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Winslow's Bungalows - Key West Historic Inns

4.4(1,267)
Hotel

About

Winslow's Bungalows offers a tranquil retreat in the heart of Key West's Old Town, just steps from Duval Street. The property features three pools nestled among tropical gardens and historic bungalows that blend island charm with modern comfort, creating a relaxed setting for small corporate gatherings.

The venue includes a lively poolside bar with live music and a complimentary continental breakfast, perfect for informal networking or team downtime. With personalized concierge services, seamless Wi-Fi, and comfortable rooms—including a private annex ideal for group stays—Winslow's balances hospitality and convenience for business travelers seeking a distinctive Key West experience.

Best for

  • Relaxed multi-night corporate stays
  • Poolside client cocktails & casual mingling
  • Quiet team retreats near Duval Street

Request a Package

Tell the venue what you're planning and they'll respond with a custom proposal within 1–2 business days.

Group Meeting

Custom request

Professional meeting space for your team — whether it's a meeting, training, workshop, or multi-day offsite. Half-day, full-day, or multi-day — with the option to request AV, catering, and your preferred room layout.

What's typically included

  • Meeting room & layout
  • Food & beverage
  • AV & technology

Room Block

Custom request

Reserve a block of rooms for your group — ideal for multi-day conferences, offsites, or any event where attendees are traveling from out of town.

What's typically included

  • Reserved guest rooms for your group
  • Flexible check-in & check-out dates
  • Negotiated group rates

Meeting + Room Block

Custom request

Bundle your meeting space and guest rooms in one request — perfect for multi-day offsites and conferences where the team meets by day and stays overnight.

What's typically included

  • Meeting room & layout
  • Food & beverage
  • AV & technology
  • Reserved guest rooms for your group

Venue Details

Standout features

Multi-building resort on historic Key West site
Historic Grounds
Multi-building resort on historic Key West site
Set on grounds that once housed Key West’s first motel and some of its oldest homes, the property carries a rich past including ties to a vaudeville venue and a fruit grove, offering guests a unique sense of place.
Three pools nestled amid tropical foliage
Outdoor Amenities
Three pools nestled amid tropical foliage
Guests can relax in a lush, private setting with three separate pools surrounded by tropical plants, providing a tranquil oasis just steps from the vibrant Old Town area.
Poolside Bungalow Bar with live music
Food & Beverage
Poolside Bungalow Bar with live music
The Bungalow Bar offers specialty cocktails and poolside bites, complemented by live performances from local musicians on select days, creating a lively yet relaxed atmosphere for business gatherings.

At a glance

Rated 4.4 on Google · 1,267 reviews