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Winslow's Bungalows - Key West Historic Inns, Key West
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Winslow's Bungalows - Key West Historic Inns — photo 2 Winslow's Bungalows - Key West Historic Inns — photo 3 Winslow's Bungalows - Key West Historic Inns — photo 4 Winslow's Bungalows - Key West Historic Inns — photo 5 Winslow's Bungalows - Key West Historic Inns — photo 6 Winslow's Bungalows - Key West Historic Inns — photo 7 Winslow's Bungalows - Key West Historic Inns — photo 8 Winslow's Bungalows - Key West Historic Inns — photo 9

Key West · FL

Winslow's Bungalows - Key West Historic Inns

★★★★☆
Provider-supplied star rating (LiteAPI)
8.6/10 2,100 reviews

Best time to visit Winslow's Bungalows - Key West Historic Inns: weather and the prices we have observed, by month →

Best time to visit

April is historically the best month for Key West

April is when Key West is at its best — 99% of days are warm with over 6 hours of sun and rain falls on just 21% of days (n=240, ERA5 2018–2025). Median sunshine: 12.5h per day.

99% warm+sunny · 21% rain days · n=240

ERA5 reanalysis 2018–2025 — historical likelihood, not a forecast. Full almanac for Key West in April →

Key West by month — ERA5 8-year history. Warm+6h sun = days ≥72°F with >6h sunshine.
Month Warm+sun Rain days Avg high n
January 56% 22% 72°F 248
February 81% 21% 74°F 226
March 90% 16% 76°F 248
April 99% 21% 78°F 240
May 95% 38% 82°F 248
June 94% 58% 84°F 240
July 96% 55% 86°F 248
August 96% 62% 86°F 248
September 94% 64% 85°F 240
October 94% 52% 82°F 248
November 88% 28% 78°F 240
December 78% 26% 75°F 248

What guests say

Verbatim from provider sentiment analysis. We publish both sides — the cons are why the pros are believable.

Praised
  • Great location
  • Friendly staff
  • Nice gardens and ambiance
Criticised
  • Room cleanliness issues
  • Room size smaller than expected
  • High price relative to value

Based on 2,100 guest reviews (provider-supplied sentiment, LiteAPI).

Facilities

37 amenities on record. Grouped by category — spa/pool/beach/golf lead.

Beach & Pool
  • Outdoor pool
  • Swimming pool
Dining
  • Bar
  • Terrace
Parking
  • Accessible parking
  • Parking
  • Private parking
30 other amenities
  • 24-hour security
  • Air conditioning
  • CCTV in common areas
  • Concierge service
  • Daily housekeeping
  • Facilities for disabled guests
  • Fire extinguishers
  • First aid kit available
  • Free WiFi
  • Garden
  • Hand sanitizer in guest room and key areas
  • Higher level toilet
  • Invoice provided
  • Key access
  • Lower bathroom sink
  • Luggage storage
  • Non-smoking rooms
  • Outdoor furniture
  • Pet bowls
  • Pets allowed
  • Picnic area
  • Public transport tickets
  • Safety deposit box
  • Security alarm
  • Smoke alarms
  • Staff adhere to local safety protocols
  • Toilet with grab rails
  • Tour desk
  • Wheelchair accessible
  • WiFi available

Room types

24 room types on record from the provider. No price shown without a live quote.

  • Winslow Mobility
    1× Extra-large double bed (Super-king size) (181-210 cm wide) 20 sqm (215 sq ft) Up to 2 guests

    Featuring free toiletries and bathrobes, this double room includes a private bathroom with a hairdryer. This double room features air conditioning and a TV. The unit has 1 bed.

  • Key Lime
    1× Queen bed (151-180 cm wide) 17 sqm (183 sq ft) Up to 2 guests

    Offering free toiletries and bathrobes, this double room includes a private bathroom with a hairdryer. This double room offers air conditioning and a TV. The unit has 1 bed.

  • Annex Mobility
    1× Extra-large double bed (Super-king size) (181-210 cm wide) 27 sqm (291 sq ft) Up to 2 guests

    The spacious double room offers air conditioning, as well as a private bathroom featuring a hairdryer. The unit offers 1 bed.

  • Blue Parrot
    2× Queen bed (151-180 cm wide) 19 sqm (205 sq ft) Up to 4 guests

    Featuring free toiletries and bathrobes, this quadruple room includes a private bathroom with a hairdryer. This quadruple room features air conditioning and a TV. The unit has 2 beds.

