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 a few moments from this villa. The Key West villa is situated 0.9 miles from Papa's Pilar Rum Distillery, while Truman Avenue & Simonton Street bus station is 500 feet away. Windward Isle Villa is in the vicinity of Key West First Legal Rum Distillery.

Food & Drinks

Offering Caribbean dishes, Better Than Sex is 5 minutes' walk away. This property is also a 10-minute drive from Key West International airport.

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

Windward Isle 1/29
Windward Isle
Windward Isle
Windward Isle
Windward Isle

Location of Windward Isle Villa Key West

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

Attractions
Great restaurants
Transportation

Places nearby

    Guest reviews of Windward Isle Villa Key West

    Write a review

    When did you travel?

    Your rating point

    Very bad
    Excellent

    Your details

    Where are you from?
    Thank you! Thank you for taking the time to share your experience. Your review will be published shortly.

    Review has not been sent.

    Please try again.

    Currency
    • USD U.S. dollar
    • EUR Euro
    • GBP Pound sterling
    • AUD Australian dollar
    • CAD Canadian dollar
    • BRL Brazilian real
    • CNY Chinese yuan
    • CZK Czech koruna
    • DKK Danish krone
    • HKD Hong Kong dollar
    • ILS Gaza Strip, Israel New Shekel
    • JPY Japanese yen
    • MYR Malaysian Ringgit
    • NZD New Zealand dollar
    • NOK Norwegian krone
    • PLN Polish zloty
    • RON Romanian new leu
    • RUB Russian ruble
    • SAR Saudi riyal
    • SGD Singapore dollar
    • ZAR South African rand
    • KRW South Korean won
    • SEK Swedish krona
    • CHF Swiss franc
    • TRY Turkish lira
    • UAH Ukrainian hryvnia
    • THB Thai Baht
    • ARS Argentina, Peso
    Select language
    • us
      us English
    • en
      en English
    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
    We're here to help
    Hi there! Have a question? Message us—our team is happy to assist.
    Your details:
    Subject:
    Message:
    Thank you for your message. We’ll get back to you shortly!
    Your message was not delivered
    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.