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About this property

Spacious Holiday Home: Tradewinds in Key West offers a spacious setting with four bedrooms and two bathrooms. The living room provides ample space for relaxation. Modern Amenities: Guests enjoy a fully equipped kitchen, hot tub, outdoor seating area, and free WiFi. Additional amenities include a work desk, TV, and private entrance. Prime Location: Located in the city center, Tradewinds is less than 0.6 mi from South Beach and Ernest Hemingway Home and Museum. Key West International Airport is 2.5 mi away. Nearby Attractions: Duval Street is a 4-minute walk, Mallory Square a 17-minute walk, and Key West Aquarium a 16-minute walk. Water sports are available in the surroundings.

Distance in property description is calculated using © OpenStreetMap

Property highlights

    • Perfect for a 3-night stay!

    • Located in the real heart of Key West, this property has an excellent location score of 9.0!


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Availability

We have no availability here between Wed, Sep 24, 2025 and Sat, Sep 27, 2025.

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Checking for other dates
Accommodation Type
Number of guests
Price
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Living room
1 sofa bed
Living room
1 sofa bed
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Managed by Vacasa

Company review score: 8.4Based on 110,826 reviews from 27375 properties
27375 managed properties

Company info

Vacation Home Management Vacasa unlocks the possibilities of how we enjoy vacation homes. We take care of managing our homeowners’ vacation houses so they can have peace of mind (and their home when they want to). And our guests book vacations confidently knowing they’re going to find exactly what they’re looking for without any surprises. Each vacation home is always cared for by our professional local teams who implement our high cleanliness and maintenance values, while the hands-off tasks of vacation rental management--marketing, filing taxes, and maintaining a website--are handled by a specialized central support team. Our passion and focus remains true: to empower our homeowners, guests, and employees to invest in vacation.

Property info

Rustle up your favorite people for a memorable trip to Key West with these two homey cottages. Sitting side-by-side in a great location, each house features two bedrooms and one bathroom, a private parking space, dog-friendly accommodations, and a tranquil garden with a private hot tub in the back - what's not to love? Located half a block from all the excitement of Duval Street, you can walk to historical landmarks like the Key West Lighthouse and The Ernest Hemingway Home and Museum, then stroll south to look out to sea from Southernmost Point. A short walk north will reveal more bars and restaurants than you could hope for on an island this size! Fuel your day with a home-cooked breakfast in your fully equipped kitchen, sip coffee in the tropical garden, and get a morning soak in the hot tub for some extra relaxation. Freshen up using the outdoor shower, have a barbecue using the gas grill, and kill some time browsing the free WiFi or surfing the flatscreen cable TV. A dog is welcome. Put life on hold for a moment and settle into paradise with these two cottages on Key West - book today!

Neighborhood info

4 dog(s), weighing 30lbs or less, are welcome in this home. No other animals are allowed without specific Vacasa approval. Parking notes: There is free parking available for 2 vehicles. Air conditioning is only available in certain parts of the home. Damage waiver: The total cost of your reservation for this Property includes a damage waiver fee which covers you for up to 3,000 dollars of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. More information can be found from the "Additional rules" on the checkout page. Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Language Spoken

English

Area info

House rules

Tradewinds takes special requests – add in the next step!
Check-in
From 4:00 PM
Guests are required to show a photo ID and credit card at check-in.
You need to let the property know what time you'll be arriving in advance.
Check-out
Until 10:00 AM
Cancellation/ prepayment
Cancellation and prepayment policies vary according to accommodation type. Check what conditions apply to each option when making your selection.
Children & Beds

Child policies

Children of all ages are welcome.

To see correct prices and occupancy info, add the number and ages of children in your group to your search.

Crib and extra bed policies

Cribs and extra beds aren't available at this property.

Age restriction
The minimum age for check-in is 25
Payments by Booking.com
Booking.com takes your payment on behalf of the property for this reservation.
Smoking
Smoking is not allowed.
Parties
Parties/events are not allowed
Quiet hours
Guests need be quiet between 10:00 PM and 8:00 AM.
Pets
Pets are allowed on request. Charges may apply.

The fine print

Must-know information for guests at this property

Guests will receive a rental agreement, which must be signed and returned directly to the property prior to arrival. If the agreement is not received, the guest should contact the property management company at the number on the booking confirmation.

Please note that only registered guests are allowed at the property.

Guests shall abide by the property's policy. Quiet hours are from 22:00 to 8:00.

Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply.

Please inform Tradewinds of your expected arrival time in advance. You can use the Special Requests box when booking, or contact the property directly using the contact details in your confirmation.

This property does not accommodate bachelor(ette) or similar parties.

Quiet hours are between 22:00:00 and 08:00:00.