Kimpton Winslow's Bungalows

Gracious Inn encompassing Grand Bahama-style historic home dating from 1854, garden cottages & poolside rooms.


  • Late check-out 2:00 pm (based on availability)
  • $50 USD value-added amenity
  • Upgrade to next room category (subject to availability)
  • Handwritten and personalized welcome card
  • Bottled water and fresh fruit/snacks in room, upon arrival
  • Turn down service
  • VIP level added into guest profile

Based on availability.

Deposit Policy: 1st night + tax at time of reservation

Kimpton Winslows Bungalows Cancellation Policy: 10 days prior to arrival, 30 days Holidays/Special Events

$35+ Tax Daily Guest Amenities Fee includes:

  • Complimentary Continental Breakfast, Coffee and Tea Service
  • Complimentary Wifi
  • Boozy welcome arrival beverage
  • Snorkel kit with mask and snorkel to use at the beach and island snorkeling spots
  • Boating towels available
  • Afternoon poolside refresher
  • Complimentary local and toll free phone calls
  • Pool access and pool towels
  • Access to Press Reader on your smart device featuring over 7,000 newspapers and magazines

Upgrade subject to availability. Click here for complete terms and conditions..

Named for landscape painter Winslow Homer, who wintered in Key West around the turn of the 19th century, this is the largest hotel in the Kimpton Key West collection comprised from multiple historic homes that make no guest room designed the same. Wander down brick walkways through vibrant greenery, stopping to play a game of corn hole or snap a photo at our “Instagram Tree”—all on grounds that were once covered in fruit groves. Today, wedding parties, families and couples enjoy coveted moments of relaxation and play in a central Old Key West locale.

Winslow's Bungalows spans a lush, landscaped campus in the heart of Old Town. Named for famous painter and summer resident Winslow Homer, this expansive haven boasts three private pools, an outdoor bar and vibrant gardens. It’s an idyllic scene for couples, families, groups and wedding parties.

With 85 guestrooms including two deluxe suites, Winslow's Bungalows is our largest Key West hotel. This expansive haven extends across several historic Key West architectural styles, with an array of past owners including an army officer, an Irish steamboat captain and a circus performer. The colorful backstory is matched by the artful, bohemian interiors and elegant touches like summer cane beds, European armoires and maritime basket lighting.