Winslow's Bungalows – Key West Resort Review
Last updated: August 28, 2026
Choose Winslow's Bungalows if...
- You want a large historic compound with three pools and resort-style amenities
- You want live music, welcome cocktails, and breakfast in a garden setting
- You're a couple or group wanting walkable Duval with a quiet retreat to return to
Skip Winslow's Bungalows if...
- You want beachfront access — there's no beach on-site
- You want adults-only exclusivity — children 13 and older are welcome
- You prefer modern, minimalist design — rooms are historically styled
AskTheKeys Traveler Match
How well does Winslow's Bungalows fit your trip?
Before you book — the one trade-off
Winslow's delivers a resort-within-Old-Town feel but no beach — you trade beachfront access for three pools and live music two blocks from Duval.
AskTheKeys Decision SummaryWinslow's Bungalows is best for travelers who want a large historic compound with three pools, live music, complimentary breakfast, and walkable Duval access at a mid-range price point. It is not ideal for guests seeking beachfront access, adults-only exclusivity, or modern minimalist design.
Winslow's Bungalows is an 85-room historic compound at 725 Truman Avenue in Old Town Key West, two blocks from Duval Street. The property spans over an acre of tropical gardens and restored historic homes — including the 1854 Robert Maloney House on the National Historic Register. Three heated pools with poolside service, the on-site Bungalow Bar, complimentary continental breakfast, welcome cocktails, and live music from resident musicians create a resort-within-Old-Town atmosphere. Rooms range from standard queens to luxury suites and poolside bungalows.
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Before You Book
The details that matter after you've narrowed down your options.
Best for
- Travelers who want a large historic compound with resort-style amenities in Old Town
- Guests who value three pools, live music, and complimentary breakfast and welcome cocktails
- Couples and groups seeking walkable Duval nightlife with a quieter garden retreat to return to
- History enthusiasts — the property includes an 1854 National Historic Register building
Not ideal for
- Guests seeking beachfront access — no beach on-site or nearby private beach
- Adults-only travelers — children ages 13+ are welcome
- Travelers who prefer modern, minimalist hotel design — rooms are historically styled
Quick facts
| Address | 725 Truman Avenue, Key West, FL 33040 |
|---|---|
| Phone | +13052945229 |
| Check-in / Out | 4:00 PM / 11:00 AM |
| Parking | On-site parking available ($30/day) |
| Pets | No |
| Beach access | No |
| Pool(s) | Yes |
| Spa | No |
| EV charging | Unknown |
Location & nearby
Winslow's Bungalows is located in Old Town / Historic District within Key West.
What's nearby
- Duval Street(0.1 mi, 2 min walk)
- Ernest Hemingway Home & Museum(0.3 mi, 8 min walk)
- Key West Butterfly & Nature Conservatory(0.4 mi, 10 min walk)
- Southernmost Point Buoy(0.5 mi, 10 min walk)
- Key West Lighthouse & Keeper's Quarters(0.3 mi, 6 min walk)
- Fort Zachary Taylor State Park & Beach(0.9 mi, 18 min walk)
- Mallory Square(0.5 mi, 10 min walk)
- South Beach (public)(0.5 mi, 10 min walk)
Amenities overview
Property highlight features
- Three heated swimming pools with poolside service
- On-site Bungalow Bar open daily 8 AM – 8 PM
- Complimentary continental breakfast served poolside daily
- 85 rooms across restored historic homes and Bahama-style buildings
- Live music from resident musicians on select days
- Welcome cocktails (2 per stay) and concierge service
Pricing positioning
Typical nightly pricing tends to fall in the $$$ range, depending on season and room type.
large historic compound with resort-style amenities
Compare current room availability and secure member-only pricing.
We handle our lodging checks through Expedia's network engine so you can lock in hidden seasonal discounts and stack your One Key™ rewards points across different island brands.
Independent Decision Engine
Florida Keys Resorts operates as a fully objective, crowdsourced review system. We do not accept paid placements from hotels to alter their scoring records. Instead, we use standardized API connections to provide transparent third-party rate checks for our community.
How Winslow's Bungalows Compares to Other Key West Resorts
Winslow's Bungalows vs Eden House
- Winslow's Bungalows wins:large 85-room compound with three pools, live music, and bungalow bar
- Eden House wins:intimate 40-room 1924 historic hotel with on-site Azur Restaurant and art deco character
Winslow's Bungalows vs Curry Mansion Inn
- Winslow's Bungalows wins:sprawling 85-room garden compound with three pools and poolside breakfast
- Curry Mansion Inn wins:intimate 28-room Victorian mansion with open bar and historic museum integration
Winslow's Bungalows vs Hyatt Centric Key West Resort & Spa
- Winslow's Bungalows wins:historic bungalow compound with three pools, live music, and independent boutique character
- Hyatt Centric Key West Resort & Spa wins:full-service branded resort with spa and fitness center
Winslow's Bungalows vs Eden House
- Winslow's Bungalows wins:intimate cottage-style bungalows with private-feeling spaces and curated design
- Eden House wins:bohemian hotel with larger tropical grounds, pool, and casual communal atmosphere
FAQs
How many pools does Winslow's Bungalows have?
Winslow's Bungalows has three heated swimming pools with poolside service. The main pool areas are surrounded by tropical gardens and sun terraces. The private Elizabeth Annex has its own pool and sun deck for guests staying in those 11 rooms.
Does Winslow's Bungalows include breakfast?
Yes. A complimentary continental breakfast is served poolside daily from 8 AM to 10 AM. The on-site Bungalow Bar also serves food and cocktails throughout the day from 8 AM to 8 PM.
How far is Winslow's Bungalows from Duval Street?
Winslow's Bungalows is at 725 Truman Avenue, two blocks from Duval Street — about a 2-minute walk. All Old Town restaurants, bars, and attractions are within easy walking distance.
Is Winslow's Bungalows family-friendly?
Children ages 13 and older are welcome and charged as adults. The property is not suited for younger children. It is popular with couples, but older teens traveling with parents are permitted.
Does Winslow's Bungalows have live music?
Yes. Resident musicians perform on select days, including weekend brunch music from 9 AM to 11 AM. The live music adds to the garden-resort atmosphere without being disruptive to quiet areas of the property.
Does Winslow's Bungalows have parking?
Yes. On-site parking is available for $30 per day. Since the property is two blocks from Duval Street, many guests walk throughout Old Town and use parking primarily for arrival and departure.
What room types are available at Winslow's Bungalows?
The property offers 85 individually furnished rooms across several categories: standard queen, superior queen, deluxe king, poolside bungalows, and luxury suites. Rooms are spread across restored historic homes and newer Bahama-style buildings.
Is Winslow's Bungalows a historic property?
Yes. The property includes the Robert Maloney House, built in 1854, which is one of the oldest buildings in Key West and listed on the National Historic Register. The property is named after landscape painter Winslow Homer, who wintered in Key West from 1888 to 1903.