Fair Winds at the Foundry - Weekly Rental

2 Bedrooms

2.5 Bathrooms

6 Guests

5.0

Bring your flip flops and walk to restaurants, shops, and attractions. Enjoy the outdoors from your fenced patio area or shared pool. This end unit townhouse is conveniently located in a gated community and offers an island vibe with modern amenities.



About the property

WEEKLY RENTAL: This property has a 7 night minimum stay.
**Beginning January, 2026, Fair Winds will be a MONTHLY (28 nights within the same month) RENTAL. 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.

***Staying for a month or longer? Request a quote for a minimum of 28 nights to see our discounted “monthly” rates.

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

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


Features & amenities

  • Type: Condominium
  • Communal Pool
  • pets not allowed
  • Truman Annex
  • Monthly
  • Nightly & Weekly
  • Air Conditioning
  • Internet Access
  • Kitchen
  • Washer / Dryer

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5.0 (48 reviews)

5.0

cozy townhome

We've been coming to KW for 20 years and have found this property to be one of the best. From its location to all the amenities - they have thought of everything. I work from home and even the wifi could keep up with all my reports. It would be nice to have a book with check in and check out information - I felt bad for asking questions, that with a little looking thru my emails, I could have found BUT when you are in Key West you forget all your worries! Great property and we will rent it again (and when we get our house built, we will send our overflow guest in this direction!).

Submitted by Purcellville VA on Mar 06, 2025

5.0

great vacation

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

Submitted by Hermitage PA on May 12, 2024

5.0

very happy!

This was our first time staying in Truman Annex & we could not be happier.
The house was perfect for my family of four. We loved the location, the patio area and my daughters loved the privacy of the third floor bedroom that they had to themselves. The house was stocked with plenty of towels, extra pillows, blankets and beach towels and plenty of paper products to last the whole week. We are looking forward to coming back!

Submitted by Ocean City NJ on Apr 05, 2024

5.0

fun @ the foudry!

Absolutely loved our week stay at the foundry! We travelled over spring break with our teen girls. The location was perfect...close to everything! We rented bikes...bikes everywhere! No need for a car. Loved the community pool and the Truman annex area is superb...by far the most beautiful area in key west.

Submitted by Van Wert OH on Mar 31, 2024

5.0

enjoyable

Terrific property in a great location. The 33 steps to the 3rd floor bedroom were a bit of an issue. The AC went out one day and the temp soared into the 90's. However, with one phone call, a maintenance man came to our unit even though it was after he had gone home for the day and within a few hours, the AC unit was repaired. The one thing I did not like was the hassle created by their check in and check out policy. You cannot gain access to your unit until 4:00pm (we arrived at noon) and must be completely out of the unit by 10:00am (our flight was at 6:00pm). The mgmt co allowed us to store our luggage at their office during the before and after hours; however, the office is two miles away from the unit. So, we had to Uber our luggage from the airport to the mgmt co's office, then Uber into town for lunch and wait the four hours until the unit became available. We then had to Uber back to the office to retrieve our luggage and then take another Uber with our luggage to our unit. We then had to repeat the process upon departure. In all, it required 8 separate Ubers - an expensive hassle. It would have been so much better service if someone at the office would have simply driven our luggage to and from the unit or if we could have stored our luggage on site. Nevertheless, I am already looking forward to our next visit.

Submitted by Muskegon MI on Mar 25, 2024

5.0

location, location, location

The location of condo #26 is outstanding. The unit at the end of a row of condos allows for three huge windows along the outside wall.
We knew that it would be a three story unit. The seemingly endless steps up and down turned out to be too strenuous for our group. A minor note: the railings are installed too high.
The living room sofas are in desperate need of replacement. There isn't anywhere comfortable to sit. At times we resorted to the wooden dinette chairs.
Since we prefer fine dining, the best meal we had all week was at Louie's Backyard.
The management company provided excellent customer service.
We were unaware and didn't research the fact that it was 'swarming season'. The termites that swarm (dusk to sunset??) can get into the house.
The unit will be recommended with the advice that thirty one some odd steps might be a drawback.

Submitted by SEATTLE WA on Mar 09, 2024

5.0

great location

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.

