Islamorada Hotels
4 Hotels Found
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Cheeca Lodge & Spa

Cheeca Lodge & Spa Rating: 4.5 Pearls

The 114-room Cheeca Lodge was one of the original luxury properties on Islamorada, dating to 1946 and earning plenty of celebrity cachet over the years (high-profile guests have included George W. Bush). The property was rebuilt after a fire gutted its main building in 2009, and now has bright, spacious rooms with tropical-luxe decor and massive bathrooms. The lush grounds are especially pretty at night, with Tiki-torch-lit paths. But the hotel's beach is manmade -- there's even a rock ledge on the water's edge -- making it muddy at times and less than ideal for swimmers and waders. And the family pool can get crowded; those traveling without children will probably prefer the much calmer adult-only pool.
Casa Morada

Casa Morada Rating: 4.0 Pearls

Inspired by a laidback Caribbean lifestyle, Casa Morada is an upscale 16-suite boutique hotel that’s perfect for couples looking for a romantic getaway, whether for a honeymoon or just because. Situated right next to the ocean in the middle of the Florida Keys on Islamorada, the hotel provides a peaceful and serene atmosphere with hanging hammocks and lots of fun and free activities like yoga classes, kayaking, and bicycle rentals. Compared to nearby hotels, this property offers great value with spacious and upscale rooms with water views.
Chesapeake Beach Resort

Chesapeake Beach Resort Rating: 3.0 Pearls

Chesapeake Beach Resort is a 65-room, mid-range hotel, offering a wide range of beach and outdoor activities. More of a family-friendly property than a romantic getaway, this hotel sits halfway between Miami and Key West, has its own private beach, and is located near plenty of restaurants and local attractions like the Windley Key Fossil Reef Geological State Park, the History of Diving Museum, and the Theater of the Sea. While the views are great, and the atmosphere is laid-back, the resort has seen better days, and could use an update. Watch out for a pesky resort fee.
Postcard Inn Beach Resort & Marina at Holiday Isle

Postcard Inn Beach Resort & Marina at Holiday Isle Rating: 3.0 Pearls

Located in Islamorada, Postcard Inn is a 150-room mid-range hotel that sits right on the water in the middle of the Florida Keys. There's lots to do on the property, with multiple dining options, happy hour with live music, boating and water-related sports, and family-friendly activities. The inn’s rates are competitive and similar to nearby hotels in the same category. Though much of the property has updated, contemporary nautical themes, some rooms, particularly bathrooms, could use further renovations.


Oyster Pearl Rating

  • Award-Winning

What's Your Style?

  • Kid-Friendly
  • Luxury
  • Beachfront
  • Romantic
  • Boutique
  • Historic
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  • Islamorada
  • Duck Key
  • Key Largo
  • Key West
  • Little Torch Key
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  • Air Conditioner
  • Babysitting Services
  • Balcony
  • Business Center
  • Cabanas at Pool
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