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Winslow's Bungalows - Key West Historic Inns

Key West · us

Winslow's Bungalows - Key West Historic Inns

8.6
Excellent1,920 reviews
  1. Hotel Collection
  2. /Hotels in Key West
  3. /Winslow's Bungalows - Key West Historic Inns
ParkingSelf parking (surcharge)Secured parkingSwimming poolExercise/lap poolConcierge service

Check-in / Check-out

From 04:00 PM · Until 11:00 AM

Classification

4-Star Hotel

Amenities

Parking, Non-smoking rooms, Air conditioning, Swimming pool, Terrace, Pets allowed

Location

Key West, us

Walkability

94
Walk
98
Bike

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!

Neighbourhood

What’s Nearby

Key West Transit - Truman & Simonton

0.1 miles

A convenient local bus stop for exploring Key West via public transit.

Santiago's Bodega

0.5 miles

A beloved tapas restaurant offering a variety of globally-inspired small plates and signature sangria in a cozy setting.

4.6

Better Than Sex - A Dessert Restaurant

0.2 miles

An award-winning, adults-only dessert restaurant known for decadent, house-made desserts and signature chocolate-rimmed wines in an intimate atmosphere.

4.7

Cuban Coffee Queen

0.4 miles

A popular spot for authentic Cuban-style coffee, refreshing iced coffee creations, smoothies, and freshly made breakfast and lunch.

4.6

Blue Heaven

0.6 miles

A famous open-air restaurant known for its Caribbean and American cuisine, live music, and resident chickens and cats.

4.6

Ernest Hemingway Home and Museum

0.2 miles

The former residence of the Nobel Prize-winning author, now a museum showcasing his life and home, famous for its polydactyl cats.

4.7

Key West Lighthouse and Keeper's Quarters Museum

0.2 miles

Climb 88 steps to the top of this historic lighthouse for panoramic views of Key West and explore the adjacent keeper's house museum.

4.7

Southernmost Point Buoy (Temporary)

0.6 miles

A full-scale replica of the iconic Southernmost Point Buoy, located at Duval Street Pocket Park while the original site undergoes renovations until late 2026.

4.5

Harry S. Truman Little White House

1.0 miles

Florida's only presidential museum, offering guided tours through the historic home where President Truman spent 175 days of his presidency.

4.6

Duval Street

0.1 miles

The vibrant heart of Key West, offering a lively mix of shops, art galleries, restaurants, and bars.

4.5

Mallory Square

0.9 miles

Famous for its nightly Sunset Celebration featuring street performers, artisans, and food vendors, with waterfront shops nearby.

4.6

The Green Parrot Bar

0.5 miles

A historic and iconic Key West dive bar known for its live music, laid-back atmosphere, and local charm.

4.7

Loading rooms and rates...

FAQs

Common Questions

Check-in is from 04:00 PM and check-out is by 11:00 AM. Early check-in and late check-out may be available upon request.

Yes, the hotel offers swimming pool for guests.

Yes, parking is available. Contact the hotel directly for current rates.

Yes, complimentary Wi-Fi is available throughout the hotel.

The nearest station is Key West Transit - Truman & Simonton, 0.1 miles from the hotel.

No promo codes needed. As a Dyme member, you automatically receive wholesale pricing up to 35% below public rates.

Sustainability

Travel That Gives Back

Every booking through Dyme directly funds clean energy infrastructure.

5,910 tons
CO₂ Avoided Annually
~271,000
Equivalent Mature Trees Per Year
15 Central Parks
Of Mature Trees Equivalent

Sustainability at Winslow's Bungalows - Key West Historic Inns

LowHigh
Medium Carbon

Winslow's Bungalows - Key West Historic Inns, part of the Key West Historic Inns Collection, has brand-wide commitments to eco-friendliness, including the use of renewable energy credits and efforts to minimize plastic. At the property level, it implements a comprehensive food waste policy, uses LED lighting, and features water-saving showers and toilets. [Note: Practices reported but not independently verified.]

Winslow's Bungalows implements a comprehensive food waste policy
The property utilizes LED bulbs
Winslow's Bungalows features showers designed to save water
The property is equipped with toilets designed to save water

Emissions estimates are calculated using the local electricity grid carbon intensity for the hotel’s region, sourced from the U.S. EPA eGRID database (for U.S. properties) and Electricity Maps (for international properties). All sustainability information is derived from publicly available data sources, including hotel websites and certification bodies, and may not reflect the hotel’s actual energy usage or specific sustainability measures. Figures are approximate and provided for indicative purposes only.

Location

How to Find Us

725 Truman Avenue

Key West · us

Policies

Good to Know

Check-in & Check-out

Check-in from 04:00 PM. Check-out by 11:00 AM. Early check-in and late checkout may be available upon request.

Cancellation

Cancellation terms vary by rate. Flexible rates allow free cancellation up to 24–48 hours before arrival. Non-refundable rates cannot be canceled or modified.

Payment

All prices are all-inclusive with taxes and fees. A valid credit card is required at check-in. No additional resort or service fees will apply.

Important Information

Please note that the property is located in a building with no elevator.Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply. Please inform of your expected arrival time in advance. You can use the Special Requests box when booking, or contact the property directly using the contact details in your confirmation.

Why Dyme

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WINSLOW'S BUNGALOWS - KEY WEST HISTORIC INNS

Guest Reviews

What Guests Say

8.6

Excellent

1,920 reviews

Highlights

  • +Great location
  • +Friendly staff
  • +Nice gardens and ambiance

Could Improve

  • –Room cleanliness issues
  • –Room size smaller than expected
  • –High price relative to value
Cleanliness8.1

Issues with room cleanliness, particularly with light fixtures and plumbing, as well as reports of pests.

Service9.5

Staff are friendly and helpful, providing a positive experience.

Location9.6

Excellent location, close to attractions but in a quieter area.

Room Quality7.5

Rooms described as small and with some maintenance issues.

Amenities8.6

Amenities such as breakfast and bar facilities are good, but issues with maintenance were noted.

Value for Money8.0

Considered a bit pricey for the quality received, especially concerning room size and cleanliness.

Food and Beverage8.6

Breakfast included is appreciated, but hours of operation could be better.

Overall Experience9.0

Overall a positive experience with notable strengths and some areas needing improvement.

Louise

Couple · May 2026

10

Great location from main attraction streets

Liked:Clean and well labeled to access pools, bar and front desk

via Nuitee

Roberta

Couple · May 2026

10

Beautiful hotel

Liked:Beautiful room, confortable bed, great location

via Nuitee

Christine

Couple · May 2026

7
Liked:Quaintness
Disliked:Small

via Nuitee

Elke

Family With Children · May 2026

8
Liked:Appartment 56 everything was perfect. Breakfast was good, we had it every morning opposite the breakfast room, on our own veranda serounded by palms and greenery.
Disliked:All good!

via Nuitee