Title: Upper Matecumbe Key Condominium Resort Rental | 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) # Find and Compare Upper Matecumbe Key Condo Resort Rentals ![](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 prices for these dates In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=CONDO_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=CONDO_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=CONDO_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=CONDO_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Upper Matecumbe Key Condo Resorts We don't have any properties that match your exact search [See all properties in Upper Matecumbe Key](https://expedia.ca/Hotel-Search?startDate=2025-10-26&endDate=2025-10-27®ionId=553248635975749648&adults=2) ## Recommended hotels in Upper Matecumbe Key ![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) ![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) ![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) ![Water view](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/8979e9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Beach Resort Matecumbe 9.2/10 Wonderful (1538) "Wonderful property, breakfast was awesome " CA $212 CA $317 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![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) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/79d31a44.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) ### Cheeca Lodge & Spa Matecumbe 9.2/10 Wonderful (1223) "Beautiful and relaxing hotel!!" CA $195 CA $314 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.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) ![Aerial view](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/0fad4f99.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) ### Sunset Inn Matecumbe 9.4/10 Exceptional (1003) "Great place to stay!" CA $141 CA $175 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Islamorada-Hotels-Sunset-Inn.h30568049.Hotel-Information) ![Private beach, fishing](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/74e26d92.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) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/ac9bc991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Jolla Resort Matecumbe 9.0/10 Wonderful (1002) "The location is great..nice beach and dock area..room was very nice.. will definitely plan to return for a longer stay" [](https://www.expedia.ca/Islamorada-Hotels-La-Jolla-Resort.h16574668.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) ![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) ![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) ### Amara Cay Resort Matecumbe 8.8/10 Excellent (1254) "Great hotel with a perfect location and friendly staff." CA $177 CA $293 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/96b58c48.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) ![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](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 (543) "Spacious rooms and location was great for what we needed. " CA $99 CA $183 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.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) ![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 Resort Matecumbe 9.2/10 Wonderful (1010) "Stunning resort with great amenities and excellent service! " CA $291 CA $422 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/6ac4045c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/a571015b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront Pool View King Room | Terrace/patio](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/a348bb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/45deddf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pines & Palms Resort Matecumbe 9.2/10 Wonderful (1002) "Very nice place to stay " [](https://www.expedia.ca/Islamorada-Hotels-Pines-Palms-Resort.h990422.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) ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/a375b426.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Siesta Resort & Villas Matecumbe 8.6/10 Excellent (1004) "Great rooms" CA $152 CA $265 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Beach nearby, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/46d4fa27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/w1009h683x7y0-80f60840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/b7eb418d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Jungles Suite](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/w762h679x132y4-fc33a6d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Morada Matecumbe 9.4/10 Exceptional (409) "The marina was clean and convenient." [](https://www.expedia.ca/Islamorada-Hotels-Casa-Morada.h900424.Hotel-Information) ![Dock](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/9afce9bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/00476fee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/61b3d4d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hadley Resort and Marina Matecumbe 7.8/10 Good (1003) "Loved the rooms very spacious. Ocean view was amazing very close to restaurants " CA $137 CA $200 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) ![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) ![Brand New Two King Bay Front | Private kitchen](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/4b05ab7b.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) ### Bayside Villas by Islander Resort Matecumbe 8.8/10 Excellent (391) "Great place to stay" CA $305 CA $437 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.Hotel-Information) ![Suite, 1 King Bed with Sofa bed, Kitchenette, Oceanfront | Terrace/patio](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/0cb6bab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, 2 Queen Beds, Refrigerator & Microwave](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/d3f952a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, 2 Queen Beds, Refrigerator & Microwave](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/b1df7837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/2b7458ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sands of Islamorada Matecumbe 8.8/10 Excellent (389) "The hotel was reasonably priced and while a little dated, the rooms were large and clean. The staff was SUPER nice. All in all, a great place to stay a couple nights in the keys at a reasonable price. Would definitely recommend!" CA $227 CA $274 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Islamorada-Hotels-Sands-Of-Islamorada.h12653483.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) ![Boating](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/a93dc7d6.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) ### The Islands of Islamorada Matecumbe 9.8/10 Exceptional (66) "Absolutely outstanding resort. Legitimate 5 star property. " CA $770 CA $944 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/64000000/63860000/63853400/63853334/w1199h900x0y0-ce43e794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/64000000/63860000/63853400/63853334/bb52c056.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/64000000/63860000/63853400/63853334/1f33ae21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/64000000/63860000/63853400/63853334/72eebe1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hidden Gem Islamorada | 1st Floor Matecumbe 10/10 Exceptional (44) "Perfect location in islamorada. Definitely recommend and will stay there again. " CA $367 CA $785 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Islamorada-Hotels-Gem-6-Hidden-Gem-Islamorada-1st-Floor-2Bed2Bath.h63853334.