Tradewinds Villa Key West Exterior photoTradewinds Villa Key West Exterior photoTradewinds Villa Key West Exterior photo
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From1 031US$ /night
Check-in
20May2026Select date
Check-out
21May2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

Property overview

529 531 Olivia St, Key West, Florida, United States, 33040
-
Close to South Beach
Very good
7.5
/10

Rooms and Amenities

This holiday home features 4 separate bedrooms and 2 bathrooms, equipped with a hairdryer and free toiletries. The unit includes 6 beds. Guests have access to a well-fitted kitchen with a stovetop, refrigerator, oven, and kitchenware. Additional amenities include tea and coffee facilities, a patio, and garden furniture. The holiday home also includes a barbecue and a private entrance. For entertainment, a TV with cable channels is provided.

Onsite Dining

The property includes onsite restaurants.

Leisure Highlights

A hot tub is available for guests.

Location Perks

Tradewinds is 5 km from Key West International Airport. Nearby landmarks include Ripley's Believe It or Not (1 km), Southernmost Point (1 km), Duval Street (0.5 km), USCGC Ingham Maritime Museum (1 km), Key West Cemetery (0.5 km), The Ernest Hemingway Home and Museum (0.5 km), Truman Little White House (1 km), San Carlos Institute (0.5 km), and Southernmost Point of the Continental US (1 km).

Living areas

This spacious holiday home comes with 2 living rooms.

“These bungalows suit groups seeking a home-like base, conveniently near Duval Street, although they are spread across separate units. Comfortable beds and clean linens are a plus. However, be mindful of potential maintenance issues and noise from the older air conditioning units.”
Hotel logo
David MillerEditor, UsFlorida
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Calendar of room availability and rates

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Facilities

Amenities are designed to ensure comfort and memorable stays
Facilities: Very good
7.4/10Review score

General

  • Wi-Fi

Guest Parking

  • Cookware/ Kitchen utensils

Room features

  • Patio
  • Tea and coffee facilities

Bathroom

  • Free toiletries

Self-catering

  • Cookware/ Kitchen utensils
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Tradewinds Villa Location

529 531 Olivia St, Key West, Florida, United States, 33040
Map view
529 531 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
Bobby's Monkey Bar
800 ft
900 Simonton St
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
Lola's Bistro
600 ft
728 Simonton St
Viva Saloon
600 ft
903 Duval St
Croissants de France and Le Bistro
700 ft
816 Duval St
Blackfin Bistro
800 ft
918 Duval St
Point 5 Tapas & Wine Bar
600 ft
915 Duval St
Key West Cuban Coffee
700 ft
517 Truman Ave Key West
Explore Key West
Explore Key West
Top Attractions
Activities
Dining
Entertainment
Key West Butterfly and Nature Conservatory
9 minutes walking
A lush habitat with hundreds of butterflies, tropical birds, and beautiful gardens. Ideal for nature lovers and photography enthusiasts.
The Ernest Hemingway Home and Museum
4 minutes walking
Historical home of the famous author, featuring guided tours showcasing his life, legacy, and the famous six-toed cats.
Southernmost Point
11 minutes walking
An iconic landmark marking the southernmost point in the continental US. Great for memorable photos and experiencing Key West's charm.
Mallory Square
17 minutes walking
Famous for its sunset celebration, live entertainment, shops, and local food vendors. A vibrant gathering place with stunning views.
Snorkeling at Western Dry Rocks
1 minute drive
Exciting snorkeling adventures just a short trip away. Gear rentals available, with options for guided tours to vibrant coral reefs.
Yoga Classes at South Beach
10 minutes walking
Relaxing yoga sessions held on the beach, offering views of the ocean. Perfect for unwinding amid the tranquility of nature.
Blue Heaven
7 minutes walking
Famed for its casual, colorful atmosphere and delicious Caribbean-inspired dishes. Signature Key Lime Pie is a must-try.
Nine One Five
3 minutes walking
Charming bistro offering a diverse menu with fresh local ingredients. Great wine selection and cozy indoor and outdoor seating.
The Studios of Key West
10 minutes walking
Art hub hosting various performances, exhibitions, and community events. A cultural hotspot showcasing local talents and artistry.
Bobby's Monkey Bar
3 minutes walking
Fun, relaxed bar featuring live music events nightly. A great place for drinks, dancing, and mingling with locals and visitors.
Local transportation
City Centre
Key West21 min  ·  1.1 mi
Airports
Key West International (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 extra beds provided in a room.  There are no cots provided in a room. 
Pets
Pets are allowed on request.

Guest ratings and reviews

Guest feedback from past stays
Review score
Based on 7 verified reviews
6.0/10
Guest rating
43%
Recommend
Cleanliness
7.5/10
Comfort
7.4/10
Facilities
7.4/10
Location
9.4/10
Staff
8.9/10
Value for money
8.8/10
Pros
Comfortable beds
Clean linens
Great location
Cons
Non-working hot tubs
Guest reviews
based on 11 reviews
7.5/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
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FAQs
About Tradewinds
What are the check-in and check-out times at Tradewinds?
Check-in is from 16:00 and check-out is by 10:00.
How far is Tradewinds from Key West International Airport?
The hotel is 4 km from Key West International Airport.
Which attractions are within walking distance from Tradewinds?
Nearby attractions include Duval Street (400 m), the Ernest Hemingway Home and Museum (300 m), and the Southernmost Point (1 km).
What amenities does Tradewinds offer for guests?
Amenities include Wi-Fi, beach access, a hot tub, and cookware/kitchen utensils.
What dining options are available near Tradewinds?
Dining options within 0.5 km include Blue Heaven, Nine One Five, and Lola's Bistro.
What room features are provided at Tradewinds?
Rooms include climate control, a multi-channel TV, and a fully equipped kitchen.
Is there a hot tub available at Tradewinds?
Yes, the hotel features an on-site hot tub for guests.
What types of room layouts can guests expect at Tradewinds?
The hotel offers a spacious 4-bedroom holiday home with 2 living rooms and 2 bathrooms.
Check-in
20May2026Select date
Check-out
21May2026Select date
Rooms and Guests2 Guests, 1 Room