Title: Upper Matecumbe Key Vacation Rentals from CA $191: Short-Term Rentals for 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)[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) # Upper Matecumbe Key Vacation Rentals ![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 prices for these dates Tonight [Sep 24 - Sep 25](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-09-24&endDate=2025-09-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 25 - Sep 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-09-25&endDate=2025-09-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in Upper Matecumbe Key ## Our top choices for Upper Matecumbe Key vacation rentals ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/98496c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Breezy Palms Resort Matecumbe 8.8/10 Excellent (540) "Spacious rooms and location was great for what we needed. " CA $106 CA $191 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.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) ![Fireplace](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/531fe0b4.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 $761 CA $933 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/30000000/29960000/29956500/29956429/c7e07388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/30000000/29960000/29956500/29956429/1feb9c6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/30000000/29960000/29956500/29956429/479e0d46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29960000/29956500/29956429/64ae72ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5 bedroom - Deep Dockage & Heated Pool in Islamorada. Matecumbe 10/10 Exceptional (118) "Wonderful location." [](https://www.expedia.ca/Islamorada-Hotels-5-Bedroom-Deep-Dockage-Heated-Pool-In-Islamorada.h29956429.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/54000000/53040000/53031600/53031525/w1924h1288x0y1-e5e79d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/54000000/53040000/53031600/53031525/34c2b128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/54000000/53040000/53031600/53031525/4a2abbee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/54000000/53040000/53031600/53031525/4afe5eac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks Matecumbe 10/10 Exceptional (58) "Fabulous house! Awesome pool, fire pit, dock. My family thoroughly enjoyed every single moment here. Plenty of room for everyone. And the wild life is awesome! Manatees, tropical fish and iguanas!" [](https://www.expedia.ca/Islamorada-Hotels-7-Bedroom-With-Dockage.h53031525.Hotel-Information) ![25-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/12c235b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/8c6c8a7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/17a61bb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/ee0752b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Treasure Harbor Islamorada 8.8/10 Excellent (105) "If you are looking for a laid back vibe with no hassle here is the place. Friendly staff. Aqualodge was cute and comfortable. Easily rented a boat for the day...found great snorkeling and beautiful views. " CA $125 CA $335 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information) ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/14000000/13280000/13279700/13279636/7f2e2269.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Room | Private kitchen](https://images.trvl-media.com/lodging/14000000/13280000/13279700/13279636/2180f342.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Room | View from room](https://images.trvl-media.com/lodging/14000000/13280000/13279700/13279636/3c8c13d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Room](https://images.trvl-media.com/lodging/14000000/13280000/13279700/13279636/29275608.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Island Bay Resort Tavernier 10/10 Exceptional (131) "Clean, friendly, has its own beach" [](https://www.expedia.ca/Tavernier-Hotels-Island-Bay-Resort.h13279636.Hotel-Information) ![Boating](https://images.trvl-media.com/lodging/24000000/23710000/23709100/23709068/461bf404.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House, 2 Bedrooms, Kitchen, Beachside](https://images.trvl-media.com/lodging/24000000/23710000/23709100/23709068/2a925366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/24000000/23710000/23709100/23709068/6c9e5462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/24000000/23710000/23709100/23709068/a4a9e792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Key Largo Cottages Key Largo 9.6/10 Exceptional (24) "Beautiful and peaceful place " [](https://www.expedia.ca/Key-Largo-Hotels-Key-Largo-Cottages.h23709068.Hotel-Information) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34020000/34015800/34015770/2b862fb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34020000/34015800/34015770/6717e112.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, table tennis, books](https://images.trvl-media.com/lodging/35000000/34020000/34015800/34015770/69382ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34020000/34015800/34015770/f37a7272.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly Islamorada 9.4/10 Exceptional (98) "Oceans views for miles! Great pool. " [](https://www.expedia.ca/Tavernier-Hotels-Oceanfront-Estate-With-Private-350-Foot-Pier.h34015770.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/119000000/118340000/118338000/118337979/9dea2f16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118340000/118338000/118337979/c769cb30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118340000/118338000/118337979/219e17c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/119000000/118340000/118338000/118337979/065f4893.