Historic Hotel in Islamorada: Best Resorts in Florida Keys

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Top Islamorada Historic Hotels

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Tavernier

Toni M.

$382 nightly

Dec 9 - Dec 10

Total with taxes and fees

Ohana Cay 2brm/2bth - Book your getaway!

Rock Harbor

Gene Z.

$725 nightly

Jan 3 - Jan 4, 2026

Total with taxes and fees

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Top Islamorada Hotel Reviews

La Siesta Resort & Villas

10/10 Excellent

"Great stay and beautiful space"

Islander Resort

10/10 Excellent

"The room was perfect and the outdoor space was great for morning coffees and reading!"

Frequently asked questions

What should a history enthusiast expect from a trip to Islamorada?

You're likely already making plans to see the sights of historical relevance during your vacation in Islamorada. And while you're here, you can check out the entertainment choices and scenic seaside. And also relish a stop at the seafood restaurants in this relaxing area.

How many historically relevant hotels will I find in Islamorada?

In Islamorada, you'll find 908 hotels and other accommodations bookable on Expedia though not many historic hotels to choose from.

What are the must-see historical sites and other places to visit in Islamorada?

Favorite places to visit include Everglades National Park, Florida Keys Brewing Co., and Bud n' Mary's Dive Center. A couple of additional sights to add to your agenda are Founders Park and Anne's Beach.

What is a historic hotel like in Islamorada?

Guests who book a historic hotel can enjoy a vacation in a place that has an official historic designation. A palace, castle, grand home or even an old police station, pub, lodge, or skyscraper can be transformed into a historic hotel as long as it's of special interest. Traditional architecture and period features are typically preserved within the guestrooms or public spaces of historic hotels in Islamorada, giving a real sense of character.

What is the difference between a historic hotel and a heritage hotel?

You'll often hear the term "heritage hotel" in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. though overall the terms are quite similar. The architecture and actual building of a historic hotel tends to be the most significant aspect. For a heritage hotel, it's often the cultural value as well as how it influenced the community.

Do historic hotels in Islamorada have modern facilities?

Hotels have the safety features and modern conveniences you expect to find, while every effort is made to preserve treasured traditions and historic facades. WiFi, heating and air conditioning, updated bathroom facilities, and the usual amenities found in most hotels will be available in a historic hotel. Rest assured that when you choose a historic hotel in Islamorada, you won't find yourself staying at a place that is rundown or uncomfortable.

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