Submitted by Meridian MS on Dec 28, 2023

5.0

perfect!

Absolutely perfect rental for our family of 4. Amazing location, everything you need!

Submitted by Chicago IL on Aug 12, 2023

5.0

relaxing vacation

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.

Submitted by Lakewood OH on May 26, 2023

5.0

fair winds at the foundry - great location in key west

Excellent stay at Fair Winds, great location, easily walkable to Old Town, harbor, Mallory Square and Zachary Taylor Park. Bonus of a parking space for our rental golf cart, a must when visiting Key West. We would certainly consider Fair Winds again on return trips.Historic Key West Vacations is a great management company, quickly responsive to questions and setting up information for arrival and departure.

Submitted by Chesterfield MO on May 25, 2023

5.0

great location

Wonderful location within Truman Annex with easy walking access to the waterfront and Mallory Square. Comfortable and charming decor.

Submitted by Silver Spring MD on Apr 17, 2023

5.0

great vacation!

We enjoyed our stay! Location was great. Very quiet.

Submitted by Hanover PA on Mar 22, 2023

5.0

great rental

This was a great unit in the Foundry. Being an end unit you get extra light from side windows but still have quiet and privacy.
The unit has everything we needed for a week stay. Beds were comfortable. It would have been nice to have a different pillow options. These were a bit too full.

Submitted by Glen Ellyn IL on Mar 06, 2023

5.0

perfect home

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.

Submitted by Fairfax VA on Feb 27, 2023

5.0

wonderful stay

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!

Submitted by Grand Rapids MI on Jan 23, 2023

5.0

excellent!

We had a delightful stay at Fair Winds @ the Foundry. The condo is kept in great shape and the kitchen is well stocked with quality utensils and appliances. There were ample supplies - coffee filters, dishwasher pads, paper towels, toilet paper, etc. so we never had to run to the store for something. Nice touch. Our bed was very comfortable and the ground floor room with the high ceilings was a pleasant space to hang out. Because this is a corner unit, there are 3 extra windows on the side for extra light, but they also have quality blinds that can be closed off completely in the evening for privacy. The decorations were very nice and it was an inviting place to come back to every day. The location is fantastic, just a short walk to Mallory square, Duval, and the seaside park. We really couldn't ask for better. Interaction with the Historic Key West staff before, during and after the stay was prompt, and always accurate. There were zero hiccups. I found them professional and trustworthy and would rent from them again.

Submitted by Northfield MN on Jan 10, 2023

5.0

fun in key west

Excellent stay at The Fair winds @ The Foundry. The unit is in Truman Annex which is perfectly situated for an easy walk to Fort Zachary and Duval Street. No need for a car or golf cart. We walked everywhere. Uber is the cheapest alternative to/from airport. Enjoyed the gulf side beach without the smelly seaweed. Snorkeling is convenient at Fort Zachary- recommend renting only one set and sharing. Chair rentals are very convenient. Great little cafe there. Beautiful sunsets from there too. Fun to see the cruise boats docked a short walk away although they made the tourist spots busy. Historic Key West Vacation Rentals provided excellent tips for a perfect vacation. The furnishing are very comfortable. Great layout with the two bedrooms on separate floors provides privacy. Comfortable beds. Very clean. Unit provided with extra tp, coffee filters and liquid soap. Instacart delivery from Publix arrived within 30 minutes of our check-in. Also, beach towels and chairs were provided. Pool is small but nice and very close to unit. Outdoor patio area is great spot to relax when not too muggy. Favorite restaurants include- Cafe Sole, Bagattelle, A&B Lobster, Louie’s Backyard, Bistro 245, Red Shoe Island Bistro, and Onlywood Pizza. Highly recommend this unit!

