Winslow's Bungalows - Key West Historic Inns

Recent Reviews: 510

• User:Craig F

  Trip type: Couples

  Beautiful Property but missed the mark with service

  07 Jun 2026

  The property and grounds were beautiful and well maintained. We enjoyed the location of our unit being close to the bar and pool. The unit was clean and comfortable but could have had some additional storage for clothes (not a big deal)We were warmly greeted upon check in by Crystal who provided us with all of the information about the property along with contact information should we need anything. The property is centrally located to everything you want to do in Key West. I highly recommend parking across the street by the Church. FREE Parking. Also, bring or rent bicycles. It's 100% easier than driving. Be aware, even Golf Carts and Scooters have to pay to park. We never used our car. We walked, biked or took and Uber.The Bar has a happy hour from 4-6 and the pools were clean and enjoyable. You can get food until 2pm.Breakfast offered limited options. Juice, Fruit, Bagels, some pastries, yogurt etc.. overall pretty good. You can order Omelets and Egg sandwiches for additional charge. There are plenty of breakfast places nearby if you are looking for more options. As this was out 35th wedding anniversary, I ordered Champagne and strawberries for our arrival and was told the strawberries would be in the refrigerator, but unfortunately a warm bottle of champagne was on the chair by the bed with no glasses. We packed the bottle in the ice bucket for a few hours and had to call for glasses. The phone in the room was not working so I texted the number provided. A woman came shortly with 2 cocktail glasses and said there are no Champagne glasses. Day 2. We were out most of the day and arrived back around 5pm to find the room had not been serviced by housekeeping. I texted the number again to ask why we didn't have service? We were told that they are making their way around.. ? at 5pm? with less than 25% occupancy at the hotel? They brought up a set of towels and left. Day 3. We left the property around 12pm and returned about 4. Once again no housekeeping and had to ask again for service. We went to the pool for about an hour while they finally cleaned up the room.Overall we enjoyed our stay but was expecting better service from a luxury property. Couple of other things we noticed. For breakfast service on Thursday morning, it had rained overnight and some of the seating was wet. It didn't appear that anyone tried to dry off the tables and chairs which made seating limited. As people were finishing up their meal, some had left their dishes on the tables. We watched the bartender do nothing while on his phone and tables needing cleaned for new guests. It took some time but the kitchen staff cleaned the tables. I found it odd the bartender would not be more helpful in keeping the area clean. This did not affect our service, but just an observation.

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• User:claudine m

  Trip type: Family

  Winslow to wins high

  30 May 2026

  Nice local place with easy access to anything around Dogs friendly ($50) expensive for the 4 stars ranking very loud AC and staff not train for this level of service breakfast could be better with a real buffet .Good morning and smiles to customers will have been appreciated!However it was pleasant.

• User:Mike J

  Trip type: Family

  Blew away expectations!

  28 May 2026

  Front desk help was amazing and professional! Great location for Duval activities. Clean room and the grounds were very nice! Pools were clean and well maintained. We found our “regular spot” when we are in Key West!! You also can book through Hilton. Parking is convenient.

• User:Pamela P

  Trip type:

  Excellence!

  28 May 2026

  Best place to stay in Key West!!Excellent accommodations, beautiful well kept, grounds, and superior staff! Top notch place. Perfectly located in the heart of Key West. Walking distance from almost everything! I would only stay here when we return.

• User:Stephanie S

  Trip type:

  Amazing Stay

  26 May 2026

  We had an amazing time at the Winslows Bungalows! The service, staff and location were wonderful and we could not have asked for anything more during our stay!