Find Historic Hotels in Islamorada, FL

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Check availability on Islamorada Historic Hotels

Tonight
3 May - 4 May
Tomorrow
4 May - 5 May
Next weekend
8 May - 10 May
In two weeks
15 May - 17 May

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 964
AED 2,080 total
includes taxes & fees
4 May - 5 May
Key Largo Kawama villa K1, 3/3
On the beach

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 1,192
AED 2,375 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 1,010
AED 1,726 total
includes taxes & fees
17 May - 18 May
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Outdoor pool, a heated pool

NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES

NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES
Rock Harbor
10.0 out of 10, Exceptional, (111 reviews)
"Nicely decorated and nice location. "
United States
Rob L.
The price is AED 2,472
AED 4,878 total
includes taxes & fees
10 May - 11 May
NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES
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 3,640 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

10/10 Excellent
"La Siesta is one of those places where the setting does most of the work. The ocean views, beach access, and relaxed atmosphere are great"
Fabiola 2-night trip
Posted 13 hours ago
La Siesta Resort & Villas
Islander Resort

Islander Resort

10/10 Excellent
"Wonderful resort. Immaculate grounds. Just a very happy place."
JAMAL 2-night trip
Posted 3 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 877 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 Robbie's of Islamorada. A couple of additional sights to add to your agenda are Anne's Beach and Fiesta Key.
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.