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~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!

Photo gallery for ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!

Bright, open, and sunny living area.
Shaded outdoor patio w/ plenty of seating.
Enjoy the private front patio and gas grill.
View of living and dining area.
Enjoy the bright cheerful decor.

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area
2 bedrooms2+ bathroomsSleeps 6141.9 sq m

Popular amenities

  • Swimming pool
  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Outdoor barbecue

Explore the area

View map
Key West, FL
  • Place, Harry S. Truman Little White House
    ‪2 min walk‬
  • Place, Duval Street
    ‪4 min walk‬
  • Place, Mallory Square
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪14 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

2 Single Beds

Other Space 1

1 Double Sofa Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Bathroom 3

Toilet

Spaces

Deck or patio
Kitchen
Balcony
Garden

About this property

~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!

MONTHLY RENTAL (28 nights within the same month). Stay a month and live like a local!

THE PROPERTY: As you open the white picket gate to this three-story townhouse, your tropical courtyard and outdoor dining area will delight you. Through the oversized French doors with transoms, you will find your living room, dining area, updated kitchen and half bath. This home has more windows than most as well as vaulted ceilings, adding sunshine and volume to the open concept living area. A comfortably furnished family room with TV lead to the dining table with seating for 4-6. The galley-style kitchen has everything you need to prepare a meal or snack.

The second-floor primary bedroom is beautifully furnished and includes bedside lamps, nightstands, TV, closet and dresser storage. The ensuite bath is tiled and has a shower/tub combination. Open the French doors enjoy morning coffee on your private balcony.
The guest bedroom is sunny and bright on the third floor. Twin beds can be combined to form a king upon request. A TV, bedside table, lamp, closet, and dresser storage are also provided.

History aficionados will appreciate The Truman Annex. Formerly an Army installation and later a Naval station, it was also President Harry S. Truman’s winter home. The park-like setting with an abundance of palm trees and white picket fences is a source of pride and splendor in Key West.

Whether you spend a day at the pool or a night on Duval Street, you won’t be disappointed with this townhouse or its unbeatable location. Come stay a while at Fair Winds at the Foundry.

BED CONFIGURATION: The primary king ensuite is on the second floor. The third floor ensuite guest bedroom has two twin beds that can be joined to create a king bed. A sleeper sofa in the living room can accommodate 2.

OUTDOOR AMENITIES: Share a fabulous pool with guests of the Foundry. Enjoy cocktails on the patio or grill up the daily catch on the gas grill.

PARKING: There is a dedicated covered parking space for one vehicle that may not exceed 18’ long x 80” wide. This is strictly enforced so be sure your vehicle is appropriately sized.

LOCATION: Tucked away in the exclusive, historic Truman Annex, this home in Old Town is close to everything. Within walking distance are galleries, shops, restaurants on and off Duval Street, sunsets at Mallory Square and the Truman Waterfront Park. Bike to Fort Zachary Taylor State Park’s beach, stroll to the Key West Harbor or walk to the Tropic Cinema and catch a film.

PETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that are pet-friendly).

SMOKING: This is a non-smoking home and property.

***Guests must be 25 years of age or older unless accompanied by an adult.

***Managed by Historic Key West Vacation Rentals***

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher

About the area

Key West

Located in Key West, this condo is in the city centre. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. USCGC Ingham Maritime Museum and Mel Fisher Maritime Museum are also worth visiting. Jet skiing, scuba diving and snorkelling offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
Map
Key West, FL

What's nearby

  • Key West Naval Station - 1 min walk - 0.2 km
  • Harry S. Truman Little White House - 2 min walk - 0.2 km
  • Duval Street - 4 min walk - 0.4 km
  • Mallory Square - 8 min walk - 0.7 km
  • Ernest Hemingway Home and Museum - 11 min walk - 0.9 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 13 min drive

Restaurants

  • ‪Green Parrot Bar - ‬6 min walk
  • ‪Key Lime Pie Factory - ‬6 min walk
  • ‪The Bull & Whistle Bar - ‬6 min walk
  • ‪Caroline's Cafe - ‬6 min walk
  • ‪La Concha Bar - ‬5 min walk

Frequently asked questions

Does ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool! have a pool?

