We stayed next door to Cheeca, and went there for a learn to fish like a local event so we didn’t use the facilities but I thought it was nice enough, especially for kids. The beach is not impressive but none are in the keys. Islamorada was not really walkable but there were enough activities a short drive away to keep the family entertained. We did a snorkel excursion, parasailing, feed the tarpons, theater of the seas is nearby too but it felt depressing to me but the kids liked the shows.
Key west is also fun but busier, more walkable, not as laid back. Definitely more restaurant options. I’m also happy go lucky and have fun wherever I go so both places are a great place to see.

Anonymous wrote:How did you get there from DC? What is the fishing pier like? How does Islamorada compare to Key West?

MIA to Key West on a nice day is a really pretty drive.

Islamorada is a nice spot if you have a boat and are into boat things. Also nice if you want to chill at the pool. As PP said, there aren't beaches in the Keys and it's not walkable outside of Key West. There really isn't much else to do. Restaurants are really average.

Key West is fun for a few days, not fun for children. My kids liked the Hemingway House (cats everywhere) and we were supposed to take the seaplane to Dry Tortugas, but there was weather and it was cancelled. Half the reason we were there.

I like Cheeca. Not super luxurious but my kids had a lot of fun. They fished, went on a boat, there was an Easter egg hunt, sailed, etc. Much more kid-focused than Key West.

Thank you this is very helpful. The web site certainly references a private beach so this is good to know as it’s quite far to travel to be disappointed.

We flew to Miami and drove. DS enjoyed the fishing pier but it was crowded. Overall, I wasn’t impressed with either Cheeca or Islamorada. Cheeca looked like it was worn and had seen better days, its pool was too crowded and generally I don’t think it was good value for the price. This was my first and only trip to the Keys, so I can’t compare it to Key West. There wasn’t much to do aside from the water and since there aren’t really beaches, you need to rent a boat. It wasn’t walkable and there weren’t great shops or restaurants.

How did you get there from DC? What is the fishing pier like? How does Islamorada compare to Key West?