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Westwinds Inn

4.2(388)
Hotel

About

Westwinds Inn offers a relaxed Victorian-style retreat with bright rooms, two pools, and lush tropical gardens that create a quiet oasis in busy Key West. The informal vibe and spacious grounds make it easy to host small business gatherings or unwind after meetings.

Rooms are comfortable and well-equipped, with options ranging from cozy queen to larger king accommodations. The inn’s convenient location puts you within walking distance of Key West’s business and cultural hubs, while included breakfast and friendly service keep your stay smooth and hassle-free.

Best for

  • Quiet multi-night group stays
  • Casual team retreats with poolside breaks
  • Walking-distance access to Key West business hubs

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

Outdoor Amenities
Two pools with lush tropical oasis setting
The venue features two pools surrounded by tropical shrubbery that create a quiet, private oasis feel, distinct from typical resort atmospheres. This setting provides a relaxed environment suitable for informal gatherings or breaks during business
Atmosphere
Informal Victorian-style charm
The hotel’s informal Victorian-style architecture and bright quarters offer a classic Key West character that blends historic charm with a comfortable, homey vibe, appealing to guests seeking a distinctive yet unpretentious setting.

At a glance

Rated 4.2 on Google · 388 reviews