Title: 4 Stars Hotels in Upper Matecumbe Key, Islamorada from CA $269 - Find Cheap Upper Matecumbe Key Hotels With 4 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) ![Islamorada which includes a beach bar](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191196-Islamorada.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 4 Stars Hotels in Upper Matecumbe Key, Islamorada from CA $269 ![](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 4 Star Hotels Tonight [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-17&endDate=2025-10-18&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-18&endDate=2025-10-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Upper Matecumbe Key 4 Star Hotels ![32-inch LCD TV with satellite channels, TV, iPod dock](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/bbdba544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/6e0cfc6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/7c755dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/1f0afa1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baker's Cay Resort Key Largo, Curio Collection by Hilton Key Largo 8.6/10 Excellent (1017) "Excellent hotel " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara CA $405 CA $533 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![5 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, premium bedding, in-room safe, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/dcef6a9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/af9b3995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/3d68eb94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hawks Cay Resort Marathon 8.0/10 Very good (1013) "Nice property with great vies and nice restaurants and great staff " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $356 CA $499 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Marathon-Hotels-Hawks-Cay-Resort.h6068.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Alligator Reef Oceanfront Accessible Room King Bed | View from room](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/1b5ced17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/60b7c04d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/28233e0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amara Cay Resort Matecumbe 8.8/10 Excellent (1259) "Great hotel with a perfect location and friendly staff." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Amir CA $172 CA $287 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/489feb58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, beach cabanas, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/d9cc2f68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/92d23e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 3 Bedrooms, Pool Access, Bay View (Balcony/Patio, Private Pool) | Beach](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/10dd6c61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Playa Largo Resort & Spa, Autograph Collection Key Largo 9.0/10 Wonderful (1013) "Very nice place to stay in the keys " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Yamilka CA $336 CA $455 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Islander Suite Ocean View Two Bedroom | Private kitchen](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/20ed25e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily full breakfast for a fee](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/3ea0faf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/6ec44483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islander Resort Matecumbe 9.2/10 Wonderful (1014) "Perfect resort for our week long honeymoon! Quiet, relaxing, plenty of activity options and great service all around. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Chloe CA $292 CA $424 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/7578de06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/a11bb47b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, Multiple Beds (Casa de Coco) | Dining room](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/9c557f5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Siesta Resort & Villas Matecumbe 8.6/10 Excellent (1006) "Excellent stay with great amenities." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $156 CA $269 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![5 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920083/8638cc9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920083/d35c4fd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920083/8e428f16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LCD TV](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920083/791c447b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villas At Hawks Cay Resort Marathon 8.6/10 Excellent (139) "Best place to stay in the Florida Keys !" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Endy [](https://www.expedia.ca/Marathon-Hotels-Villas-At-Hawks-Cay-Resort.h99920083.Hotel-Information) ![2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/61575cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/5be55ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/fa0090c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/531fe0b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Islands of Islamorada Matecumbe 9.8/10 Exceptional (66) "Absolutely outstanding resort. Legitimate 5 star property. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Craig CA $773 CA $947 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/61000000/60290000/60289900/60289884/4c18eaad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Multiple Beds, Private Pool, Garden View | Living room](https://images.trvl-media.com/lodging/61000000/60290000/60289900/60289884/5f28c00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/61000000/60290000/60289900/60289884/1d5cc14d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Multiple Beds, Private Pool, Garden View | Living room](https://images.trvl-media.com/lodging/61000000/60290000/60289900/60289884/f68ce2f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Caribbean Resort Coconut Palm North Matecumbe [](https://www.expedia.ca/Islamorada-Hotels-The-Caribbean-Resort-Hemingway-House-North.h60289884.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%2F4Star-Upper-Matecumbe-Key-Hotels.s40-0-d553248635975749648.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Upper-Matecumbe-Key-Hotels.s40-0-d553248635975749648.Travel-Guide-Filter-Hotels) ## Explore similar 5-star hotels Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Upper Matecumbe Key. ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Cheeca Lodge & Spa 81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL CA $195 CA $315 total Oct 26 - Oct 27 includes taxes & fees 9/10 Wonderful! (1,222 reviews) [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Condo in the Keys](https://images.trvl-media.com/lodging/94000000/93070000/93061400/93061348/9b3c41b7_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Condo in the Keys 500 Burton Dr, 1313, Tavernier, FL [Get rates](https://expedia.ca/Hotel-Search?startDate=31%2F10%2F2025&endDate=01%2F11%2F2025&selected=93061348&PinnedHotelID=93061348&HadPinnedHotel=true®ionId=553248635975749648) 8.4/10 Very Good! (10 reviews) [](https://expedia.ca/Tavernier-Hotels-Condo-In-The-Keys.h93061348.Hotel-Information) ![Waterfront House with Boat Dock](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/691ffb10_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Waterfront House with Boat Dock 213 Aberdeen Ct, Tavernier, FL [Get rates](https://expedia.ca/Hotel-Search?startDate=31%2F10%2F2025&endDate=01%2F11%2F2025&selected=109724487&PinnedHotelID=109724487&HadPinnedHotel=true®ionId=553248635975749648) 6/10 (1 review) [](https://expedia.ca/Tavernier-Hotels-Waterfront-House-With-Boat-Dock.h109724487.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=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=553248635975749648&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=553248635975749648&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=553248635975749648&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=553248635975749648&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=553248635975749648&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=553248635975749648&star=40&star=40&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 Bud n' Mary's Dive Center and Florida Keys Brewing Co.. [See all hotels in Upper Matecumbe Key](https://www.expedia.ca/Hotel-Search?startDate=2025-10-31&endDate=2025-11-01&adults=2®ionId=553248635975749648) ![Islamorada which includes a beach bar](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191196-Islamorada.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Upper Matecumbe Key Hotel Reviews ![Baker's Cay Resort Key Largo, Curio Collection by Hilton](//images.trvl-media.com/lodging/1000000/20000/14100/14042/bbdba544_y.jpg) ### Baker's Cay Resort Key Largo, Curio Collection by Hilton 10/10 Excellent "Excellent hotel " [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Amara Cay Resort](//images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 10/10 Excellent "It was great weekend! Clean room, nice service" [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![La Siesta Resort & Villas](//images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg) ### La Siesta Resort & Villas 10/10 Excellent "Excellent stay with great amenities." [](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Islander Resort](//images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "Amazing property! We’ve been going for years!!" [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Hawks Cay Resort](//images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555_y.jpg) ### Hawks Cay Resort 10/10 Excellent "Impeccable cleanliness. The Salt and Ash dining was one of the best meals of my life." [](https://expedia.ca/Marathon-Hotels-Hawks-Cay-Resort.h6068.Hotel-Information) ![The Islands of Islamorada](//images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/61575cce_y.jpg) ### The Islands of Islamorada 10/10 Excellent "Beautiful property!" [](https://expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) ## Find out more about Upper Matecumbe Key If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Upper Matecumbe Key are calling your name. Known for providing first-rate service in amazing locations, each of the Upper Matecumbe Key 4 Stars hotels lets discerning travelers bask in an unforgettable experience. Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day. It’s all waiting for you at the top four star hotels in Upper Matecumbe Key. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Upper Matecumbe Key, Islamorada, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Upper Matecumbe Key hotels with 4 Stars provide everything you need to unwind in style. ## 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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