Title: Book the Best Hotels with BARS in Islamorada in 2025 | 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 showing a sandy beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191197-Islamorada.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Bar in Islamorada, FL from CA $179 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Islamorada Hotels with Bar ## Top Islamorada Hotels with Bar ![Room, 1 King Bed, Bay View | Beach/ocean view](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/68e30233.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 8 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/c604580a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/c052003d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/66659102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Key Largo Manatee Bay Key Largo 8.8/10 Excellent (1006) "The place was very clean safe and enjoyable. Perfect little paradise." CA $159 CA $179 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.Hotel-Information) ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/9b929f51.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) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/79d31a44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheeca Lodge & Spa Matecumbe 9.2/10 Wonderful (1216) "Beautiful and relaxing hotel!!" CA $166 CA $281 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.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) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/fa9b6bdf.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 (1531) "Wonderful property, breakfast was awesome " CA $182 CA $284 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/af88a0b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/19311fed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/9a9545cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marina Del Mar Resort and Marina Key Largo 8.4/10 Very good (1613) "We loved the area. We were not impressed with beach options " CA $127 CA $183 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/430000/428800/428789/02e7cbc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Refrigerator & Microwave (Wet bar)](https://images.trvl-media.com/lodging/1000000/430000/428800/428789/9df88559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/430000/428800/428789/c0da6cad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/428800/428789/1b910ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Marathon - Florida Keys Marathon 9.0/10 Wonderful (1005) "Our quick family getaway was great and this hotel was a great option . Staff was excellent . " CA $183 CA $206 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Marathon-Hotels-Hampton-Inn-Marathon-Florida-Keys.h428789.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) ![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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/4b49fc53.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 (1074) "So close to the ocean was amazing. " CA $157 CA $240 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.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) ![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) ### Ocean Pointe Suites at Key Largo Tavernier 8.2/10 Very good (1005) "Excellent place. Room super clean, staff very welcoming." CA $169 CA $216 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Tavernier-Hotels-Ocean-Pointe-Suites-At-Key-Largo.h5502.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/b513b652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Islander Suite Ocean View Two Bedroom | Private kitchen](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/20ed25e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily full breakfast for a fee](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/3ea0faf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islander Resort Matecumbe 9.2/10 Wonderful (1003) "Stunning resort with great amenities and excellent service! " CA $268 CA $396 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Private beach, sun loungers, beach towels, scuba diving](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/cb9f9f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/c5948ba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4dfe75fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort Islamorada 9.0/10 Wonderful (91) "Beautiful place to stay" CA $260 CA $385 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/489feb58.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) ![On the beach, beach cabanas, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/8f8fe319.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 Key Largo 9.0/10 Wonderful (1003) "Very nice place to stay in the keys " CA $333 CA $452 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-20&endDate=2025-10-21®ionId=10768&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Islamorada Hotel Reviews ![Pines & Palms Resort](//images.trvl-media.com/lodging/1000000/1000000/990500/990422/6ac4045c_y.jpg) ### Pines & Palms Resort 10/10 Excellent "Campground feel. Staff was incredible. " [](https://expedia.ca/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information) ![Drop Anchor](//images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d_y.jpg) ### Drop Anchor 10/10 Excellent "Clean, comfortable room, friendly staff. Grounds clean and properly taken care of. Would stay here again. " [](https://expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) ![Cheeca Lodge & Spa](//images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "Yes" [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Coconut Cove Resort and Marina](//images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/667446d9_y.jpg) ### Coconut Cove Resort and Marina 10/10 Excellent "⭐️⭐️⭐️⭐️⭐️ We had such a wonderful stay at Coconut Cove Resort! The room was spotless, comfortable, and had everything we needed. The staff was incredibly friendly and made us feel right at home from the moment we arrived. Breakfast was fresh and delicious each morning, the perfect way to start the day. The best part was the beautiful ocean view—waking up to that scenery was unforgettable. We can’t wait to come back!" [](https://expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information) ![Chesapeake Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Excellent recommendation for a small budget." [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](//images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort 10/10 Excellent "Truly enjoyed our visit to this property. Lots to do and great dining options! We will be back." [](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Amara Cay Resort](//images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 10/10 Excellent "Loved the stay at Amara Cay! Will be back. Staff was amazing." [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.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 "Nice location and very spacious suite!" [](https://expedia.ca/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) ![Islander Resort](//images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "Stunning resort with great amenities and excellent service! " [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Islamorada? > If you're searching for a hotel where you can enjoy a drink after a day of exploring, Islamorada features 905 hotels and other properties, including 12 accommodations with an onsite bar. While you're here, consider a visit to Bud n' Mary's Dive Center and Islamorada County Park. ### What are the best hotels with bars in Islamorada? > Here's some of the top Islamorada hotels with bars: [Chesapeake Beach Resort](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information): Enjoy the bar, free breakfast, and free WiFi. [Cheeca Lodge & Spa](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information): Resort with 3 restaurants. Enjoy the 2 poolside bars, free parking, and 3 outdoor pools. [Amara Cay Resort](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information): Resort with 2 restaurants. Enjoy the 3 bars, private beach, and breakfast. [Islander Resort](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information): Hotel with 3 restaurants. Enjoy the beach bar, poolside bar, and free WiFi. [Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://www.expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information): Resort with 4 restaurants. Enjoy the beach bar, poolside bar, and free WiFi. ### How many hotels with bars should I expect to find in Islamorada? > Expedia has 12 hotels with a bar in Islamorada. ### What is there to do in Islamorada? > In the area, you can visit Bud n' Mary's Dive Center, Islamorada County Park, and Anne's Beach, then find a cozy spot for a nightcap. Other places to see include Fiesta Key and Everglades National Park. Islamorada is popular for its entertainment choices and seafood restaurants. ### When is the best time to visit Islamorada? > Visiting local bars in Islamorada is better when you know what the weather holds. These rainfall averages and temperatures can help you choose the best time for bar hopping. The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 72°F. Average annual precipitation for Islamorada is 44 inches. ### How can I get to Islamorada and around the area? > Here are some of your transportation choices in and around Islamorada: Fly into Marathon, FL (MTH-Florida Keys Marathon), which is located 30 mi (48.2 km) away from the heart of the city. 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