Windward Isle Villa

531 Olivia St, Downtown Key West, Key West, United States of America - Show on map

Offering a location 8 minutes' stroll from San Carlos Institute, Windward Isle Villa Key West gives access to various tourist spots in the area.

Location

Guests can reach the center of Key West within 20 minutes' walk, and The Ernest Hemingway Home and Museum is just near this villa. USCGC Ingham Maritime Museum is located 0.8 miles from the Key West villa, and Truman Avenue & Simonton Street bus station is 500 feet away. Windward Isle Villa is situated a stone's throw from the historic Key West Lighthouse.

Food & Drinks

Better Than Sex as one of dining choices lies 5 minutes' walk away.

Important information

Check-in:
from 16:00 until 23:59
Check-out:
until 10:00
  • Children and extra beds
  • There are no cribs provided in a room.

Enter dates to see availability

From USD 312 per night
Check-in 30 Sept 2026
Check-out 1 Oct 2026
Guests 2 guests

Adults:

2

Children:

0
All rates verified
How we verified prices Our team regularly checks prices to make sure you see the lowest available rates. We compare them with hotel prices and other providers. If discounts or promotions appear, prices on our site are updated accordingly.

Rooms

Current offers Editor's Pick
Up to 10% off

Mobile Rates

Book in a few taps and save a little more for the places, tastes, and moments waiting throughout your stay.
Book via mobile Includes special rates from Booking.com
Up to 15% off

Longer Stays

A few extra nights let you slow down, find favorite spots, and experience the place beyond the highlights.
3 nights or more Discount will be applied to your results
Up to 20% off

Early Bird

Reserve while the right dates are open, then enjoy planning everything that comes after stress-free, step by step.
Book 30+ days ahead Some dates already include an extra discount

Photos of Windward Isle Villa Key West

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Windward Isle Holiday home Key West
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Windward Isle Holiday home Key West
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Windward Isle Holiday home *
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Location of Windward Isle Villa Key West

531 Olivia St, Downtown Key West, Key West, United States of America

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Great restaurants
Transportation

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    Enter dates to see availability
    From USD 312 per night
    Check-in 30 Sept 2026
    Check-out 1 Oct 2026
    Guests 2 guests

    Adults:

    2

    Children:

    0
    All rates verified
    How we verified prices Our team regularly checks prices to make sure you see the lowest available rates. We compare them with hotel prices and other providers. If discounts or promotions appear, prices on our site are updated accordingly.
    Check-in & out
    30 Sept 2026
    —
    1 Oct 2026
    Guests
    2 guests
    Check availability
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    Important information
    Windward Isle
    Check-in:
    from 16:00 until 23:59
    Check-out:
    until 10:00
    • Children and extra beds
    • There are no cribs provided in a room.