Title: Islamorada Chalets from CA $143 | Expedia.ca [Islamorada Travel Guide](https://expedia.ca/Islamorada.dx10768)[Hotels in Islamorada](https://expedia.ca/Islamorada-Hotels.d10768.Travel-Guide-Hotels)[Vacation Rentals in Islamorada](https://expedia.ca/Islamorada-Vacation-Rentals.d10768.Travel-Guide-VacationRentals)[Flights to Islamorada](https://expedia.ca/Cheap-Flights-To-Islamorada.d10768.Travel-Guide-Flights)[Things to do in Islamorada](https://expedia.ca/Things-To-Do-In-Islamorada.d10768.Travel-Guide-Activities)[Islamorada Car Rentals](https://expedia.ca/Car-Rentals-In-Islamorada.d10768.Car-Rental-Guide)[Islamorada Vacation Packages](https://expedia.ca/Islamorada.d10768.Destination-Travel-Guides) ![Islamorada which includes tropical scenes and a sandy beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63860-Islamorada.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Chalets in Islamorada from CA $143 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Islamorada Chalets No exact matches found, but these alternatives could be just right ## Recommended hotels in Islamorada ![Front of property - evening/night](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/1508fc00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, snorkeling, kayaking](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/f3e504e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, snorkeling, kayaking](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/70c7ac71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/0065f64e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drift Hotel Key Largo 9.0/10 Wonderful (1001) "The rooms are very nice, staff is friendly. The back is absolutely breathtaking. My boyfriend and I will be back here for sure. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea CA $113 CA $143 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Key-Largo-Hotels-Drift-Hotel.h13209518.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/b5cef261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/9192d0b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/f35b06df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite | Beach/ocean view](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/ae06d5c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Pelican Key Largo Cottages Key Largo 8.8/10 Excellent (1004) "We were delighted with everything The Pelican said it was. The staff was friendly and courteous throughout the property. THE VIEWS were stunning! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ramiro CA $140 CA $158 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information) ![Dock](https://images.trvl-media.com/lodging/112000000/111560000/111555900/111555855/cc89f8fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111560000/111555900/111555855/e8b845d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111560000/111555900/111555855/cb9ea3a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111560000/111555900/111555855/9aaf0d80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seafarer Key Largo Rock Harbor 9.4/10 Exceptional (124) "Everything was especially clean and the breakfast was incredible " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) FATIMA CA $118 CA $152 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Key-Largo-Hotels-Seafarer-Key-Largo.h111555855.Hotel-Information) ![Superior Bungalow, Multiple Beds, Beachfront (Ground Level Sleeps 6) | Terrace/patio](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/6747175b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/ac9bc991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/31d6a642.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, fishing](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/74e26d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Jolla Resort Matecumbe 9.0/10 Wonderful (1000) "Great place to stay lovely staff Easy to find " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) diane CA $99 CA $151 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Islamorada-Hotels-La-Jolla-Resort.h16574668.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/6f2246e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room | Private kitchen](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/4077334d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Waterfront Standard King Bed](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/e7a0378c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/393ff3a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lime Tree Bay Resort Long Key 9.2/10 Wonderful (1097) "Excellent stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joshua [](https://www.expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information) ![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) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/fa9b6bdf.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) ![1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/43f5c138.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Beach Resort Matecumbe 9.2/10 Wonderful (1579) "Great breakfast very well kept grounds" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $147 CA $244 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Premier Cottage, Bay View | Terrace/patio](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/0c81ecd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Suite](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/w1485h1001x15y0-19c35a33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Cabin, 1 King Bed, Bay View](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/w1498h1001x2y0-11d0c529.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, beach towels, kayaking](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/528adcf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rock Reef Resort Rock Harbor 9.2/10 Wonderful (1061) "Everything was perfect. Very clean great staff beautiful place to relax ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miguel CA $133 CA $149 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/419b7787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/8e763282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier One Bedroom Waterfront Suite Bayview with Sofabed](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/dd3dbaaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/46aade65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Inn Key Largo Key Largo 8.6/10 Excellent (1605) "Great location and helpful staff !