Find Historic Hotels in Islamorada, FL

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Check availability on Islamorada Historic Hotels

Our top choices for Islamorada historic hotels

Room, 1 King Bed, Bay View | Beach/ocean view

Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay
2.5 star property
Key Largo
8.8 out of 10, Excellent, (1,014 reviews)
"Great location."
United States
Linda
The price is AED 458
AED 516 total
includes taxes & fees
2 Jun - 3 Jun
Hampton Inn Key Largo Manatee Bay
Bar (on property)

Fairfield Inn & Suites by Marriott Marathon Florida Keys

Fairfield Inn & Suites by Marriott Marathon Florida Keys
3.0 star property
Marathon
9.2 out of 10, Wonderful, (1,133 reviews)
"Staff and rooms and breakfast were great!"
United States
peggy
The price is AED 625
AED 703 total
includes taxes & fees
31 May - 1 Jun
Fairfield Inn & Suites by Marriott Marathon Florida Keys
3 restaurants, breakfast, lunch, dinner served; American cuisine

Reefhouse Resort & Marina

Reefhouse Resort & Marina
4.5 star property
Key Largo
9.4 out of 10, Exceptional, (1,440 reviews)
"Our visit to the Reefhouse was wonderful, staff was top notch and we loved the property."
United States
Michele
The price is AED 951
AED 1,217 total
includes taxes & fees
21 May - 22 May
Reefhouse Resort & Marina
Private beach, white sand, sun loungers, beach towels

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,730 reviews)
"Great breakfast and very friendly staff "
United States
Larry
The price is AED 634
AED 920 total
includes taxes & fees
8 Jun - 9 Jun
Chesapeake Beach Resort
Sundeck

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,137 reviews)
"Had a great stay just what we wanted "
Canada
Elizabeth
The price is AED 438
AED 493 total
includes taxes & fees
21 May - 22 May
Rock Reef Resort
Hibiscus Waterfront 2-Bedroom, Two Bath Master Suite (Brand New) | Terrace/patio

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1,297 reviews)
"Had a great time, this location was wonderful"
United States
John
The price is AED 475
AED 699 total
includes taxes & fees
26 May - 27 May
Lime Tree Bay Resort
Exterior

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very Good, (1,009 reviews)
"Beautiful scenery and well-maintained."
United States
Cindy Everhart
The price is AED 496
AED 678 total
includes taxes & fees
3 Jun - 4 Jun
Fisher Inn Resort & Marina
Exterior

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
8.8 out of 10, Excellent, (1,001 reviews)
"Can recommend the location, good breakfast, nice restaurants"
Germany
Hanspeter
The price is AED 1,260
AED 1,620 total
includes taxes & fees
2 Jun - 3 Jun
Playa Largo Resort & Spa, Autograph Collection
On the beach, sun loungers, snorkeling, kayaking

Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,000 reviews)
"Great family atmosphere definitely will be back again "
United States
ELIO
The price is AED 658
AED 781 total
includes taxes & fees
21 May - 22 May
Drift Hotel
Balcony

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,315 reviews)
"Amazing place and wonderful stay. "
United States
Danielle
The price is AED 996
AED 1,389 total
includes taxes & fees
3 Jun - 4 Jun
Cheeca Lodge & Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Islamorada Hotel Reviews

Islander Resort

Islander Resort

6/10 Okay
"Was not worth the 1200 per night we spent! "
Thomas 2-night trip
Posted 6 hours ago
Islander Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

6/10 Okay
"La Siesta has so much potential. Beautiful grounds, spacious rooms, pool and views. The front counter staff and bike staff were very nice. Unfortunately they don’t clean up the trash around the compound. To either side of our entrance was trash that had been there before us and Is probably still there. Our room had black sharpie all over the floors. There were no cups, plates, silverware… to use with the small kitchen. The couch and drapes were dirty. The freezer was a block of ice. Need more hangers in the closet. The bicycles, kayaks were not available for use until 9:30am and had to be back by 4pm (hottest part of a Florida day). The snack shack/bar at the pool opened late and closed early. Our room was cleaned once in six days. For the cost I shouldn’t be typing any of this."
Timothy 5-night trip
Posted 2 days ago
La Siesta Resort & Villas

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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 841 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, Bud n' Mary's Dive Center, and Islamorada County Park. A couple of additional sights to add to your agenda are Robbie's of Islamorada 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.