Islamorada Hotels

    13 Hotels Found
    1. Cheeca Lodge & Spa
      Islamorada, Florida Keys, Florida
      • Beachfront
      • Historic
      • Kid-Friendly
      • Luxury
      • Resort
      • Romantic
      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…
    2. Casa Morada
      Islamorada, Florida Keys, Florida
      • Boutique
      • Luxury
      • Romantic
      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…
    3. Postcard Inn Beach Resort & Marina at Holiday Isle
      Islamorada, Florida Keys, Florida
      • Beachfront
      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…
    4. Islander Resort, a Guy Harvey Outpost
      Islamorada, Florida Keys, Florida
      • Beachfront
      • Kid-Friendly
      • Party
      • Romantic
      The Islander Resort, a Guy Harvey Outpost, is a mid-range, 114-room Islamorada property decorated in artist Guy Harvey's vibrant sea-themed artwork. The borderline kitsch style won't please everyone, but tourists flock to the hotel for its man-made beach, fishing pier, and abundant water-sports offerings…
    5. Chesapeake Beach Resort
      Islamorada, Florida Keys, Florida
      • Beachfront
      • Kid-Friendly
      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…
    6. Pelican Cove Resort Marina Hotel Islamorada
      Islamorada, Florida Keys, Florida
      • Beachfront
      • Boutique
      • Business
      • Kid-Friendly
      • Romantic
      Pelican Cove Resort Marina Hotel Islamorada is an upper-middle-range waterfront property within an easy drive of Islamorada's sights. Following 2014 renovations, this property offers 63 sleek and stylish rooms equipped with private balconies, mini-fridges, and coffeemakers. Along with a private beach…
    7. The Caribbean Resort at Sea Isle
      Islamorada, Florida Keys, Florida
      • Boutique
      • Kid-Friendly
      • Romantic
      The Caribbean Resort at Sea Isle is a stunning three-and-a-half pearl property offering 16 homes with individualized decor and impressive, modern kitchens. This picturesque venue -- a frequent spot for weddings -- also offers some unusual features, such as a microclimate pool surrounded by fruit trees…
    8. Amara Cay Resort
      Islamorada, Florida Keys, Florida
      • Beachfront
      • Kid-Friendly
      • Value
      The Islamorada Resort is in the process of transforming from a typical value hotel into a unique waterfront property located in the middle of The Florida Keys. With all of the activities and water sports available (including kayaking, boating, fishing, and diving), there is tons of stuff for guests to…
    9. Pines & Palms Resort
      Islamorada, Florida Keys, Florida
      • Beachfront
      • Boutique
      • Kid-Friendly
      • Value
      Set on a beach shaded by palm trees, Pines & Palms Resort is a mid-range resort on Islamorada made up of 26 bungalows that range from Budget Efficiencies to Three-Bedroom Cottages and villas. All of the bright and airy units have kitchens, and most have private patios or balconies plus daily housekeeping…
    10. Sands of Islamorada
      Islamorada, Florida Keys, Florida
      • Beachfront
      • Kid-Friendly
      • Value
      Sands of Islamorada is a nine-room budget property with a candy-pink facade and a charming Old Florida vibe. This quiet, relaxed hotel has a small private beach and fishing pier, a waterfront pool and hot tub, and beautifully landscaped grounds with coconut palms and tropical flowers. Rooms are basic…
    11. Drop Anchor Resort
      Islamorada, Florida Keys, Florida
      • Beachfront
      • Boutique
      • Kid-Friendly
      • Value
      The two-and-a-half pearl, 18-room Drop Anchor Resort is located on Windley Key in Islamorada, "the fishing capital of the world." The resort, very much in the laid-back "Old Keys" style, includes a man-made beach surrounded by thatched-roof umbrellas, hammocks, palm trees, loungers, picnic tables, and…
    12. Coral Bay Resort
      Islamorada, Florida Keys, Florida
      • Beachfront
      • Kid-Friendly
      • Value
      Coral Bay Resort -- a 17-room, budget hotel located in Islamorada -- offers a simple, bayside stay that's ideal for families and boaters. The waters surrounding the Coral Bay are excellent for fishing and snorkeling, and many guests park their boats right at the hotel for free. Rooms are clean and spacious…
    13. La Siesta Resort and Marina
      Islamorada, Florida Keys, Florida
      • Beachfront
      • Kid-Friendly
      La Siesta Resort and Marina is a waterfront hotel with a stellar location on the ocean, access to water sports, and a spacious pool deck with a tropical vibe. However, the majority of the hotel's 54 rooms are unimpressive, outdated, and more expensive than other nearby properties with the same location…

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