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Condo

Shaded outdoor patio w/ plenty of seating.

Enjoy the private front patio and gas grill.

Overview
Amenities
Policies
Location
Host

9.6

Exceptional

2 bedrooms2+ bathroomsSleeps 6142 sq m

Popular amenities

Barbecue grill

Washer

Kitchen

Air conditioning

Dryer

Outdoor space

Check-in time

4:00 PM

Check-out time

10:00 AM

Explore the area

Key West, Florida

Duval Street5 min walk
Mallory Square7 min walk
Ernest Hemingway Home and Museum12 min walk
Key West, FL (EYW-Key West Intl.)14 min drive

Most relevant reviews

10/10 Excellent

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the locat...

Fred B.

Mar 26, 2024

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!

WEEKLY RENTAL: This property has a 7 night minimum stay.

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***

Property manager

Historic Key West Vacation Rentals

Premier Host

Languages

English

Amenities

Kitchen

Washer

Dryer

Air conditioning

Outdoor space

Barbecue grill

Kitchen

Washer

Dryer

Free WiFi

House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

No pets allowed

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 not indicated whether there is a smoke detector on the property

About the area

Key West

Located in Key West, this condo is in the city centre. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. 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.

Key West, Florida

What's nearby

Duval Street - 5 min walk
Mallory Square - 7 min walk
Ernest Hemingway Home and Museum - 12 min walk
Southernmost Point - 19 min walk
Fort Zachary Taylor Historic State Park - 4 min drive

Getting around

Key West, FL (EYW-Key West Intl.) - 14 min drive

Restaurants

‪Margaritaville - ‬6 min walk
‪Bull & Whistle Bar - ‬6 min walk
‪Green Parrot Bar - ‬9 min walk
‪Caroline's Cafe - ‬6 min walk
‪Mattheessen's - ‬5 min walk

Frequently asked questions

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.

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 is within a 5-minute walk of Harry S. Truman Little White House and Duval Street. Mallory Square and Florida Keys Beaches are also within 15 minutes.

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

10/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Denise T.

13 May 2024

Great vacation

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kelly O.

6 Apr 2024

Very happy!

Rating Details: The property manager was very helpful. The vacation rental was very clean. 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: 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!

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Fred B.

26 Mar 2024

Enjoyable

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: 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.

10/10 Excellent

REBECCA A., VAN WERT

18 Mar 2024

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

This review comes from a trusted partner site and has not been verified.

8/10 Good

Geri G.

10 Mar 2024

Location, location, location

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 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.

10/10 Excellent

Kathleen T.

3 Mar 2024

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

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

William S.

29 Dec 2023

Great Location

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

KATHY S.

11 Dec 2023

Wonderful Rental

Rating Details: The property manager was very helpful. The vacation rental was very clean. 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: Wonderful rental and location. Comfortable beds and bedding including clean blankets and newer pillows. Bedrooms have nice, clean furniture with plenty of storage. Plenty of hangers which is a nice touch. Bathrooms are tight but clean. Kitchen is stocked and the drawers are clean and not full of old junk. Bonus! Appreciated the outside seating with comfy swivel rockers/side table and a small table/chairs all newer and a bonus. Unit is very clean other than the first floor tile and family room rug which needs to be addressed. Also, it's time to do a little updating. Replace the family room sofa pillows and get rid of the carpet on the staircase. Front porch is tight with the step location off to one side which makes it awkward to exit and probably an accident waiting to happen. All easy fixes for a great rental.

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Jacqueline P., Chicago, IL

13 Aug 2023

Perfect!

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Aleksandar V., Lakewood

27 May 2023

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.

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Rob G., St. Louis, MO

26 May 2023

Fair Winds at the Foundry - great location in Key West

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Melissa C.

18 Apr 2023

Great location

10/10 Excellent

Michelle K.

19 Mar 2023

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

Key west

Wonderful week.

Stayed 8 nights in Mar 2023

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Lisa N.

7 Mar 2023

Great rental

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Ellen H.

28 Feb 2023

Perfect Home

This review comes from a trusted partner site and has not been verified.

8/10 Good

Terri Z.

24 Jan 2023

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!

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Matt S., Northfield, MN, USA

12 Jan 2023

Excellent!

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 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.

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Matt S., Northfield, MN, USA

11 Jan 2023

Excellent!

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 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.

10/10 Excellent

Danielle E., Flagler Beach, Florida

19 Nov 2022

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

Nice townhouse

Pretty townhome centrally located in old town.

Stayed 7 nights in Nov 2022

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Laureen M., Richmond, VA

1 Aug 2022

Fun in Key West

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: 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!

10/10 Excellent

Jennifer M.

12 July 2022

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

Great House! Great Location!

This property is exactly as it appears online! You access the front door through a white picket fence and enclosed patio. Once you enter, the living room and kitchen area are downstairs and comfortably fit our family of 4. The master bedroom is on the 2nd floor and the other bedroom is on the 3rd floor. We all slept comfortably and felt like we had our own separate spaces. This house is also immaculately clean and stays so cool in the hot and humid key west climate. My husband said he would give the AC unit alone a “5+ star rating” as the house was so cool! It is close to so many shops and restaurants as well as Mallory Square for breathtaking views of the sunset. My family and I would stay here again in a heartbeat!

Stayed 7 nights in Jul 2022

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Lisa M.

19 May 2022

Fun at the Foundry

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: 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.

This review comes from a trusted partner site and has not been verified.