Condo

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

Condo with kitchen, a short walk to Duval Street

Shaded outdoor patio w/ plenty of seating.

Enjoy the private front patio and gas grill.

Overview
Amenities
Policies
Location

Exceptional

2 bedrooms2+ bathroomsSleeps 61527 sq ft

Popular amenities

Dryer
Washer
Kitchen
Pool
Barbecue grill

Explore the area

Key West, FL

Place, Duval Street
‪5 min walk‬
Place, Mallory Square
‪6 min walk‬
Place, Southernmost Point
‪18 min walk‬
Airport, Key West, FL (EYW-Key West Intl.)
‪10 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!

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***

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

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 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 Fort Zachary Taylor Historic State Park 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, FL

What's nearby

Duval Street - 5 min walk - 0.4 km
Mallory Square - 6 min walk - 0.6 km
Ernest Hemingway Home and Museum - 11 min walk - 0.9 km
Southernmost Point - 18 min walk - 1.6 km
Fort Zachary Taylor Historic State Park - 3 min drive - 1.4 km

Getting around

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

Restaurants

‪Caroline's Cafe - ‬6 min walk
‪General Horseplay - ‬5 min walk
‪Garbo's Grill - ‬5 min walk
‪Gator Joe's Coffee - ‬4 min walk
‪First Flight Island Restaurant & Brewery - ‬4 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.

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 building is within a 5-minute walk of Harry S. Truman Little White House and Duval Street. Mallory Square and Ernest Hemingway Home and Museum are also within 15 minutes.

9.8

Exceptional

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

Learn more

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

JILL T.

27 Aug, 2025

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

10/10 Excellent

michelle b.

1 Aug, 2025

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

10/10 Excellent

John F.

29 Aug, 2025

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

10/10 Excellent

KATIE F.

9 Jun, 2025

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

Great location!!

Stayed 7 nights in May 2025

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

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

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

Denise T.

13 May, 2024

Great vacation

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

Ronda P.

6 Mar, 2025

Cozy townhome

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

10/10 Excellent

Tom D.

5 Feb, 2020

The Foundery

Stayed 7 nights in Jan 2020

10/10 Excellent

Luke M.

15 Feb, 2025

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

The Perfect Vacation Rental

We had an excellent stay at The Foundry in Key West! Its location cannot be beat as it is within walking distance of just about everything you might want to do while visiting the city. We were only minutes from the excitement of Duval street, but when back at the property you wouldn’t know it. The Foundry was always peaceful and relaxing at any given time of day. We also loved all the amenities it provided us. The full kitchen and gas grill were perfect for nights when we didn’t feel like going out to a restaurant. We loved how each bedroom was on its own floor with a full bathroom attached and that there was even a half bath on the ground floor as well. Having a washer and dryer in the unit was especially convenient for a week long stay. The staff were very helpful any time we had questions and we felt right at home the whole time. Would definitely book a property with Historic Key West Vacation Rentals again!

Stayed 7 nights in Feb 2025

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

10/10 Excellent

Melissa C.

18 Apr, 2023

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.

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

10/10 Excellent

Ellen H.

28 Feb, 2023

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.

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

8/10 Good

Terri Z.

24 Jan, 2023

Wonderful Stay

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

10/10 Excellent

Aleksandar V., Lakewood

27 May, 2023

Relaxing vacation

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

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

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

John R.

19 May, 2022

Island Charm

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: 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.

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

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.

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.

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

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!