Title: Book the Best Hotels with POOL in Upper Matecumbe Key in 2025 | 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 showing art](https://images.trvl-media.com/place/10768/3219f098-cff5-4a89-b5cb-f20e360451df.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Upper Matecumbe Key, FL - ![](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 Hotels with a Pool Tonight [Nov 7 - Nov 8](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-11-07&endDate=2025-11-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 8 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-11-08&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Upper Matecumbe Key Hotels with a Pool ![Superior Bungalow, Multiple Beds, Beachfront (Ground Level Sleeps 6) | View from room](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/f30bc378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 2 Queen Beds, Kitchenette, Bay View](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/c0d44f4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, fishing](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/d330cb53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/31d6a642.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Jolla Resort Matecumbe 9.0/10 Wonderful (1001) "Great place to stay lovely staff Easy to find " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) diane [](https://www.expedia.ca/Islamorada-Hotels-La-Jolla-Resort.h16574668.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Oceanfront Suite King](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/2f598fe7.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) ### Amara Cay Resort Matecumbe 8.8/10 Excellent (1243) "Great hotel with a perfect location and friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amir CA $200 CA $319 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/12d77a84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/fa9b6bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/43f5c138.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, white sand, sun loungers, beach towels](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Beach Resort Matecumbe 9.2/10 Wonderful (1552) "Clean room, friendly staff, perfect setting, good breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dwight CA $200 CA $304 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/98496c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Cottage | Living area](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/7a0bffa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Bedroom, Kitchen, Pool View | Living area](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/5e728c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Cottage](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/b8fa0acc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Breezy Palms Resort Matecumbe 8.8/10 Excellent (558) "Love this resort. Friendly check-in, room is always spotless and lovely outside area with beautiful views of the water. We have stayed here multiple times now - best spot in the keys! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gemma CA $98 CA $161 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/8f06ee9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, beach towels, kayaking](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/8952c233.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/61b3d4d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dock](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/9afce9bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hadley Resort and Marina Matecumbe 7.8/10 Good (1000) "Super " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michel CA $164 CA $230 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) ![Outdoor pool, free cabanas](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/25606792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/711b38d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Double Beds, Kitchenette](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/4c5cb130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/0fad4f99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Inn Matecumbe 9.4/10 Exceptional (1000) "Conveniently located to dining options and attractions to explore and do." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tony CA $183 CA $206 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Islamorada-Hotels-Sunset-Inn.h30568049.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/a375b426.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) ### La Siesta Resort & Villas Matecumbe 8.8/10 Excellent (1001) "Clean rooms, great ambiance and service. Would definitely go again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary CA $190 CA $308 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/981feca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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 (1252) "This resort was amazing!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $253 CA $380 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![2 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/b513b652.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 (1002) "Awesome stay! Well recommended!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Juan Andre CA $294 CA $426 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/641fc549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/29faa902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/70514579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/8ad54011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Villas by Islander Resort Matecumbe 8.8/10 Excellent (392) "Beautiful property loads of thing to do or do nothing. Great restaurao" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie CA $302 CA $435 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.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=2025-11-22&endDate=2025-11-23®ionId=553248635975749648&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Upper Matecumbe Key Hotel Reviews ![Breezy Palms Resort](//images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/96b58c48_y.jpg) ### Breezy Palms Resort 10/10 Excellent "Love this resort. Friendly check-in, room is always spotless and lovely outside area with beautiful views of the water. We have stayed here multiple times now - best spot in the keys! " [](https://expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) ![Amara Cay Resort](//images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 10/10 Excellent "Water Taxi is the best perk ever .. " [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Islander Resort](//images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "Quiet, beautiful resort. Pools, beach and beach bars were clean and accessible. Prices are a little high especially for drinks. Great location. " [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Holiday Inn Key Largo by IHG](//images.trvl-media.com/lodging/1000000/10000/7300/7230/160ba216_y.jpg) ### Holiday Inn Key Largo by IHG 10/10 Excellent "Clean room, great pool and tiki bar and skippers was a great short walk for happy hour " [](https://expedia.ca/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.Hotel-Information) ![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 "clean room, great staff " [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Chesapeake Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Friendly staff clean room!!!" [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Marina Del Mar Resort and Marina](//images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885_y.jpg) ### Marina Del Mar Resort and Marina 10/10 Excellent "The staff was friendly and helpful throughout my stay, always greeting guests with a smile and offering great local recommendations. My room was clean, comfortable, and had everything I needed for a relaxing trip. I especially loved waking up to the peaceful marina view every morning! The pool area and hot tub were beautiful, and the atmosphere was calm and inviting. Having restaurants and water activities just steps away made everything super convenient — we even took a sunset cruise right from the marina!" [](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ![Pines & Palms Resort](//images.trvl-media.com/lodging/1000000/1000000/990500/990422/6ac4045c_y.jpg) ### Pines & Palms Resort 10/10 Excellent "Very recently updated rooms with great facilities in a beautiful location" [](https://expedia.ca/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information) ![Cheeca Lodge & Spa](//images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "Always a great stay at Cheeca. Lovely property, great restaurants, clean rooms and wonderful service by the staff. 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