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Winslow's Bungalows - Key West Historic Inns

Property class: 4

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Photo gallery for Winslow's Bungalows - Key West Historic Inns

A two-story building with a covered entrance, palm trees, and a bench outside. - Winslow's Bungalows - Key West Historic Inns (Key West)
A white picket fence, a wooden bench with cushions, and a concrete pathway surrounded by lush greenery. - Winslow's Bungalows - Key West Historic Inns (Key West)
A white building with a sign reading 'Kimpton Key West Winslow's Bungalow.' - Winslow's Bungalows - Key West Historic Inns (Key West)
A poolside area with lounge chairs, umbrellas, and a covered seating area with hanging lights. - Winslow's Bungalows - Key West Historic Inns (Key West)
A bright room with a staircase, two windows overlooking a pool area, and two wicker chairs with cushions. - Winslow's Bungalows - Key West Historic Inns (Key West)
Close to Ernest Hemingway Home and Museum and Duval Street, 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

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Skip the crowds, keep the savings. AARP members save more after Labor Day. Book by Oct 7, 2026.

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
(56 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
(51 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

8.4 out of 10
Very good
(6 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
(15 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

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 - 0.3 miles
  • A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.
    Ernest Hemingway Home and Museum
    8 min walk - 0.4 miles
  • 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 - 0.4 miles
  • A beach with people sunbathing, palm trees, and a multi-story building in the background.
    South Beach
    9 min walk - 0.5 miles
  • 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 - 0.6 miles

Getting around

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

Restaurants

  • Circle K
    7 min walk
  • 801 Bourbon Bar
    9 min walk
  • Old Town Tavern
    7 min walk
  • El Siboney Restaurant
    6 min walk
  • Better Than Sex
    4 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

  • 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.

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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Reviews

Winslow's Bungalows - Key West Historic Inns Reviews

9.2

Wonderful

9.4

Cleanliness

9.2

Amenities

9.4

Staff & service

9.2

Property conditions & facilities
Rating 10 - Excellent. 1034 out of 1404 reviews
Rating 8 - Good. 232 out of 1404 reviews
Rating 6 - Okay. 93 out of 1404 reviews
Rating 4 - Poor. 28 out of 1404 reviews
Rating 2 - Terrible. 17 out of 1404 reviews

Reviews

Verified review

10/10 Excellent

Stacey

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful resort with amazing staff!
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Julia

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent hotel Friendly helpful staff Great location
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Deanna

Liked: Cleanliness, staff & service, property conditions & facilities
The staff was fantastic and we loved the hotel!!! Great location!
Stayed 5 nights in Aug 2026
Verified review

10/10 Excellent

Cathy

Liked: Cleanliness, staff & service, property conditions & facilities
Lovely place and helpful staff. Rooms are very private feeling.
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Teresa

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful property. Walking distance to Duval. Friendly helpful staff. Highly recommend!!
Stayed 3 nights in Sep 2026
Verified review

8/10 Good

Lisa

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very private and personal. Breakfast and Bar was very nice and relaxing.
Stayed 3 nights in Aug 2026
Verified review

8/10 Good

Julie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Small room but clean and functional. Grounds are beautiful and well maintained. Only complaint was the chemicals in the pool bleached two of my swimsuits- so beware of that.
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

Owen

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Really nice rooms, always clean. Pools are nice, wish they were cooler in temp but it is what it is. "free" breakfast if that's your thing. Good amount of parking. Easy to get anywhere from this location.
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Elizabeth

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was particularly wonderful. Helpful and friendly. And the place is lovely and so centrally located.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Stephanie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I had a wonderful stay. Amazing location. Three pools cleaned regularly. Staff was super helpful, Keith at the bar offered great service. Overall an enjoyable trip. I hope to return again soon.
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Kerry

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved this place! Beautiful hotel and great location.
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Jack

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

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 review

10/10 Excellent

Mayra

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Our stay was absolutely amazing from beginning to end! The service was truly over the top—everyone went above and beyond to make sure we had an incredible experience. The hospitality and attention to detail were exceptional. We loved all the amenities, including the bicycle rental option, complimentary breakfast, three beautiful pools, and the bar. There was always something to enjoy, and the live music created such a fun and relaxing atmosphere. Everything was wonderful—the service, amenities, atmosphere, and overall experience. We honestly didn’t want to leave! We would absolutely stay here again and highly recommend this place to anyone looking for a memorable getaway. Five stars all the way!
Stayed 4 nights in Aug 2026
Verified review

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 review

8/10 Good

Theresa

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room was clean, but very small, and no hooks for towels or clothes. Pool and bar areas were very nice and well maintained. The free breakfast was great every day. Would definitely stay here again.
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

MP

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We stayed here for two nights in June and had an amazing experience! The weather was very hot, but having three different pools to choose from made it easy to cool off and relax. The breakfast was delicious—we especially loved the Belgian waffles and the fresh fruit. The entire resort had a peaceful, relaxing atmosphere, making it the perfect place to unwind. We would definitely stay here again!
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Jennifer

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The hotel felt quiet and quaint. The three small pools offered a more private feel. The staff was very welcoming and the property was clean. My husband and I enjoyed having a pool side bar at our convenience. The location was perfect and very close to many attractions and restaurants. We loved our stay here.
Stayed 2 nights in Jun 2026
Verified review

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 review

10/10 Excellent

Ashley

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was awesome! We went for my fiancé's birthday, they provided a cake and individual champagne. It was all complementary. The staff out and got the cake from a local bakery for me. We would recommend this resort. We plan to visit again.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Edmar

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
a historical building, with comfortable rooms, on a pleasant street. staff absolutely welcoming. and the restaurant has excellent options.
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Kimberly

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved this place. 2 blocks from duval st. Three different pools to choose from. Was told this was the off season so it wasn’t that crowded. Two of the nights it rained but we sat out on the patio and enjoyed a relaxing dinner. Because we were so close to duval st, we did A LOT of walking. My only complaint about the hotel is that the walls are very thin. You can hear your neighbors and they can hear you 😁 other than that, would highly recommend.
Stayed 4 nights in Aug 2026
Verified review

10/10 Excellent

Raymond

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

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 review

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