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Entire condo

Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach

Condo with kitchen, 6-minute walk to Duval Street

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Beach - Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach (Key West)
Smart TV, DVD player, books - Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach (Key West)
Outdoor dining - Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach (Key West)
Pool - Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach (Key West)
Property grounds - Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach (Key West)
In the heart of Truman Annex, this fully furnished condominium offers a serene retreat with a private balcony overlooking the swimming pool and another facing the courtyard. Enjoy comfortable outdoor furniture, a full kitchen, and two spacious bedrooms with custom bedspreads. The property is steps from Duval Street's vibrant action and sunset celebrations.

Reviews

9.6 out of 10
Exceptional

Entire condo

2 bedrooms1 bathroomSleeps 6

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Add dates for prices

About this property

Entire place

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

Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach

This condo has been grandfathered in to allow for weekly rentals. One of only a few with City approval. This 2 bedroom, fully furnished condominium with brand new living room furniture and dining room table set is located in the Truman Annex, a gated community of private homes and condominiums. Located inside the Truman Annex is Truman's Little White House Museum, Eco-Discovery Center, Water Park for small children and Fort Zachary State Park. Freshly painted and upgraded with custom bedspreads, new key west style furniture, all flat screen televisions, comfortable outdoor furniture, queen bed with two twin beds that are easily converted to a king sleeper, a sofa sleeper, full kitchen, living room, washer/dryer and two private balconies one overlooking the swimming pool and the other facing the courtyard. Free assigned parking spot and Free Wi-fi. Steps from famous Duval Street, sunset celebration and all the downtown action one desires. High demand book early.

Property amenities

Ski

  • Close to skiing

Pool/Spa

  • Communal pool

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Car not required
  • Parking on site

Kitchen

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

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Towels provided

Living spaces

  • Living room

Entertainment

  • Books
  • DVD player
  • Smart 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

Location highlights

  • In the city center
  • Near a health/beauty spa
  • Near a hospital
  • Near the marina

Things to do

  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Water skiing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • No carbon monoxide detector or gas appliances (host has indicated there are no carbon monoxide detectors or gas appliances on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 27

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

Check-out instructions

The host requires you complete the following before checking out:
Load the dishwasher
Strip any used beds and gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights, lock the doors, and return the keys
Full detail check-out instructions are inside the owners manual.
Make sure you text me @ 305-797-5263 copy of both sets of keys.
The garbage and recycle cans are located next to your parking bay.
Failure to complete these may result in a negative review from the host.

Pets

Pets not allowed

Children and extra beds

Children are welcome

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 indicated there are no carbon monoxide detectors or gas appliances on the property
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 has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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

We should mention

A car is not required for transportation to and from this property

Property is also known as

Early December Rent Five Days get Two Days Free-discount Applied
Early December Rent Five Days get Two Days Free-discount Applied

About the neighborhood

Located in Key West, this condo is in the city center. 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 Florida Keys Eco - Discovery Center are also worth visiting. Be sure to check out the area's animals with activities such as game walks and birdwatching. Visit our Key West travel guide
View more Condo Rentals in Key West
Map
FL, Key West

What's nearby

  • Duval Street featuring signage
    Duval Street
    6 min walk - 0.5 km
  • Ernest Hemingway Home and Museum featuring heritage elements and a house
    Ernest Hemingway Home and Museum
    6 min walk - 0.5 km
  • Fort Zachary Taylor Historic State Park showing military items, heritage elements and interior views
    Fort Zachary Taylor Historic State Park
    8 min walk - 0.7 km
  • Mallory Square featuring outdoor art, a square or plaza and signage
    Mallory Square
    11 min walk - 1.0 km
  • Florida Keys National Marine Sanctuary
    5 min walk - 0.4 km

Getting around

  • Key West Intl. Airport (EYW)
    19 min drive

Restaurants

  • Green Parrot Bar
    4 min walk
  • Willie T's
    6 min walk
  • Blue Heaven
    8 min walk
  • Mangoes Restaurant
    7 min walk
  • Moondog Cafe & Bakery
    8 min walk

Frequently asked questions

Does Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach have a pool?

Yes, this property has a pool.

Is Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach?

Check-in begins at 4:00 PM.

What time is check-out at Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach?

Check-out is at 10:00 AM.

Where is Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach located?