Yes, this property has a pool.

How much does it cost to stay at ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!?

As of 23 Apr 2026, prices found for a 1-night stay for 2 adults at ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool! on 25 Apr 2026 start from AU$337, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool! pet-friendly?

No, pets are not allowed at this property.

How much is parking at ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!?

On-site parking is available at the property.

What time is check-in at ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!?

Check-in begins at 4:00 PM.

What time is check-out at ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!?

Checkout is at 10:00 AM.

Where is ~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool! located?

Located in Old Town Key West, this condo building is within a 5-minute walk of Harry S. Truman Little White House and Duval Street. Florida Keys Beaches and Mallory Square are also within 15 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 78 out of 89 reviews
Rating 8 - Good. 9 out of 89 reviews
Rating 6 - Okay. 0 out of 89 reviews
Rating 4 - Poor. 0 out of 89 reviews
Rating 2 - Terrible. 2 out of 89 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

KATIE F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location!!
Stayed 7 nights in May 2025
From a partner site

10/10 Excellent

suzan s.

Quiet and lovely venue

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Such a beautiful and peaceful location. A quiet place but so very close to everything we were looking for: easy walk to beach, Mallory Square, Duval Street restaurants, Truman Little White House, and Hemingway House. We hardly used our car! We would definitely stay here again.
Response from VrboOwner on 12 Dec 2025
Starting in December 22, 2025, Fair Winds @ the Foundry will be a monthly rental; we hope you'll come and stay with us for a month and live like a local! ~ The Team @ Historic Key West Vacation Rentals
Verified

10/10 Excellent

JILL T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful and clean property in the heart of Key West. Walkable to everything.
Stayed 7 nights in Aug 2025
Response from VrboOwner on 30 Aug 2025
We appreciate your taking the time to review us so kindly! We hope you're already making plans to come back and see us again, and soon! ~ The Team @ Historic Key West Vacation Rentals
Verified

10/10 Excellent

michelle b.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay. Most everything was walking distance. HKWVR staff very frinedly and helpful answering questions. Would definitely stay again!
Stayed 7 nights in Jul 2025
Response from VrboOwner on 4 Aug 2025
Thank you so much for the kind review of Fair Winds ~ and we hope you're already making plans to come back! ~ The Team @ Historic Key West Vacation Rentals
Verified

10/10 Excellent

John F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was beautiful and very clean. Plenty of room for my family of four. The check in process was easy and the seamless. The location is close enough to Duval Street but far enough to not hear the noise. The pool is nice but small. We enjoyed our stay!!
Stayed 7 nights in Aug 2025
Response from VrboOwner on 30 Aug 2025
We hope you're already making plans to come and stay with us again! ~ The Team @ Historic Key West Vacation Rentals
Verified

10/10 Excellent

Nirza C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

The house look exactly in the photos. Very clean and a great location.

Very pleased with our booking.
Stayed 7 nights in Aug 2021
Response from VrboOwner on 18 Aug 2021
So happy you were pleased!! Come and stay with us again! (and again). ;) ~ Jennifer & Team @ Historic Key West Vacation Rentals
Verified

10/10 Excellent

REBECCA A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A perfect getaway

Loved our stay! Fair winds is a perfect location for key west! Quiet and easy accessibility to everything nearby. Very safe and comfortable.
Stayed 7 nights in Mar 2024
Response from VrboOwner on 3 Apr 2024
What a great review and we thank you for taking the time to do so! Hope we'll see you again, and soon! There's still more memories to be made in Key West. Jennifer & Team @ Historic Key West Vacation Rentals
Verified

