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Winslow's Bungalows - Key West Historic Inns

4.0 star property
Three outdoor pools await at this Key West retreat near Duval Street, where guests can enjoy breakfast in a garden setting or relax at the poolside bar

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Front of property - Winslow's Bungalows - Key West Historic Inns (Key West)
Lobby - Winslow's Bungalows - Key West Historic Inns (Key West)
Restaurant - Winslow's Bungalows - Key West Historic Inns (Key West)
King Suite with Sofa Bed | Premium bedding, in-room safe, individually decorated - Winslow's Bungalows - Key West Historic Inns (Key West)
3 outdoor pools, open 7:00 AM to 10:00 PM, sun loungers - Winslow's Bungalows - Key West Historic Inns (Key West)
Winslow's Bungalows offers a peaceful retreat in Key West's historic district. Start your day with a continental breakfast in the garden, then lounge by one of the three outdoor pools. The helpful staff creates a welcoming environment that keeps guests returning.

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Pool
  • Breakfast included
  • Pet friendly
  • Free WiFi
  • Restaurant
  • Air conditioning

Room options

Available filters for rooms
Showing 11 of 11 rooms

View all photos for Premier King with Patio or Balcony

Premium bedding, in-room safe, individually decorated

Premier King with Patio or Balcony

9.0 out of 10
Wonderful
(54 reviews)
  • 17 sq m
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for King Suite with Sofa Bed

King Suite with Sofa Bed | Premium bedding, in-room safe, individually decorated

King Suite with Sofa Bed

9.4 out of 10
Exceptional
(3 reviews)
  • 46 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Twin Sofa Bed
  • Free WiFi

View all photos for King Suite with Soaking Tub

Premium bedding, in-room safe, individually decorated

King Suite with Soaking Tub

10.0 out of 10
Exceptional
(2 reviews)
  • 37 sq m
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for King Mobility

Premium bedding, in-room safe, individually decorated

King Mobility

9.6 out of 10
Exceptional
(12 reviews)
  • 29 sq m
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Two Queens

Premium bedding, in-room safe, individually decorated

Two Queens

8.8 out of 10
Excellent
(10 reviews)
  • 22 sq m
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

View all photos for Classic King

Premium bedding, in-room safe, individually decorated

Classic King

8.8 out of 10
Excellent
(46 reviews)
  • 22 sq m
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Single Queen

Premium bedding, in-room safe, individually decorated

Single Queen

8.0 out of 10
Very good
(3 reviews)
  • 22 sq m
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

View all photos for Treehouse King Suite

Treehouse King Suite | Premium bedding, in-room safe, individually decorated

Treehouse King Suite

10.0 out of 10
Exceptional
(2 reviews)
  • 39 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Bungalow King

Premium bedding, in-room safe, individually decorated

Bungalow King

9.6 out of 10
Exceptional
(5 reviews)
  • 22 sq m
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Annex King

Premium bedding, in-room safe, individually decorated

Annex King

9.4 out of 10
Exceptional
(13 reviews)
  • 22 sq m
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Annex King Mobility

Arcade

Annex King Mobility

10.0 out of 10
Exceptional
(3 reviews)
  • 29 sq m
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

About the neighborhood

Located in Old Town Key West, a neighborhood in Key West, Winslow's Bungalows - Key West Historic Inns is in the entertainment district and near a boardwalk/promenade. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and skydiving nearby. Visit our Key West travel guide
Map
725 Truman Avenue, Key West, FL, 33040

What's nearby

  • Duval Street
    Duval Street
    5 min walk - 0.3 miles
  • Ernest Hemingway Home and Museum
    Ernest Hemingway Home and Museum
    8 min walk - 0.4 miles
  • South Beach
    South Beach
    9 min walk - 0.5 miles
  • Key West Butterfly and Nature Conservatory
    Key West Butterfly and Nature Conservatory
    9 min walk - 0.5 miles
  • Southernmost Point
    Southernmost Point
    11 min walk - 0.6 miles

Getting around

  • Key West Intl. Airport (EYW)
    9 min drive

Restaurants

  • Circle K
    7 min walk
  • Old Town Tavern
    7 min walk
  • Better Than Sex
    4 min walk
  • El Siboney Restaurant
    6 min walk
  • Ocean Grill & Bar
    5 min walk

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Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transportation

