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Upscale end unit home @ Truman Annex close to Duval St

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Beach nearby
Property grounds
Property grounds
Dining
Fridge, microwave, oven, stovetop

Reviews

10 out of 10
Exceptional

Entire condo

1 bedroom1 bathroomSleeps 3

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Parking available

Explore the area

View in a map
Key West, FL
  • Place, Florida Keys National Marine Sanctuary
    ‪5 min walk‬
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Fort Zachary Taylor Historic State Park
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪14 min drive‬

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About the neighborhood

Key West

Located in Old Town Key West, this condo is within a 10-minute walk of popular sights such as Duval Street and Fort Zachary Taylor Historic State Park. The condo includes a kitchen, a balcony, and a sofa bed.
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What's nearby

  • Florida Keys National Marine Sanctuary - 5 min walk - 0.3 miles
  • Duval Street - 6 min walk - 0.4 miles
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.4 miles
  • Ernest Hemingway Home and Museum - 9 min walk - 0.5 miles
  • Mallory Square - 12 min walk - 0.7 miles

Getting around

  • Key West Intl. Airport (EYW) - 15 min drive

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Margaritaville - ‬7 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪La Concha Bar - ‬8 min walk

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

Upscale end unit home @ Truman Annex close to Duval St

Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We inspect our homes multiple times each month and follow the AHLA Stay Safe Guidelines to ensure your stay is safe and comfortable. You will also find an initial supply of cleaning and paper products along with handsoap and toiletries. The home has a private entrance and contactless Check-In/Out.

Need to stay connected during your trip? We offer high speed cable internet.

This upscale home has been meticulously renovated with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape and pool while only 2 blocks from the excitement of Duval St. We are just outside the entrance to Ft Zachary Taylor State Park and Beach and so close to many of Key West’s popular attractions. After a full day of taking in many of the island's wonderful experiences, come back to all the comforts of home. This open airy home offers a fully furnished kitchen, eating area, living room and bedroom with a queen size bed and full bath. There are televisions in both the bedroom and living room along with wireless internet access. Two sets of French doors bring in lots of light and open to a large balcony where you can enjoy a meal or relax and sip umbrella drinks on the chaise lounges in your own private tropical paradise. Gated parking lot with one reserved space. (For reviews on our other homes, please see Listing # 877318 Sunset on Southard)

Amenities

- Televisions in bedroom and living area
- 2 Bicycles for Guests to use during their stay
- Bed Linens, Bath & Beach Towels
- Hairdryer
- Beach Chairs & Cooler
- Access to Shipyard Pool
- Partially covered oversize deck
- Reserved parking place
- Secure high speed wireless internet in condo
- Only a few short blocks from Duval Street and Mallory Square
- Short walk to the Fort Zachary Taylor State Park Beach
- Fully equipped Kitchen with Silestone counter and eat in bar- Silverware, Dishes, Cooking Utensils Provided, Stove/Oven, Refrigerator, Microwave, Dishwasher, Coffee Maker & Blender
The condo is air-conditioned and features a kitchen and a balcony, and there's space to spread out with a separate bedroom. Other standard amenities include a washing machine, a sofa bed, and a coffee maker. Limited housekeeping is available.

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Property amenities

Pool/Spa

  • Communal pool
  • Heated pool

Internet

  • Available in the condo: Internet access

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • Bedroom
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Wood stove

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board
  • Limited housekeeping
  • Phone

Things to do

  • Bicycles
  • Golf
  • Heated pool

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Bicycles

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

Events

No events 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
Onsite 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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a fire extinguisher, a smoke detector, and a deadbolt lock.

Property is also known as

New Upscale Rental Truman Annex Condo Key West
New Upscale Rental Truman Annex Condo
New Upscale Rental Truman Annex Key West
Upscale Rental Truman Annex
New Upscale Rental in Truman Annex!
¡nuevo Alquiler de Lujo en Truman Annex!
Upscale end Unit Home in Truman Annex Close to Duval St
Upscale end Unit Home @ Truman Annex Close to Duval St Condo
Upscale end Unit Home @ Truman Annex Close to Duval St Key West
2509-167209

Frequently asked questions

What's there to do around this condo?

This condo is situated in Old Town Key West within a 10-minute walk of Duval Street, Fort Zachary Taylor Historic State Park, and Ernest Hemingway Home and Museum. You'll also find Florida Keys Beaches and Mallory Square less than a mile away.

Is there parking available at Upscale end unit home @ Truman Annex close to Duval St?

