Title: Holiday Rentals Islamorada from £103: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [Islamorada Travel Guide](https://expedia.co.uk/Islamorada.dx10768)[Hotels in Islamorada](https://expedia.co.uk/Islamorada-Hotels.d10768.Travel-Guide-Hotels)[Flights to Islamorada](https://expedia.co.uk/Cheap-Flights-To-Islamorada.d10768.Travel-Guide-Flights)[Things to do in Islamorada](https://expedia.co.uk/Things-To-Do-In-Islamorada.d10768.Travel-Guide-Activities)[Islamorada Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Islamorada.d10768.Car-Hire-Guide)[Islamorada Holidays](https://expedia.co.uk/Islamorada.d10768.Holidays-City-Breaks) ![Islamorada showing a beach and tropical scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63860-Islamorada.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Holiday Rentals in Islamorada ![price find illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.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 Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![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 [21 Sept - 22 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=10768&startDate=2025-09-21&endDate=2025-09-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [22 Sept - 23 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=10768&startDate=2025-09-22&endDate=2025-09-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [26 Sept - 28 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=10768&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [3 Oct - 5 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=10768&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Holiday Rentals in Islamorada ## Our top choices for Islamorada holiday rentals ![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) ![25-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/92a650b5.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) ![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) ### Treasure Harbor Islamorada 8.8/10 Excellent (104) "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. " £180 includes taxes & fees 24 Sept - 25 Sept [](https://www.expedia.co.uk/Islamorada-Hotels-Treasure-Harbor.h91743042.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 | 1 bedroom, free WiFi](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/b8fa0acc.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) ![Standard Room, 1 Bedroom, Kitchen, Pool View | Living area | TV](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/5e728c12.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. " £103 includes taxes & fees 6 Oct - 7 Oct [](https://www.expedia.co.uk/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) ![2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/61575cce.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) ![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) ### The Islands of Islamorada Matecumbe 9.8/10 Exceptional (66) "Absolutely outstanding resort. Legitimate 5 star property. " £500 includes taxes & fees 23 Sept - 24 Sept [](https://www.expedia.co.uk/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.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) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/33000000/32590000/32583400/32583358/a9bfcbbf.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) ### Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7 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.co.uk/Islamorada-Hotels-Oceanfront-165ft-Beach-Dock-Heated-Pool-4K-Sqft-4-Bed5-Bath-Next-Avail-8925.h32583358.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33501900/33501813/932e7e7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33510000/33501900/33501813/0d21a2f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33510000/33501900/33501813/80ad41b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/34000000/33510000/33501900/33501813/6c41bbd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars Islamorada 10/10 Exceptional (195) "We just got back from Islamorada and cannot stop talking about our trip. This property was clean and comfortable and the private development had everything we wanted. Everyone was very nice. I will definitely rent again if/when we return." [](https://www.expedia.co.uk/Islamorada-Hotels-OCEAN-VIEW-ANGLERS-REEF-POOL.h33501813.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/90000000/89670000/89661200/89661122/009106c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89670000/89661200/89661122/0d92c0bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89670000/89661200/89661122/0cc8876e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89670000/89661200/89661122/50479bb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada Matecumbe 9.6/10 Exceptional (32) "Nice property . Well kept. Good management " [](https://www.expedia.co.uk/Islamorada-Hotels-Bungalow-4-2-Bed1-Bath-Pool-In-Islamorada.h89661122.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) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29960000/29956500/29956429/64ae72ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/30000000/29960000/29956500/29956429/34468839.