Find Hotels with a Pool in Upper Matecumbe Key, FL

"Great location close to the bay. Road noise was a little disturbing, but overall relaxing location. Restaurant on site made for a complete destination. Room was somewhat small, but fine for 2 people. "

"⭐⭐⭐⭐⭐ Perfect Stay – Already Want to Go Back! We had an amazing stay at Islander Resort and honestly didn’t want to leave! From the moment we arrived (even with a late check-in), Angela at the front desk set the tone for the entire trip. She was incredibly welcoming, fun, and went above and beyond—giving us a full tour of the property and even personally driving us to our villa since we had no idea where we were going. She immediately put us in vacation mode, and that level of service continued throughout our stay. We stayed in an oceanfront villa, which was absolutely beautiful. The setup was perfect—one king bedroom separate from the living area, plus a pullout couch that would easily work for kids or teens. The view was stunning, and having a front porch lounge area right on the water made it even better. What really stood out about this resort is how it manages to feel both secluded and social at the same time. There are so many little tucked-away lounging areas where you can relax in peace, but also plenty of space for larger groups to gather and enjoy. It’s perfect whether you’re traveling as a couple, with friends, or with kids. Speaking of kids/teens—the amount of activities available is incredible. There’s truly something for everyone, which made it a great fit for our family. Another unexpected highlight was the golf cart taxi service around the property—such a unique and convenient touch. Plus, using the Freebee app to get around Islamorada made everything so"

"Amazing! Loved everything can’t wait to go back!!"

"The suite was spotlessly clean and the air conditioner worked great. The sitting area and kitchen are downstairs. The bedroom and full bath are upstairs. The stairs to the bedroom are very steep so that should be a consideration for anyone with mobility issues."

"Small shops "

"The best "

"I would have liked blackout curtains and the sliding closet doors were a total wrestling match to open to the point of us just deciding to leave our clothes next to us on the beds rather than hang anything up."

"What a GREAT place. The kids had a blast and well… so did I. Lots of fun and very relaxing it’s my go to place in Key Largo. "

"We were very surprized at the size of our unit- large bedroom- kitchen- living room- lanai- beach front- spotless and updated very nicely. Location was great. Felt it was a good price for an ocean front room. Would definitely come back. "