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Hotels in Islamorada
15 Hotels
Postcard Inn Beach Resort & Marina
84001 Overseas Hwy

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.

Chesapeake Beach Resort
83409 Overseas Hwy, P.O. Box 909

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. 

Islander Resort
82100 Overseas Highway, Mile Marker 82.1 Oceanside

The Islander Resort is a mid-range, 114-room Islamorada property decorated in artist Guy Harvey's vibrant sea-themed artwork. Tourists flock to the hotel for its man-made beach, fishing pier, and abundant water-sports offerings. Set on 22 acres, the hotel has a waterside seafood restaurant and bar, two outdoor pools, and a hot tub plus barbecue grills and hammocks for laid-back evenings. Oceanfront rooms and suites feature kitchenettes or kitchens plus screened-in patios. While the hotel was badly damaged during Hurricane Irma in 2017, that gave the property a chance to renovate and rooms are now fresh and modern. Travelers may want to also check out the Pelican Cove Resort Marina Hotel Islamorada, where rooms are more modern.

Coral Bay Resort
75690 Overseas Hwy, MM 75.5 Bayside

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, with flat-screen TVs and microwaves, but the style is simple and dated -- expect to see tropical floral prints and faded wall art. Sunset views are great, and the atmosphere is laid-back, but the low(ish) rates here mean few frills. Rooms at the Pelican Cove Resort are more modern, but expect higher rates.