The Florida Keys Hotels

Throughout the Keys, the types of accommodations are remarkably varied, from 1950s-style motels to cozy inns to luxurious resorts. Most are on or near the oc... Read More

9 Matching Hotels

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1. Casa Morada

$$ | MM 82 BS, 136 Madeira Rd., Islamorada, Florida, 33036, United States

This relic from the 1950s has been restyled into a suave, design-forward, all-suites property with outdoor sho... Read More

2. Cheeca Lodge & Spa

$$ | MM 82 OS, Islamorada, Florida, 33036, United States

At 27 acres, this may be the largest resort in the Keys, and it's also big on included amenities. In the main... Read More

3. Chesapeake Beach Resort

$ | MM 83.5, 83409 Overseas Hwy., Islamorada, Florida, 33036, United States

This boutique hotel on the beach mixes modern conveniences with a retro look. High-tech gadgets like flat-scre... Read More

4. Drop Anchor Resort and Marina

$ | MM 85 OS, 84959 Overseas Hwy., Islamorada, Florida, 33036, United States

Immaculately maintained, this place has the feel of an old friend's beach house. And it's easy to find your un... Read More

5. Ocean House

$$$ | MM 82 OS, 82885 Old Hwy., Islamorada, Florida, United States

Islamorada's newest adult boutique hotel is situated right on the Atlantic, yet it's hidden from passersby ami... Read More

6. Postcard Inn Beach Resort & Marina at Holiday Isle

$$ | MM 84 OS, 84001 Overseas Hwy., Islamorada, Florida, 33036, United States

After an $11-million renovation that encompassed updating everything from the rooms to the public spaces, this... Read More

7. Ragged Edge Resort

$ | MM 86.5 OS, 243 Treasure Harbor Rd., Islamorada, Florida, 33036, United States

Nicely tucked away in a residential area at the ocean's edge, this family-owned hotel draws returning guests w... Read More

8. The Islander, A Guy Harvey Outpost Resort

$$ | MM 82.1 OS, 82200 Overseas Hwy., Islamorada, Florida, 33036, United States

Guests here get to choose between a self-sufficient town home on the bay with room for a boat, or an oceanfron... Read More

9. The Moorings Village

$$$$ | MM 81.6 OS, 123 Beach Rd., Islamorada, Florida, 33036, United States

This tropical retreat is everything you imagine when you think of the Keys—from hammocks swaying between tower... Read More

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