Winslow's Bungalows - Key West Historic Inns

Top rated by guests
Exterior view
Swimming pool [outdoor]
Bathroom
Lobby
Bathroom
Don't miss out! Price and availability may change
8.9 / 10.0
Excellent(67 Ratings)

Hotel in Key West, FL

4-Star Hotel

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this hotel

Winslow's Bungalows - Key West Historic Inns offers top-notch services and amenities, ensuring guests experience utmost comfort. Share your photos and respond to emails at your convenience, thanks to the free Wi-Fi internet access offered by hotel. Visitors can take advantage of the accessible parking options directly at the hotel. The accommodating team at the reception will aid you with amenities such as concierge service. Securing top-notch tickets and snagging sought-after dining reservations become effortless, thanks to the hotel's ticket service and tours. Room amenities feature daily housekeeping, allowing you to unwind and make the most of your visit.

The hotel maintains a completely smoke-free zone, providing a breathable atmosphere. Each accommodation at Winslow's Bungalows - Key West Historic Inns is thoughtfully created and adorned to provide visitors with a comfortable, home-like atmosphere. In select rooms of the hotel, guests can enjoy the advantage of having linen service available for their convenience.

Rest assured, in a few chosen rooms, the presence of a refrigerator can be found.

Understanding the significance of bathroom facilities in enhancing visitor contentment, hotel offers a hair dryer, toiletries and bathrobes within a few chosen chambers. Begin your holiday on a high note. At Winslow's Bungalows - Key West Historic Inns, your mornings are greeted with a delightful, free breakfast. Experience an unforgettable evening with your fellow travelers just a short distance away, at hotel's bar. Throughout the day, engage in the entertaining activities available at Winslow's Bungalows - Key West Historic Inns.

Each day at hotel, immerse yourself in the invigorating waters of the pool, perfect for a rejuvenating plunge or a series of revitalizing laps.

Bypass the formal attire and choose a laid-back mixed drink or brew at hotel's waterside lounge.


Amenities at Winslow's Bungalows - Key West Historic Inns

Free WiFi/internet
Free breakfast
Air conditioning
Pool
Non-smoking
Pets allowed
Wheelchair accessible
WiFi/Internet
Parking Available
Garden
Cleaning products

Map of Key West, FL


Available Rooms

Things to know

Check-in: 4:00 PM
Check-out: 11:00 AM
Early check-ins and late check-out requests will be accommodated upon request and based upon availability. Unauthorized early check-ins and late checkouts will incur a penalty fee.
House rules
  • Pets allowed, fees apply
  • Kids allowed, fees apply
  • No parties or events allowed without prior approval, fees apply
  • Must be 25 or older to rent

Additional fees to expect

Cleaning & other feesWe include all stay related fees in the Cleaning Fee line, which may include cleaning, property manager, resort, tourism and other stay related fees. All Vogo properties are professionally cleaned after each stay.
Booking feeNo booking fees, easy credit card payments.
Service feeThis helps Vogo provide a safer and more secure booking experience.
TaxesTaxes on accommodation such as Occupancy Tax, VAT, or GST. May also include tourism fees.

