Winslow's Bungalows
Old Key West character meets island-chic ease. Historic Conch homes, Victorian architecture, and Bahama-style cottages share lush grounds once used as a fruit grove. Eclectic, unhurried, and genuinely tropical without being kitsch.
Guests of any Key West Historic Inns property can use ALL five inns' pools, bars, and breakfast — worth knowing if you want to explore Merlin's Afternoon Tea at Ella's Cottages nearby
Why It Matters
Member of Small Luxury Hotels of the World. One of Key West's largest boutique properties with 85 individually decorated rooms across a multi-structure campus established in 1856. The property's layered history includes residents like Colonel Walter Maloney, a circus performer, a cigar maker, and a steamboat captain — plus alleged buried pirate loot under the grounds. Family-friendly, unlike two adult-only inns in the same collection.
Winslow's Bungalows is the largest of five Key West Historic Inns properties, with 85 rooms spread across multiple historic structures — the former Key Lime Inn and Chelsea House — on both sides of Truman Avenue. Three outdoor pools, a poolside bar, and winding brick walkways through tropical gardens make it feel more like a lush compound than a hotel. Named for American maritime painter Winslow Homer, who wintered on the island between 1888 and 1903.
Where You'll Stay
11 room types available
Annex
Located in the Elizabeth Annex — a charming Victorian home adjacent to the main Winslow's grounds. Either a king or queen bed. Access to a tranquil private pool and sun deck separate from the main property. Great for guests who want a quieter corner of the campus.
King or QueenAnnex Mobility
ADA-accessible room in the Victorian Elizabeth Annex building. Lush landscaping surrounds it, with access to the private Annex pool. 312 square feet with accessible bathroom features.
KingBungalow
The most intimate room type on the property — just 150 square feet — but set in authentic Key West conch homes with a sun-filled outdoor space. Think of it as your own little porch-fronted cottage. Tight inside, but the outdoor area makes it work.
KingClassic King
A solid mid-tier option. Plush king bed, bathed in natural light. Comfortable and well-appointed without the step up to a patio or balcony. Popular choice for couples who want a generous room without paying suite prices.
KingKing Mobility
ADA-accessible room designed for comfort and safety, with stylish decor that brings in the tropical surroundings. Either a king or two queen beds depending on unit. 175–225 sq ft range.
King or Two QueensKing Suite with Soaking Tub
The biggest upgrade in the standard suite range — a spacious 400-square-foot room with a king bed and a proper soaking tub. Known in some internal references as the Maloney Suite. Quiet luxury without the full Treehouse price tag.
KingKing Suite with Sofa Bed
Pool and Basilica views from this 325-square-foot suite. King bed plus a sofa bed for a third guest, and a private patio for island living. Wake up to the spires of St. Mary Star of the Sea from your window.
KingPremier King with Patio or Balcony
Steps up to a private outdoor space — either a patio or balcony depending on the unit. King bed with luxe bath amenities. The private outdoor space is what you're paying for here, and on a Key West morning it's worth it.
KingSingle Queen
Inspired by the legacy of the Key Lime Inn, this is the entry-level room at Winslow's. One queen bed in a compact, well-appointed setting. Good for a solo traveler or couple who plan to spend most of the day outside.
QueenTreehouse Suite
The largest and most impressive suite on the property at 425 square feet. Separate living area, full bath with shower, and a spacious treetop balcony where tropical birds serenade you in the morning. The artwork (including pieces by Janet Hill) and two-sink bathroom make it feel genuinely indulgent. This is the room people remember.
KingTwo Queen
The go-to for families or friends sharing a room. Two queen beds in a relaxed layout, sleeping up to four. Same footprint as the Single Queen, so two beds in 240 square feet means a snug but functional stay.
Two QueensThe Property
Eat & Drink
1 venue on property
Restaurant
Spa & Wellness
Treatment Menu
On Property
How you'll actually spend your days.
Complimentary afternoon poolside refreshers served daily. Part of the included amenities package for all Winslow's guests.
Partnered with Island Safari Rentals. Cruiser bikes, e-bikes, scooters, and golf carts available. Scan the QR code on bike signage around the property or visit the front desk for reservations.
Dedicated concierge Jenny Berube can design your itinerary, arrange local excursions, and recommend restaurants. Contact available via email directly with Key West Historic Inns.
A private area of the property with its own pool, sun deck, and 11 king guest rooms. Available for full group bookings — family reunions, milestone birthdays, wedding parties. Separate from the main grounds for full privacy.
The grounds include hammocks, swings, and multiple shaded outdoor seating areas across the former fruit grove campus. Winding brick walkways with directional signs connect the different pools and buildings.
Resident fiddler or clarinet player performs Saturday and Sunday mornings 9–11 AM during breakfast. Additional live music performances from local Key West musicians on select days — schedule posted on the hotel events calendar.
All Key West Historic Inns guests — including Winslow's guests — can attend Merlin's Afternoon Tea at sister property Ella's Cottages. Serves mini pastries, tea sandwiches, smoked salmon crostini, house-made iced tea, and canned cocktails. Casual dress; no reservations needed.
Three outdoor pools spread across the grounds. The main pool sits outside the historic lobby building; a second, more intimate pool is adjacent to Bungalow Bar; and the third is in the private Elizabeth Annex. Open 7 AM to 10 PM. All Key West Historic Inns guests can use any of the five properties' pools.
Every guest receives a pirate-coin-style token redeemable for two welcome cocktails at Bungalow Bar. Choose between Rum Punch or a Paloma. Redeem anytime during bar hours (8 AM – 8 PM).
A full 3D walkthrough of the property is available online via Visiting Media, accessible from the official website.
Amenities & Practical Info
The details that matter for planning.
The property is located in historic buildings and has no elevator. Guests with mobility needs should book accessible ground-floor rooms (King Mobility or Annex Mobility).
Served daily at Bungalow Bar 8–10 AM. Includes pastries, muffins, croissants, fresh fruit, yogurt, sliced meats and cheeses, wellness shots, and smoothies. Made-to-order hot items available for an additional charge.
Available around the clock in the lobby area at no charge.
Pets welcome at $50/night. No size, weight, or number limits. Guests receive plush pet-bed loaners, food/water bowls, door hangers, and courtesy bags. Pet-friendly restaurant/park/groomer recommendations provided.
Three outdoor pools open daily 7 AM–10 PM. One main pool by the lobby, one intimate pool beside Bungalow Bar, and one private pool in the Elizabeth Annex.
Personalized concierge services for trip planning. 24-hour front desk.
Limited on-site parking available at $30/night. Inquire at check-in. Additional street parking and city lot parking available nearby. No parking at Ridley House or Fitch Lodge locations.
Yoga mats available for in-room or poolside use.
BUILD YOUR WINSLOW'S BUNGALOWS - KEY WEST HISTORIC INNS PLAN
Rooms, dining, spa, and resort experiences — organized into one trip plan.
Start Planning