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) ### 5 bedroom - Deep Dockage & Heated Pool in Islamorada. Matecumbe 10/10 Exceptional (118) "Wonderful location." [](https://www.expedia.co.uk/Islamorada-Hotels-5-Bedroom-Deep-Dockage-Heated-Pool-In-Islamorada.h29956429.Hotel-Information) ![Sun-loungers](https://images.trvl-media.com/lodging/114000000/113320000/113313700/113313657/362909f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113320000/113313700/113313657/660dcd95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113320000/113313700/113313657/fbce4b7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/114000000/113320000/113313700/113313657/2eebfb00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BeachFront Paradise/By The Glam Homes Matecumbe [](https://www.expedia.co.uk/Islamorada-Hotels-BeachFront-ParadiseBy-The-Glam-Homes.h113313657.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34080000/34074700/34074635/3effc76f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/35000000/34080000/34074700/34074635/23f2f79c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34080000/34074700/34074635/528b8783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/35000000/34080000/34074700/34074635/d3da3c21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY! Matecumbe 9.6/10 Exceptional (83) "Great property and great location!" [](https://www.expedia.co.uk/Islamorada-Hotels-WOW-WATERFRONT-CANAL-HOME-RELAXING.h34074635.Hotel-Information) ![On the beach, sun-loungers, beach towels](https://images.trvl-media.com/lodging/36000000/35270000/35265400/35265387/56c8be3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35270000/35265400/35265387/8c530ac0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/36000000/35270000/35265400/35265387/ab7b3ad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35270000/35265400/35265387/9d3eacfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views Matecumbe 10/10 Exceptional (105) "Chauncey was awesome and very accommodating." [](https://www.expedia.co.uk/Islamorada-Hotels-Private-Oceanfront-Heated-Pool.h35265387.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) ![Smart TV](https://images.trvl-media.com/lodging/54000000/53040000/53031600/53031525/4afe5eac.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) ### 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.co.uk/Islamorada-Hotels-7-Bedroom-With-Dockage.h53031525.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/26000000/25090000/25088000/25087966/a399288a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/26000000/25090000/25088000/25087966/1ab96f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children’s area](https://images.trvl-media.com/lodging/26000000/25090000/25088000/25087966/5266da3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/26000000/25090000/25088000/25087966/5c0cbd2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards Islamorada 10/10 Exceptional (185) "Great property. Very clean and had everything we needed. The whole complex is very nice and loved our stay. Owners very good with communication and friendly." [](https://www.expedia.co.uk/Islamorada-Hotels-OCEANFRONT-ANGLERS-REEF-ISLAMORADA-HOME-Pool.h25087966.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34530000/34520800/34520723/b6691c8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/35000000/34530000/34520800/34520723/62cb2b9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34530000/34520800/34520723/4af3e774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34530000/34520800/34520723/dc3d65ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker Venetian Shores 10/10 Exceptional (38) "Was a nice property and pleasant enough for our stay." [](https://www.expedia.co.uk/Islamorada-Hotels-Paradise-In-Venetian-Shores-Pool-SPA-Heater-Chiller-Commercial-Ice-Maker.h34520723.Hotel-Information) ![Smart TV, books, stereo, printers](https://images.trvl-media.com/lodging/112000000/111850000/111848500/111848403/8b8b2523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111850000/111848500/111848403/e475ebbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/112000000/111850000/111848500/111848403/059fe8f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111850000/111848500/111848403/w1024h682x0y1-f558126f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning Oceanfront Estate with Private Pool ~ Beach. Matecumbe [](https://www.expedia.co.uk/Islamorada-Hotels-NEW-Stunning-Oceanfront-Estate-With-Private-Pool-Beach-2026-Calendar-Only.h111848403.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117370000/117360600/117360591/41466dc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, ping pong, stereo](https://images.trvl-media.com/lodging/118000000/117370000/117360600/117360591/f60fb0cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117370000/117360600/117360591/e906dcf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117370000/117360600/117360591/79f4d875.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony Islamorada 10/10 Exceptional (1) "This property was amazing basically brand new definitely recommend " [](https://www.expedia.co.uk/Islamorada-Hotels-NEW-Oceanfront-FL-Keys-Home-WPool.h117360591.