Customer support

Customer support is handled by our partner Vogo

    Ratings and reviews

    8.9 / 10.0
    Excellent(67 Ratings)
    8.0 / 10.0Excellent·Apr 2026
    Nice location and fun facility. Room are extremely small but nice.
    10.0 / 10.0Outstanding·Feb 2026
    Loved staying at Winslow bungalows. Attention to detail AAA+++ Breakfast was always great. Would highly recommend it.
    8.0 / 10.0Excellent·May 2025
    The hotel is in a great location, just steps from Main Street, and the staff were friendly and welcoming. The room was cleaned daily, breakfast was good, and free water was a nice bonus. However, the room itself was quite small and lacked a wardrobe, which made storage inconvenient. The front yard was not well maintained, with overgrown grass and common lizards around, with not cleaned chairs. While the service and location were definite positives, the overall comfort could be improved with better upkeep and more in-room amenities.
    6.8 / 10.0Average·Nov 2025
    We’re Floridians and reside about 3+ hours south. We visit Key West very often and stayed at Winslow Bungalows back in June for the first time. We enjoyed our time so much when we had family visiting from out of state this past week that had never been to the Keys before, we immediately thought this place would be the perfect experience and booked 2 rooms, 2 nights - 3 days. Check-in was supposed to be @ 4pm but unfortunately their room was not ready. We wanted to catch sunset @ 5:30 and Mallory sq for which was a mile away. We were advised they did not know when the room would be ready. Next, at check-in, we were advised they offer "complimentary" happy hour from 3-4pm at the bar - we were thrilled! When we went to the bar during this time, we asked for the happy hour menu and we were advised by the tender that it offered beer, wine, and well drinks. After getting our drinks and leaving a tip, we were asked if the charge should be added to our room? Huh? The bar tender advised us the "free" happy hour is only for “refreshers” and that what we had was half off! WOW! Why didn’t the bar tender mention that when we inquired about happy hour? Both reception and the bar tender never mentioned the word “refreshers” until we questioned being charged. I still don’t know what their refreshers consist of. Oh, and in the rooms, they offer a bottle water for $5 each. The next morning, we went to "breakfast” which was mediocre. Previously it had much more to offer and I’d in fact bragged about it to my family when we booked that it wasn’t your typical continental setup. Unfortunately, there were no scrambled eggs, no bacon or sausage but hardboiled eggs. And I do love the wellness shots. Then, we tried to retreat back to our rooms after breakfast, about 9am. Cousin had to take his medication now that he’d eaten and his wife had an upset stomach and hungover from the night before. Unfortunately, unbeknownst to them, they’d accidentally locked themselves out of their room as there are 2 doors. The door they didn't go out of, they'd had deadbolted from the inside and that door was also the only of the 2 doors the room key opened. At check in, no one mentioned the multiple doors or to be mindful of potentially locking themselves out. It took over an hour to retrieve the master key. We were lied to numerous times about what was happening. We were eventually told the truth that the key was being brought from another location and that it is located elsewhere “for our safety.” I work in the insurance industry, and this is a serious hazard at its finest. Had there been a fire, you would need to get into the room quickly. In an hour, the entire building would be burnt down. What if a child accidentally locked the door and could not figure out how to unlock it? What if a mentally unstable person was in there about to make a life changing decision, etc. There are many potential risks that could arise. Accidents happen and a key should be present, locked in a safe as having it on site is a potential concern for the guest’s safety. Their insurance carrier would not be happy about this. I’d expressed my concerns to management and suggested they make this experience right, but nothing came of that. This place has great potential, and we thought we’d found the perfect spot when we visit Key West. I was embarrassed and disappointed. I can only hope they make changes in their policies & procedures and it does not take a tragedy to realize this is unacceptable practice. This should and could have been a quick / simple fix, leaving us with a positive experience. We didn’t get anything but frustration out of this and hopefully this spares someone a hardship or tragedy in the future.

    $$$$
    Enter dates for accurate pricing

    FAQs

    Is parking included with this hotel?

    Yes, parking is listed as an amenity at Winslow's Bungalows - Key West Historic Inns. For more information, we encourage you to contact the property about where to park.

    Is there a pool at this hotel?

    Yes, a swimming pool is available for use at Winslow's Bungalows - Key West Historic Inns. Enjoy the water!

    Is Winslow's Bungalows - Key West Historic Inns pet friendly?

    Yes! This hotel is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

    What amenities are available at Winslow's Bungalows - Key West Historic Inns?

    We found 11 amenities for this rental. This includes free wifi/internet, free breakfast, air conditioning, pool, and non-smoking.

    What payment types are supported?

    This property accepts Visa, Mastercard, American Express, Discover, and Diners Club. Some card brands may not be accepted if you are located in a country or using a currency they don't support.


    Explore similar stays in Key West

    Explore all stays