  • Truman King Patio
    1× Sofa bed (Variable Size), 1× Queen bed (151-180 cm wide) 33 sqm (355 sq ft) Up to 3 guests

    Featuring free toiletries and bathrobes, this suite includes a private bathroom with a hairdryer. This suite features air conditioning and a TV. The unit has 2 beds.

  • Bungalow
    1× Extra-large double bed (Super-king size) (181-210 cm wide) 14 sqm (151 sq ft) Up to 2 guests

    Providing free toiletries and bathrobes, this double room includes a private bathroom with a hairdryer. This double room provides air conditioning and a TV. The unit offers 1 bed.

  • Maloney King
    1× Extra-large double bed (Super-king size) (181-210 cm wide) 38 sqm (409 sq ft) Up to 2 guests

    Featuring free toiletries and bathrobes, this suite includes a private bathroom with a bath and a hairdryer. This suite features air conditioning and a TV. The unit has 1 bed.

  • Annex
    1× Extra-large double bed (Super-king size) (181-210 cm wide) 20 sqm (215 sq ft) Up to 2 guests

    Featuring free toiletries and bathrobes, this double room includes a private bathroom with a hairdryer. This double room features air conditioning and a TV. The unit has 1 bed.

  • Treehouse Suite
    1× Extra-large double bed (Super-king size) (181-210 cm wide), 1× Sofa bed (Variable Size) 40 sqm (431 sq ft) Up to 2 guests

    Featuring free toiletries and bathrobes, this suite includes a private bathroom with a bath and a hairdryer. This suite features air conditioning and a TV. The unit has 2 beds.

  • Room, 1 Queen Bed, Patio (Elizabeth Annex)
    22 m2 (237 sq ft) Up to 2 guests

    <p><strong>1 Queen Bed</strong></p><p>240-sq-foot individually decorated room with a furnished balcony/patio </p><br/><p><b>Internet</b> - Free WiFi </p><p><b>Entertainment</b> - 55-inch LED TV with cable channels</p><p><b>Food & Drink</b> - Mini-fridge</p><p><b>Sleep</b> - Premium bedding and bed sheets </p><p><b>Bathroom</b> - Private bathroom, bathrobes, designer toiletries, and a hair dryer</p><p><b>Practical</b> - Safe, phone, and iron/ironing board (on request); free cribs/infant beds available on request</p><p><b>Comfort</b> - Climate-controlled air conditioning, daily housekeeping, and heating</p><p><b>Accessibility</b> - Hardwood flooring in room</p><p><b>Eco-friendly</b> - Eco-friendly toiletries, eco-friendly cleaning supplies, recycling bin, and LED light bulbs</p><p>Non-Smoking</p><p>Room is accessed via exterior corridors </p>

  • Room, 2 Queen Beds, Patio, Poolside
    20 m2 (215 sq ft) Up to 4 guests

    <p><strong>2 Queen Beds</strong></p><p>220-sq-foot individually decorated room with a patio </p><br/><p><b>Internet</b> - Free WiFi </p><p><b>Entertainment</b> - 55-inch LED TV with cable channels</p><p><b>Food & Drink</b> - Mini-fridge</p><p><b>Sleep</b> - Premium bedding and bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower, bathrobes, and designer toiletries</p><p><b>Practical</b> - Safe, phone, and iron/ironing board (on request); free cribs/infant beds available on request</p><p><b>Comfort</b> - Climate-controlled air conditioning, daily housekeeping, and heating</p><p><b>Accessibility</b> - Wheelchair accessible</p><p><b>Eco-friendly</b> - Eco-friendly toiletries, eco-friendly cleaning supplies, recycling bin, and LED light bulbs</p><p>Non-Smoking</p><p>Room is accessed via exterior corridors </p>