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Piece of Paradise located at Hawks Cay in Duck Key Duck Key 9.6/10 Exceptional (4) "Amazing place. " [](https://www.expedia.ca/Marathon-Hotels-Piece-Of-Paradise-Located-At-Hawks-Cay-In-Duck-Key.h118337979.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/103000000/102250000/102242200/102242195/430a28a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/103000000/102250000/102242200/102242195/f086b42f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/103000000/102250000/102242200/102242195/9573e9d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102250000/102242200/102242195/3f852982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys. Tavernier 9.8/10 Exceptional (57) "Great unit, nicely renovated and a good weekend! " [](https://www.expedia.ca/Tavernier-Hotels-Relax-In-Your-One-Bedroom-Oceanfront-Suite-In-Tavernier-FL-Florida-Keys.h102242195.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/31000000/30020000/30011700/30011621/w2048h1364x0y1-d4421f55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/31000000/30020000/30011700/30011621/606fc243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30020000/30011700/30011621/3bc598c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/31000000/30020000/30011700/30011621/6adbb23f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl, Marathon 10/10 Exceptional (179) "We always stay here. Location, house, yard, and a the dock make this place great. Always clean and size is perfect for us. Owner is great to deal with as well. Thanks again for another great stay." [](https://www.expedia.ca/Marathon-Hotels-Best-Deals-In-Duck-Key-2-Bedroom-2-Bath-W40-Dock.h30011621.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/45000000/44080000/44079000/44078971/172890e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/45000000/44080000/44079000/44078971/ddcabe47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/45000000/44080000/44079000/44078971/eebfd124.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers](https://images.trvl-media.com/lodging/45000000/44080000/44079000/44078971/52ee15e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo Tavernier 9.8/10 Exceptional (224) "We found the condo very nicely located to Key Largo, Islamorada, and Tavernier. Enjoyed restaurants with sunset bayside, snorkeling excursion off John Pennecamp state park, and the pool and tiki hut on resortPremises! Would return here if back in the area. " [](https://www.expedia.ca/Tavernier-Hotels-Two-Panoramic-Ocean-Views-From-The-Living-Room-And-Master-Bedroom-In-This-Condo.h44078971.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/34000000/33570000/33568800/33568760/b543b616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/34000000/33570000/33568800/33568760/be2db90c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33570000/33568800/33568760/0fe74234.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/34000000/33570000/33568800/33568760/5f289790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe Tavernier 9.8/10 Exceptional (186) "Cute apartment perfectly located in the complex with proximity to the pool and beach areas. Comfortable for 4 adults " [](https://www.expedia.ca/Tavernier-Hotels-Ocean-Front-Private-Beach.h33568760.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/36000000/35140000/35132500/35132443/382a8bcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/36000000/35140000/35132500/35132443/4f978649.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/36000000/35140000/35132500/35132443/5887df5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35140000/35132500/35132443/194b23b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### VOTED BEST KEY LARGO VACATION RENTAL Key Largo 10/10 Exceptional (82) "Wonderful property! Very clean, plenty of space, and updated interior. Access to many amenities across the whole property with multiple pools, a swimming lagoon, fishing equipment, bikes, kayaks, and more. Great location to everything in Key Largo and southern Florida activities. Would highly recommend. " [](https://www.expedia.ca/Key-Largo-Hotels-VOTED-BEST-KEY-LARGO-VACATION-RENTAL.h35132443.Hotel-Information) ![55-inch Smart TV with digital channels, books](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/96d842c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/a7f8b8c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, individually furnished, blackout drapes](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/dc4f4949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108750000/108743400/108743380/f15964b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Premium Floating Bungalow by Stay Ombi Key Largo CA $1,106 CA $1,244 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Key-Largo-Hotels-Premium-Floating-Bungalow-By-Stay-Ombi.h108743380.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/94241dd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/95c54ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/b3fdbd21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/006a1068.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Home in Key Largo Key Largo 9.8/10 Exceptional (25) "Great location. Very clean very nice, stay there again" CA $96 CA $441 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Key-Largo-Hotels-Charming-Home-In-Key-Largo.h99961430.Hotel-Information) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/115000000/114470000/114469100/114469045/a4739b6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114470000/114469100/114469045/9e703d6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114470000/114469100/114469045/4beca01b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/115000000/114470000/114469100/114469045/aa42431b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5 Star Coastal Luxury: Key Largo 2BR Condo w/Lagoon, Golf Cart, Pools& Amenities Key Largo 10/10 Exceptional (15) "Great vacation spot , only thing missing is a good saltwater beach." [](https://www.expedia.ca/Key-Largo-Hotels-Coastal-Luxury-Key-Largo-2BR-Condo-W-Lagoon.h114469045.