Title: TOP Upper Matecumbe Key Beach Resorts for 2026 - Hotels on the Beach in Upper Matecumbe Key, FL | Expedia.co.uk [Upper Matecumbe Key Travel Guide](https://expedia.co.uk/Upper-Matecumbe-Key.dx553248635975749648)[Hotels in Upper Matecumbe Key](https://expedia.co.uk/Upper-Matecumbe-Key-Hotels.d553248635975749648.Travel-Guide-Hotels)[Holiday Rentals in Upper Matecumbe Key](https://expedia.co.uk/Upper-Matecumbe-Key-Holiday-Rentals.d553248635975749648.Travel-Guide-HolidayRentals)[Flights to Upper Matecumbe Key](https://expedia.co.uk/Cheap-Flights-To-Upper-Matecumbe-Key.d553248635975749648.Travel-Guide-Flights)[Upper Matecumbe Key Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Upper-Matecumbe-Key.d553248635975749648.Car-Hire-Guide)[Upper Matecumbe Key Holidays](https://expedia.co.uk/Upper-Matecumbe-Key.d553248635975749648.Holidays-City-Breaks) ![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=1200&h=500&q=medium) Photo by Cameron Abbott ![](https://images.trvl-media.com/place/10768/414c55a9-82b2-4829-857c-fd7c26e0bd48.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 Beach Resorts & Hotels Tonight [29 Jan - 30 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=553248635975749648&startDate=2026-01-29&endDate=2026-01-30&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Tomorrow [30 Jan - 31 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=553248635975749648&startDate=2026-01-30&endDate=2026-01-31&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) This weekend [30 Jan - 1 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248635975749648&startDate=2026-01-30&endDate=2026-02-01&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Next weekend [6 Feb - 8 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248635975749648&startDate=2026-02-06&endDate=2026-02-08&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) ## Our top choices for Upper Matecumbe Key beach hotels ![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) ![43-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/77344fea.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) ![Deluxe Ocean View Two Queen Suite | Balcony](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/1d1a1984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Beach Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) Matecumbe 9.2/10 Wonderful (1,649 reviews) "Wonderful breakfast with omelettes cooked to order, great pancakes, fresh fruit, etc. very pleasant staff and beautiful beach area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kurt £223 includes taxes & fees 3 Feb - 4 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Alligator Reef Oceanfront Room King Lanai with Queen Sofabed | View from room](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/4186365f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/af6ef0d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Oceanfront Suite Two Queens Lanai | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/a737b04b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Alligator Reef Oceanfront Room King | Beach/ocean view](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/43c465e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amara Cay Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) Matecumbe 8.8/10 Excellent (1,259 reviews) "Beautiful place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keith £245 includes taxes & fees 11 Feb - 12 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Daily full breakfast for a fee](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/b210c979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/387633fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/981feca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4cbd70d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheeca Lodge & Spa [](https://www.expedia.co.uk/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) Matecumbe 9.2/10 Wonderful (1,290 reviews) "Nice resort " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danilo £274 includes taxes & fees 3 Feb - 4 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/19240ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Bedroom, Kitchen, Pool View | Living area | TV](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/3602f78f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/98989626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Room | 1 bedroom, free WiFi](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/f0ed1fc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Breezy Palms Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) Matecumbe 8.8/10 Excellent (615 reviews) "Friendly staff, beautiful peaceful beach, great room with a big comfy bed and all that you might need. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexander £175 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) ![Outdoor pool, pool loungers](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/7578de06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool loungers](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eed3d949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Ocean View | Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/c134a889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Siesta Resort & Villas [](https://www.expedia.co.uk/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) Matecumbe 8.6/10 Excellent (1,001 reviews) "Great accommodations, very peaceful setting " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan £217 includes taxes & fees 3 Feb - 4 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Beach umbrellas, beach towels](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/f85a3b04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, 2 Queen Beds, Refrigerator & Microwave | In-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/c8c3e07d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/fb0a23a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Kitchenette, Oceanfront | Terrace/patio](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/22976423.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sands of Islamorada [](https://www.expedia.co.uk/Islamorada-Hotels-Sands-Of-Islamorada.h12653483.Hotel-Information) Matecumbe 8.8/10 Excellent (397 reviews) "Great place! Very clean! We'll be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) peter e £175 includes taxes & fees 3 Feb - 4 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Sands-Of-Islamorada.h12653483.Hotel-Information) ![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) ![Balcony view](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/ed6e1255.