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Winslow's Bungalows - Key West Historic Inns

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Luxury
VIP Access
4.0 star property
9.2

Wonderful

Upscale hotel near Duval Street

Close to Ernest Hemingway Home and Museum and South Beach, Winslow's Bungalows - Key West Historic Inns provides free continental breakfast, a poolside bar and a garden. Free in-room WiFi and a bar are available to all guests.

Popular amenities

  • Pool
  • Breakfast included
  • Pet-friendly
  • Free Wi-Fi
  • Restaurant
  • Air-conditioning
The current price is AU$362
includes taxes & fees
25 May - 26 May

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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

Special check-in instructions

The front desk is open daily from 7:00 AM - 11:00 PM

Front desk staffed during limited hours

For any questions, please contact the property using the information on the booking confirmation

Information provided by the property may be translated using automated translation tools

Access methods

Front desk (limited hours)

Pets

Pets are allowed for an extra charge of USD 50 per pet, per night

Service animals are welcome, and are exempt from fees

Food and water bowls are available

Children and extra beds

Children are welcome

Rollaway/extra beds are not available.

Free cots are available on request at the property

Payment types

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • Deposit: USD 50 per accommodation, per night
  • Resort fee: USD 50.63 per accommodation, per night
The resort fee includes:
  • Additional inclusions
  • Concierge service
  • In-room safe
  • Phone calls
  • Pool access

We have included all charges provided to us by the property.

Optional extras

  • 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.

You need to know

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
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 property accepts credit cards; cash is not accepted
This property uses eco-friendly cleaning products
Safety features at this property include a carbon monoxide detector, a fire extinguisher, a smoke detector and outdoor lighting
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Please note that cultural norms and guest policies may differ by country and by property; the policies listed are provided by the property
This hotel requires written authorization in advance for any payment using a credit card whose name differs from the registered guest.

We should mention

This property does not have any lifts
Pool access available from 7:00 AM to 10:00 PM
This property welcomes guests of all sexual orientations and gender identities (LGBTQ+ friendly)

Frequently asked questions

Does Winslow's Bungalows - Key West Historic Inns have a pool?

Yes, this property has 3 outdoor pools. Pool access is from 7:00 AM to 10:00 PM.

How much does it cost to stay at Winslow's Bungalows - Key West Historic Inns?

As of 21 May 2026, prices found for a 1-night stay for 2 adults at Winslow's Bungalows - Key West Historic Inns on 25 May 2026 start from AU$362, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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

Yes, pets are allowed at this property. There's a fee of USD 50 per pet, per night. Service animals are exempt from fees.

How much is parking at Winslow's Bungalows - Key West Historic Inns?

Self-parking is available for USD 30 per day.

What time is check-in at Winslow's Bungalows - Key West Historic Inns?

Check-in start time: 4:00 PM; check-in end time: anytime.

What time is check-out at Winslow's Bungalows - Key West Historic Inns?

Checkout is at 11 AM.

Where is Winslow's Bungalows - Key West Historic Inns located?

Located in Old Town Key West, this hotel is within a 5-minute walk of Saint Mary Star of the Sea and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 15 minutes.

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on selected room rates because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

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Reviews

Reviews

9.2

Wonderful

9.4

Cleanliness

9.2

Amenities

9.4

Staff & service

9.2

Property conditions & facilities
Rating 10 - Excellent. 938 out of 1286 reviews
Rating 8 - Good. 218 out of 1286 reviews
Rating 6 - Okay. 87 out of 1286 reviews
Rating 4 - Poor. 28 out of 1286 reviews
Rating 2 - Terrible. 15 out of 1286 reviews

Reviews

Verified

10/10 Excellent

Adam Scott

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything was on point at this property. Pools, bar, breakfast, staff, etc...
Stayed 4 nights in Apr 2026
Verified

10/10 Excellent

Donna

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great staff and location. Breakfast was also wonderful.
Stayed 4 nights in Feb 2026
Verified

10/10 Excellent

Raymond

Liked: Cleanliness, staff & service, property conditions & facilities
Great accommodations and staff !
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Rebecca

Liked: Cleanliness, staff & service, property conditions & facilities
Winslow’s Bungalows offers a delightful stay for guests. It is centrally located for exploring Key West. The staff were very helpful.
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Melissa or Jeffrey