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/56000000/55190000/55186000/55185936/88377e50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/56000000/55190000/55186000/55185936/9f308d75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/56000000/55190000/55186000/55185936/f0dca02d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/56000000/55190000/55186000/55185936/a381fdfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Tiny House w Pool, Beach, and Boat Dock Key Largo 9.6/10 Exceptional (59) "Excelent place " CA $163 CA $508 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Key-Largo-Hotels-Tiny-House-On-The-Water-Pool.h55185936.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/63000000/63000000/62990400/62990381/278234d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/63000000/63000000/62990400/62990381/d8edae43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/63000000/63000000/62990400/62990381/296570b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/63000000/63000000/62990400/62990381/3663ec76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxurious 2BR Beachfront Condo | Steps to Pool & Ocean | Ocean Pointe Resort Tavernier 9.0/10 Wonderful (67) "This was the perfect place to stay!Nice & clean!Close to activities and restaurants!The owner was very easy to communicate with!We will definitely stay here again next time we are in the Keys!" [](https://www.expedia.ca/Tavernier-Hotels-Key-Largo-Luxurious-2BR2BA-Amazing-Pool-And-Large-Pool.h62990381.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/33000000/32590000/32583400/32583358/38e83c14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32590000/32583400/32583358/d743bb5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32590000/32583400/32583358/19a40742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32590000/32583400/32583358/0b2a8558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront 165ft Beach-Dock-Pool-4K sq.ft 4 bed-5 bath - Islamorada Matecumbe 10/10 Exceptional (85) "Wonderful place to stay for families. We loved it. Rooms and bathrooms were fantastic. Michele was a great host that made sure our stay was perfect. " [](https://www.expedia.ca/Islamorada-Hotels-Oceanfront-165ft-Beach-Dock-Heated-Pool-4K-Sqft-4-Bed5-Bath-Next-Avail-8925.h32583358.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=2025-10-08&endDate=2025-10-09®ionId=553248635975749648&adults=2&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-Vacation-Rentals.d553248635975749648.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FUpper-Matecumbe-Key-Vacation-Rentals.d553248635975749648.Travel-Guide-VacationRentals) ## Top Upper Matecumbe Key Hotel Reviews ![Waterside Suites & Marina](//images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg) ### Waterside Suites & Marina 10/10 Excellent "Love the location and the room. Made for a great fishing trip with my son & grand daughter. Well be return in the near future." [](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information) ![Sunset Inn](//images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/25606792_y.jpg) ### Sunset Inn 10/10 Excellent "Great place to stay!" [](https://expedia.ca/Islamorada-Hotels-Sunset-Inn.h30568049.Hotel-Information) ![Pines & Palms Resort](//images.trvl-media.com/lodging/1000000/1000000/990500/990422/6ac4045c_y.jpg) ### Pines & Palms Resort 10/10 Excellent "Very nice place to stay " [](https://expedia.ca/Islamorada-Hotels-Pines-Palms-Resort.h990422.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 "Great rooms" [](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.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 "Bakers Cay was a wonderful place to stay and unwind. The service was outstanding and location perfect. Thank you" [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Cheeca Lodge & Spa](//images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "Beautiful and relaxing hotel!!" [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Islander Resort](//images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "Alot of fun things to do including kayaking, paddle board, vollyball,ping pong and bikes." [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.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 "Loved " [](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.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 "Loved the rooms very spacious. Ocean view was amazing very close to restaurants " [](https://expedia.ca/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) ## Find out more about Upper Matecumbe Key **Everything you need to know about** **Upper Matecumbe Key** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Upper Matecumbe Key vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upper Matecumbe Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Upper Matecumbe Key vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Upper Matecumbe Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upper Matecumbe Key vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upper Matecumbe Key vacation rentals we have selected for you start as low as CA $191 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Upper Matecumbe Key rentals** At Expedia, we put the best Upper Matecumbe Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Upper Matecumbe Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upper Matecumbe Key vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upper Matecumbe Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Upper Matecumbe Key ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - 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