Submitted by Richmond VA on Jul 31, 2022

5.0

a piece of paradise

From opening the front gate, you can sense something special. Then you enter the setting room, the calming blue colors, touches of orange, and pleasant seating arrangement, and then you smile, understanding the serenity you have entered.
Mornings I worked on my computer, with coffee, on the patio until my family awoke. Breakfast prep followed.
A day of adventure would begin. I have never enjoyed a house and its surroundings as much as I enjoyed this one...thanks

Submitted by Ashburn VA on Jan 31, 2022

5.0

ideal location

Located in Truman Annex, this house is surrounded by stunningly beautiful homes, meticulously maintained lush landscaping and terrific historical landmarks. The community is very quiet and yet Duval Street is just a short stroll away. Our favorite spot, Hank’s, is just a 5 minute walk. The house is very clean, brightly decorated and comfortable. The management staff responded quickly to our inquiries and arranged our bike rentals. We are a family of five (all adults) and everyone enjoyed the accommodations. The pool area is small but well maintained. We wholeheartedly recommend this property.

Submitted by Virginia Beach VA on Dec 31, 2021

5.0

awesome end unit townhome

This was an awesome townhome. Very private , gated and so peaceful at night. Conveniently located near Duval St, a short walk to ft Zachary and adjacent to a great sunset spot by the former cruise port. There is a bike rental shop just outside the main entry point as well. The place accommodated 5 adults comfortably. The only drawback is the pool. It's very small but ft Zachary made up for it, as there is a beautiful beach along with food/drink bar onsite and a rock formation that we spent hours snorkeling. Overall great place to stay !

Submitted by Nashville TN on Sep 28, 2021

5.0

location location location

This was our first time to Key West. I think your experience on the island is dictated by the location of your stay. This property is in the perfect location (2 blocks from Duval) and is located in pristine complex (Truman Annex). The property was clean, well maintained and well equipped. The Annex had a very tropical feel with all of the palm trees and well maintained grounds. The property is within walking distance to everything Key West has to offer. We will definitely be back ... hopefully sooner than later.

Submitted by Cumming GA on Sep 10, 2021

5.0

one of our best vacations

Very happy with our stay. The house was very clean. In a great location. Would definitely comeback and recommend. One of our best vacations.

Submitted by Denville NJ on Sep 02, 2021

5.0

perfect place in the heart of paradise

We loved our condo! It was exactly as described. Loved the location close to the pool and within walking distance of everything. Enjoyed the the patio in the morning to have a cup of coffee and read a book. Kitchen had everything we needed to have a meal even though we didn’t do a lot of cooking certainly could have easily made a meal. Beds and sheets were super comfy. Beach chairs were a nice bonus for our day trips too! Would definitely stay in this exact unit again because of the location.

Submitted by Imlay City MI on May 19, 2021

5.0

perfect month away

We had a wonderful at The Fair Winds @ The Foundry! The house was immaculate, the beds were very comfortable, we had all the comforts of home!
Loved the location, we only used our car if we went to Fort Zachary,which you could walk or bike!
One simple thing, I wish they had something more comfortable to sit on off the balcony of the second floor bedroom. Other than that it was simply marvelous ��

Submitted by Reston VA on Mar 29, 2021

5.0

great get-away to key west

Our stay at the Foundry in the Truman Complex was fantastic! The location and condition of the property was excellent. Would highly recommend this spot for someone who is looking for a quaint, peaceful and quite place that is minutes from all the hot spots on Duval.

Submitted by Tulsa OK on Mar 24, 2021

5.0

truman annex retreat

Lovely townhouse in the foundry building in Truman Annex. This is the 4th townhouse in the foundry we stayed in, they are all very nice but being a corner unit was the best. Very clean, very well furnished and exactly as shown in the pictures. We were very happy with our stay! Historic Key West Vacation Rentals are a fantastic company to work with!

Submitted by Warren OH on Nov 28, 2020

5.0

wonderful property!! two thumbs up . . .

We cannot say enough about FairWinds at the Foundry! The property is fantastic - super close to everything in Old Town but you feel like you are in the midst of the jungle with all of the tropical plants/trees. The layout of the townhome is great for families or two couples - and it was spotless. I really appreciated the way that Historic Key West Vacation Rentals worked with us as we were booking for the time right after the island opened back up in June. They were super accommodating and very transparent with everything they did/said. We will definitely stay there again and highly recommend!

Submitted by Fairhope AL on Jun 25, 2020

5.0

find at the foundry

Had to leave early because of the pandemic. Close to the action but off the beaten path. Spacious and comfortable. All the accompaniments to make the stay worry free. Had an AC issue the second day there, but management dispatched a maintenance man within 20 minutes to rectify the problem. No detail for an enjoyable stay was overlooked.







