Upscale end unit home @ Truman Annex close to Duval St in Key West

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Entire condo

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Where to?

Dates

May 2025

June 2025

Overview
Amenities
Policies
Location
Host

Exceptional

Entire condo

1 bedroom1 bathroomSleeps 3

Popular amenities

Dryer
Washer
Parking available
Kitchen
Air conditioning

Explore the area

Key West, Florida

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

Room options

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.

View more Condo Rentals in Key West

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

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.

Property manager

Key West Property Services, LLC

Languages

English

Similar properties

Pool
Kitchen
Washer
Dryer

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
Microwave
Oven
Refrigerator
Stovetop
Toaster

Bedrooms

Bedroom
Bedsheets provided
Sofa bed

Bathroom

1 bathroom
Hair dryer
Shower
Towels provided

Living spaces

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

This property doesn't allow pets

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.

Will I be able to park at this condo?

No, there isn't parking available at the 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.

What amenities will couples enjoy at Upscale end unit home @ Truman Annex close to Duval St?

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

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

No, but this condo does have a heated pool.

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 this condo have connecting rooms?

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 unit 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

Exceptional

10/10

Cleanliness

10/10

Staff & service

10/10

Amenities

8.8/10

Property conditions & facilities

10/10

Eco-friendliness

8/10 Good

John M.

Mar 24, 2025

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.

Dec 15, 2024

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

Dec 8, 2024

Liked: Cleanliness

Stayed 7 nights in Nov 2024

10/10 Excellent

Teresa C.

Nov 19, 2024

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.

Nov 13, 2024

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.

Sep 21, 2024

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

Aug 17, 2024

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.

Aug 15, 2024

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.

Jul 20, 2024

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.

May 11, 2024

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.

May 4, 2024

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.

Dec 10, 2023

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

Nov 14, 2023

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

Nov 9, 2023

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.

May 8, 2023

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.

Dec 28, 2022

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.

Dec 10, 2022

Liked: Cleanliness

Mice

Nice

Stayed 7 nights in Dec 2022

10/10 Excellent

Thomas C., Cleveland

Dec 7, 2022

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.

Sep 17, 2022

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.

Sep 11, 2022

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.

Aug 31, 2022

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.

Aug 28, 2022

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.

Aug 6, 2022

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.

Aug 2, 2022

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