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From312US$ /night
Check-in
14Feb2026Select date
Check-out
15Feb2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

Property overview

531 Olivia St, Key West, Florida, United States, 33040
-
Close to Duval Street
Very good
7.5
/10

Holiday Home Features

Windward Isle is a holiday home located in Duval. It features two bedrooms and one bathroom with a hairdryer and free toiletries. Standout feature is the hot tub. The unit includes two beds. A well-fitted kitchen contains a stovetop, refrigerator, oven, and kitchenware. Other amenities include air conditioning, a TV with cable channels, a private entrance, a patio, and tea and coffee facilities.

Dining at Windward Isle

Windward Isle in Duval offers unique, island-inspired small plates with bold Caribbean spices and fresh local seafood.

Leisure and Extras

Guests can use the barbecue facilities.

Location and Access

Windward Isle is 200 metres from the Ernest Hemingway Home and Museum, 500 metres from Duval Street, and 700 metres from Southernmost Point. Key West International Airport is 4 km away. Nearby landmarks include Southernmost Point (1 km), Key West Shipwreck Treasure Museum (1 km), Mallory Square (1 km), Key West Cemetery (0.5 km), Duval Street (0.5 km), Southernmost Point of the Continental US (1 km), Truman Little White House (1 km), and Key West Butterfly and Nature Conservatory (0.5 km) and Key West Aquarium (1 km).

Essential Services

WiFi is available in all areas. Guests must be 25 years of age or older. Quiet hours are from 22:00. A rental agreement must be returned directly to the property.

“The location stands out, a short walk to Duval Street with the added convenience of on-site parking-a true advantage in Key West. Accommodations provide the essentials for a comfortable stay, though some aspects could use refreshing. In my view, its prime location makes it a worthwhile consideration.”
Hotel logo
David MillerEditor, UsFlorida
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Choose your preferred room

The property features double rooms, family rooms, and suites, often including breakfast, free cancellation, and special offers
Two Bedroom Holiday Home
2 persons
810 sq. feet 
1 King-size bed
Coffee machine

Calendar of room availability and rates

See current availability and pricing for your dates

Facilities

Amenities are designed to ensure comfort and memorable stays

General

  • No smoking on site
  • Wi-Fi
  • Pets allowed
  • Smoke detectors
  • Fire extinguishers

Guest Parking

  • Cookware/ Kitchen utensils

Spa & Leisure

  • BBQ facilities
  • Jacuzzi

Room features

  • Patio
  • Tea and coffee facilities

Bathroom

  • Free toiletries

Self-catering

  • Cookware/ Kitchen utensils
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Windward Isle Villa Location

531 Olivia St, Key West, Florida, United States, 33040
Map view
531 Olivia St, Key West, Florida, United States, 33040
Nearby
Museum
The Ernest Hemingway Home and Museum
1100 ft
Duval Street
Duval Street
1300 ft
Event hall
San Carlos Institute Casa Cuba
2000 ft
Garden
Nancy Forrester's Secret Garden
1900 ft
Church
Saint Mary Star of the Sea
1200 ft
938 Whitehead St
Key West Lighthouse and Keeper's Quarters Museum
1400 ft
Museum
Tennessee Williams Key West Exhibit
500 ft
1100 Simonton St
Historic E. H. Gato Building
600 ft
Gallery
Wild Side Gallery
700 ft
Gallery
Art On Duval Key West
800 ft
Gallery
Wyland Galleries
1000 ft
Gallery
Zazoo Fine Art Gallery
1000 ft
Gallery
Guild Hall Gallery
1100 ft
Restaurants
Better Than Sex
500 ft
926 Simonton Street
Blue Heaven
1700 ft
729 Thomas St
Nine One Five
700 ft
915 Duval St
Sugar Apple Health Food Store
400 ft
917 Simonton St
Duffy's Steak & Lobster House
500 ft
1007 Simonton St
Viva Saloon
600 ft
903 Duval St
Point 5 Tapas & Wine Bar
600 ft
915 Duval St
Explore Key West
Local Highlights
Top Attractions
Activities
Dining
Entertainment
The Ernest Hemingway Home and Museum
4 minutes' walk
A historic site where the author lived, featuring beautiful gardens and guided tours showcasing Hemingway's life and works.
Southernmost Point
11 minutes' walk
Iconic landmark marking the southernmost tip of the continental US, popular for photo ops and scenic views of the ocean.
Key West Butterfly and Nature Conservatory
9 minutes' walk
An enchanting sanctuary with hundreds of butterflies in a tropical habitat, ideal for nature lovers and families.
Mallory Square
17 minutes' walk
A vibrant waterfront plaza known for sunset celebrations featuring street performers, local artisans, and food vendors.
Snorkeling Adventures
5 minutes' drive
Thrilling snorkeling excursions to vibrant reefs and wrecks. Rentals and guided tours available from local operators.
Yoga on the Beach
6 minutes' drive
Relaxing beach yoga sessions offered at sunrise, promoting wellness and mindfulness with scenic ocean views.
Self-Guided Bike Tours
10 minutes' walk
Explore the charming streets of Key West on a bike. Rentals available nearby for easy access to local attractions.
Better Than Sex
2 minutes' walk
An intimate dessert bar offering indulgent sweet treats and craft cocktails in a cozy, romantic setting.
Blue Heaven
7 minutes' walk
A lively eatery famous for its breakfast and outdoor seating, featuring fresh, local ingredients and Key West flair.
Duffy's Steak & Lobster House
2 minutes' walk
Casual dining experience specializing in steaks and fresh seafood. Great for families with several gluten-free options.
Green Parrot Bar
10 minutes' walk
A lively local bar with live music and a laid-back vibe, perfect for enjoying drinks with a mix of locals and visitors.
Key West Theater
5 minutes' drive
Host to comedy shows and live performances, offering a unique cultural experience for all ages, with regular events.
Local transportation
City Centre
Key West21 min  ·  1.1 mi
Airports
Key West International Airport (EYW)9 min  ·  3.7 mi
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Property information and rules
Check-in
from 16:00-23:59
Check-out
until 10 am
Guest Parking
Paid Public parking is possible on site.
Internet
Wireless internet is available in the entire villa for free.
Children & extra beds
There are no cots provided in a room. 
Pets
Pets are allowed on request.
FAQs
About Windward Isle
What popular attractions are close to Windward Isle?
Nearby attractions include Ernest Hemingway Home and Museum (0.5 km), Duval Street (0.5 km), and Southernmost Point (0.5 km).
What is the check-in and check-out policy at Windward Isle?
Check-in is at 16:00 and check-out is by 10:00.
What amenities are available in the rooms at Windward Isle?
Rooms feature air conditioning, a TV with satellite channels, kitchenware, and hot tub access.
What dining options are available at Windward Isle?
The property offers a kitchen for self-catering, and popular nearby restaurants include Better Than Sex (0.5 km) and Blue Heaven (0.5 km).
What are the main features and highlights of Windward Isle?
Highlights include Wi-Fi availability, a hot tub, and kitchen facilities with cookware.
How far is Windward Isle from Key West International Airport?
Windward Isle is located 4 km from Key West International Airport.
What are the quiet hours at Windward Isle?
Quiet hours are observed from 22:00.
Are there any amenities for cooking at Windward Isle?
The holiday home includes a fully equipped kitchen with an oven and microwave.
What type of property is Windward Isle?
Windward Isle is a holiday home located in the Duval district of Key West.
Check-in
14Feb2026Select date
Check-out
15Feb2026Select date
Rooms and Guests2 Guests, 1 Room
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