10/10 Excellent

Mark S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Truman Annex

We enjoyed our week here. Property was accurately described and the location is perfect. Plenty of room to stretch out and nice quiet area but still walking distance to Duval.
Stayed 7 nights in Feb 2022
Response from VrboOwner on 25 Feb 2022
We are so happy you enjoyed your time at Fair Winds! We think it's a pretty great home and in a great location as well. Hope you're already making plans to come and see us again, and soon! ~ Jennifer & Team Historic Key West Vacation Rentals
Verified

10/10 Excellent

Joseph V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Destination wedding

Our son married in Key West and our family stayed at Truman Annex. Our place was amazing and the location was walking distance to anything we wanted to see or do.
Stayed 7 nights in Jun 2019
Response from VrboOwner on 18 Mar 2020
Thank you for your great review. Key West is a beautiful island for a wedding. We're so happy that everything was wonderful for your family. We look forward to your next visit with us. Smiles, Mary Ann & the HKWVR team
Verified

10/10 Excellent

Vern N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Location

Great Location. Everything was great until the A/C quit working but they were on top of it and had it working in no time.
Stayed 10 nights in Apr 2022
Response from VrboOwner on 31 May 2022
Sorry to hear the A/C quit but so happy to hear we got right on it! A/C is important. :) Let us know when you're coming back to see us again! ~ Jennifer & Historic Key West Vacation Rentals Team
Verified

10/10 Excellent

Danielle E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice townhouse

Pretty townhome centrally located in old town.
Stayed 7 nights in Nov 2022
Response from VrboOwner on 19 Nov 2022
Danielle, thank you for your review! Fairwinds is in a great location and the parking space and shared pool are great amenities! Come back to our little island paradise when you can! Cindy & the HKWVR team
Verified

10/10 Excellent

Kathleen T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful time in Key West

The rental property was comfortable, clean, well appointed and in a terrific neighborhood...easy access to all that Key West has to offer. We didn't even need a car. Key West is a fun and happy place!
Stayed 28 nights in Feb 2024
Response from VrboOwner on 7 Mar 2024
Thank you for the nice review of Fair Winds at the Foundry! Please tell us when you'll be back to make some more memories. ~ Jennifer & Team @ Historic Key West Vacation Rentals
Verified

10/10 Excellent

Michelle K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key west

Wonderful week.
Stayed 8 nights in Mar 2023
Response from VrboOwner on 20 Mar 2023
Oh, that's so nice to hear! Come and stay at Fair Winds at the Foundry again and have another wonderful week! We're here. ~ Jennifer @ Historic Key West Vacation Rentals
Verified

10/10 Excellent

Heather K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely gem close walking distance to duval.

Such a great location! Of all our stays so far in Key West (which is many) this was one of my top choices. Easy to get anywhere and parking for the unit was right outside and covered. I would recommend it to anyone unless you can’t climb stairs ;)
Stayed 7 nights in Oct 2021
Response from VrboOwner on 5 Nov 2021
Heather, thank you very much for your review. Fairwinds is in a great location and the parking space is a great perk. We are pleased you enjoyed your stay. Please come back soon for more Key West adventures! Cindy & the HKWVR team
From a partner site

10/10 Excellent

Denise T.

Great vacation

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our second time at Fair Winds and we are very pleased. It is clean and located close to all the best places to see. We will definitely be going back
Response from VrboOwner on 14 May 2024
Third time will definitely be the charm, so please hurry back! ~ Jennifer & Team @ HKWVR
From a partner site

10/10 Excellent

Jacqueline P.

Perfect!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Absolutely perfect rental for our family of 4. Amazing location, everything you need!
Response from VrboOwner on 22 Aug 2023
So nice to hear that you enjoyed your time at Fair Winds! Please bring the family back soon and make some more memories. ~ Jennifer & Team HKWVR
From a partner site

10/10 Excellent

Melissa C.

