Home of the 'Rum Runner", the World Famous Tiki Bar still exists and has had a bit of a facelift. The days of "Bartenders Week" and wet t-shirt contests may be over, but when you have a location as sweet as the rum they serve, it will forever be a gold mine. Facing the ocean on one side while bordering Whale Harbor Channel on the other side, this location at Postcard in is the most famous hotel bar Islamorada has ever had.
The Islander Hotel, home to the largest beach in the Keys, did a fantastic job creating their beautiful outdoor bar and restaurant, Waves. In addition to the huge beach, there are two adjacent large pools that allows you to lounge in the sun while a server takes your order.
Cheeca Lodge added a great circular Tiki Bar that sits oceanfront close to their pier and next to the pool. Cheeca, being one of the more upscale hotels in Islamorada, is great place to visit as the property boasts many luxuries. The large round tiki bar is a cool place to chit chat with fellow guests as everybody is facing each other, but not too close where its uncomfortable. Sometimes I enjoy ordering a drink at the bar and take a stroll on their massive beach and to the end of their pier.
The Amara Cay property has come a long way since it was an old Hampton Inn. The moment you walk in the front door you can feel the elegance. You'll notice they have a nice bar inside by the lobby area, but my preference is to take it outside by their pool which is also only steps from the ocean. At the end of their pool area, they have an awesome tiki bar and restaurant for guest to enjoy
The Kokomo Poolside Bar is the only swim up pool bar in Islamorada, so of course it has to make our list. In addition, you'll notice that it is on the same property as the World Famous Tiki Bar, Postcard Inn (which again, is the old Holiday Isle). The poolside bar sets itself on the northern/central end of the property and has wonderful ocean views in all directions. It is important to note that the poolside bar is for hotel guests only. However, Postcard Inn has three sister properties in Islamorada which all allow you access to each hotel property: Amara Cay, La Siesta and Pelican Cove (adjacent to Postcard). So if you stay at any of these places, you can enjoy three of the five bars we put on this list!
The Pines and Palms pool area is a great place to hang out and often times listen to live music. They have a great pool bar that is open to guests. Pines and Palms is a bit different than your normal resort as its not too fancy. However, it is in a stellar location in Islamorada, most rooms come with a full kitchen and the overall price point is less than most other hotels. This is the type of place we LOVE here in the Keys....old school and real.