  • Self parking on site (USD 30 per day; includes in/out privileges)

Food and drink

  • Free continental breakfast available daily 8:00 AM to 11:00 AM
  • A bar/lounge
  • A poolside bar
  • Coffee and tea in common areas

Restaurants on site

  • Bungalow Bar

Things to do

  • 3 outdoor pools

Family friendly

  • 3 outdoor pools
  • In-room crib
  • Mini-fridge

Conveniences

  • Limited-hour front desk
  • Luggage storage
  • Shared microwave
  • Water dispenser

Guest services

  • Concierge services
  • Housekeeping (daily)
  • Tour and ticket assistance

Outdoors

  • Garden
  • Outdoor furniture
  • Pool loungers

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Front entrance ramp
  • Hardwood flooring in room
  • Pool hoist on site
  • Upper floors accessible by stairs only
  • Well-lit path to entrance
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible path of travel
  • Wheelchair-accessible pool
  • Wheelchair-accessible registration desk (30 inches high)

More

  • 15 buildings
  • 2 floors
  • At least 80% lighting from LEDs
  • Built in 1857
  • Comprehensive food waste policy
  • Eco-friendly cleaning products used
  • Locally-owned and organized tours and activities
  • Smoking not allowed
  • Vegan dining options
  • Vegetarian dining options
  • Water dispenser usage encouraged

Room amenities

Bedroom

  • Free crib
  • Premium bedding

Bathroom

  • Bathrobes
  • Designer toiletries
  • Hair dryer
  • Private bathroom
  • Shampoo
  • Soap
  • Toilet paper
  • Toothbrush and toothpaste (on request)
  • Towels provided

Entertainment

  • 55-inch LED TV with cable channels

Food and drink

  • Mini-fridge

More

  • Access via exterior corridors
  • Air conditioning (climate-controlled)
  • Ceiling fan
  • Cleaning products are eco-friendly
  • Eco-friendly toiletries
  • Free local calls
  • Heating
  • Individual decor
  • Individual furnishings
  • Iron/ironing board on request
  • LED lighting
  • Phone
  • Recycling
  • Safe
  • Water-efficient showers
  • Water-efficient toilets

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 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 cribs are available on request at the property

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
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, 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
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 elevators
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–10:00 PM.

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?

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?

Check-out 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 Southernmost Point are also within 15 minutes.

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

Yes, this property offers free cancellation on select 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

Winslow's Bungalows - Key West Historic Inns Reviews

9.2

Wonderful

9.4

Cleanliness

9.0

Amenities

9.4

Staff & service

9.2

Property conditions & facilities
Rating 10 - Excellent. 962 out of 1318 reviews
Rating 8 - Good. 222 out of 1318 reviews
Rating 6 - Okay. 91 out of 1318 reviews
Rating 4 - Poor. 28 out of 1318 reviews
Rating 2 - Terrible. 15 out of 1318 reviews

Reviews

Verified

10/10 Excellent

Jack

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location and good property.
Stayed 5 nights in May 2026
Verified

10/10 Excellent

offri

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location and facilities. The breakfast was excellent.
Stayed 2 nights in May 2026
Verified

10/10 Excellent

Les

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff/Service was great...... facilities are beautiful..... perfect location...... would definitely stay again.
Stayed 3 nights in Jun 2026
Verified

10/10 Excellent

Bridget

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful property, nice location. Friendly staff.
Stayed 4 nights in Mar 2026
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

Nigel

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful cottage bedroom - very comfortable!! Outstanding free continental breakfast. Staff were very helpful; barman Keith was attentive during happy hour and full of great suggestions for our trip. Highly recommended!
Stayed 2 nights in May 2026
Verified

6/10 Okay

carol

Liked: Property conditions & facilities
Disliked: Cleanliness, staff & service
Beautiful foliage
Stayed 3 nights in May 2026
Verified

10/10 Excellent

Stephen Harlow

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This is a beautiful tropical property, along with being quaint. We loved being able to walk and ride bikes to many places but still in a quiet area. Every one of the staff are very nice and pleasant. Sonya at the front desk is outstanding!
Stayed 6 nights in May 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

Jessica

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was a lovely room and the breakfasts were great.
Stayed 5 nights in Jul 2024
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

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

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

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

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

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

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
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

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

10/10 Excellent

Patricia

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