Located in Old Town Key West, this condo building is within a 10-minute walk of We Cycle Key West, Duval Street, and Ernest Hemingway Home and Museum. Florida Keys Beaches and Mallory Square are also within 15 minutes.

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Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 104 out of 131 reviews
Rating 8 - Good. 18 out of 131 reviews
Rating 6 - Okay. 7 out of 131 reviews
Rating 4 - Poor. 2 out of 131 reviews
Rating 2 - Terrible. 0 out of 131 reviews

9.4

Cleanliness

10

Location

9.4

Property conditions & facilities

Reviews

10/10 Excellent

David O.

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

Great Stay

Great location, close to the action on Duval St as well as the water front.
Stayed 9 nights in Oct 2024

10/10 Excellent

Michael G.

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

Awesome stay at the Truman Annex

The stay at the Truman Annex was great. The location, facilities available and the staff are all commented for the nice appearance and wonderful environment.....
Stayed 8 nights in May 2024

10/10 Excellent

Amy B.

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

Great place

Love the location, couldn’t ask for a better place!
Stayed 7 nights in Oct 2023

10/10 Excellent

Bob C., Marysville, MI

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

Quiet but Close

great location and close to all the activities we were interested in
Stayed 7 nights in Nov 2023

10/10 Excellent

Jesica W.

Liked: Check-in, communication, location, listing accuracy

Great Key West getaway

Loved the place and can’t beat the price. Excellent location, walking distance to almost everything and easy for kids. Loved the pool and the fun community at Truman Annex.
Stayed 10 nights in Jul 2023

10/10 Excellent

Brian K.

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

Amazing Week

This was a great vacation and this unit/location was amazing!!! Literally walk to everything and in the complex the pool was just outside the door, 2 balconies so you could always find shade and relax
Stayed 7 nights in Aug 2024

10/10 Excellent

Missy C.

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

Perfect location

This property checked every box. The place was clean, and just the right size. Everything we needed for a two week stay was there from beach towels, linens, pans, dishes, even hand soap and dish soap was provided. The few questions I had were answered immediately. The location is absolutely perfect. Within walking distance to everything. The pool was cleaned daily and the grounds were immaculate. I highly recommend this place.
Stayed 14 nights in Mar 2025

10/10 Excellent

Sue D.

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

Perfect location and host

Roberta was wonderful to work with. Extremely responsive. The unit was spectacularly clean. We could not have asked for a better location.
Stayed 7 nights in Oct 2024

10/10 Excellent

Mitchell K.

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

Close to everything and lots of friends to be made

Enjoyed the closeness of the unit to all things downtown and proximity to pool with so many friendly people
Stayed 7 nights in Oct 2023

10/10 Excellent

Michael R.

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

summer family vacation

This is a very nice place in a very good location close to everything. Beaches are close by (walkable, less than 1 mile). Higgs beach was probably the best one. Plenty of shopping and restaurants on Duval St. Overall, it was a great Key West vacation.
Stayed 7 nights in Jul 2023

10/10 Excellent

Jonathan M.

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

Walking distance to Duval

Property is exactly as described. Easy check in/out. Walking distance to Duval.
Stayed 7 nights in Jun 2024

10/10 Excellent

Carolynn M.

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

Great location… nice property

We had a great stay… loved being overlooking the pool as it was quiet and pretty. Lots of Key West chickens about and nice to hear the national anthem at 8 am every morning from the nearby military base. Many good restaurants within walking distance and the parking for a car/golf cart was really handy. The unit is cute and clean. Everything you need is available. Loved the two porches although they were being painted for much of our stay. The unit could do with a spot of paint but overall it was wonderful.
Stayed 9 nights in Sep 2024

10/10 Excellent

Linda M.

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

Close to everything

We had an amazing time at this condo. The place had everything we needed. Having two balconies and one that overlooked the pool was a plus. We walked everywhere, this condo was right in the middle of town. You just needed to decide everyday go right or left. Take a Sunset cruise!!! Visit Hemingway house and Butterfly Exhibit. Oh yeah and Irish Kevin’s on Duvall St. Thank you Roberta.
Stayed 7 nights in Oct 2024

10/10 Excellent

Peggy W.