Submitted by Atlantic City NJ on Apr 02, 2020

5.0

foundry fun

Great location, close to pool, nicely furnished rental, clean. Attentive staff. Not for people who have trouble with stairs, as bedrooms are on 2nd and 3rd levels.

Submitted by Worthington OH on Feb 05, 2020

5.0

the foundery

Very good. Very Enjoyable.

Submitted by Washington DC on Feb 04, 2020

5.0

had a good week

All went well once we got into the unit. We had to wait 4 hours to get into it.
Also, the $3000 deposit, which I hope to get back, is excessive considering that you already had my credit card for any damages (there were none).

Submitted by South Amboy NJ on Dec 09, 2019

5.0

convient location

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

Submitted by South Park PA on Aug 12, 2019

5.0

island charm

Lovely condo within walking distance to Key West landmarks, great restaurants, Mallory Square, art galleries and just fun places to catch a cocktail (we walked around 41 miles in 7 days). I enjoyed a sailfishing trip with my son and relaxed the rest of the time with my family. Although we didn't sit in the condo much, the accommodations are stunning and well appointed. It was also nice enjoying a quick dip in the pool which is just across the street.

Submitted by Batavia IL on May 27, 2019

5.0

beautiful truman annex

We couldn’t have chosen a more perfect location to experience Key West. The Truman Annex was a treat!

My only suggestion is to clean the interior of the front loading washing machine. While it smells clean, the odor left in my clothes is horrible. I’m rewashing and rewashing in vinegar and still haven’t gotten the smell out.

Submitted by Grand Rapids MI on Mar 29, 2019

5.0

key west january 2019

Very Good

Submitted by Indianapolis IN on Feb 04, 2019

5.0

wonderful stay

Great place in a great location. Forget your rental car you don’t need it!

Submitted by Greensboro NC on Dec 18, 2018

5.0

fantastic vacation

Our vacation at The Fairwinds @ The Foundry vacation during Thanksgiving week was a wonderful experience. The accommodations were top notch. The living area and bedrooms were large, everything was updated and spotless. You could not ask for a better location. It was very tranquil but was walking distance to Mallory Square and Duval Street. The property management staff were very accommodating. Check in and check out was a breeze. We would definitely stay here again

Submitted by Cocoa FL on Nov 29, 2018

5.0

paradise

The property was perfect. Easy check in and out. Art work in the condo was fantastic. Condo was well stocked and location was perfect.

Submitted by Burlington CT on Nov 15, 2018

5.0

great stay

Very quite area but within 10 minutes walk from main street with restaurants and bars. The house was clean and well equipped.

Submitted by L'Assomption QC on Sep 08, 2018

5.0

wonderful stay!

We have been coming to the Keys for many years, but this is our first time to stay in Key West. We found the property to be the perfect place to stay. It was quiet and peaceful, but still very close to all the action. The property was very comfortable and clean and we would definitely recommend it to anyone who is able to climb stairs, because there are three stories. There is so much to enjoy in Key West and we had a wonderful stay.

Submitted by Dallas GA on Jun 21, 2018

5.0

great condo in beautiful key west

Our stay at Fairwinds @ The Foundry was wonderful. The condo afforded us ample space for spending a week with our two grown sons. Every room was well appointed and clean. The small courtyard was a great space to enjoy Cuban coffee in the morning and a glass of wine in the evening.

It is also close to so many of the Key West attractions and fabulous restaurants. We walked everywhere!

Submitted by Batavia IL on May 14, 2018

5.0

perfect location

The condo was in a perfect location for walking everywhere. The parking spot was directly across from the condo and very convenient. The unit I stayed in was sold in the middle of my stay so I lost tv and internet for a day while management installed a new system. There was a sink plumbing issue that got addressed promptly. There were no lamps on the third floor so I had to move one from the second floor. The only floor with window or door screens was the top floor. It would have been nice to have been able to open windows and doors and let in that lovely breeze. The outdoor furniture comprised of two small rusted chairs, a rusted bistro table and two beatup Adirondack chairs that were very uncomfortable. They need new outdoor furniture so that the patio can be enjoyed. In a month I probably only used the patio two or three times. We balanced the food on our laps and sat on the edge of the Adirondack chairs. The condo was clean and the indoor furnishings were fine. Perhaps the new owners will fix up the outdoors and get some screens. Otherwise it was paradise!

