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Upscale end unit home @ Truman Annex close to Duval St

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Beach nearby
Exterior
Fridge, microwave, oven, stovetop
Property grounds
A heated pool

Reviews

10 out of 10
Exceptional

Entire condo

1 bedroom1 bathroomSleeps 3

Popular amenities

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

Explore the area

Map
Key West, Florida
  • Duval Street
    ‪6 min walk‬
  • Ernest Hemingway Home and Museum
    ‪7 min walk‬
  • Mallory Square
    ‪9 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪15 min drive‬

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About the neighborhood

Key West

Seaside stay .Within a 10-minute walk of this Old Town Key West condo, you'll find Duval Street and Fort Zachary Taylor Historic State Park. Mallory Square and Jackson Square are also within half a mile (1 km).
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What's nearby

  • Duval Street - 6 min walk - 0.3 miles
  • Fort Zachary Taylor Historic State Park - 9 min walk - 0.5 miles
  • Ernest Hemingway Home and Museum - 9 min walk - 0.5 miles
  • Mallory Square - 11 min walk - 0.6 miles
  • Southernmost Point - 16 min walk - 0.9 miles

Getting around

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

Restaurants

  • ‪Margaritaville - ‬7 min walk
  • ‪Blue Heaven - ‬9 min walk
  • ‪Green Parrot Bar - ‬6 min walk
  • ‪Willie T's - ‬6 min walk
  • ‪Mangoes Restaurant & Island Cuisine - ‬7 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

Property manager

Key West Property Services, LLC

Languages

English

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Property amenities

Beach

  • Beach nearby

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

  • Smoke-free property

Services and conveniences

  • Housekeeping (limited availability)
  • Iron/ironing board
  • Phone

Location highlights

  • Near a hospital
  • Near the sea

Things to do

  • Bicycles
  • Golf
  • Heated pool
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby

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

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.

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

How close is Upscale end unit home @ Truman Annex close to Duval St to the airport?

This condo is 4.3 mi (15-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does Upscale end unit home @ Truman Annex close to Duval St have an airport shuttle?

Airport shuttle services are not available at this condo.

How close is Upscale end unit home @ Truman Annex close to Duval St to the beach?

This condo is a short 11-minute walk from Florida Keys Beaches and 14-minute walk from Truman Beach. Don't forget your sunscreen!

Does Upscale end unit home @ Truman Annex close to Duval St offer free breakfast?

This condo does not offer free breakfast.

Is there a casino at Upscale end unit home @ Truman Annex close to Duval St?

No, there is no casino at this condo.

What time is check-in at Upscale end unit home @ Truman Annex close to Duval St?

Check-in begins at 4:00 PM.

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

Free parking is not available at this condo.

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

Yes, there's a heated pool.

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

There are no spa services available at this condo.

How close is Upscale end unit home @ Truman Annex close to Duval St to downtown Key West?

This condo is 0.2 mi away from Key West.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 109 out of 115 reviews
Rating 8 - Good. 6 out of 115 reviews
Rating 6 - Okay. 0 out of 115 reviews
Rating 4 - Poor. 0 out of 115 reviews
Rating 2 - Terrible. 0 out of 115 reviews

10/10

Cleanliness

10/10

Staff & service

10/10

Amenities

8.8/10

Property conditions & facilities

10/10

Eco-friendliness

Reviews

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

10/10 Excellent

Jessica C.

Liked: Cleanliness

best location

this was our fav location yet and the bicycles were a great addition.
Stayed 7 nights in Dec 2022

10/10 Excellent

David L.

Liked: Cleanliness

Mice

Nice
Stayed 7 nights in Dec 2022

10/10 Excellent

Thomas C., Cleveland

Liked: Cleanliness

Awesome stay

Great location, very clean and updated. I would love to make this a regular stay. I have stayed in the same complex for years with friends, this time it was just my wife and I this condo was perfect.
Stayed 7 nights in Nov 2022

10/10 Excellent

Michelle Beaumont O.

Liked: Cleanliness

Great week in Key West

The condo was adorable and within walking distance to all the fun places on Duval. Truman Annex neighborhood was very pretty and quiet, loved the pool to cool off. Great communication with Tracey. Thank you, we will be back!
Stayed 7 nights in Sep 2022

10/10 Excellent

Donna C.

Liked: Cleanliness

Clean, updated condo

The unit was updated and clean. Had everything we needed and a large balcony. Location was close to Duval St, Mallory Square and Fort Zachary State park.
Stayed 7 nights in Sep 2022

10/10 Excellent

Syn S.

Liked: Cleanliness

Stay

This property is awesome! Second year in a row we have stayed there. It is clean and in a convenient spot. It was easy to communicate with the owners and they were very responsive. Hoping to go back soon!!! Would look to stay here if available.
Stayed 7 nights in Aug 2022

10/10 Excellent

Sonia V.

Liked: Cleanliness

Relaxing, peaceful

Southward Breeze was a great getaway. Walking distance to so much shopping, restaurants, museums and beach. The shared pool was perfect for those unbearably hot days. Would definitely go back!
Stayed 7 nights in Aug 2022

10/10 Excellent

Isaac D.

Liked: Cleanliness

LOVED

Planning on making key west a regular vacation spot and staying here everytime!
Stayed 7 nights in Jul 2022

8/10 Good

Kathleen V.

Liked: Cleanliness

Cozy condo with great balcony

This condo had everything you would need for your stay. I think it’s best suited for a couple, my sister and I took turns with the bed and sofa bed but neither mattress was comfortable. We enjoyed the pool which was a short walk. We didn’t cook as too many great places to eat but it was nice to have a kitchen for snacks and wine.
Stayed 7 nights in Jul 2022