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Our top choices for Islamorada historic hotels

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Key Largo Kawama villa K1, 3/3

Key Largo Kawama villa K1, 3/3
Key Largo
9.8 out of 10, Exceptional, (188 reviews)
"Great place, the lake outside was amazing. Would stay here again. "
United States
Spencer H.
The price is AED 1,157
AED 2,341 total
includes taxes & fees
19 May - 20 May
Key Largo Kawama villa K1, 3/3
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Key largo Kawama Villa N2

Key largo Kawama Villa N2
Key Largo
9.6 out of 10, Exceptional, (134 reviews)
"The condo was perfectly appointed with everything we would want or need, including some snorkel masks, beach towels, bikes. Really a wonderful stay. Thanks."
United States
Wendy R.
The price is AED 1,138
AED 2,319 total
includes taxes & fees
19 May - 20 May
Key largo Kawama Villa N2
Fridge, microwave, oven, stovetop

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

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Tavernier
9.8 out of 10, Exceptional, (217 reviews)
"Our stay was amazing, I highly recommend Heidi and this location!"
United States
Becky S.
The price is AED 909
AED 1,601 total
includes taxes & fees
24 May - 25 May
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
On the beach, sun loungers, beach towels

NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS
Key Largo
9.8 out of 10, Exceptional, (199 reviews)
"The place is beautiful love having the golf cart also."
United States
Tina W.
The price is AED 1,737
AED 3,480 total
includes taxes & fees
31 May - 1 Jun
NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS
Beach

SOMBRERO BEACH LARGE 4/3 HOME w/ HEATED POOL, 40 ft BOAT DOCK, BEACH NEARBY

SOMBRERO BEACH LARGE 4/3 HOME w/ HEATED POOL, 40 ft BOAT DOCK, BEACH NEARBY
Marathon
9.8 out of 10, Exceptional, (63 reviews)
"This was our second time staying in this house lots of room great location."
United States
Anonymous traveler
The price is AED 1,095
AED 3,794 total
includes taxes & fees
30 May - 31 May
SOMBRERO BEACH LARGE 4/3 HOME w/ HEATED POOL, 40 ft BOAT DOCK, BEACH NEARBY
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

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 20 hours ago
La Siesta Resort & Villas
Islander Resort

Islander Resort

10/10 Excellent
"Yes"
Loyce 2-night trip
Posted 2 days ago
Islander Resort

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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.