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful property, nice staff, clean rooms, relaxing atmosphere. We definitely recommend.
Stayed 5 nights in Mar 2026
Verified

8/10 Good

James

Liked: Cleanliness, amenities, property conditions & facilities
Friendly staff, great location and clean rooms.
Stayed 4 nights in Feb 2026
Verified

10/10 Excellent

Andrew

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Second time we have stayed here.Staff is excellent, accommodating. The property is very well maintained and a great location.
Stayed 4 nights in Mar 2026
Verified

10/10 Excellent

Joseph

Liked: Cleanliness, amenities, property conditions & facilities
Great rooms , beautiful grounds,and amazing staff
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

John

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
My wife and I had a great stay at the Winslow‘s. All the staff was really friendly and we love the bartender Kurt definitely will stay here again.
Stayed 5 nights in Mar 2026
Verified

10/10 Excellent

Jennifer

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property was beautifully laid out! The breakfast was delicious, more than we expected and the staff was very friendly. I would and probably will stay here again!
Stayed 4 nights in Mar 2026
Verified

10/10 Excellent

Mark

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Such a cool, boutique style property walkable to all the Old Town Key West attractions, but far enough away so that it feels peaceful and quiet! Has 3 different pools on property and a great little poolside bar area. Great for couples!
Stayed 4 nights in Apr 2026
Verified

10/10 Excellent

Monina S

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property was beautiful with all the trees and greenery. Sonia at the front desk was very helpful and I love the coffee and continental breakfast every morning. The location was ideal. It was close enough to Duval if you wanted to party and far enough for privacy.
Stayed 6 nights in Apr 2026
Verified

8/10 Good

John

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Property was nice, clean, breakfast good and the pool was nice. We would stay there again.
Stayed 7 nights in Feb 2026
Verified

10/10 Excellent

Jerri

Liked: Cleanliness
Pet friendly, great staff, clean room and pools
Stayed 5 nights in Mar 2026
Verified

10/10 Excellent

Mark

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nicely situated. Comfy room. Neat swimming pool(s). Breakfast and bar areas did the job!
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Kristi

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Absolutely love the property. The landscaped paths to each bungalow were absolutely beautiful. It was very quaint place to stay. Location was perfect. Close to the waterfront and Duval Street. The bartender Keith gave us great places to visit and eat and made delicious drinks. We will be back.
Stayed 3 nights in Apr 2026
Verified

8/10 Good

Carolyn

Liked: Cleanliness, staff & service, property conditions & facilities
Cute bungalows in a good location. Staff is very helpful. Pools and rooms are very small, - but you’re getting the bungalow vibe vs hotel room. We walked everywhere from here.
Stayed 2 nights in Apr 2026
Verified

10/10 Excellent

Patricia

Liked: Cleanliness, staff & service, amenities
Clean great staff great breakfast
Stayed 5 nights in Jan 2026
Verified

10/10 Excellent

Lori

Liked: Cleanliness, staff & service, amenities
We enjoyed the resort and the staff was very accommodating. The continental breakfast was excellent, fresh fruit, eggs, waffles, juices, bagels, etc. more than usual!
Stayed 3 nights in Mar 2026
Verified

8/10 Good

Tom

Liked: Cleanliness, staff & service, amenities
We enjoyed our stay very much at the Bungalows. Clean and comfortable location, great walkable from everything in Key West.
Stayed 4 nights in Feb 2026
Verified

10/10 Excellent

Alan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean. Convenient location, staff was very courteous.
Stayed 6 nights in Mar 2026
Verified

10/10 Excellent

Pamela

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nicely maintained grounds and amenities. Bungalow room was a little small for 2 but clean and nicely decorated. Excellent breakfast and poolside bar.
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

John

Staff was awesome
Stayed 5 nights in Feb 2026
Verified

10/10 Excellent

Lisa

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent choice for our 3 night stay. The property is beautiful, the bungalows are charming and the staff is friendly. The daily breakfast options are fresh and beautiful displayed. The property is quiet and is within walking distance to shops, historic places, and many restaurants. I give this property an A+
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Marcel

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The hotel was very cozy. I enjoyed relaxing by the pool which is right next to the bar. Definitely had the vacation I wanted.
Stayed 4 nights in Mar 2026