Title: Book the Best Hotels with BARS in Islamorada in 2026 | 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 featuring a sunset and general coastal views](https://images.trvl-media.com/place/10768/7014979e-dcd6-42fa-a69b-b138a0a93305.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/10768/7014979e-dcd6-42fa-a69b-b138a0a93305.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 availability on Islamorada Hotels with Bar ## Our top choices for Islamorada hotels with a bar ![Hibiscus Waterfront 2-Bedroom, Two Bath Master Suite (Brand New) | Terrace/patio](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/55bf0b8b.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) ![Room](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/9e920762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 outdoor pools, open 7:30 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/ca18911f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lime Tree Bay Resort [](https://www.expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information) Long Key 9.2/10 Wonderful (1,182 reviews) "Excellent location, beautiful property, friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $322 CA $424 total includes taxes & fees Mar 4 - Mar 5 [](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) ![Water view](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/8979e9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/c2caabe9.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.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) Matecumbe 9.2/10 Wonderful (1,663 reviews) "Awesome place!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $461 CA $596 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Classic Room, Patio, Garden View](https://images.trvl-media.com/lodging/111000000/110690000/110683500/110683445/5d3fac38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Room, Mobility Accessible, Patio](https://images.trvl-media.com/lodging/111000000/110690000/110683500/110683445/f4617abf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Room, Patio, Garden View](https://images.trvl-media.com/lodging/111000000/110690000/110683500/110683445/5f27ae80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/111000000/110690000/110683500/110683445/01400ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ocean View Inn & Pub [](https://www.expedia.ca/Islamorada-Hotels-The-Ocean-View-Inn-Pub.h110683445.Hotel-Information) Islamorada 9.0/10 Wonderful (17 reviews) "Great stay! Loved this property and staff. Clean and convenient. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela CA $333 CA $374 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Islamorada-Hotels-The-Ocean-View-Inn-Pub.h110683445.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256350/9bc23a15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256350/079f8926.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256350/b17c222a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/79000000/78260000/78256400/78256350/w1284h942x0y5-9b978d1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3212 Across from Pool \* King & Queen/Twin Bunk Bed [](https://www.expedia.ca/Tavernier-Hotels-Modern-Coastal-Renovation.h78256350.Hotel-Information) Tavernier 9.8/10 Exceptional (152 reviews) "Great stay lovely home " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yezenia CA $237 CA $621 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Tavernier-Hotels-Modern-Coastal-Renovation.h78256350.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, sun loungers](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/af6ef0d3.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) ![One Bedroom Oceanfront Suite Two Queens Lanai](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/a737b04b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amara Cay Resort [](https://www.expedia.ca/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 CA $407 CA $558 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Outdoor pool, open 8:00 AM to 11:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/5600/5502/7f240362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, beach towels](https://images.trvl-media.com/lodging/1000000/10000/5600/5502/0c2736d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/1000000/10000/5600/5502/dfb81707.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 [](https://www.expedia.ca/Tavernier-Hotels-Ocean-Pointe-Suites-At-Key-Largo.h5502.Hotel-Information) Tavernier 8.4/10 Very good (1,012 reviews) "I love this place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rosemary CA $326 CA $392 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Tavernier-Hotels-Ocean-Pointe-Suites-At-Key-Largo.h5502.Hotel-Information) ![Suite, 1 King Bed with Sofa bed, Ocean View](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) ![Suite, 1 King Bed with Sofa bed, Ocean View | Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/b304e7ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/7578de06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Siesta Resort & Villas [](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) Matecumbe 8.8/10 Excellent (1,001 reviews) "excellent location very nice simple breakfast close to liz’s of activities great poool " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kurt CA $364 CA $510 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.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) ![Property grounds](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/981feca1.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.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) Matecumbe 9.2/10 Wonderful (1,299 reviews) "Great staff and beautiful property " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie CA $703 CA $891 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/8c74658c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves lunch and dinner](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/bb9d7ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, beach cabanas, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/d9cc2f68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/92d23e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Playa Largo Resort & Spa, Autograph Collection [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) Rock Harbor 8.8/10 Excellent (1,003 reviews) "We had a wonderful six night stay at Playa Largo Resort. Exceptional staff and resort amenities. Beautiful beach and Key Largo property. Definitely coming back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debra CA $621 CA $774 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.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) ![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) ![3 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/2bff44ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islander Resort [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) Matecumbe 9.2/10 Wonderful (1,009 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 CA $562 CA $725 total includes taxes & fees Mar 26 - Mar 27 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.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=2026-03-17&endDate=2026-03-18®ionId=10768&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_10768) ## Top Islamorada Hotel Reviews ![Coconut Cove Resort and Marina](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/667446d9_y.jpg) ### Coconut Cove Resort and Marina 10/10 Excellent "It was wonderful " [](https://expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information) ![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "Our king room was spacious and clean with a very comfortable bed and nice linens. Very well maintained grounds and a nice bar by the pool with a great view of the ocean. I would definitely recommend! " [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Very comfortable with nice rooms. Attentive on site management." [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.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 "Sarah the night manager was so very helpful as we checked in on Monday evening. The pool area was ideal for our toddler. All of the staff were delightful and so friendly. Love the resort ambiance." [](https://expedia.ca/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.Hotel-Information) ![Breezy Palms Resort](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/96b58c48_y.jpg) ### Breezy Palms Resort 10/10 Excellent "location was excellent, room was awesome, grounds were the best" [](https://expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) ![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/4186365f_y.jpg) ### Amara Cay Resort 10/10 Excellent "Staff excellent. Clean room and surroundings " [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4671ebc2_y.jpg) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort 10/10 Excellent "Fun outdoor tiki bar. Beautiful beach access. Nice room. " [](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "This Resort is unbelievable from the rooms to the beach, walking & biking trails, golf course 27 acres of lush property. Lots of shops & restaurants nearby including Bass Pro Shop, small artists shops & brewery within walking/biking distance. " [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Drop Anchor](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d_y.jpg) ### Drop Anchor 10/10 Excellent "My stay at Drop Harbor was excellent. The room was spotless and the location couldn’t have been better. I opened my door and the water was right there — absolutely beautiful. The front desk staff was very friendly and welcoming. Overall, a fantastic experience!" [](https://expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Islamorada? ### What are the best hotels with bars in Islamorada? ### How many hotels with bars should I expect to find in Islamorada? ### What is there to do in Islamorada? ### When is the best time to visit Islamorada? ### How can I get to Islamorada and around the area? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Cheap-Hotels.0-0-d553248635083902001-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Luxury-Hotel.0-0-d553248635083902001-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Brickell ](https://www.expedia.ca/Brickell-Miami-Hotels-Adults-Only-Resorts.0-n6240961-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Casino Hotels in Brickell ](https://www.expedia.ca/Brickell-Miami-Hotels-Casino-Hotel.0-n6240961-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - 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