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27140000/27138100/27138031/270-181d1b05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/28000000/27140000/27138100/27138031/b8d2c60e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27140000/27138100/27138031/270-9647ee10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/28000000/27140000/27138100/27138031/c4cf9e8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Breathtaking ocean views for your Paradise vacations Matecumbe 10/10 Exceptional (91) "Great place to hang by the ocean with tons of dining choices in every direction! Clean and open layout - you won’t be disappointed!" [](https://www.expedia.co.uk/Islamorada-Hotels-Breathtaking-Ocean-Views-For-Your-Paradise-Vacations.h27138031.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/27000000/26850000/26841500/26841407/c21b836d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/27000000/26850000/26841500/26841407/772ff74c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/27000000/26850000/26841500/26841407/19539bcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/26850000/26841500/26841407/b2ff04e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Venetian Shores Escape! Heated Pool, 3BR, 70ft Dock, Dog-Friendly! Venetian Shores 9.6/10 Exceptional (58) "The property is central location in Islamorada, best location....The outdoor area is perfect,pool heated very enjoyable.. great neighborhood..Friendly Host JoAnn is amazing, and prompt response, a delightful person, and a wonderful host!" [](https://www.expedia.co.uk/Islamorada-Hotels-Venetian-Tropics-Weekly-Pvt-Home-Wheated-Pool.h26841407.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/77000000/76260000/76257400/76257359/6ab2d73c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun-loungers, beach towels](https://images.trvl-media.com/lodging/77000000/76260000/76257400/76257359/a5518809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76260000/76257400/76257359/28b21330.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/77000000/76260000/76257400/76257359/1955b8a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islamorada Boaters Paradise with 70' Dock and private beach access.. Matecumbe 10/10 Exceptional (24) "We loved this house. It had plenty of space for all 8 of us. We enjoyed fishing off the dock, the pool and the private beach. " [](https://www.expedia.co.uk/Islamorada-Hotels-Islamorada-Boaters-Paradise-With-70-Dock-And-Private-Beach-Access.h76257359.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/60000000/59200000/59193600/59193507/87d82598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/60000000/59200000/59193600/59193507/2ae7152a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/60000000/59200000/59193600/59193507/1628bedb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, ping pong, books, stereo](https://images.trvl-media.com/lodging/60000000/59200000/59193600/59193507/4a3a2525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Iconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage. Matecumbe 10/10 Exceptional (67) "Ted’s Place was a 10! Mark and Theresa were wonderful! Easy to communicate with and made sure that the home had everything one might need. Our family absolutely loved the outdoor space and the location in Islamorada couldn’t be better! " [](https://www.expedia.co.uk/Islamorada-Hotels-Iconic-Ted-Williams-Estate-Bayfront.h59193507.Hotel-Information) ![On the beach, sun-loungers, beach towels](https://images.trvl-media.com/lodging/88000000/87380000/87373500/87373500/4b78f6ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/88000000/87380000/87373500/87373500/924a536c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87380000/87373500/87373500/abc1e84a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/88000000/87380000/87373500/87373500/c7b0dea4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront 4-BR w/ private 31' Boat Slip Included, Pool & Beach, gourmet kitchen Islamorada 9.8/10 Exceptional (34) "We had a great family trip! The house was perfect and so comfortable " [](https://www.expedia.co.uk/Islamorada-Hotels-Oceanfront.h87373500.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=2025-10-06&endDate=2025-10-07®ionId=10768&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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FIslamorada-Holiday-Rentals.d10768.Travel-Guide-HolidayRentals)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FIslamorada-Holiday-Rentals.d10768.Travel-Guide-HolidayRentals) ## Top Islamorada Hotel Reviews ![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.co.uk/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Sunset Inn](//images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/25606792_y.jpg) ### Sunset Inn 10/10 Excellent "It was a wonderful stay. The ladies at the front desk are more than amazing. The room is super cute and clean. Pool was wonderful We are looking forward to staying here again. Also, lots of places to eat are walkable. " [](https://expedia.co.uk/Islamorada-Hotels-Sunset-Inn.h30568049.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.co.uk/Islamorada-Hotels-Islander-Resort.h475438.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.co.uk/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) ![Chesapeake Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Very clean property, good breakfast included and the views are spectacular!! Beautiful beach location!! Would go back anytime!! " [](https://expedia.co.uk/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![La Jolla Resort](//images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/74e26d92_y.jpg) ### La Jolla Resort 10/10 Excellent "Little hidden jewel of the keys. " [](https://expedia.co.uk/Islamorada-Hotels-La-Jolla-Resort.h16574668.