Old Town Rentals USA Florida Key West Old Town

Winslow's Bungalows - Key West Historic Inns | Hotel in Key West

| 9.2 (1018 Reviews) |   Pet Friendly  1 Bathroom  Stay&Play
Old Town Hotel | Winslow's Bungalows - Key West Historic Inns

Hotel in Old Town, Key West

Hotel with 3 outdoor swimming pools, a short walk to Duval Street
Along with 3 outdoor pools, this smoke-free hotel has a bar/lounge and a poolside bar. Free continental breakfast and free WiFi in public areas are also provided. Other amenities include self parking, coffee/tea in a common area, and a microwave in a common area.
Winslow's Bungalows - Key West Historic Inns offers 85 accommodations, which are accessible via exterior corridors and feature safes and bathrobes. Each accommodation is individually furnished and decorated. Beds feature premium bedding. 55-inch LED televisions come with cable channels. Bathrooms include designer toiletries, complimentary toiletries, and hair dryers.

This Key West hotel provides complimentary wireless Internet access. Business-friendly amenities include phones along with free local calls (restrictions may apply). Housekeeping is offered daily and irons/ironing boards can be requested.


3 outdoor swimming pools are on site.

The recreational activities listed below are available either on site or nearby; fees may apply.

Show more

Unique Amenities

  • Air Conditioner
  • Parking
  • Pet Friendly
  • Pool
  • TV
  • Balcony/Terrace
  • Accessibility
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
  • Bar
  • Toiletries
  • Guest Services
  • Breakfast
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
Read More Read Less

Policies

Check-in Check-in start time: 4:00 pm; check-in end time: anytime minimum check-in age: 21
Check-out Check-out before 11 am
Payment Policy Self parking fee: usd 30 per day (in/out privileges) pet fee: usd 50 per pet, per night service animals are exempt from fees the above list may not be comprehensive. fees and deposits may not include tax and are subject to change.
Child Policy Children are welcome. rollaway/extra beds are not available. free cribs (infant beds)!
Pet Policy Food and water bowls are available pets allowed for an extra charge of usd 50 per pet, per night service animals are welcome, and are exempt from fees
Other Policy Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card may be required at check-in for incidental charges please note that cultural norms and guest policies may differ by country and by property; the policies listed are provided by the property safety features at this property include a carbon monoxide detector, a fire extinguisher, a smoke detector, and outdoor lighting special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed the name on the credit card used at check-in to pay for incidentals must be the primary name on the guestroom reservation this hotel requires written authorization in advance for any payment using a credit card whose name differs from the registered guest. this property accepts credit cards; cash is not accepted this property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room this property uses eco-friendly cleaning products
 
725 Truman Avenue, Key West, 33040, USA

What Our Guests say 500 + Reviews

Sep 6, 2025 07:12:19 AM
Summary: Great room, spacious and private
Chris Chris
Aug 11, 2025 04:37:58 AM
Summary: Amazing, clean, beautifully decorated. Loved everything!
Robert Robert
Jul 18, 2025 06:35:45 PM
Summary: Very outdated, wood floors were soft and extremely uneven. Hotel bar closes really early at 7pm. Pools are tiny. Breakfast was just ok. Location was great.
Jul 5, 2025 12:06:42 AM
Summary: My husband and I had a vacation getaway. I have been to Key West before and it was his first time. I wanted him to have a great experience. Winslow Bungalow did not disappoint. The breakfast was amazing, the rooms were impeccably clean and the staff were friendly. We would stay at the Winslow again and again.
Pamela Pamela
Jun 24, 2025 11:49:45 PM
Summary: Amazing accommodations. Loved the cute little bungalow we were in with a front porch. Staff was friendly and responsive.
Jun 18, 2025 06:12:58 AM
Summary: Amazing place for out honeymoon! Quiet, clean and well decorated room. Very comfortable also. Two things I suggest for improvement: the bathroom door didn't close and everynight there was a cockroach waiting for us in the room... :( We were in the first floor, I imagine it is normal.
Roberta Roberta
Jun 16, 2025 08:53:47 PM
Summary: We had a wonderful stay!
Ada Ada
Jun 16, 2025 02:02:25 AM
Summary: Great place to stay, staff was amazing, very close to everything .
Bryan Bryan
Jun 15, 2025 11:08:38 PM
Summary: The property is beautiful but the room we had definitely needed some repairs.
Tatiana Tatiana
Jun 15, 2025 03:24:44 PM
Summary: When we arrived our bank flagged our account for fraud, the staff was super understanding and patient until we got it figured out.
Candy Candy

FAQ's

Is this Old Town hotel pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Old Town hotel have a swimming pool?

Yes, this Old Town hotel has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Old Town hotel?

Best-rates for the Old Town hotel starts from $223 per night with includes Parking, Pool, Fireplace/Heating, Guest Services, Breakfast, Child Friendly, Internet, Kitchen, Air Conditioner, Security/Safety, Wellness Facilities, Balcony/Terrace, Bar, Laundry, Pet Friendly, TV, Accessibility, Bedding/Linens, Toiletries StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Old Town hotel a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this hotel 4 stars or guests have recommended them suitable for families. As reported by the owner or manager, the hotel has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Old Town hotel wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Old Town hotel has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Old Town hotel?

Based on the information reported by the owner or manager, the Old Town hotel indicates 1 day stay policy at this hotel. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Old Town hotel?

Based on the information reported by the owner or manager, details for the cancellation policy for the Old Town hotel are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

People Also Ask

Check Hotel Availability
Nightly rates from:
US $223
Price Details
You will be redirected to  
Hot Deal - It has been viewed 212 times today
Not the right fit? Check out our other properties in Old Town
view more places to stay

Recently Booked Locations

Recently Booked Properties