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 [Jan 16 - Jan 17](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-01-16&endDate=2026-01-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 17 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-01-17&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-01-23&endDate=2026-01-25&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) ![Marina](https://images.trvl-media.com/lodging/33000000/32800000/32791200/32791186/7959b4f4.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) ### 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 (210 reviews) "Absolutely wonderful property in every way!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher K. CA $417 CA $686 total includes taxes & fees Jan 30 - Jan 31 [](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 (170 reviews) "Everything was clean and in good condition. The owner responded right away to any questions. Golf Cart is a plus! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $754 CA $1,441 total includes taxes & fees Jan 29 - Jan 30 [](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) ![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33493000/33492930/758d3015.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) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33500000/33493000/33492930/107bfadb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW OCEANFRONT RESORT CASA MAR-NO RESORT OR MANAGEMENT FEES WHEN BOOKING WITH ME [](https://www.expedia.ca/Key-Largo-Hotels-CASA-MAR-OCEAN-VIEW-VOTED-1-2-King-Ensuites.h33492930.Hotel-Information) Rock Harbor 10/10 Exceptional (104 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 $935 CA $1,844 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Key-Largo-Hotels-CASA-MAR-OCEAN-VIEW-VOTED-1-2-King-Ensuites.h33492930.Hotel-Information) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34150000/34140800/34140748/2ef98d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, music library, video library](https://images.trvl-media.com/lodging/35000000/34150000/34140800/34140748/8cebb21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34150000/34140800/34140748/87625d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34150000/34140800/34140748/5d0da2ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS [](https://www.expedia.ca/Key-Largo-Hotels-Casa-Azul-THE-Salt-Life-Meets-Luxury-Chic-With-Beachy-Vibes-Free-Golf-Cart.h34140748.Hotel-Information) Key Largo 9.8/10 Exceptional (194 reviews) "We had a wonderful experience. The house had everything we needed for our family of 8\. We had the security of a gated community with the freedom to explore like it was a little private island. The house was clean and very accommodating. Host was so nice and communicated promptly anytime we needed her. We had so much fun and we are so thankful for the host and her property. Will visit again if given the opportunity. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alyssa I. CA $893 CA $1,616 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Key-Largo-Hotels-Casa-Azul-THE-Salt-Life-Meets-Luxury-Chic-With-Beachy-Vibes-Free-Golf-Cart.h34140748.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/33000000/32180000/32179700/32179681/4c8b67b3_edited_416f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/33000000/32180000/32179700/32179681/ceb45735_edited_dfad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/33000000/32180000/32179700/32179681/9ce2d3fd_edited_d426.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/33000000/32180000/32179700/32179681/9da6d310_edited_0408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 4BR/3BA • 8 Beds • Mariner’s Club Community • Perfect for Large Groups [](https://www.expedia.ca/Key-Largo-Hotels-Spacious-4BR3BA-8-Beds-Mariners-Club-Community-Perfect-For-Large-Groups.h32179681.Hotel-Information) Rock Harbor 10/10 Exceptional (71 reviews) "very clean, lots of beds, very comfortable common areas, great all around" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joe F. CA $813 CA $1,849 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Key-Largo-Hotels-Spacious-4BR3BA-8-Beds-Mariners-Club-Community-Perfect-For-Large-Groups.h32179681.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=2026-01-30&endDate=2026-01-31®ionId=10768&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Islamorada Hotel Reviews ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg) ### La Siesta Resort & Villas 10/10 Excellent "The kitchen had nothing in it, so plan ahead. No silverware at all. The room was as pictured, and the pool.and beach areas were very nice. Lots of restaurants super close. Shopping nearby as well" [](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "So much luxury!" [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.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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