No, there isn't parking at this condo.

Is this condo adjacent to a casino?

No, this condo is not connected to a casino.

Will I find an indoor pool at this condo?

No, there is no indoor pool at this condo.

Is Upscale end unit home @ Truman Annex close to Duval St a good place to stay for couples?

At this historic condo, amenities that appeal to couples include a kitchen, a kitchen in some condo, as well as a heated pool.

Does Upscale end unit home @ Truman Annex close to Duval St have a hot tub?

No, but guests can enjoy a heated pool at this condo.

Does this condo offer breakfast?

No, this condo doesn't offer breakfast.

Will this condo allow pets to stay for free?

No, pets aren't allowed at this condo.

Does Upscale end unit home @ Truman Annex close to Duval St have connecting rooms available?

No, this condo doesn't feature connecting guestrooms.

How close is the airport from this condo?

The closest major airport to this condo is Key West Intl. Airport (EYW), which is 4.3 mi away (15 minutes by car).

Are there rooms with balconies at Upscale end unit home @ Truman Annex close to Duval St?

Yes, every condo at Upscale end unit home @ Truman Annex close to Duval St comes with a balcony.

Upscale end unit home @ Truman Annex close to Duval St Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 118 out of 125 reviews
Rating 8 - Good. 7 out of 125 reviews
Rating 6 - Okay. 0 out of 125 reviews
Rating 4 - Poor. 0 out of 125 reviews
Rating 2 - Terrible. 0 out of 125 reviews

10/10

Cleanliness

10/10

Staff & service

10/10

Amenities

8.8/10

Property conditions & facilities

Reviews

10/10 Excellent

Melissa G.

Liked: Cleanliness
What a great location and able to walk to everything you would want to see with ease! The home was spotless, cozy, and comfortable and would highly recommend!
Stayed 7 nights in Dec 2025

10/10 Excellent

Frank B.

Liked: Cleanliness
Room was very nice and newly renovated. Decor was beachy. Location was near everything. Host communicated well.
Stayed 7 nights in Nov 2025

10/10 Excellent

Kristyn S.

Liked: Cleanliness
Great location and beautiful place.
The outside of our condo.
The living room
The view from our balcony.
Stayed 7 nights in Oct 2025

10/10 Excellent

Brian G.

Liked: Cleanliness
Great condo! Was very clean and had everything we needed. The location could not be beat and communication with host was excellent.
Stayed 7 nights in Oct 2025

10/10 Excellent

Janet H.

Liked: Cleanliness
Perfect for our needs.
Stayed 7 nights in Aug 2025

10/10 Excellent

Colleen B.

Liked: Cleanliness
Stayed 7 nights in Jun 2025

10/10 Excellent

Meghan W.

Liked: Cleanliness
Stayed 7 nights in Jun 2025

8/10 Good

Yancy T.

Liked: Cleanliness
Stayed 7 nights in Jul 2025

10/10 Excellent

Thomas D.

Liked: Cleanliness

Excellent experience

My wife and I have been lucky enough to be able to visit Key West over 30 times in the last 25 years and we love staying at Truman Annex! This visit we stayed for two weeks at the Southard Breezes property for two weeks and we had an excellent experience. Where do we start? Above all, we loved how clean the condo was, the location, and all of “included” amenities; bikes, beach chairs, starter amounts of toiletries, kitchen and cloths washing detergent, etc. The deck was a great size and place to sit out and relax. The roof overhangs part of the deck which makes it ideal for sitting out even when it’s sprinkling outside. The porthole window in the bedroom lets in a ton of light and if you like to sleep in, you might have to improvise a curtain, as we did by taping a pillow case over it. Sleep in - no problem. We look forward to be staying here again!!!!!
A beautiful view from the deck
Stayed 14 nights in May 2025

10/10 Excellent

Michelle

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Nice unit, good location & well maintained
Stayed 7 nights in Mar 2025

8/10 Good

John M.

Liked: Cleanliness

Shipyard 2nd floor condo. Great location

We had a nice 3 weeks, everything we needed was supplied except a step stool
Stayed 21 nights in Mar 2025

10/10 Excellent

Michael L.

Liked: Cleanliness

Southard Breeze

Loved our stay here, super clean, super convenient to walk everywhere and comes with 2 bikes if you dont want to walk. Very comfortable place to stay and would definitely stay here again
Stayed 7 nights in Dec 2024

8/10 Good

Brad

Liked: Cleanliness
Stayed 7 nights in Nov 2024

10/10 Excellent

Teresa C.