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/118000000/117560000/117550900/117550857/w792h683x116y0-96afa1d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/118000000/117560000/117550900/117550857/w1009h683x7y0-89ba4a66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117560000/117550900/117550857/0f0a77eb_edited_d3e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117560000/117550900/117550857/w865h663x80y0-887c2bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite Matecumbe CA $4,202 CA $5,276 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Islamorada-Hotels-Private-Island-Suite-W-Terrace-Balcony-Islamorada-Coconut-Palm-Suite.h117550857.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/118000000/117560000/117551400/117551306/w792h683x116y0-4f6c00d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117560000/117551400/117551306/3edaac92_edited_0f36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117560000/117551400/117551306/w865h663x80y0-f5d66c5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117560000/117551400/117551306/w836h683x94y0-cccfe5f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite Matecumbe CA $2,798 CA $3,514 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Islamorada-Hotels-Jacuzzi-Suite-Overlooking-The-Sea-Islamorada-Iguana-Suite.h117551306.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/118000000/117560000/117551800/117551749/w792h683x116y0-8979e8e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117560000/117551800/117551749/w865h663x80y0-f5af0e82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/118000000/117560000/117551800/117551749/w1009h683x7y0-0c5c0daa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117560000/117551800/117551749/w962h680x31y3-3a73e5da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite Matecumbe CA $2,280 CA $2,865 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Islamorada-Hotels-Terrace-Florida-Bay-View-Suite-Islamorada-Shangri-La-Suite.h117551749.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/118000000/117560000/117552000/117551960/w792h683x116y0-c9518e40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/118000000/117560000/117552000/117551960/w1009h683x7y0-686fbd92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117560000/117552000/117551960/w1024h728x0y73-136d79a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117560000/117552000/117551960/fb8ef6dd_edited_a7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite Matecumbe CA $2,268 CA $2,849 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Islamorada-Hotels-Oceanfront-Manatee-Suite-W-Private-Patio-Islamorada-Manatee-Suite.h117551960.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/118000000/117530000/117525600/117525589/w792h683x116y0-b196f56e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117530000/117525600/117525589/w865h663x80y0-99d56dac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117530000/117525600/117525589/078e3a39_edited_78aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117530000/117525600/117525589/w796h683x114y0-c357f0e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite Matecumbe CA $2,101 CA $2,639 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Islamorada-Hotels-Serene-Moon-Suite-W-Jacuzzi-Garden-View-Islamorada-Moon-Suite.h117525589.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=2025-10-26&endDate=2025-10-27®ionId=553248635975749648&adults=2&lodging=CONDO_RESORT&sort=RECOMMENDED&openPlayBack=true) ![](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%2FUpper-Matecumbe-Key-Condominium-Resort.d553248635975749648-aaCondominiumResort.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FUpper-Matecumbe-Key-Condominium-Resort.d553248635975749648-aaCondominiumResort.Travel-Guide-Accommodation) ## Top Upper Matecumbe Key Hotel Reviews ![Sunset Inn](//images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/25606792_y.jpg) ### Sunset Inn 10/10 Excellent "Staff was very friendly and room was very clean. Location was ideal for our needs. " [](https://expedia.ca/Islamorada-Hotels-Sunset-Inn.h30568049.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 "Excelent service " [](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Pines & Palms Resort](//images.trvl-media.com/lodging/1000000/1000000/990500/990422/6ac4045c_y.jpg) ### Pines & Palms Resort 10/10 Excellent "Yes and yes. Loved this place. " [](https://expedia.ca/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information) ![Playa Largo Resort & Spa, Autograph Collection](//images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/489feb58_y.jpg) ### Playa Largo Resort & Spa, Autograph Collection 10/10 Excellent "Staff was great, pool area was beautiful. Great Food and drink options. Very relaxing, did not need to leave the resort. Shout out to Matt the bartender who was amazing!" [](https://expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ![Hadley Resort and Marina](//images.trvl-media.com/lodging/1000000/20000/12200/12200/9afce9bd_y.jpg) ### Hadley Resort and Marina 10/10 Excellent "Super " [](https://expedia.ca/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) ![Islander Resort](//images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "My son and his new wife had an amazing time on their honeymoon! They said everything was top notch and have gone on & on about what an amazing time they had! ⭐️⭐️⭐️⭐️⭐️" [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Cheeca Lodge & Spa](//images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "Staff was extremely accommodating, Property is stunning with numerous activities. " [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.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 "Excelent" [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.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 "used tge dock very easy " [](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ## Find out more about Upper Matecumbe Key ## Upper Matecumbe Key Condo Resorts information | Number of reviews | | | --- | --- | | Accommodation | Condo Resorts | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - 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[Flights from Toronto to Islamorada](https://www.expedia.ca/lp/flights/178314/10768/toronto-to-islamorada) - [Hurricane Monument](https://www.expedia.ca/Hurricane-Monument-Matecumbe.d6063543.Vacation-Attraction) - [Islamorada Vacations](https://www.expedia.ca/Islamorada.d10768.Destination-Travel-Guides) - [Visit Islamorada](https://www.expedia.ca/Islamorada.dx10768) - [Car rental Islamorada](https://www.expedia.ca/Car-Rentals-In-Islamorada.d10768.Car-Rental-Guide) - [Convertible Car Rentals in Islamorada](https://www.expedia.ca/Convertible-Car-Rentals-In-Islamorada.d10768-tConvertible.Car-Rental-Guide-Class) - [Sixt Rental Cars in Islamorada](https://www.expedia.ca/Sixt-Car-Rentals-In-Islamorada.d10768-c35.Car-Rental-Guide-Suppliers) - [Islamorada Vacation Rentals](https://www.expedia.ca/Islamorada-Vacation-Rentals.d10768.Travel-Guide-VacationRentals) - [Things to do in Islamorada](https://www.expedia.ca/Things-To-Do-In-Islamorada.d10768.Travel-Guide-Activities) - [Book Condo Resorts in Upper Matecumbe Key on Expedia.com](https://www.expedia.com/Upper-Matecumbe-Key-Condominium-Resort.d553248635975749648-aaCondominiumResort.Travel-Guide-Accommodation)