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

| 9.2 (1260 Reviews) |   Pet Friendly  1 Bathroom
Old Town Hotel | Winslow's Bungalows - Key West Historic Inns

Hotel in Old Town, Key West

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

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

Samuel
Apr 13, 2026 09:20:46 PM
Review Score:   6
Summary: Pros: The staff are excellent! Everyone, front desk, bartender, cleaning lady, all went out of their way over and above to be helpful. Best staff ever. The property is lovely, with beautiful landscaping throughout. Cons: The place is old and the rooms show it. Fixtures are very dated and our room had an old and tired feel. Old air conditioner, old bathroom fixtures. Nothing particularly nice. Worst is the walls are paper thin. We were kept up late by our neighbors having loud sex, and woken up early (at 6:30!) by construction. Don't even think of staying here without quality ear plugs. The breakfast is quite below average. There is no hot protein, just the usual sweet carbs. Every cheap two-star hotel these days has a hot plate with scrambled eggs and sausage, or something. Why would a place like this be so stingy? Overall: Despite the amazing people working here, we would not go back.
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Room Arrangement

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

General

Ping - 7, Shower only, Square feet - 240, Bed count minimum 1, Bed count maximum 1, Square meters - 22
Premier King with Patio or Balcony
Room Size: 180 square feet m2
1 King Bed
Premier King with Patio or Balcony

General

Patio, Ping - 5, Square feet - 180, Square meters - 17, Shower only, Bed count minimum 1, Bed count maximum 1
King Suite with Sofa Bed
Room Size: 500 square feet m2
2 King Bed and Twin Sofa Bed
King Suite with Sofa Bed

General

Square feet - 500, Patio, Number of bedrooms - 1, Shower only, Ping - 14, Square meters - 46, Bed count minimum 2, Bed count maximum 2
King Suite with Soaking Tub
Room Size: 400 square feet m2
1 King Bed
King Suite with Soaking Tub

General

Separate bathtub and shower, Ping - 11, Square meters - 37, Square feet - 400, Bed count minimum 1, Bed count maximum 1
King Mobility
Room Size: 312 square feet m2
1 King Bed
King Mobility

General

Ping - 9, Patio, Square meters - 29, Shower only, Extra bed count 0, Square feet - 312, Wheelchair accessible, Bed count minimum 1, Bed count maximum 1
Annex King Mobility
Room Size: 312 square feet m2
1 King Bed
Annex King Mobility

General

Ping - 9, Square meters - 29, Shower only, Square feet - 312, Bed count minimum 1, Bed count maximum 1
Two Queens
Room Size: 240 square feet m2
2 Queen Beds
Two Queens

General

Ping - 7, Shower only, Square feet - 240, Bed count minimum 2, Square meters - 22, Bed count maximum 2
Treehouse King Suite
Room Size: 425 square feet m2
1 King Bed
Treehouse King Suite

General

Square feet - 425, Furnished patio, Number of bedrooms - 1, Square meters - 39, Shower only, Ping - 12, Separate sitting area, Bed count minimum 1, Bed count maximum 1
Classic King
Room Size: 240 square feet m2
1 King Bed
Classic King

General

Ping - 7, Shower only, Square feet - 240, Bed count minimum 1, Bed count maximum 1, Square meters - 22
Annex King
Room Size: 240 square feet m2
1 King Bed
Annex King

General

Furnished balcony or patio, Ping - 7, Shower only, Square feet - 240, Extra bed count 0, Bed count minimum 1, Bed count maximum 1, Square meters - 22
Single Queen
Room Size: 240 square feet m2
1 Queen Bed
Single Queen

General

Ping - 7, Shower only, Square feet - 240, Bed count minimum 1, Bed count maximum 1, Square meters - 22

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 $409 per night with includes Balcony/Terrace, Accessibility, Fireplace/Heating, Bar, Breakfast, Laundry, Air Conditioner, Toiletries, Guest Services, TV, Security/Safety, Bedding/Linens, Wellness Facilities, Parking, Pet Friendly, Pool, Child Friendly, Internet, Kitchen with all other facilities. matches every traveler with their perfect accommodation, 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?

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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USD409
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