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Winslow's Bungalows - Key West Historic Inns

Property class: 4

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A short walk from Duval Street and Southernmost Point, Winslow's Bungalows - Key West Historic Inns provides a poolside bar, a garden and a bar. Guests can connect to free in-room WiFi.

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Air-conditioning
The current price is AU$364
includes taxes & fees
14 Sept - 15 Sept

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Room options

Available filters for rooms
Showing 14 of 14 rooms

View all photos for Premier King with Patio or Balcony

A wooden bench with cushions, a small table with glasses, and a white gate in a garden with various plants.

Premier King with Patio or Balcony

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

View all photos for King Suite with Sofa Bed

A modern hotel room with a bed, sofa, and a desk with a lamp.

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 Single Sofa Bed
  • Free Wi-Fi

View all photos for King Suite with Soaking Tub

A bedroom with a large bed, a wicker chair, a desk with a lamp, and a painting on the wall.

King Suite with Soaking Tub

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

View all photos for King Mobility

A neatly made bed with a floral pillow, a wooden headboard, and two bedside lamps. There are two framed pictures on the wall above the bed.

King Mobility

9.6 out of 10
Exceptional
(13 reviews)
  • 29 sq m
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Two Queens

A hotel room with two beds, a wooden headboard, a bedside table with a lamp, a wicker chair, and a large window with shutters.

Two Queens

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

View all photos for Classic King

A modern bedroom with a bed, bedside table, lamp, and a ceiling fan.

Classic King

9.0 out of 10
Wonderful
(50 reviews)
  • 22 sq m
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Single Queen

Premium bedding, in-room safe, iron/ironing board (on request)

Single Queen

8.8 out of 10
Excellent
(5 reviews)
  • 22 sq m
  • Sleeps 2
  • 1 Queen Bed
  • Free Wi-Fi

View all photos for Treehouse King Suite

A modern bedroom with a bed, a sofa, a ceiling fan, and a wall-mounted mirror.

Treehouse King Suite

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

View all photos for Bungalow King

A bedroom with a large bed, a wicker chair, a desk with a lamp, and a painting on the wall.

Bungalow King

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

View all photos for Annex King

Premium bedding, in-room safe, iron/ironing board (on request)

Annex King

9.4 out of 10
Exceptional
(14 reviews)
  • 22 sq m
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Annex King Mobility

A two-story white house with a balcony, surrounded by lush greenery and a white picket fence.

Annex King Mobility

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

Room

  • Sleeps 9
  • Free Wi-Fi

View all photos for Bungalow

A bedroom with a bed, a desk, a chair, a dresser, a door, and a wall-mounted lamp.

Bungalow

  • 28 sq m
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

Room

  • Sleeps 9
  • Free Wi-Fi

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About the area

Located in Old Town Key West, a neighbourhood in Key West, Winslow's Bungalows - Key West Historic Inns is in the entertainment district and near a boardwalk. Ernest Hemingway Home and Museum and Southernmost Point 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 skydiving and ecotours nearby. Visit our Key West travel guide
Map
725 Truman Avenue, Key West, FL, 33040

What's nearby

  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    5 min walk - 0.4 km
  • A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.
    Ernest Hemingway Home and Museum
    8 min walk - 0.7 km
  • A lighthouse with a white exterior and a black top, surrounded by lush green trees.
    Key West Lighthouse and Keeper's Quarters Museum
    8 min walk - 0.7 km
  • A beach with people sunbathing, palm trees, and a multi-story building in the background.
    South Beach
    9 min walk - 0.8 km
  • A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.
    Southernmost Point
    11 min walk - 1.0 km

Getting around

  • Key West, FL (EYW-Key West Intl.)
    9 min drive

Restaurants

  • Moondog Cafe & Bakery
    9 min walk
  • Circle K
    7 min walk
  • Cuban Coffee Queen (Duval)
    8 min walk
  • Mangoes Restaurant
    10 min walk
  • 801 Bourbon Bar
    9 min walk

About this property

Winslow's Bungalows - Key West Historic Inns

  • Upscale hotel near Duval Street
  • Close to Ernest Hemingway Home and Museum and Southernmost Point, Winslow's Bungalows - Key West Historic Inns provides a poolside bar, a garden and a bar. Guests can connect to free in-room WiFi.
  • You'll also find perks such as:
    • 3 outdoor pools, along with sunloungers
    • Continental breakfast (surcharge), self-parking (surcharge) and coffee/tea in reception
    • A water dispenser, outdoor furniture and concierge services
    • Tour/ticket information, smoke-free property and bike parking
    • Guest reviews give top marks for the breakfast, pool and helpful staff
  • Room features
  • All 85 individually furnished rooms include thoughtful touches such as premium bedding and air conditioning, in addition to amenities such as free WiFi and safes. Guest reviews speak positively of the cleanliness rooms at the property.
  • Other conveniences in all rooms include:
    • Heating and ceiling fans
    • Recycling, LED light bulbs and eco-friendly cleaning products
    • Bathrooms with designer toiletries and hairdryers
    • 55-inch LED TVs with cable channels
    • Mini fridges, free infant beds and daily housekeeping

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Property amenities

Internet

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

Parking and transport

  • Parking on site (USD 30 per day; includes in/out privileges)
  • Limited on-site self parking

Food and drink

  • Daily continental breakfast available 8:00 AM to 10:00 AM for a fee
  • 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 cot
  • 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 (76 centimetre high)

More

  • 15 buildings
  • 2 floors
  • Built in 1857
  • Comprehensive food waste policy
  • Eco-friendly cleaning products used
  • Locally-owned and organised tours and activities
  • Smoking not allowed
  • Some LED lighting used
  • Vegan dining options
  • Vegetarian dining options
  • Water dispenser usage encouraged

Room amenities

Bedroom

  • Free cot
  • Premium bedding

Bathroom

  • Designer toiletries
  • Dressing gowns
  • 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 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
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 19 Aug 2026, prices found for a 1-night stay for 2 adults at Winslow's Bungalows - Key West Historic Inns on 14 Sept 2026 start from AU$364, 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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