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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 AED 716
AED 992 total
includes taxes & fees
23 Aug - 24 Aug

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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 WiFi

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 Twin Sofa Bed
  • Free WiFi

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 WiFi

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 WiFi

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 WiFi

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 WiFi

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 WiFi

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 WiFi

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 WiFi

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 WiFi

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 WiFi

BUNGALOW KING SIZE BED

  • Sleeps 9
  • Free WiFi

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 WiFi

BUNGALOW STANDARD

  • Sleeps 9
  • Free WiFi

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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. 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 Intl. Airport (EYW)
    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 like:
    • 3 outdoor pools along with sun loungers
    • Continental breakfast (surcharge), self parking (surcharge), and coffee/tea in the lobby
    • A water dispenser, outdoor furniture, and concierge services
    • Tour/ticket assistance, smoke-free premises, and bicycle parking
    • Guest reviews say great things about the breakfast, pool, and helpful staff
  • Room features
  • All 85 individually furnished rooms include perks such as premium bedding and air conditioning, in addition to amenities like free WiFi and safes. Guest reviews speak positively of the clean 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 hair dryers
    • 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 transportation

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

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 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
  • Built in 1857
  • Comprehensive food waste policy
  • Eco-friendly cleaning products used
  • Locally-owned and organized tours and activities
  • Smoking not allowed
  • Some LED lighting used
  • 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.

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

As of 19 August 2026, prices found for a 1-night stay for 2 adults at Winslow's Bungalows - Key West Historic Inns on 23 August 2026 start from AED 716, excluding 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?

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 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 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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