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 [](https://www.expedia.co.uk/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) Matecumbe 7.6/10 Good (1,002 reviews) "Friendly staff and they did have breakfast. Room was right on the water beautiful view" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynne £202 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/7f55fd9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5d218fa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/d49c45e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/f8d2863e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islander Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) Matecumbe 9.2/10 Wonderful (1,001 reviews) "Rooms are clean, staff is friendly and the place is beautifull" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James £292 includes taxes & fees 4 Feb - 5 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Islander-Resort.h475438.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) ![Dock](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/95229722.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/a51334f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Villas by Islander Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.Hotel-Information) Matecumbe 8.8/10 Excellent (407 reviews) "Staff was very responsive. Great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) rebecca £319 includes taxes & fees 4 Feb - 5 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/a40f819e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shangri-La Suite | Terrace/patio](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/58abb15a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/180cb0c9.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) ### Casa Morada [](https://www.expedia.co.uk/Islamorada-Hotels-Casa-Morada.h900424.Hotel-Information) Matecumbe 9.4/10 Exceptional (422 reviews) "Friendly staff! Laid back place! We enjoyed our stay here! We will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Neal £401 includes taxes & fees 11 Feb - 12 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Casa-Morada.h900424.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.co.uk/Hotel-Search?startDate=2026-02-12&endDate=2026-02-13®ionId=553248635975749648&adults=2&travelerType=beach&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at beach hotels in Upper Matecumbe Key Pool Sea view Family-friendly Air conditioning Pet-friendly ## Beach hotels with pools 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) ![43-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/77344fea.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) ![Deluxe Ocean View Two Queen Suite | Balcony](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/1d1a1984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Beach Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) Matecumbe 9.2/10 Wonderful (1649) £223 includes taxes & fees 3 Feb - 4 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Alligator Reef Oceanfront Room King Lanai with Queen Sofabed | View from room](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/4186365f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/af6ef0d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Oceanfront Suite Two Queens Lanai | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/a737b04b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Alligator Reef Oceanfront Room King | Beach/ocean view](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/43c465e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amara Cay Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) Matecumbe 8.8/10 Excellent (1259) £245 includes taxes & fees 11 Feb - 12 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/f8d2863e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5d218fa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/d49c45e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/7f55fd9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islander Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) Matecumbe 9.2/10 Wonderful (1001) £292 includes taxes & fees 4 Feb - 5 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/387633fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily full breakfast for a fee](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/b210c979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4cbd70d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheeca Lodge & Spa [](https://www.expedia.co.uk/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) Matecumbe 9.2/10 Wonderful (1290) £274 includes taxes & fees 3 Feb - 4 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Oceanfront Three Bedroom Villa | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/43a6a6d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront Three Bedroom Villa | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/d76c74b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/45b47efd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/992a1942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pines & Palms Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information) Matecumbe 9.2/10 Wonderful (1005) [](https://www.expedia.co.uk/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information) ![Suite, 1 King Bed with Sofa bed, Ocean View | Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool loungers](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eed3d949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool 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/c134a889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Siesta Resort & Villas [](https://www.expedia.co.uk/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) Matecumbe 8.6/10 Excellent (1001) £217 includes taxes & fees 3 Feb - 4 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Balcony view](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/ed6e1255.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) ![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) ![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 [](https://www.expedia.co.uk/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) Matecumbe 7.6/10 Good (1002) £202 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/180cb0c9.