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 "Everything was good, the place is super familiar, secure and the service was incredible." [](https://expedia.co.uk/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Fisher Inn Resort & Marina](//images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9_y.jpg) ### Fisher Inn Resort & Marina 10/10 Excellent "Two night stay . Advertised paddle boards and kayaks but although front desk employee was nice she didn’t get up or go out of her way to offer much additional info on anything. Never saw the kayaks or paddle boards and wasn’t an actual beach right there so no clue where you go to do that. Heard another customer say they were told one kayak was broke? Also had to put key in the wall to power certain thinks which is fine and we figured it out but would’ve taken less time if she explained that. She was very nice at checking though. " [](https://expedia.co.uk/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) ![Bayside Villas by Islander Resort](//images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/70514579_y.jpg) ### Bayside Villas by Islander Resort 10/10 Excellent "Beautiful property loads of thing to do or do nothing. Great restaurao" [](https://expedia.co.uk/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.Hotel-Information) ## Find out more about Islamorada **Everything you need to know about** **Islamorada** **holiday rentals** Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Islamorada holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/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 Islamorada holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Islamorada holiday rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Islamorada. 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 Islamorada holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Islamorada holiday rentals we have selected for you start as low as £103 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Islamorada rentals** At Expedia, we put the best Islamorada holiday 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 Islamorada 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 Islamorada holiday. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Islamorada. 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.co.uk - All accommodation types in Islamorada ### Trending destinations on Expedia.co.uk - [Holiday Rentals in the Cotswold](https://www.expedia.co.uk/lp/b/vr/cotswold) - [Holiday Rentals in Lake District](https://www.expedia.co.uk/lp/b/vr/lake-district) - [Devon Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Devon.d6046196.Holiday-Rental-Destinations) - [Norfolk Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Norfolk.d6046223.Holiday-Rental-Destinations) - [Bedfordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Bedfordshire.d6046189.Holiday-Rental-Destinations) - [Dorset Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Dorset.d6046198.Holiday-Rental-Destinations) - [Northumberland Holiday Rentals](https://www.expedia.com/Destinations-In-Northumberland.d6046225.Vacation-Rental-Destinations) - [Herefordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Herefordshire.d6046203.Holiday-Rental-Destinations) - [Essex Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Essex.d6046201.Holiday-Rental-Destinations) - [Cumbria Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cumbria.d6046194.Holiday-Rental-Destinations) - [Yorkshire Holiday Rentals](https://www.expedia.co.uk/Yorkshire-Holiday-Rentals.d6342462.Travel-Guide-HolidayRentals) - [South Wales Holiday Rentals](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals) - [North Wales Holiday Rentals](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals) - [London Holiday Rentals](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals) - [York Holiday Rentals](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals) - [Blackpool Holiday Rentals](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals) - [Isle of Wight Holiday Rentals](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations) - [Scarborough Holiday Rentals](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals) - [Edinburgh Holiday Rentals](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals) - [Bath Holiday Rentals](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals) - [Bournemouth Holiday Rentals](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals) - [England Holiday Rentals](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations) - [Scotland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations) - [Cornwall Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations) - [Wales Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations) - [Northern Ireland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations) - [Holiday Homes in Islamorada](https://expedia.co.uk/Islamorada-Private-Holiday-Homes.d10768-aaPrivateHolidayHomes.Travel-Guide-Accommodation) - [Apartments in Islamorada](https://expedia.co.uk/Islamorada-Apartments.d10768-aaApartments.Travel-Guide-Accommodation) - [Villas in