  • Room, 1 King Bed (Elizabeth Annex)
    22 m2 (237 sq ft) Up to 2 guests

    <p><strong>1 King Bed</strong></p><p>240 sq feet </p><br/><p><b>Internet</b> - Free WiFi </p><p><b>Entertainment</b> - 55-inch LED TV with cable channels</p><p><b>Food & Drink</b> - Mini-fridge</p><p><b>Sleep</b> - Premium bedding and bed sheets </p><p><b>Bathroom</b> - Private bathroom, bathrobes, designer toiletries, and a hair dryer</p><p><b>Practical</b> - Safe, phone, and iron/ironing board (on request); free cribs/infant beds available on request</p><p><b>Comfort</b> - Climate-controlled air conditioning, daily housekeeping, and heating</p><p><b>Accessibility</b> - Hardwood flooring in room</p><p><b>Eco-friendly</b> - Eco-friendly toiletries, eco-friendly cleaning supplies, recycling bin, and LED light bulbs</p><p>Non-Smoking</p><p>Room is accessed via exterior corridors </p>

  • Room, 1 King Bed, Patio (Elizabeth Annex Garden, Gated Patio)
    23 m2 (248 sq ft) Up to 2 guests

    <p><strong>1 King Bed</strong></p><p>249-sq-foot individually decorated room with a furnished balcony/patio </p><br/><p><b>Internet</b> - Free WiFi </p><p><b>Entertainment</b> - 55-inch LED TV with cable channels</p><p><b>Food & Drink</b> - Mini-fridge</p><p><b>Sleep</b> - Premium bedding and bed sheets </p><p><b>Bathroom</b> - Private bathroom, bathrobes, designer toiletries, and a hair dryer</p><p><b>Practical</b> - Safe, phone, and iron/ironing board (on request); free cribs/infant beds available on request</p><p><b>Comfort</b> - Climate-controlled air conditioning, daily housekeeping, and heating</p><p><b>Accessibility</b> - Hardwood flooring in room</p><p><b>Eco-friendly</b> - Eco-friendly toiletries, eco-friendly cleaning supplies, recycling bin, and LED light bulbs</p><p>Non-Smoking</p><p>Room is accessed via exterior corridors </p>

  • Room, 1 King Bed, Balcony (Elizabeth Annex, Wrap Around Balcony)
    41 m2 (441 sq ft) Up to 2 guests

    <p><strong>1 King Bed</strong></p><p>440-sq-foot individually decorated room with a furnished balcony/patio </p><br/><p><b>Internet</b> - Free WiFi </p><p><b>Entertainment</b> - 55-inch LED TV with cable channels</p><p><b>Food & Drink</b> - Mini-fridge</p><p><b>Sleep</b> - Premium bedding and bed sheets </p><p><b>Bathroom</b> - Private bathroom, bathrobes, designer toiletries, and a hair dryer</p><p><b>Practical</b> - Safe, phone, and iron/ironing board (on request); free cribs/infant beds available on request</p><p><b>Comfort</b> - Climate-controlled air conditioning, daily housekeeping, and heating</p><p><b>Accessibility</b> - Hardwood flooring in room</p><p><b>Eco-friendly</b> - Eco-friendly toiletries, eco-friendly cleaning supplies, recycling bin, and LED light bulbs</p><p>Non-Smoking</p><p>Room is accessed via exterior corridors </p>

  • Room, 1 King Bed, Patio, Poolside
    22 m2 (237 sq ft) Up to 1 guests

    <p><strong>1 King Bed</strong></p><p>240-sq-foot individually decorated room with a patio </p><br/><p><b>Internet</b> - Free WiFi </p><p><b>Entertainment</b> - 55-inch LED TV with cable channels</p><p><b>Food & Drink</b> - Mini-fridge</p><p><b>Sleep</b> - Premium bedding and bed sheets </p><p><b>Bathroom</b> - Private bathroom, bathrobes, designer toiletries, and a hair dryer</p><p><b>Practical</b> - Safe, phone, and iron/ironing board (on request); free cribs/infant beds available on request</p><p><b>Comfort</b> - Climate-controlled air conditioning, daily housekeeping, and heating</p><p><b>Accessibility</b> - Hardwood flooring in room</p><p><b>Eco-friendly</b> - Eco-friendly toiletries, eco-friendly cleaning supplies, recycling bin, and LED light bulbs</p><p>Non-Smoking</p><p>Room is accessed via exterior corridors </p>

  • Winslow
    1× Extra-large double bed (Super-king size) (181-210 cm wide) 14 sqm (151 sq ft) Up to 2 guests

    Offering free toiletries and bathrobes, this double room includes a private bathroom with a hairdryer. This double room offers air conditioning and a TV. The unit offers 1 bed.