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nikki CA $171 CA $228 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/4ac8a422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/340e7f1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/eec761cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/aed267ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dove Creek Resort & Marina, Trademark Collection by Wyndham Key Largo 7.6/10 Good (1002) "clean room nice balcony view nice staff nice breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Manuel CA $134 CA $195 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Key-Largo-Hotels-Dove-Creek-Resort-Marina.h1186162.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/7c261d0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/449b99c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, individually decorated](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9e08c794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fisher Inn Resort & Marina Islamorada 8.2/10 Very good (1005) "Great experience, highly recommend staying at the Fisher Inn." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eduardo CA $104 CA $163 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/98989626.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 (568) "Best hotel for the price" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) luzdari CA $107 CA $194 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/ee0752b0.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) ![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) ![Outdoor pool](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/1641bbd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Treasure Harbor Islamorada 9.0/10 Wonderful (111) "The houseboat was so cute! The staff was very friendly and helpful. We really enjoyed out stay. The pool was new and clean. We would definitely come back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tracie [](https://www.expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/1c677271.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/8147c88b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/be3c8b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/b10fe59f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coconut Cove Resort and Marina Islamorada 9.0/10 Wonderful (141) "Really great facility, very relaxing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ken CA $188 CA $212 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/10000/5600/5502/c6c81bd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/1000000/10000/5600/5502/849a6a27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 8:00 AM to 11:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/5600/5502/8bacb368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/10000/5600/5502/084177d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Pointe Suites at Key Largo Tavernier 8.4/10 Very good (1009) "Super happy with the staying " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alejandro CA $191 CA $241 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Tavernier-Hotels-Ocean-Pointe-Suites-At-Key-Largo.h5502.Hotel-Information) ![Water view](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/d461c69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/4743fa46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Queen Beds Water View](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/d6bb28b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Creekside Inn Tavernier 8.0/10 Very good (1000) "We will definitely stay here again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DANIEL CA $175 CA $197 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Tavernier-Hotels-Creekside-Inn-Islamorada.h1576773.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/711b38d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/0fad4f99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, free cabanas](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/25606792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Double Beds, Kitchenette](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/4c5cb130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Inn Matecumbe 9.4/10 Exceptional (1003) "Great place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather CA $169 CA $206 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Islamorada-Hotels-Sunset-Inn.h30568049.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/75000000/74510000/74501700/74501641/2278ee21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite | Living area](https://images.trvl-media.com/lodging/75000000/74510000/74501700/74501641/4ae3e8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed | Terrace/patio](https://images.trvl-media.com/lodging/75000000/74510000/74501700/74501641/bf338fd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74510000/74501700/74501641/fcd75612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kona Kai Resort and Gallery - Adults Only Rock Harbor 9.8/10 Exceptional (285) "The Kona Kai Resort was perfect for us. We especially appreciated the small resort with quiet spaces to relax, read and admire the view. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bastianella CA $171 CA $232 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Key-Largo-Hotels-Kona-Kai-Resort-And-Gallery.h74501641.Hotel-Information) ![Gazebo](https://images.trvl-media.com/lodging/6000000/5030000/5027500/5027403/fe271bae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/6000000/5030000/5027500/5027403/484a28a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage 3 Not Pet-Friendly](https://images.trvl-media.com/lodging/6000000/5030000/5027500/5027403/9ba18998.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5030000/5027500/5027403/28719020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Cove Beach Resort Key Largo 9.0/10 Wonderful (1002) "Always a great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $218 CA $245 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Key-Largo-Hotels-Sunset-Cove-Beach-Resort.h5027403.Hotel-Information) ![Oceanfront King Suite w/ Kitchen & Private Balcony | Water view](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/3997e962.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront King Suite w/ Kitchen & Private Balcony](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/d0b4fd2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/29680b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/f44c6b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drop Anchor Islamorada 8.8/10 Excellent (1001) "Beautiful property and the staff was amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $129 CA $195 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/078f0b06.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) ![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) ![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) ### Charming Home in Key Largo Key Largo 9.8/10 Exceptional (26) "It was clean and a very nice place to stay. Plenty of room and awesome amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric M. CA $154 CA $554 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Key-Largo-Hotels-Charming-Home-In-Key-Largo.h99961430.