Winslow's Bungalows - Key West Historic Inns | Hotel in Key West

| 9.2 (1005 Reviews) |   Pet Friendly  1 Bathroom
Old Town Hotel | Winslow's Bungalows - Key West Historic Inns

Hotel in Old Town, Key West

Hotel with 3 outdoor swimming pools, a short walk to Duval Street
Along with 3 outdoor pools, this smoke-free hotel has a bar/lounge and a poolside bar. Free continental breakfast and free WiFi in public areas are also provided. Other amenities include self parking, coffee/tea in a common area, and a microwave in a common area.
Winslow's Bungalows - Key West Historic Inns offers 85 accommodations, which are accessible via exterior corridors and feature safes and bathrobes. Each accommodation is individually furnished and decorated. Beds feature premium bedding. 55-inch LED televisions come with cable channels. Bathrooms include designer toiletries, complimentary toiletries, and hair dryers.

This Key West hotel provides complimentary wireless Internet access. Business-friendly amenities include phones along with free local calls (restrictions may apply). Housekeeping is offered daily and irons/ironing boards can be requested.


3 outdoor swimming pools are on site.

The recreational activities listed below are available either on site or nearby; fees may apply.

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725 Truman Avenue, Key West, 33040, United States

Amenities

Air Conditioner
Parking
Pet Friendly
Pool
TV
Balcony/Terrace
Accessibility
Security/Safety
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Bar
Toiletries
Guest Services
Breakfast
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Bathrooms
  • Bathrobes
  • Hair dryer
  • Soap
  • Toilet paper
  • Private bathroom
  • Toothbrush and toothpaste (on request)
  • Shampoo
  • Designer toiletries
  • Towels
Bedroom
  • Premium bedding
  • Ceiling fan
  • Bed sheets
  • Heating
  • Free cribs/infant beds
  • Air conditioning (climate-controlled)
  • Iron/ironing board (on request)
  • Phone
  • Water-efficient toilets only
  • Water-efficient showers only
  • Recycling
  • Eco-friendly cleaning products provided
  • Individually furnished
  • Free local calls
  • Individually decorated
  • Safe
  • LED light bulbs
  • Access via exterior corridors
Breakfast
  • Free continental breakfast available daily 8:00 AM–11:00 AM
  • 1 poolside bar and 1 bar
  • Coffee/tea in common area(s)
  • Mini-fridge
Parking
  • Self parking on site (USD 30 per day; includes in/out privileges)
Accessibility
  • Wheelchair-accessible pool
  • Hardwood flooring in room
  • Well-lit path to entrance
  • Wheelchair-accessible path of travel
  • This property does not have elevators
  • Pool hoist on site
  • Front entrance ramp
  • Upper floors accessible by stairs only
  • Wheelchair-accessible registration desk height (inches): 30
  • Wheelchair-accessible registration desk
  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
Activities
  • Fishing
  • Parasailing
  • Windsurfing
  • Marina
  • Motor boating
  • Beach access
  • Sailing
  • Scooter/moped rentals
  • Kayaking
  • Scuba diving
  • Snorkeling
  • Swimming
  • Jet skiing
  • Boat tours
  • Canoeing
  • Skydiving
  • Golfing
  • Ecotours
  • 3 outdoor pools
  • Bike parking
Entertainment
  • Cable channels
  • 55-inch LED TV
General
  • Water dispenser
  • English
  • Locally-owned & organized tours & activities
  • At least 80% lighting from LEDs
  • Vegan dining options
  • Water dispenser
  • Smoke-free property
  • Vegetarian dining options
  • Comprehensive food waste policy
  • Shared microwave
Guest Services
  • Free cribs/infant beds
  • 3 outdoor pools
  • Mini-fridge
  • Daily housekeeping
  • Front desk (limited hours)
  • Concierge services
  • Tour/ticket assistance
  • Luggage storage
Internet
  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi
Outdoors
  • Pool sun loungers
  • Garden
  • Outdoor furniture

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
Child Policy
Children are welcome. rollaway/extra beds are not available. free cribs (infant beds)!
Payment Policy
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.
Pet Policy
Food and water bowls are available pets allowed for an extra charge of usd 50 per pet, per night service animals are welcome, and are exempt from fees
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 please note that cultural norms and guest policies may differ by country and by property; the policies listed are provided by the property safety features at this property include a carbon monoxide detector, a fire extinguisher, a smoke detector, and outdoor lighting 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 hotel requires written authorization in advance for any payment using a credit card whose name differs from the registered guest. this property accepts credit cards; cash is not accepted 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 this property uses eco-friendly cleaning products

Reviews

Pamela
Jul 5, 2025 12:06:42 AM
Review Score:   10
Summary: My husband and I had a vacation getaway. I have been to Key West before and it was his first time. I wanted him to have a great experience. Winslow Bungalow did not disappoint. The breakfast was amazing, the rooms were impeccably clean and the staff were friendly. We would stay at the Winslow again and again.
See All Reviews