Great location

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Wonderful location within Truman Annex with easy walking access to the waterfront and Mallory Square. Comfortable and charming decor.
Response from VrboOwner on 21 Apr 2023
We are so happy you enjoyed Fair Winds at the Foundry, and we agree on its comfort and charm! We hope you're already making plans to come back and see us again, and soon. ~ Jennifer & Team HKWVR
From a partner site

10/10 Excellent

Tom D.

The Foundery

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Very good. Very Enjoyable.
Stayed 7 nights in Jan 2020
Response from VrboOwner on 18 Mar 2020
Tom we are so happy you enjoyed Fairwinds at the Foundry and you stayed with us once again. Key West is a lovely place to enjoy the warm weather & get away from the ice cold winds.We look forward to seeing you whenever you can come back. Hoping it wil be soon! Cindy & the HKWVR team
From a partner site

8/10 Good

Terri Z.

Wonderful Stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great place to stay. Truman Annex is very quiet. The Foundry is a cool building and the kids enjoyed having their own separate space. We will be re-booking for next year!
Response from VrboOwner on 25 Jan 2023
Thank you Peter for your kind review of Fair Winds. We agree that the building is cool and the layout is great! We can't wait to see you again in sunny Key West! ~Lori and the Team @ HKWVR
From a partner site

10/10 Excellent

Joseph F.

Paradise

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The property was perfect. Easy check in and out. Art work in the condo was fantastic. Condo was well stocked and location was perfect.
Response from VrboOwner on 28 May 2022
Dear Joseph, Thank you so much for taking the time to share your feedback in regards with your most recent stay with us. We strive to provide all of our guests with an unforgettable experience and we are delighted to have accomplished that objective during your stay. We are thrilled you enjoyed your visit with us and hope to welcome you back for another great stay soon! Happy Holidays! Sincerely, Yoli and the HKWVR Team
From a partner site

10/10 Excellent

Joseph F.

Paradise

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The property was perfect. Easy check in and out. Art work in the condo was fantastic. Condo was well stocked and location was perfect.
Response from VrboOwner on 18 Mar 2020
Dear Joseph, Thank you so much for taking the time to share your feedback in regards with your most recent stay with us. We strive to provide all of our guests with an unforgettable experience and we are delighted to have accomplished that objective during your stay. We are thrilled you enjoyed your visit with us and hope to welcome you back for another great stay soon! Happy Holidays! Sincerely, Yoli and the HKWVR Team
From a partner site

10/10 Excellent

Aleksandar V.

Relaxing vacation

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our vacation was so relaxing. The condo was very clean and spacious for the four of us. It was within walking distance to lots of very good restaurants and shopping. I would absolutely recommend this place to my friends.
Response from VrboOwner on 3 June 2023
Relaxing vacations are our goal for our guests. Please come and relax with us anytime! ~ Jennifer & Team HKWVR
From a partner site

10/10 Excellent

Ellen H.

Perfect Home

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The house has a great location, is well maintained and tastefully decorated, and has a delightful patio. The staff at Historic Key West Vacation were the best we have ever dealt with in renting vacation homes.
Response from VrboOwner on 4 Mar 2023
Wow! Thank you for the super kind review of Fair Winds *and* us. I will pass this along to our crew ~ we love happy, nice guests. ~ Jennifer & Team HKWVR
From a partner site

8/10 Good

Convient location

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location, close to everything Property worked very well for family The kitchen is somewhat under equipped and guest bedroom could use better lighting (as per the boys) Would stay at property again, over all satisfied
Stayed 7 nights in Aug 2019
From a partner site

10/10 Excellent

William S.

Great Location

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We loved the location. The condo was clean worked well for our family of 4. Historic Key West did a great job of keeping us apprised of the check-in process, kept our bags when we arrived early and coordinated our bike drop off. Very happy with our stay. We will be back.
Response from VrboOwner on 5 Jan 2024
We are so happy you enjoyed your time and that we met (exceeded?) your expectations! Please come and stay with us again, anytime, but hopefully soon. ~ Jennifer & Team @ HKWVR

About the host

Hosted by Historic Key West Vacation Rentals

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