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=2025-12-03&endDate=2025-12-04®ionId=10768&adults=2&lodging=CHALET&sort=RECOMMENDED&openPlayBack=true) ## Find vacation rentals that suit your style Condos [](https://www.expedia.ca/Hotel-Search?destination=Islamorada%2C+Florida%2C+United+States+of+America®ionId=10768&latLong=24.924294%2C-80.627838&adults=2&startDate=2026-02-16&d1=2026-02-16&endDate=2026-02-19&d2=2026-02-19&lodging=CONDO) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Islamorada%2C+Florida%2C+United+States+of+America®ionId=10768&latLong=24.924294%2C-80.627838&adults=2&startDate=2026-02-16&d1=2026-02-16&endDate=2026-02-19&d2=2026-02-19&lodging=VACATION_HOME) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Islamorada%2C+Florida%2C+United+States+of+America®ionId=10768&latLong=24.924294%2C-80.627838&adults=2&startDate=2026-02-16&d1=2026-02-16&endDate=2026-02-19&d2=2026-02-19&lodging=APARTMENT) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Islamorada%2C+Florida%2C+United+States+of+America®ionId=10768&latLong=24.924294%2C-80.627838&adults=2&startDate=2026-02-16&d1=2026-02-16&endDate=2026-02-19&d2=2026-02-19&lodging=HOUSE_BOAT) Villas [](https://www.expedia.ca/Hotel-Search?destination=Islamorada%2C+Florida%2C+United+States+of+America®ionId=10768&latLong=24.924294%2C-80.627838&adults=2&startDate=2026-02-16&d1=2026-02-16&endDate=2026-02-19&d2=2026-02-19&lodging=VILLA) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Islamorada%2C+Florida%2C+United+States+of+America®ionId=10768&latLong=24.924294%2C-80.627838&adults=2&startDate=2026-02-16&d1=2026-02-16&endDate=2026-02-19&d2=2026-02-19&lodging=APART_HOTEL) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Islamorada%2C+Florida%2C+United+States+of+America®ionId=10768&latLong=24.924294%2C-80.627838&adults=2&startDate=2026-02-16&d1=2026-02-16&endDate=2026-02-19&d2=2026-02-19&lodging=COTTAGE) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Islamorada%2C+Florida%2C+United+States+of+America®ionId=10768&latLong=24.924294%2C-80.627838&adults=2&startDate=2026-02-16&d1=2026-02-16&endDate=2026-02-19&d2=2026-02-19&lodging=CABIN) ![](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%2FIslamorada-Chalets.d10768-aaChalets.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FIslamorada-Chalets.d10768-aaChalets.Travel-Guide-Accommodation) ## Top Islamorada Hotel Reviews ### Islander Resort 10/10 Excellent "Beautiful facility and grounds, wonderful location for quiet get away. The room was very clean. We really enjoyed sitting by the pool and also lounging on our private patio. Would definitely stay here again if we were in the area. A broom on the patio would be helpful to sweep away any insects." [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ### La Jolla Resort 10/10 Excellent "Room was nice and clean. Beach area was beautiful to watch sunset. " [](https://expedia.ca/Islamorada-Hotels-La-Jolla-Resort.h16574668.Hotel-Information) ### Cheeca Lodge & Spa 10/10 Excellent "Amazing!" [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ### Chesapeake Beach Resort 10/10 Excellent "Room was clean, breakfast and staff were good " [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ### Coconut Cove Resort and Marina 10/10 Excellent "Really really enjoyed the laid back style at this resort and what a beautiful property. Will be back soon!" [](https://expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information) ### Amara Cay Resort 10/10 Excellent "Very nice resort! Nice pool and the tiki bar was amazing. Great service and so close to Bud and Mary’s since we were fishing a few days. Definitely will return." [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ### Fisher Inn Resort & Marina 10/10 Excellent "We stay here about 3-4 times a year. Always great. Nice rooms. Parking is easy and right in front of the rooms. Comp breakfast. Can fish from anywhere on the property and spot to clean your catch, hands and rods. Dog friendly! We love this spot. " [](https://expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort 10/10 Excellent "We had the best family stay at this resort in the Keys. The rooms were spotless, comfortable, and perfect for winding down after a day in the sun. The pool was the real star for us… our kiddo didn’t want to get out. The whole place felt relaxed and welcoming, Truly one of our favorite family trips. Highly recommend!" [](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ### Breezy Palms Resort 10/10 Excellent "This is one of my top 5 spot to stay in the keys, clean, friendly and budget friendly, mimi is awesome " [](https://expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) ## Find out more about Islamorada ## Islamorada Chalets information | Number of reviews | 16,588 | | --- | --- | | Accommodation | 0 Chalets | | Lowest Price | CA $143 | | Highest Price | CA $554 | ## Explore a world of travel with Expedia - Lodging - Packages - Cars - Other - More ways to book - [Hotels near Bud n' Mary's Dive Center](https://www.expedia.ca/Bud-N-Marys-Dive-Center-Hotels.0-l6069243-0.Travel-Guide-Filter-Hotels) - [B&B in Coopertown](https://www.expedia.ca/Coopertown-Bed-And-Breakfast.d6177715-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Coopertown](https://www.expedia.ca/Coopertown-Guest-Houses.d6177715-aaGuestHouses.Travel-Guide-Accommodation) - 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[Hurricane Monument](https://www.expedia.ca/Hurricane-Monument-Matecumbe.d6063543.Vacation-Attraction) - [Visit Matecumbe](https://www.expedia.ca/Islamorada-Matecumbe.dx855587555438403584) - [Visit Upper Matecumbe Key](https://www.expedia.ca/Upper-Matecumbe-Key.dx553248635975749648) - [Windley Key Fossil Reef Geological State Park](https://www.expedia.ca/Windley-Key-Fossil-Reef-Geological-State-Park-Islamorada.d6282211.Vacation-Attraction) - [Drive-A-Matic Rental Cars in Windley Key](https://www.expedia.ca/Drive-A-Matic-Car-Rentals-In-Windley-Key.d553248635976197663-c1082.Car-Rental-Guide-Suppliers) - [Easirent.com Rental Cars in Upper Matecumbe Key](https://www.expedia.ca/Easirentcom-Car-Rentals-In-Upper-Matecumbe-Key.d553248635975749648-c1017.Car-Rental-Guide-Suppliers) - [Zezgo Rental Cars in Windley Key](https://www.expedia.ca/ZezGo-Car-Rentals-In-Windley-Key.d553248635976197663-c1122.Car-Rental-Guide-Suppliers) - [Things to do in Windley Key](https://www.expedia.ca/Things-To-Do-In-Windley-Key.d553248635976197663.Travel-Guide-Activities) - [Book Chalets in Islamorada on Expedia.com](https://www.expedia.com/Islamorada-Chalets.d10768-aaChalets.Travel-Guide-Accommodation)