Room Arrangement

Room Info Facilities
Bungalow
Room Size: 240 square feet m2
1 King Bed
Bungalow

General

Ping - 7, Shower only, Square feet - 240, Bed count minimum 1, Bed count maximum 1, Square meters - 22, Number of bathrooms - 1
Room (Winslet)
Room Size: 180 square feet m2
1 King Bed
Room (Winslet)

General

Number of living rooms 0, Patio, Number of bedrooms - 0, Ping - 5, Square feet - 180, Square meters - 17, Shower only, Bed count minimum 1, Bed count maximum 1, Number of bathrooms - 1
Room (Truman)
Room Size: 500 square feet m2
2 King Bed and Twin Sofa Bed
Room (Truman)

General

Number of living rooms 0, Square feet - 500, Patio, Number of bedrooms - 0, Shower only, Ping - 14, Square meters - 46, Bed count minimum 2, Number of bathrooms - 1, Bed count maximum 2
Room (Maloney)
Room Size: 400 square feet m2
1 King Bed
Room (Maloney)

General

Number of living rooms 0, Separate bathtub and shower, Number of bedrooms - 0, Ping - 11, Square meters - 37, Square feet - 400, Bed count minimum 1, Bed count maximum 1, Number of bathrooms - 1
Room, Mobility Accessible (Winslow)
Room Size: 312 square feet m2
1 King Bed
Room, Mobility Accessible (Winslow)

General

Number of living rooms 0, Ping - 9, Patio, Number of bedrooms - 0, Square meters - 29, Shower only, Extra bed count 0, Square feet - 312, Wheelchair accessible, Bed count minimum 1, Bed count maximum 1, Number of bathrooms - 1
Room, Mobility Accessible (Annex)
Room Size: 312 square feet m2
1 King Bed
Room, Mobility Accessible (Annex)

General

Number of living rooms 0, Ping - 9, Number of bedrooms - 0, Square meters - 29, Shower only, Square feet - 312, Bed count minimum 1, Bed count maximum 1, Number of bathrooms - 1
Room (Blue Parrot)
Room Size: 240 square feet m2
2 Queen Beds
Room (Blue Parrot)

General

Number of living rooms 0, Number of bedrooms - 0, Ping - 7, Shower only, Square feet - 240, Bed count minimum 2, Square meters - 22, Number of bathrooms - 1, Bed count maximum 2
Tree House (Suite)
Room Size: 425 square feet m2
1 King Bed
Tree House (Suite)

General

Square feet - 425, Number of living rooms 0, Furnished patio, Number of bedrooms - 1, Square meters - 39, Shower only, Ping - 12, Separate sitting area, Bed count minimum 1, Bed count maximum 1, Number of bathrooms - 1
Room (Winslow)
Room Size: 240 square feet m2
1 King Bed
Room (Winslow)

General

Number of living rooms 0, Number of bedrooms - 0, Ping - 7, Shower only, Square feet - 240, Bed count minimum 1, Bed count maximum 1, Square meters - 22, Number of bathrooms - 1
Room (Annex)
Room Size: 240 square feet m2
1 King Bed
Room (Annex)

General

Number of living rooms 0, Furnished balcony or patio, Number of bedrooms - 0, Ping - 7, Shower only, Square feet - 240, Extra bed count 0, Bed count minimum 1, Bed count maximum 1, Square meters - 22, Number of bathrooms - 1
Room (Key Lime)
Room Size: 240 square feet m2
1 Queen Bed
Room (Key Lime)

General

Number of living rooms 0, Number of bedrooms - 0, Ping - 7, Shower only, Square feet - 240, Bed count minimum 1, Bed count maximum 1, Square meters - 22, Number of bathrooms - 1

FAQ's

Is this Old Town hotel pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Old Town hotel have a swimming pool?

Yes, this Old Town hotel has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Old Town hotel?

Best-rates for the Old Town hotel starts from $270 per night with includes Kitchen, Balcony/Terrace, Fireplace/Heating, Laundry, Parking, Bedding/Linens, Wellness Facilities, Guest Services, Air Conditioner, Pet Friendly, TV, Security/Safety, Toiletries, Child Friendly, Pool, Accessibility, Bar, Breakfast, Internet with all other facilities. Hotala.co.nz matches every traveler with their perfect hotel, resort, or rental and whether you are traveling with a group, friends, family, or pets.

Is Old Town hotel a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this hotel 4 stars or guests have recommended them suitable for families. As reported by the owner or manager, the hotel has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Old Town hotel wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Old Town hotel has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Old Town hotel?

Based on the information reported by the owner or manager, the Old Town hotel indicates 1 day stay policy at this hotel. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Old Town hotel?

Based on the information reported by the owner or manager, details for the cancellation policy for the Old Town hotel are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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