Resort pool with blue water, lounge chairs, patterned umbrellas, white cottages, and palm trees
Resort swimming pool with blue water, white loungers, palm trees, wooden fence, and poolside seating
Residential pool area with white deck chairs, thatched umbrellas, white railings, and palm trees
Poolside dining with fresh salads, sandwiches, fruit bowls, and colorful tropical drinks
Resort pool deck with white lounge chairs, thatched umbrella, palm trees, and cottage-style buildings
Resort poolside lounge with white umbrellas, loungers, and coastal architectural style building
Resort pool area with white cabanas, thatched umbrellas, tropical landscaping and deck seating

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Winslow's Bungalows - Key West Historic Inns

4.9 (8)

Key West, Florida

4 star property

Enchantment awaits in the vibrant heart of Old Town, just steps from Duval Street and the best of Key West. Discover this inviting resort-like retreat with three pools, nestled on historic grounds that once housed Key West’s first motel and some of its oldest homes.

Experiences

Day Pass

Soak up Old Town charm across three heated pools with live music setting the Key West mood.

Day Pass

From

$25

Property details

Location

725 Truman Ave, Key West, FL 33040

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Amenities

Outdoor Pool

Free Parking

Towels

Luggage Storage

Pool

Food Service

Drink Service

Pool

Daily 10:00am - 7:00pm

Bungalow Bar

Daily 11:00am - 7:00pm

Good to know

What happens when I get there?

Check in at the front desk with your confirmation and a photo ID — the same way any hotel guest would. The hotel knows you’re coming.

What’s included in the price listed?

Your booking covers everything listed on the experience page — no hidden fees. Some properties offer food, drinks, or extras you can add on once you're there, but nothing is required unless noted.

Can I cancel if my plans change?

Yes, most bookings can be canceled for a full refund. Cancellation windows and refund eligibility details are found on the experience page. Read our full cancellation policy.

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