  • Winslet
    1× Extra-large double bed (Super-king size) (181-210 cm wide) 17 sqm (183 sq ft) Up to 2 guests

    Featuring free toiletries and bathrobes, this double room includes a private bathroom with a hairdryer. This double room features air conditioning and a TV. The unit has 1 bed.

  • Queen Room With Two Queen Beds And Mobility Accessible Roll-In Shower
    2× Large bed (151-180 cm wide) 20 m2 (215 sq ft) Up to 4 guests

    The quadruple room provides air conditioning, a private entrance, a balcony with garden views as well as a private bathroom featuring a shower. The unit offers 2 beds.

  • Deluxe King Room
    1× Extra-large double bed (Super-king size) (181-210 cm wide) 22 m2 (237 sq ft) Up to 2 guests

    The double room offers air conditioning, a private entrance, a balcony with garden views as well as a private bathroom boasting a shower. The unit has 1 bed.

  • Deluxe Double Room
    1× Extra-large double bed (Super-king size) (181-210 cm wide) 22 m2 (237 sq ft) Up to 1 guests

    The single room offers air conditioning, a private entrance, a balcony with garden views as well as a private bathroom featuring a shower. The unit offers 1 bed.

  • Essential King Room With Balcony
    1× Extra-large double bed (Super-king size) (181-210 cm wide) 20 m2 (215 sq ft) Up to 2 guests

    The double room offers air conditioning, a private entrance, a balcony with garden views as well as a private bathroom featuring a shower. The unit offers 1 bed.

  • Deluxe Queen Room
    1× Large bed (151-180 cm wide) 22 m2 (237 sq ft) Up to 2 guests

    The double room features air conditioning, a private entrance, a balcony with garden views as well as a private bathroom boasting a shower. The unit has 1 bed.

  • Double Room
    1× Extra-large double bed (Super-king size) (181-210 cm wide) 40 m2 (431 sq ft) Up to 2 guests

    The spacious double room features air conditioning, a private entrance, a balcony with garden views as well as a private bathroom boasting a shower. The unit has 1 bed.

  • King Room With Garden View
    1× Extra-large double bed (Super-king size) (181-210 cm wide) 25 m2 (269 sq ft) Up to 2 guests

    The spacious double room offers air conditioning, a private entrance, a balcony with garden views as well as a private bathroom featuring a shower. The unit offers 1 bed.

Nearby

  • Duval Street
    District
    0.4 mi
  • Southernmost Point (buoy)
    Landmark
    0.6 mi
  • Ernest Hemingway Home and Museum
    Museum
    0.4 mi
  • Mallory Square (Sunset Celebration)
    Entertainment
    0.6 mi
  • Fort Zachary Taylor Historic State Park
    Park
    0.9 mi
  • Truman Little White House
    Museum
    0.4 mi
  • Key West Bight / Ferry Terminal
    Transit
    0.5 mi
  • Key West Butterfly & Nature Conservatory
    Nature
    0.6 mi
  • Key West International Airport (EYW)
    Airport
    2.8 mi

About the property

Luxurious Amenities:
Winslow's Bungalows offers 3 swimming pools for ultimate relaxation and enjoyment. Free WiFi access throughout the property ensures you stay connected during your stay.

Convenient Location:
Situated just 1 km from the Southernmost Point and 750 meters from Duval Street, Winslow's Bungalows provides easy access to Key West's popular attractions.

Tranquil Surroundings:
Enjoy the serene landscaped gardens and unwind on the sun terrace with lounge chairs. The inn also features hammocks, swings, and 3 outdoor pools for a peaceful retreat.

To experience the luxury and tranquility of Winslow's Bungalows, book your stay now!

Description from provider (LiteAPI). Not generated or paraphrased.

Stay details

Check-out
11:00 AM
Pets
Not permitted
Children
Welcome
Parking
PAID

Weather in Key West

4-day run 7–10 Nov, 4.2% rain-affected · 1 clear, rain on 11 of 16 forecast days (132h)

View Key West weather forecast & all hotels

Property data from LiteAPI, including photos, facilities, rooms, policies and sentiment analysis. Star rating is provider-supplied. Guest rating shown only when a review count is available — never invented. No price is shown without a live quote. No awards are claimed that are not in the provider record. Weather data from ERA5 reanalysis (Open-Meteo); almanac figures are 8-year historical likelihoods, not forecasts. All model logic is on our methodology page.