Windward Isle Villa

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

Windward Isle Villa Key West offers easy access to such tourist spots as the historical Key West Lighthouse, located merely 5 minutes' walk away.

Location

Located in 0.2 miles from The Ernest Hemingway Home and Museum, this Key West holiday home awaits you in the Duval district of Key West. The Harry S. Truman Little White House is in proximity to the villa, and Key West Butterfly and Nature Conservatory is approximately a 10-minute drive away. Located 0.8 miles from Ripley's Believe It or Not Museum, Windward Isle Villa is also only 0.9 miles from entertainment venues like Papa's Pilar Rum Distillery.

Food & Drinks

Experience ultimate comfort in this property's kitchen, supplied with coffee and tea making facilities, a fridge, and a kitchenware. Caribbean dishes are served at Better Than Sex situated steps away from Windward Isle Villa. Thanks to Truman Avenue & Simonton Street bus stop, located about 500 feet away, guests can easily explore Key West.

Why choose Windward Isle Villa Key West

Select room

Main amenities

  • Wi-Fi

General
  • Wi-Fi
1/6

Internet

  • Wi-Fi

Parking options

  • Parking

In the kitchen

  • Cookware/ Kitchen utensils

In the rooms

  • Patio
  • Tea and coffee facilities

In the bathroom

  • Free toiletries

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 5 Jun 2026
Check-out 6 Jun 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.
Special offers & deals Limited offer

Mobile-Only Deal

An exclusive discount – get up to 10% off when you book from your phone.

Summer Deal

Up to 15% off
Make the most of summer with up to 15% off and free breakfast – limited-time offer.

Early Booking Discount

Up to 20% off
Save up to 20% when you book at least 30 days before your trip.

Members Only Rate

Up to 15% off
Join now to unlock up to 15% off on your dates – visible to members only.

Family Package Deal

Up to 20% off
Save up to 20% with special family packages that include your stay, meals, and fun for the kids..

Rooms

Photos of Windward Isle Villa Key West

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Windward Isle

Location of Windward Isle Villa Key West

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

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    Select language
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    Enter dates to see availability
    From USD 312 per night
    Check-in 5 Jun 2026
    Check-out 6 Jun 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
    5 Jun 2026
    —
    6 Jun 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.