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Winslow's Bungalows is a Small Luxury Hotels of the World member in Old Town Key West, offering self-contained bungalows that blend Victorian architecture with modern styling. The 84-room property features one restaurant, three outdoor pools, and a location steps from Duval Street and Key West's historic attractions. Designed as a base for exploring the island, the hotel combines period character with contemporary comfort.
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Winslow's Bungalows sits in the heart of Old Town, Key West's historic neighborhood. The location provides immediate access to Duval Street, where the hotel staff offers curated restaurant recommendations for daytime and evening dining. The Basilica of St. Mary Star of the Sea is visible from select rooms, including the King Suite with Sofa Bed.
Key West connects to broader attractions within reach of the hotel. Fort Jefferson at Dry Tortugas National Park, known for sea turtle encounters and the Windjammer Wreck on Loggerhead Reef, is accessible by boat or seaplane. The former residence of Ernest Hemingway, notable for its population of six-toed cats, is also nearby.
The hotel operates 84 rooms across 3 floors, arranged as self-contained bungalows with leafy walkways connecting units to front porches. Room types include the Single Queen, Classic King, Premier King with Patio or Balcony, Two Queens, Annex King, and mobility-accessible variants of these configurations.
Suites feature the King Suite with Soaking Tub and the King Suite with Sofa Bed, with the latter offering views of the Basilica of St. Mary Star of the Sea. The Treehouse Suite features a secluded balcony positioned among the treetops, accompanied by tropical birdsong. Some bungalows occupy the former home of historian Colonel Walter Maloney, preserving the property's historic character.
The hotel offers one on-site restaurant. Breakfast includes fresh croissants, coffee, and a full continental breakfast. The Bungalow Bar provides a social hub, while three outdoor pools feature poolside refreshers served each afternoon.
Duval Street lies within walking distance, where the concierge desk provides restaurant recommendations to guide choices for daytime and evening meals beyond the property.
The property features three outdoor pools. Facilities include a 24-hour front desk, concierge desk, full-service housekeeping, air conditioning, Wi-Fi in public areas, on-site parking with accessible spaces, 24-hour security, a doctor on call, wakeup service, and wedding services. The hotel is fire safety compliant and pet-friendly.
The self-contained bungalows and poolside setting appeal to those seeking privacy within a social environment. The family-friendly designation and multi-bed room options accommodate groups. Pet owners will find the hotel's pet-friendly policy accommodating.
Visitors interested in Key West's bohemian culture, historic sites, and water-based activities will find the hotel's location and concierge services supportive of exploration. Wedding services indicate suitability for celebration events.
Editorial verification: Winslow's Bungalows is affiliated with Small Luxury Hotels of the World; this was confirmed on the brand's own website or hotel list, and the hotel was matched to its official website by our editorial board.
Winslow's Bungalows is located in Old Town Key West at 725 Truman Avenue, Florida 33040. The property sits steps from Duval Street and near the Basilica of St. Mary Star of the Sea.
The hotel offers Single Queen, Classic King, Premier King with Patio or Balcony, Two Queens, Annex King, King Suite with Soaking Tub, King Suite with Sofa Bed, and the Treehouse Suite. Mobility-accessible versions of most room types are available.
Yes, the hotel has one restaurant serving continental breakfast, fresh croissants, and coffee. The Bungalow Bar is available, and poolside refreshers are served each afternoon. Duval Street restaurants are within walking distance.
Yes, the hotel is pet-friendly, allowing guests to bring animals with them.
Facilities include three outdoor pools, 24-hour front desk, concierge desk, full-service housekeeping, on-site parking with accessible spaces, Wi-Fi in public areas, a doctor on call, wedding services, and 24-hour security.
Nearby attractions include the Basilica of St. Mary Star of the Sea, Ernest Hemingway's former residence, and Fort Jefferson at Dry Tortugas National Park, reachable by boat or seaplane. Duval Street offers restaurants and nightlife.
Yes, the hotel is designated family-friendly with rooms offering multiple beds suitable for families. Wedding services are also available.
Winslow's Bungalows is affiliated with Small Luxury Hotels of the World; this was confirmed on the brand's own website or hotel list, and the hotel was matched to its official website by our editorial board.
Winslow's Bungalows is in Key West, United States. Address: Truman Avenue 725, Old Town, Key West, Florida, 33040, United States.
| Location | Key West, United States |
|---|---|
| Address | Truman Avenue 725, Old Town, Key West, Florida, 33040, United States |
| Brand / alliance | Small Luxury Hotels of the World |
| Official website | slh.com |
| Area guide | Key West luxury hotels |
| Verified | by the editorial board |
Sources: slh.com/hotels/winslows-bungalows
Map data © OpenStreetMap contributors. Hotel data: Wikidata (CC0), OpenStreetMap (ODbL), official websites.