Title: 5 Stars Hotels in Upper Matecumbe Key, Islamorada from CA $432 - Find Cheap Upper Matecumbe Key Hotels With 5 Stars | Expedia.ca [Upper Matecumbe Key Travel Guide](https://expedia.ca/Upper-Matecumbe-Key.dx553248635975749648)[Hotels in Upper Matecumbe Key](https://expedia.ca/Upper-Matecumbe-Key-Hotels.d553248635975749648.Travel-Guide-Hotels)[Vacation Rentals in Upper Matecumbe Key](https://expedia.ca/Upper-Matecumbe-Key-Vacation-Rentals.d553248635975749648.Travel-Guide-VacationRentals)[Flights to Upper Matecumbe Key](https://expedia.ca/Cheap-Flights-To-Upper-Matecumbe-Key.d553248635975749648.Travel-Guide-Flights)[Upper Matecumbe Key Car Rentals](https://expedia.ca/Car-Rentals-In-Upper-Matecumbe-Key.d553248635975749648.Car-Rental-Guide)[Upper Matecumbe Key Vacation Packages](https://expedia.ca/Upper-Matecumbe-Key.d553248635975749648.Destination-Travel-Guides) ![Florida Keys Brewing Co. showing signage](https://images.trvl-media.com/place/553248635997958830/30b22f53-286f-436b-ae7a-d035c9062e6c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Upper Matecumbe Key, Islamorada from CA $432 - ![](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 Upper Matecumbe Key 5 Star Hotels Tonight [Dec 20 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-12-20&endDate=2025-12-21&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 21 - Dec 22](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-12-21&endDate=2025-12-22&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-12-26&endDate=2025-12-28&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-01-02&endDate=2026-01-04&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Upper Matecumbe Key 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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/e32d7e53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/9b929f51.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 [](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) Matecumbe 9.2/10 Wonderful (1272) "It was awesome, great service, staff members are helpful, clean and tidy room with excellent views!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sami CA $523 CA $690 total includes taxes & fees Jan 3 - Jan 4, 2026 [](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/ab76abc3.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) ![Exterior](https://images.trvl-media.com/lodging/94000000/93070000/93061400/93061348/0917a41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in the Keys [](https://www.expedia.ca/Tavernier-Hotels-Condo-In-The-Keys.h93061348.Hotel-Information) Tavernier 8.0/10 Very good (13) "Love the location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela [](https://www.expedia.ca/Tavernier-Hotels-Condo-In-The-Keys.h93061348.Hotel-Information) ![Design Villa, Canal View | Balcony](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/5d9195bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design Villa, Canal View | Living area](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/8c99be49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/w1024h1021x0y3-63c47ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design Villa, Canal View](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/264ca003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront House with Boat Dock [](https://www.expedia.ca/Tavernier-Hotels-Waterfront-House-With-Boat-Dock.h109724487.Hotel-Information) 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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew [](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-Upper-Matecumbe-Key-Hotels.s50-0-d553248635975749648.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Upper-Matecumbe-Key-Hotels.s50-0-d553248635975749648.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 Upper Matecumbe Key. ![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hawks Cay Resort 61 Hawks Cay Blvd Marathon FL CA $349 CA $489 total Jan 4 - Jan 5, 2026 includes taxes & fees 8/10 Very Good! (1,002 reviews) [](https://expedia.ca/Marathon-Hotels-Hawks-Cay-Resort.h6068.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 $302 CA $432 total Jan 4 - Jan 5, 2026 includes taxes & fees 8.8/10 Excellent! (1,263 reviews) [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![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 $553 CA $699 total Jan 8 - Jan 9, 2026 includes taxes & fees 8.6/10 Excellent! (1,005 reviews) [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) Still don't see what you're looking for? [See all properties in Upper Matecumbe Key.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=21%2F12%2F2025&endDate=22%2F12%2F2025®ionId=553248635975749648&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=21%2F12%2F2025&endDate=22%2F12%2F2025®ionId=553248635975749648&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=21%2F12%2F2025&endDate=22%2F12%2F2025®ionId=553248635975749648&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=21%2F12%2F2025&endDate=22%2F12%2F2025®ionId=553248635975749648&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=21%2F12%2F2025&endDate=22%2F12%2F2025®ionId=553248635975749648&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=21%2F12%2F2025&endDate=22%2F12%2F2025®ionId=553248635975749648&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 Upper Matecumbe Key Check out the local area in Upper Matecumbe Key—home to attractions like Florida Keys Brewing Co. and Bud n' Mary's Dive Center. [See all hotels in Upper Matecumbe Key](https://www.expedia.ca/Hotel-Search?startDate=2026-01-03&endDate=2026-01-04&adults=2®ionId=553248635975749648) ![Islamorada Florida. Beautiful Beach and Amazing Fishing. What else can you ask for.](https://images.trvl-media.com/place/10768/414c55a9-82b2-4829-857c-fd7c26e0bd48.jpg?impolicy=fcrop&w=900&h=592&p=1&q=high) Photo by Cameron Abbott ## Top Upper Matecumbe Key Hotel Reviews ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "Everything was awsome" [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ## Find out more about Upper Matecumbe Key Luxury is the name of the game at the best 5 Stars hotels in Upper Matecumbe Key. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top Upper Matecumbe Key 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them. Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars Upper Matecumbe Key hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels Upper Matecumbe Key without giving up even an inch of quality. Everything your heart desires (and a few perks designed to make it skip a beat): That’s what’s on offer when you plan a trip to the hotels with 5 Stars in Upper Matecumbe Key. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [1 Star Hotels in Eden Pines ](https://www.expedia.ca/1Star-Eden-Pines-Big-Pine-Key-Hotels.s10-n553248635976471710-0.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Riviera Estates ](https://www.expedia.ca/1Star-Riviera-Estates-Miami-Hotels.s10-n553248635976469340-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Coconut Grove ](https://www.expedia.ca/2Star-Coconut-Grove-Miami-Hotels.s20-n11937-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Kendall ](https://www.expedia.ca/2Star-Kendall-Miami-Hotels.s20-n8226-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Key Largo ](https://www.expedia.ca/2Star-Key-Largo-Hotels.s20-0-d8369.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Plantation Key ](https://www.expedia.ca/2Star-Plantation-Key-Hotels.s20-0-d553248635083898347.Travel-Guide-Filter-Hotels) - 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