Islamorada](https://expedia.co.uk/Islamorada-Villas.d10768-aaVillas.Travel-Guide-Accommodation) - [Houseboats in Islamorada](https://expedia.co.uk/Islamorada-Houseboats.d10768-aaHouseboats.Travel-Guide-Accommodation) - [Motels in Islamorada](https://expedia.co.uk/Islamorada-Motels.d10768-aaMotels.Travel-Guide-Accommodation) - [B&B in Islamorada](https://expedia.co.uk/Islamorada-Bed-And-Breakfasts.d10768-aaBedAndBreakfasts.Travel-Guide-Accommodation) ## Frequently asked questions ### Can I find a holiday rental in Islamorada? > Yes, there are holiday rentals close to the most popular sights in Islamorada, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Islamorada like the scenic seaside and entertainment choices this destination is known for. While you're here, grab a bite or have a drink at the seafood restaurants. ### What are some of the best holiday rentals that Islamorada has to offer? > [Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7](https://www.expedia.co.uk/Islamorada-Hotels-Oceanfront-165ft-Beach-Dock-Heated-Pool-4K-Sqft-4-Bed5-Bath-Next-Avail-8925.h32583358.Hotel-Information): This highly rated holiday home rental in Islamorada is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a rooftop terrace, a private garden and a selection of games so that you can immerse yourself in your holiday. Some other homes for rent in Islamorada include [OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars](https://www.expedia.co.uk/Islamorada-Hotels-OCEAN-VIEW-ANGLERS-REEF-POOL.h33501813.Hotel-Information) and [Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada](https://www.expedia.co.uk/Islamorada-Hotels-Bungalow-4-2-Bed1-Bath-Pool-In-Islamorada.h89661122.Hotel-Information). ### How many holiday rentals are there in Islamorada? > With 493 Expedia holiday rentals, you're guaranteed to find just the right place for your Islamorada stay. ### What can I see and do in Islamorada? > Enjoy the outdoors at Islamorada County Park and Anne's Beach, or simply take in cultural attractions like History of Diving Museum and MoradaWay Arts & Cultural District. Other places in town to visit include Bud n' Mary's Dive Center and Fiesta Key. ### What’s a holiday rental in Islamorada like? > Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Islamorada. Holiday rentals feature extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips. ### Expedia's Latest Trends Hotels - [Hotels in Key West](https://expedia.co.uk/Key-West-Hotels.d1187.Travel-Guide-Hotels) - [Hotels in Sanibel](https://expedia.co.uk/Sanibel-Hotels.d9791.Travel-Guide-Hotels) - [Hotels in Sarasota](https://expedia.co.uk/Sarasota-Hotels.d602719.Travel-Guide-Hotels) - [Hotels in Cocoa Beach](https://expedia.co.uk/Cocoa-Beach-Hotels.d6549.Travel-Guide-Hotels) - [Hotels in Daytona Beach](https://expedia.co.uk/Daytona-Beach-Hotels.d6023995.Travel-Guide-Hotels) - [Hotels in Destin](https://expedia.co.uk/Destin-Hotels.d6906.Travel-Guide-Hotels) - [Hotels in Naples](https://expedia.co.uk/Naples-Hotels.d602724.Travel-Guide-Hotels) - [Hotels in Key Largo](https://expedia.co.uk/Key-Largo-Hotels.d8369.Travel-Guide-Hotels) Flights - [Flights to Sarasota](https://expedia.co.uk/Cheap-Flights-To-Sarasota.d602719.Travel-Guide-Flights) - [Flights to Christmas](https://expedia.co.uk/Cheap-Flights-To-Christmas.d6154232.Travel-Guide-Flights) - [Flights to Melbourne](https://expedia.co.uk/Cheap-Flights-To-Melbourne.d2342.Travel-Guide-Flights) - [Flights to Tallahassee](https://expedia.co.uk/Cheap-Flights-To-Tallahassee.d6048214.Travel-Guide-Flights) - [Flights to Fort Myers](https://expedia.co.uk/Cheap-Flights-To-Fort-Myers.d602729.Travel-Guide-Flights) - [Flights to Davenport](https://expedia.co.uk/Cheap-Flights-To-Davenport.d6301.Travel-Guide-Flights) - [Flights to Cape Canaveral](https://expedia.co.uk/Cheap-Flights-To-Cape-Canaveral.d6484.Travel-Guide-Flights) - [Flights to Pensacola](https://expedia.co.uk/Cheap-Flights-To-Pensacola.d6023331.Travel-Guide-Flights) - [Flights to Sanford](https://expedia.co.uk/Cheap-Flights-To-Sanford.d9845.Travel-Guide-Flights) - [Flights to Palm Beach](https://expedia.co.uk/Cheap-Flights-To-Palm-Beach.d9061.Travel-Guide-Flights) - [Flights to Daytona Beach](https://expedia.co.uk/Cheap-Flights-To-Daytona-Beach.d6023995.Travel-Guide-Flights) - [Flights to Key West](https://expedia.co.uk/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights) Cars - [Car hire in Key West](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Key-West.d1187.Car-Hire-Guide) Activities - [Things to do in Winter Garden](https://expedia.co.uk/Things-To-Do-In-Winter-Garden.d7898.Travel-Guide-Activities) - [Things to do in Holiday](https://expedia.co.uk/Things-To-Do-In-Holiday.d10343.Travel-Guide-Activities) Packages - [Naples Holidays](https://expedia.co.uk/Naples.d602724.Holidays-City-Breaks) - [Panama City Beach Holidays](https://expedia.co.uk/Panama-City-Beach.d8021.Holidays-City-Breaks) - [Siesta Key Holidays](https://expedia.co.uk/Siesta-Key.d6881.Holidays-City-Breaks) - [Heathrow Holidays](https://expedia.co.uk/Heathrow.d11967.Holidays-City-Breaks) - [Key West Holidays](https://expedia.co.uk/Key-West.d1187.Holidays-City-Breaks) General - [Visit Tallahassee](https://expedia.co.uk/Tallahassee.dx6048214) - [Visit Boca Raton](https://expedia.co.uk/Boca-Raton.dx6317) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)