Winslow's Bungalows - Key West Historic Inns

"A quaint, historic, and beachy spot just steps away from all the action." - Amber Love Bond

"A campus of multiple, white-washed cottages and former homes cast predominantly in classic Key West architectural style, Winslow’s Bungalows is a history-steeped retreat two blocks from Duval Street. Formerly part of the Kimpton portfolio, the 85-unit property still oozes retro-chic decor and draws a cool (often pet-obsessed) crowd. Not much has changed since reintegrating into Key West Historic Inns Collection in January 2024: Winslow’s retains an intimate setting, where you’ll feel more like a guest in a private home than in a hotel. Several pools, including a large heated one, and lots of relaxation nooks (hello: hammocks) dot the beautifully landscaped enclave, and continental breakfast is a standard inclusion in all stays. Though Winslow’s remains pet-friendly in life after Kimpton, there is a nightly fee worth noting ($50 per pet, per night). Considering the campus houses one of Key West’s oldest homes and oldest lodging, dating to 1856, it’s worth asking the front desk for a quick primer in Winslow’s history." - Paul Rubio, Nancy DePalma

"A campus of multiple, white-washed cottages and former homes cast predominantly in classic Key West architectural style, Winslow’s Bungalows is a history-steeped retreat two blocks from Duval Street. Formerly part of the Kimpton portfolio, the 85-unit property still oozes retro-chic decor and draws a cool (often pet-obsessed) crowd. Not much has changed since reintegrating into Key West Historic Inns Collection in January 2024: Winslow’s retains an intimate setting, where you’ll feel more like a guest in a private home than in a hotel. Several pools, including a large heated one, and lots of relaxation nooks (hello: hammocks) dot the beautifully landscaped enclave, and continental breakfast is a standard inclusion in all stays. Though Winslow’s remains pet-friendly in life after Kimpton, there is a nightly fee worth noting ($50 per pet, per night). Considering the campus houses one of Key West’s oldest homes and oldest lodging, dating to 1856, it’s worth asking the front desk for a quick primer in Winslow’s history." - Paul Rubio, Nancy DePalma

"Why book? Don't have a home in Key West? No problem—book a room here for that residential feel. Set the scene Winslow’s Bungalows is downright cool. The place just oozes a hip vibe with its retro-chic decor and intimate setting that makes you feel like you have the run of the place. The backstory It’s a boutique resort occupying several historic homes in the heart of Old Key West. Named for Winslow Homer, who wintered in town, it feels like it has a story behind it, and indeed the homes once belonged to a cast of characters. The rooms There may be 85 accommodations, but you’ll feel more like a guest in a private home than in a hotel here. There’s a hint of the tropics (think mod graphic prints of palm leaves) but it’s more Architectural Digest than kitschy Florida. Food and drink Breakfast is complimentary and the bar by the pool keeps thirst at bay, but you’ll need to venture off property for lunch and dinner. The neighborhood/area You’re smack dab in the middle of the Key West Historic District when staying at Winslow’s Bungalows. The service Low-key, but the onsite concierge is there to help when you need it. Accessibility ADA accessible. Anything left to mention? The daily resort fee covers the usual suspects, including towels at the resort’s three pools, but it also includes a kit with a mask and snorkel for getting up close and personal with the local marine life. Ask the concierge for the best snorkeling spots." - Nancy DePalma

"Winslow’s Bungalows is downright cool. The place just oozes a hip vibe with its retro-chic decor and intimate setting that makes you feel like you have the run of the place. It’s a boutique resort occupying several historic homes in the heart of Old Key West. Named for Winslow Homer, who wintered in town, it feels like it has a story behind it, and indeed the homes once belonged to a cast of characters. There may be 85 accommodations, but you’ll feel more like a guest in a private home than in a hotel. The resort fee covers the usual suspects, including towels at the resort’s three pools, but it also includes a kit with a mask and snorkel for getting up close and personal with the local marine life. Ask the concierge for the best snorkeling spots. —Nancy DePalma" - Jamie Spain