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) ![Shangri-La Suite | Terrace/patio](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/58abb15a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/2237ce7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Morada [](https://www.expedia.co.uk/Islamorada-Hotels-Casa-Morada.h900424.Hotel-Information) Matecumbe 9.4/10 Exceptional (422) £401 includes taxes & fees 11 Feb - 12 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Casa-Morada.h900424.Hotel-Information) ![On the beach, sun-loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/dd7d4fab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillow-top beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/a064415d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/55a08207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/95dbc957.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Islands of Islamorada [](https://www.expedia.co.uk/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) Matecumbe 9.8/10 Exceptional (70) £771 includes taxes & fees 4 Feb - 5 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/19240ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Bedroom, Kitchen, Pool View | Living area | TV](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/3602f78f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/98989626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Room | 1 bedroom, free WiFi](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/f0ed1fc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Breezy Palms Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) Matecumbe 8.8/10 Excellent (615) £175 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) [View all properties](https://expedia.co.uk/Hotel-Search?startDate=2026-02-12&endDate=2026-02-13®ionId=553248635975749648&adults=2&travelerType=beach&sort=RECOMMENDED&amenities=POOL&openPlayBack=true) ## Beach hotels with ocean views 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) ![43-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/77344fea.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) ![Deluxe Ocean View Two Queen Suite | Balcony](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/1d1a1984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Beach Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) Matecumbe 9.2/10 Wonderful (1649) £223 includes taxes & fees 3 Feb - 4 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Alligator Reef Oceanfront Room King Lanai with Queen Sofabed | View from room](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/4186365f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/af6ef0d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Oceanfront Suite Two Queens Lanai | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/a737b04b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Alligator Reef Oceanfront Room King | Beach/ocean view](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/43c465e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amara Cay Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) Matecumbe 8.8/10 Excellent (1259) £245 includes taxes & fees 11 Feb - 12 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/387633fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily full breakfast for a fee](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/b210c979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4cbd70d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheeca Lodge & Spa [](https://www.expedia.co.uk/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) Matecumbe 9.2/10 Wonderful (1290) £274 includes taxes & fees 3 Feb - 4 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/f8d2863e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5d218fa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/d49c45e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/7f55fd9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islander Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) Matecumbe 9.2/10 Wonderful (1001) £292 includes taxes & fees 4 Feb - 5 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Oceanfront Three Bedroom Villa | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/43a6a6d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront Three Bedroom Villa | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/d76c74b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/45b47efd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/992a1942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pines & Palms Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information) Matecumbe 9.2/10 Wonderful (1005) [](https://www.expedia.co.uk/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information) ![Suite, 1 King Bed with Sofa bed, Ocean View | Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool loungers](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eed3d949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool 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/c134a889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Siesta Resort & Villas [](https://www.expedia.co.uk/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) Matecumbe 8.6/10 Excellent (1001) £217 includes taxes & fees 3 Feb - 4 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Balcony view](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/ed6e1255.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) ![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) ![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 [](https://www.expedia.co.uk/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) Matecumbe 7.6/10 Good (1002) £202 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) ![On the beach, sun-loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/dd7d4fab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillow-top beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/a064415d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/55a08207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/95dbc957.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Islands of Islamorada [](https://www.expedia.co.uk/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) Matecumbe 9.8/10 Exceptional (70) £771 includes taxes & fees 4 Feb - 5 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/19240ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Bedroom, Kitchen, Pool View | Living area | TV](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/3602f78f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/98989626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Room | 1 bedroom, free WiFi](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/f0ed1fc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Breezy Palms Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) Matecumbe 8.8/10 Excellent (615) £175 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.