A campus of historic Key West cottages two blocks from Duval Street — 85 units in white-washed buildings dating to 1856, with retro-chic décor, several heated pools, hammock-filled relaxation nooks, and a continental breakfast included. Pet-friendly (nightly fee). CNT Readers' Choice 2021.
Why We Chose It
Winslow's Bungalows is a Key West Historic Inns property — an 85-unit campus of white-washed historic cottages and former homes two blocks from Duval Street, with buildings dating to 1856 (among the oldest lodging on the island). The retro-chic décor and intimate feel — more private home than hotel — draws a cool, often pet-obsessed crowd. Several pools including a large heated one, hammock-filled relaxation nooks in beautifully landscaped grounds, and continental breakfast included in all stays. Pet-friendly ($50 per pet per night). Formerly a Kimpton property; now part of the Key West Historic Inns Collection. CNT Readers' Choice 2021.
What Stands Out
- Historic cottages dating to 1856 — among Key West's oldest lodging
- 85 units two blocks from Duval Street — walkable to everything
- Continental breakfast included; intimate home-like atmosphere
- Several heated pools and hammock-filled relaxation nooks
- Pet-friendly · CNT Readers' Choice 2021