Title: Book the Best HISTORIC Hotels in Islamorada in 2026 | Expedia.ca [Islamorada Travel Guide](https://expedia.ca/Islamorada.dx10768)[Hotels in Islamorada](https://expedia.ca/Islamorada-Hotels.d10768.Travel-Guide-Hotels)[Vacation Rentals in Islamorada](https://expedia.ca/Islamorada-Vacation-Rentals.d10768.Travel-Guide-VacationRentals)[Flights to Islamorada](https://expedia.ca/Cheap-Flights-To-Islamorada.d10768.Travel-Guide-Flights)[Things to do in Islamorada](https://expedia.ca/Things-To-Do-In-Islamorada.d10768.Travel-Guide-Activities)[Islamorada Car Rentals](https://expedia.ca/Car-Rentals-In-Islamorada.d10768.Car-Rental-Guide)[Islamorada Vacation Packages](https://expedia.ca/Islamorada.d10768.Destination-Travel-Guides) ![Islamorada featuring a sunset and general coastal views](https://images.trvl-media.com/place/10768/7014979e-dcd6-42fa-a69b-b138a0a93305.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/10768/7014979e-dcd6-42fa-a69b-b138a0a93305.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Islamorada Historic Hotels Tonight [Mar 2 - Mar 3](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-03-02&endDate=2026-03-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 3 - Mar 4](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-03-03&endDate=2026-03-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-03-13&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Islamorada historic hotels ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/03c452e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/dd3c2d84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/dcaa469a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/7959b4f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures [](https://www.expedia.ca/Tavernier-Hotels-Florida-Keys-Luxury-Houseboat.h32791186.Hotel-Information) Tavernier 9.8/10 Exceptional (214 reviews) "Absolutely wonderful property in every way!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher K. CA $542 CA $860 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Tavernier-Hotels-Florida-Keys-Luxury-Houseboat.h32791186.Hotel-Information) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34150000/34143300/34143275/ee01b3bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/35000000/34150000/34143300/34143275/237e34eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34150000/34143300/34143275/b96653e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/35000000/34150000/34143300/34143275/cdbcc55f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS [](https://www.expedia.ca/Key-Largo-Hotels-Casa-Palma-Live-THE-Lavish-Keys-Life-Vibrant.h34143275.Hotel-Information) Key Largo 9.8/10 Exceptional (172 reviews) "Loved this place and will stay again if we go back to the Keys. Gated community with golf cart to go to the pier with great community resources, grills and sitting areas. Favorite part was the lagoon in the middle of the community not far from the screened in back porch. Full of fish you can swim with and calm beach area that is clean and nice with shade when you need it. We didn’t want to leave this place. Highly recommend!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chandler G. CA $877 CA $1,587 total includes taxes & fees Mar 18 - Mar 19 [](https://www.expedia.ca/Key-Largo-Hotels-Casa-Palma-Live-THE-Lavish-Keys-Life-Vibrant.h34143275.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33500000/33493000/33492930/d09fe7c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33500000/33493000/33492930/81254fdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33500000/33493000/33492930/3bcaca6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33493000/33492930/758d3015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES [](https://www.expedia.ca/Key-Largo-Hotels-CASA-MAR-OCEAN-VIEW-VOTED-1-2-King-Ensuites.h33492930.Hotel-Information) Rock Harbor 9.8/10 Exceptional (107 reviews) "Loved the location, the decor and the pool area!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laureen h. CA $1,248 CA $2,226 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Key-Largo-Hotels-CASA-MAR-OCEAN-VIEW-VOTED-1-2-King-Ensuites.h33492930.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-16&endDate=2026-03-17®ionId=10768&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_10768) ## Top Islamorada Hotel Reviews ![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "Our king room was spacious and clean with a very comfortable bed and nice linens. Very well maintained grounds and a nice bar by the pool with a great view of the ocean. I would definitely recommend! " [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg) ### La Siesta Resort & Villas 10/10 Excellent "Great staff. Coffee machine in room was defective. Curtains dirty and faulty closing. Everything else clean and convenient." [](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to Islamorada? ### How many historically relevant hotels will I find in Islamorada? ### What are the must-see historical sites and other places to visit in Islamorada? ### What is a historic hotel like in Islamorada? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Islamorada have modern facilities? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Cheap-Hotels.0-0-d553248635083902001-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Luxury-Hotel.0-0-d553248635083902001-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Brickell ](https://www.expedia.ca/Brickell-Miami-Hotels-Adults-Only-Resorts.0-n6240961-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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