Winslow’s Bungalows - Historic Key West Hotel & Pet-Friendly Stay

Winslow’s Bungalows stands as one of the most distinctive historic Key West hotels, offering a refined blend of preserved 19th-century architecture and upscale tropical living. Spread across multiple Victorian-era homes and landmark structures dating back to the 1880s, the property reflects the island’s evolution—from shipbuilders and cigar makers to steamboat captains and circus performers—while delivering elevated comforts such as premium linens, rainfall showers, and smart climate control in every room and bungalow. The meandering shell pathways and original Dade County pine details enrich the stay with authentic Key West character.

Three uniquely designed pool areas create a boutique resort atmosphere with an intimate pool-to-room ratio. The Main Pool serves as a lively social lounge framed by bougainvillea and palms, featuring underwater seating ideal for cocktails. The Garden Pool offers a quieter sanctuary with hammocks and deep greenery, while the heated saltwater pool at the Elizabeth Annex provides an exclusive hideaway for guests of the adults-preferred wing. This private Annex includes 11 oversized guestrooms, each over 450 square feet, along with the expansive 900-sq-ft Grand Margaret Suite, wraparound veranda, private check-in, and concierge services.

The Bungalow Bar enhances the guest experience with craft cocktails inspired by local lore. Drinks such as the Colonel’s Old Fashioned and Circus Performer’s Punch pair with classic Key West bites like conch fritters, fish tacos, and the signature Bungalow Burger. The bar’s reclaimed cypress, sourced from a 19th-century steamboat, adds historical intrigue to every visit.

Winslow’s Bungalows also features tailored packages and exclusive perks. Florida and Georgia resident discounts offer up to 20% off select stays, while pet-friendly accommodations welcome dogs of all sizes with complimentary treats, bowls, and a dedicated play area. Additional benefits include extended stay savings for 7+ nights, daily housekeeping credits, and curated romance upgrades such as champagne and chocolate-covered Key limes.

Positioned just two blocks from Duval Street and a short walk to Mallory Square, the Hemingway Home, and the Historic Seaport, the location offers immediate access to iconic attractions without sacrificing tranquility. Complimentary beach cruisers make island exploration simple and scenic.

Winslow’s Bungalows continues to be recognized among the best Key West bungalows thanks to its deep sense of place, its generous pet policy, three distinct pools for 65 rooms, and environmentally conscious initiatives including solar-heated pools, rainwater irrigation, and wildlife conservation partnerships. This historic Key West hotel appeals to couples, extended-stay travelers, pet owners, and locals seeking a relaxing, story-filled retreat.

For current room options, rates, and direct reservations, use the Reserve a Room button above.