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

Truman annex

It was clean, spacious for a 2 bedroom. It had 2 balconies which we loved. Had breakfast every morning outside over looking the pool. The beds were comfortable. The unit came with a washer and dryer which I think is a bonus. Roberta was very easy to get a hold of and responded very quickly no matter what or when I asked questions. The property was well maintained and quiet. Great location for us since we prefer that side of Key West.
Stayed 12 nights in Dec 2023

10/10 Excellent

Susan D.

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

Great location, loved two balconies

The unit is more dated than others I’ve stayed in, but met all of our needs. Well equipped, plenty of towels and extra bedding. We loved having two balconies to relax on. The location is great within the complex, right next to the pool, it was easy to look out and see how busy it was. It’s an end until which makes it quieter, and the bedrooms are on the outside wall thankfully because the walls are thin and our neighbors were loud talkers. Super quiet at night. Thank you!
Stayed 7 nights in Oct 2023

10/10 Excellent

Stacey C.

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

Excellent Location

You can't beat this location. It is quiet, safe, and within walking distance from nearly everything you want to do in Key West. We saw a manatee at the waterfront right next to the complex the second night we were there. We also spent several days at Fort Zachary Taylor State Park, which is walking distance from the property if you don't have a lot of items to carry. This is a great spot for families. Despite the heat, we also spent a lot of time reading on the balcony overlooking the pool. The pool is clean and very quiet during this time of year. There were several points during our 10 day trip when we had the pool to ourselves. The complex property is immaculate and everyone was very friendly. Property manager was responsive and helpful.
Stayed 10 nights in Jul 2024

10/10 Excellent

Molly D.

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

A perfect location for seeing Old Town on foot...

We loved the architecture and location of the Shipyard Condos. We were revisiting Key West after 30 years and wanted to do it on foot. This sweet place was central to all Old Town had to offer: we walked to the beach at Fort Zachary Taylor, to the great old aquarium, sat on benches across from the Green Parrot listening to their live music, had Cuban lunch with the roosters. We caught the air-conditioned Duval Loop free bus when it got too hot to enjoy walking. We appreciated Roberta making it possible for an early arrival to the condo; were grateful to be close to the pool and enjoyed both verandas at dusk and dawn. Our stay was too short and we intend to do it again!
Stayed 5 nights in Oct 2023

4/10 Poor

Susan B.

Liked: Check-in, location, listing accuracy
Disliked: Cleanliness, communication

Tatty and tired property with a lot wrong with it

The Truman complex is lovely, great location and very well maintained. But the property is very tired (as per other reviews) and needs a major overhaul to bring it up to a reasonable standard. The experience was pretty awful. From getting the dates on our booking messed up (and host was no help to get this resolved - had to escalate through to Directors at VRBO to get help), through to broken floor tiles in every room, fridge door held on by sticky tape, dirty and discoloured kitchen sink, dangerous looking electrics, wall tile hanging off the wall in the bathroom, dirty bottom bed sheet in the master bedroom, sofa bed that you cannot sleep on as the mattress is so bad and the springs make it totally impossible to sleep on. Made the host aware of all these issues and she did nothing.
Stayed 4 nights in Apr 2024

10/10 Excellent

Stacie K.

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

Excellent Location

Safe location, great for families! Steps from the community pool. Plus a really nice neighborhood walk to local attractions like the aquarium and museums.
Stayed 10 nights in Jun 2025

10/10 Excellent

Jamie W.

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

Great location

Love Key West and this is a fantastic location in the middle of everything, making all entertainment very walkable if you choose. Great pool and very friendly people.
Stayed 7 nights in Apr 2025

10/10 Excellent

Kenneth L.

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

Always great

Great stay, great unit and great location. Host was great as always
Stayed 12 nights in Apr 2025

10/10 Excellent

Melissa P.

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

Great location and property!

Great location and property!
Stayed 7 nights in Aug 2022

10/10 Excellent

Kim R.

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

Great spot

Super location, easy check in, great spot for a week of vacation.
Stayed 7 nights in Feb 2022

10/10 Excellent

Elizabeth M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Just as advertized !
Stayed 7 nights in May 2025

10/10 Excellent

Joey C.

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

Our Favorite Place

This property was a wonderful stay. The beds were comfy, the showers were refreshing, the air conditioning was cold. Perfect place to come "home" to after a hot day out on the water. A dip in the pool was greatly enjoyed after getting used to the initial chill of the water, a little colder than previous years, but tolerable. We look forward to more visits to this complex in the coming years!
Stayed 7 nights in May 2025