Liked: Cleanliness

Cozy Condo

This cozy condo is ideally located and is great for two people. The area is generally safe and quieter than two blocks away on Duval. Fort Zach Beach and restaurants are only minutes away. Upon arrival, the house was immaculate, and contactless check-in was easy. The house has quality finishes and is well-appointed. Two bicycles and Tommy Bahama beach chairs are available, which is a nice touch. The queen bed was comfy. There are wood blinds on the bedroom window but no blackout curtains, so I will bring an eye mask if we go again. Having the washer/dryer available is convenient, and starter amounts of products are provided. The partially covered balcony expands the living space and was a nice spot on a rainy morning. There is a designated parking space, but we did not use it. We would stay there again if it were a couple's trip.
Stayed 7 nights in Nov 2024

10/10 Excellent

Jen H.

Liked: Cleanliness

Great choice for 2 people

Southard Breezes was very nice for me and my husband. The deck was large and had both shade and sun so it was convenient to have coffee or an afternoon cocktail. Bed and pillows were comfortable. The washer and dryer were a little loud but we would do the laundry when we were not in the bedroom! Having laundry available was a plus, though! Truman Annex is close to everything but just far enough away! Thanks for the great week!
Stayed 7 nights in Nov 2024

10/10 Excellent

Leslie R.

Liked: Cleanliness

Key west vaca

Loved the condo. Close to everything. Really enjoyed having the bikes. Comfortable bed. We had a great week!
Stayed 7 nights in Sep 2024

10/10 Excellent

Tom and Valerie W., Simpsonville

Liked: Cleanliness

Awesome unit and location

The unit was in a perfect location and was very nice. The entire unit has been updated with new appliances and furnishings. All the action on Duval St is close but not too close. And Ft. Zachary Taylor is in close walking distance or a short bike ride using the nice bikes that were supplied. We would definitely stay here again!
Stayed 7 nights in Aug 2024

10/10 Excellent

Kathy J.

Liked: Cleanliness

Perfect location

Great location-10 minute walk to Duval Street, Mallory Square, Fort Zachary Taylor park, southernmost point. Rental had everything we needed. Would definitely go back!
Stayed 7 nights in Aug 2024

10/10 Excellent

Tim S.

Liked: Cleanliness

Nice place, great location

Enjoyed our stay at the Truman Annex. Short walk to Duval street and the park and beach behind the annex are nice too. Would stay again - no complaints!
Stayed 7 nights in Jun 2024

10/10 Excellent

John M.

Liked: Cleanliness

Great location in Key West

Great vacation in Key West at a great condo that worked very well for my wife and I. Location is close to everything in Old Town and having bikes was great as well !
Stayed 7 nights in May 2024

10/10 Excellent

Katie Todd F.

Liked: Cleanliness

25th Anniversary Trip

Southward Breezes was perfect for our trip! Close in distance to everything we wanted to do on the west end of the island! Easy in and out and great access to pool and bikes. Definitely a place we would come back to!
Stayed 7 nights in Apr 2024

10/10 Excellent

Michelle S.

Liked: Cleanliness

November 25 2023

Enjoyed our stay & we'll be back! Property is amazing, condo clean & beautiful, location fantastic.
Stayed 7 nights in Nov 2023

10/10 Excellent

June L., Hanover Park, IL

Liked: Cleanliness

Key West vacation

The condo was exactly like the photos. The porch was perfect for morning coffee!
Stayed 7 nights in Oct 2023

10/10 Excellent

Verified traveler

Liked: Cleanliness

Fantastic location, bonus to have use of bicycles

The condo is within walking distance to everything that we wanted; Beach, restaurants, and shops. The bikes were in great shape and we used them to get to the beach, just used the picnic tables there.
Stayed 7 nights in Oct 2023

10/10 Excellent

Susan and Philip K.

Liked: Cleanliness

Already dreaming of a return stay

Great location, we walked everywhere. The unit was well stocked with everything and well thought out. There were plenty of toiletries, even sunscreen; and great to have beach chairs and towels. Kitchen had everything we needed. Clean, comfortable, convenient. It was our first time in Key West, and if we ever make it back, we want to be here. The only downside was our assigned parking space. It was a bit of a walk from the unit - which we thought maybe was a perk because we realized we were in the shade, and we only used the car once all week. However the Cuban Mahagony tree we were underneath drops large, hard as rocks seed pods, and we were dismayed to find two dents to our vehicle. Beware the tree!
Stayed 7 nights in Apr 2023

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