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) ![Dock](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/95229722.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/a51334f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Villas by Islander Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.Hotel-Information) Matecumbe 8.8/10 Excellent (407) £319 includes taxes & fees 4 Feb - 5 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.Hotel-Information) [View all properties](https://expedia.co.uk/Hotel-Search?startDate=2026-02-12&endDate=2026-02-13®ionId=553248635975749648&adults=2&travelerType=beach&sort=RECOMMENDED&amenities=OCEAN_VIEW&openPlayBack=true) ## Family-friendly beach hotels in Upper Matecumbe Key ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/387633fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily full breakfast for a fee](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/b210c979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4cbd70d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheeca Lodge & Spa [](https://www.expedia.co.uk/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) Matecumbe 9.2/10 Wonderful (1290) £274 includes taxes & fees 3 Feb - 4 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/f8d2863e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5d218fa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/d49c45e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/7f55fd9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islander Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) Matecumbe 9.2/10 Wonderful (1001) £292 includes taxes & fees 4 Feb - 5 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Balcony view](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/ed6e1255.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) ![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) ![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 [](https://www.expedia.co.uk/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) Matecumbe 7.6/10 Good (1002) £202 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) ![Suite, 1 King Bed with Sofa bed, Ocean View | Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool loungers](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eed3d949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool 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/c134a889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Siesta Resort & Villas [](https://www.expedia.co.uk/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) Matecumbe 8.6/10 Excellent (1001) £217 includes taxes & fees 3 Feb - 4 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![On the beach, sun-loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/dd7d4fab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillow-top beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/a064415d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/55a08207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/95dbc957.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Islands of Islamorada [](https://www.expedia.co.uk/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) Matecumbe 9.8/10 Exceptional (70) £771 includes taxes & fees 4 Feb - 5 Feb [](https://www.expedia.co.uk/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.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) ![Dock](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/95229722.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/a51334f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Villas by Islander Resort [](https://www.expedia.co.uk/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.Hotel-Information) Matecumbe 8.8/10 Excellent (407) £319 includes taxes & fees 4 Feb - 5 Feb [](https://www.expedia.co.uk/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.co.uk/Hotel-Search?startDate=2026-02-12&endDate=2026-02-13®ionId=553248635975749648&adults=2&travelerType=beach&sort=RECOMMENDED&travelerType=family_friendly&openPlayBack=true) ## Top Upper Matecumbe Key Hotel Reviews ![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555_y.jpg) ### Hawks Cay Resort 10/10 Excellent "Great atmosphe" [](https://expedia.co.uk/Marathon-Hotels-Hawks-Cay-Resort.h6068.Hotel-Information) ![Waterside Suites & Marina](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg) ### Waterside Suites & Marina 10/10 Excellent "Nice " [](https://expedia.co.uk/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information) ![Lime Tree Bay Resort](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/6f2246e8_y.jpg) ### Lime Tree Bay Resort 10/10 Excellent "We stay one night but it was great. It was very clean and it had the space we need it. The front desk staff were friendly and welcoming. This is the 4th time we stay at The Lime Tree Bay Resort." [](https://expedia.co.uk/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information) ![Bayside Villas by Islander Resort](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/70514579_y.jpg) ### Bayside Villas by Islander Resort 10/10 Excellent "Staff was very responsive. Great location " [](https://expedia.co.uk/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.Hotel-Information) ![Marina Del Mar Resort and Marina](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885_y.jpg) ### Marina Del Mar Resort and Marina 10/10 Excellent "Room was clean and spacious. People were friendly and amenities were pleasing " [](https://expedia.co.uk/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Staff was very nice. Nice to use the complimentary clear bottom kayaks. Breakfast was good, Didi made a great omelette!" [](https://expedia.co.uk/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 10/10 Excellent "Beautiful place!" [](https://expedia.co.uk/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg) ### La Siesta Resort & Villas 10/10 Excellent "We stayed in one of the bungalows and absolutely loved it! It was awesome to walk right out of your room onto the beach. We really enjoyed the kayaking. " [](https://expedia.co.uk/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "This palce is awesome. Clean rooms. 2 large pools with a view. Covered garage spot. 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