bar, and Zen garden with rock grotto all contribute to the serene vibe. The crown jewel of the hotel is its own small private island, which is accessed by a white footbridge and features a freshwater pool and secluded cabana with panoramic views of the Florida Bay. Guests at Casa Morada can expect lots of freebies, including bicycle rentals, kayaks, paddleboards, snorkel equipment, Wi-Fi, and a daily gourmet breakfast.


Cheeca Lodge & Spa

Islamorada, Florida, United States

The 214-room Cheeca Lodge & Spa offers plenty of on-site features, like a nine-hole golf course, a pretty beach with a long fishing pier, a full-service spa, six tennis courts, and two pools (one for adults only). Three restaurants serve tasty seafood, sushi, and Italian fare, respectively, and there's a fun tiki bar on the beach. Spacious guest rooms with elegant tropical decor have private furnished balconies (some with outdoor jetted tubs), while suites add separate living rooms and some have full kitchens. There's a resort fee and it's steep, but covers a lot. Romantics looking for a more upscale and intimate (and adults-only) experience might prefer nearby Casa Morada, though it lacks a full-service restaurant.