Title: 5 Stars Hotels in Islamorada, Florida from CA $226 - Find Cheap Islamorada Hotels With 5 Stars | 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 which includes tropical scenes and a sandy beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63860-Islamorada.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Islamorada, Florida from CA $226 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 5 Star Hotels Tonight [Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2025-09-28&endDate=2025-09-29&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 29 - Sep 30](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2025-09-29&endDate=2025-09-30&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2025-10-03&endDate=2025-10-05&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Islamorada 5 Star Hotels ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/981feca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/e32d7e53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/79d31a44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheeca Lodge & Spa Matecumbe 9.2/10 Wonderful (1214) "Beautiful and relaxing hotel!!" CA $117 CA $226 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/94000000/93070000/93061400/93061348/9b3c41b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/94000000/93070000/93061400/93061348/2c922f43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/94000000/93070000/93061400/93061348/5de75c93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/94000000/93070000/93061400/93061348/ab76abc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in the Keys Tavernier 8.8/10 Excellent (9) "Thoroughly enjoyed our stay! The pool, beach area and pickleball courts were fantastic! Also enjoyed the premium cable. " [](https://www.expedia.ca/Tavernier-Hotels-Condo-In-The-Keys.h93061348.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/691ffb10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, memory foam beds](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/478c87a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![75-inch Smart TV with digital channels, Netflix, streaming services](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/e85faba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/cc96c50e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront House with Boat Dock Hammer Point 6.0/10 (1) "Covered porch was nice for time outside. Inside was in need of work. Closets unfinished, no place to put any luggage, advertises a king bed and a queen bed, but only had a king and a full, no tp, or tissue products when we arrived. None of the above were deal breakers but just allot of small things that add up to frustration." [](https://www.expedia.ca/Tavernier-Hotels-Waterfront-House-With-Boat-Dock.h109724487.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Islamorada-Hotels.s50-0-d10768.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Islamorada-Hotels.s50-0-d10768.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Islamorada. ![Baker's Cay Resort Key Largo, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/bbdba544_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Baker's Cay Resort Key Largo, Curio Collection by Hilton 97000 Overseas Hwy, Key Largo, FL CA $365 CA $488 total Sep 30 - Oct 1 includes taxes & fees 8.6/10 Excellent! (1,021 reviews) [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Amara Cay Resort 80001 Overseas Hwy, Islamorada, FL CA $227 CA $348 total Oct 1 - Oct 2 includes taxes & fees 8.8/10 Excellent! (1,258 reviews) [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Islander Resort 82100 Overseas Highway, Islamorada, FL CA $261 CA $387 total Oct 2 - Oct 3 includes taxes & fees 9/10 Wonderful! (1,014 reviews) [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) Still don't see what you're looking for? [See all properties in Islamorada.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=29%2F09%2F2025&endDate=30%2F09%2F2025®ionId=10768&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=29%2F09%2F2025&endDate=30%2F09%2F2025®ionId=10768&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=29%2F09%2F2025&endDate=30%2F09%2F2025®ionId=10768&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=29%2F09%2F2025&endDate=30%2F09%2F2025®ionId=10768&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=29%2F09%2F2025&endDate=30%2F09%2F2025®ionId=10768&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=29%2F09%2F2025&endDate=30%2F09%2F2025®ionId=10768&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Islamorada The turquoise waters between the Keys offer world-class fishing that even beginners can enjoy with knowledgeable local guides. Spend mornings snorkelling coral reefs teeming with tropical fish, then unwind at waterfront restaurants where chefs cook your fresh catch. [See all hotels in Islamorada](https://www.expedia.ca/Hotel-Search?startDate=2025-10-12&endDate=2025-10-13&adults=2®ionId=10768) ![Islamorada which includes tropical scenes and a sandy beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63860-Islamorada.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Islamorada Hotel Reviews ![Cheeca Lodge & Spa](//images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "I love it" [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ## Find out more about Islamorada ## Five Star Hotels in Islamorada There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Islamorada so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Islamorada and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Islamorada Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Islamorada The results are in, and Islamorada 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Islamorada! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Islamorada today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### What are the best 5-star hotels in Islamorada? > Step into a world of luxury at [Cheeca Lodge & Spa](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information). This is among the leading 5-star hotels in Islamorada based on Expedia customer reviews. From its premium amenities and services to its prime location, you can look forward to the best of everything. ### How much does it cost to stay in a 5-star hotel in Islamorada? > You'll find various pricing options for a 5-star hotel in Islamorada on Expedia. How much you'll pay will depend on when you travel, length of your trip and other factors. Compare available accommodations for your desired dates and make use of our pricing and other filters to lock in the ideal luxury stay. > > > > - Search for the lowest price per night from CA $348 ### What makes a hotel 5 stars in Islamorada? > From fine dining venues and all-day fitness centres to pools and luxury bedding, the 5-star experience in Islamorada is all about indulgence and comfort. But it calls for more than just top-notch perks to receive a 5-star rating. 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