Submitted by Fairport NY on Mar 16, 2018

5.0

great location

Great location, located just 2 to 4 blocks from Mallory Square and my favorite bars on Duvall Street. Air conditioner needs service or an upgrade, it ran continuously and the temperature was always a couple of degrees warmer than I would have liked it. Small bedrooms, kinda felt like I have more room on a cruise ship for clothing and stuff, but the beds were comfortable, 2 twins upstairs and a queen bed in the middle level.

Submitted by Fort Collins CO on Nov 17, 2017

5.0

great location, air conditioning broke twice

Great unit. Best location. Went for boat races. Walk everywhere we needed to be. Two years ago, we stayed here and air broke. Booked again cause great location. Air broke twice. First night we relocated and next time broke, they fixed same day. They responded quickly to fix and took care of us. When there, they got estimate to replace so hopefully that happens because we would stay there again. If plan to book, make sure AC unit was replaced. Third floor got up to 88 degrees. Management company was great trying to fix it. This was after Hurricane so contractors busy but they got someone out there.

Submitted by Shorewood IL on Nov 16, 2017

5.0

our wedding week in key west

We stayed in the condo during our wedding week from May 29th - June 5th. The condo met our needs perfectly. It is in a lovely location and we love staying in Truman Annex. There were a few small issues with the TVs and then with the dishwasher but nothing that would make or break our stay. The condo was very clean and comfortable and we loved the high ceilings! We would definitely stay here again!

Submitted by south plainfield NJ on Jun 21, 2017

5.0

first time to key west

Overall we had a great experience in Key West and our vacation rental in the Foundry at Truman Annex was a major part of that. The location was excellent. A very quiet area within 2 blocks of all the hustle and bustle of Duval Street. The rental was generally in good shape although we did have a couple of teething problems. The staff were very responsive and so there was little to no inconvenience. We shared with another couple and the two bed two bath arrangement worked really well so that each couple had their own space. Undercover parking meant that the car didn't get too hot although we didn't use it much as everything was so close. Great booking experience and useful app added to make our stay very enjoyable. Only minor draw back was that in my opinion this particular property could do with some firmer mattresses on the beds, as they were a little soft for our liking. Will definitely return to Key West and Truman Annex.

Submitted by LEXINGTON SC on Dec 02, 2016

5.0

fun at the foundry

Stayed for 8 nights with my parents, husband and baby boy. The townhouse was as depicted in the description and pictures. Very clean and spacious (we fit a full size crib in the 3rd floor bedroom). Location was fantastic, easily accessible to everything you needed (sites, pool, beach, restaurants, cafes, shops, grocery store, and most tourist attractions). We did not rent a car nor did we need one. Did a hop on hop off bus tour one day to get to see some of the sites further away. The property managers/owners provided all the staples you needed for the week (detergent, soap, toilet paper, etc.). The only thing that potentially could be improved were the pillows but that of course is a very personal choice.
The property managers were very professional and were in constant communication with me from the day I sent in my first inquiry on the property online to the day we landed. We even exchanged text messages the day of arrival to ensure we didn't get lost. The property manager met us at the house to provide the keys and some basic information. They also were in contact with the baby furniture rental company so everything was delivered and set up before we arrived. Wifi was very stable and fast. But I don't think there was a working phone so I would suggest bringing a cell phone. The Truman Annex area is beautiful and we all felt safe walking around day or night. I would recommend this property to friends and family and would stay there again.

Submitted by Willowdale South, Toronto ON on Feb 03, 2016

5.0

key west vacation

First time to Key West at a busy time of year between Christmas and New Years Day. Really enjoyed visiting Key West and we were fortunate to have great weather the entire time. Our rental was in the Truman Annex, a great location to walk to downtown area and restaurants. During our stay we snorkled, kayaked, visited Hemingway House, Ft Zach and beaches.

Submitted by Cincinnati OH on Jan 20, 2016

Location

May 14-14, 2025
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