The Reach Key West, Curio Collection by Hilton

The honest review

Key West is a complicated family destination. The island's primary draw — Duval Street's bars, the late-night entertainment culture, the adult party-town energy — is not particularly family-oriented. But there is a real family case for Key West: it's a unique place in the United States, genuinely unlike anywhere else, with excellent snorkeling and water activities, accessible marine life (manatees, reef fish, sea turtles), interesting history, and an architecture and character that older kids and teens find genuinely memorable.

The Reach Key West is positioned at the better end of the family-practical hotel spectrum on the island. Most Key West hotels are on the Gulf of Mexico side or on the interior of the island, with no beach access — you walk to the seawall or take a taxi to a public beach. The Reach is on the Atlantic side near Smathers Beach, and it has an actual sandy private beach, which is genuinely uncommon. Watersports rentals operate directly off the beach, so snorkel equipment, kayaks, and paddleboards are accessible without planning or driving anywhere. For a family that wants to be on the water (not just near it), this is a meaningful advantage.

The pool is compact by resort standards but functional — Key West properties generally don't have the sprawling pool complexes of Destin or Kissimmee, and the ocean swimming and watersports largely substitute for it here. The Sands Beach Bar provides poolside and beachside food and drink service without requiring a dress code or long wait.

Room sizing is the most consistent family complaint about The Reach and about Key West hotels generally: rooms are not generous. A family of four in a Double Queen room will feel the space limitation by day three. Suites are available but push the rate meaningfully higher in an already-expensive market. Families who need significant space should either book the suite category or consider a vacation rental through VRBO, which has a reasonable Key West inventory.

Old Town and the most historically interesting parts of Key West are about 1.5 miles from The Reach — easily bikeable (Key West is flat and very bike-friendly), or a short rideshare. The resort's concierge can arrange sunset sail tickets, reef snorkeling charters, and the Dry Tortugas day ferry, which is one of the most memorable day trips available from Key West for older kids.