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Entire condo

THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard!

Condo with a water park, 6-minute walk to Duval Street

Photo gallery for THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard!

Fridge, microwave, oven, stovetop - THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard! (Key West)
Property grounds - THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard! (Key West)
TV - THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard! (Key West)
A heated pool - THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard! (Key West)
2 bedrooms, iron/ironing board, free WiFi, bed sheets - THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard! (Key West)
In the heart of Old Town Key West, The Quarterdeck offers a vibrant retreat with colorful patterns and comfortable furnishings. Relax on the sunny deck with ocean views or unwind in the community pool just a block away from Fort Zachary's beach. With ample seating for your group, this condo features an open floor plan, fully equipped kitchen and designated parking space.

Reviews

9.4 out of 10
Exceptional

Entire condo

2 bedrooms1 bathroomSleeps 4680 sq ft

Popular amenities

  • Dryer
  • Washer
  • Pool
  • Kitchen
  • Parking available
  • Outdoor Space

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.

THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard!

PLEASE BE AWARE...
We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nights if your arrival is 12/22 or before.

COMFORT AND VALUE IN TRUMAN ANNEX…
This newly renovated 2nd floor two bedroom condo is located in The Shipyard, a neighborhood of Truman Annex in the heart of Old Town Key West! Colorful, fun patterns fill the rental with life while the furnishings provide a comfortable gathering space for your group. The sunny deck overlooks the distance views of the ocean through the lush trees but can also be a shady retreat with the help of an awning.  This unit is accessed via one flight of stairs.
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE

FURNISHINGS…
The Quarterdeck’s open floor plan and ample seating provides the perfect space for your group to enjoy together. Curl up on the couch and watch a movie on the flat screen, gather around the dining table to play a game or cook together in the fully equipped kitchen!

SLEEPING ARRANGEMENTS…
Both guest rooms have a comfortable queen bed with extra drawers built into the bed frames for maximum storage space! Each room has a closet with lots of hanging space a flat screen TV, tile throughout and new paint for a fresh, clean feel. 

DETAILS AND AMENITIES…
Settled in the manicured, gated community of The Shipyard, this location offers guests a peaceful spot to relax just a block from all the action! You will be in walking distance from Fort Zachary’s gorgeous beach and picnic area, Duval Street, Mallory Square and more! The Shipyard also offers a beautiful community pool lined with lounge chairs perfect for soaking up the sun. Parking is always an issue in Old Town, but this condo comes with its own designated parking space (vehicle cannot exceed 18 ft.)

OUTDOOR LIVING…
Open the French doors to the back deck letting in the great breezes and sun rays that fill the space throughout the day. This wonderful extension to the living space has a table for two where you can have your morning coffee or enjoy a cocktail after a long day of exploring. On hot summer days pull out the awning to push back the sun so you can enjoy the views without sitting in the direct sunlight.

PETS...
The is not a pet friendly home.

MULTI MONTH RESERVATIONS...
For monthly reservations, the following fees will be added PER MONTH:
Mid-stay clean

BOOKING DATES...
This home is only available as a monthly rental (28 night minimum) as of Dec 23, 2025. We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.

PARKING!
This home does offer parking for one vehicle (cannot exceed 18 ft), but oversized trucks and extra large SUV's are not permitted and will have to park outside of this community.

CANCELLATION...
Bookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.

CONCIERGE SERVICES...
Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!

COME STAY A WHILE...

Property amenities

Pool/Spa

  • Communal pool
  • Heated pool

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Concierge services
  • Iron/ironing board

Location highlights

  • In the city center
  • Near a hospital
  • Near the marina
  • Near the sea

Things to do

  • Heated pool
  • Water park
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Jet skiing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Water skiing nearby
  • Windsurfing 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

  • Garden
  • Gated community
  • Unit size: 680 square feet

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Exterior detail

THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool!

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
9.6 out of 10, Exceptional, 21 reviews
THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool!

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

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 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
Property Registration Number 25230-132478

Property is also known as

"the Quarterdeck" Colorful Comfortable 2ba/ Condo
"the Quarterdeck" Colorful Comfortable 2ba/ 1Ba Unit Shipyard
"the Quarterdeck" Colorful Comfortable 2ba
"the Quarterdeck" Colorful Comfortable 2ba/ Condo
"the Quarterdeck" Colorful Comfortable 2ba/ 1Ba Unit Shipyard
"the Quarterdeck" Colorful Comfortable 2ba/ Condo
"the Quarterdeck" Colorful Comfortable 2ba/ 1Ba Unit Shipyard
2450-154441
"the Quarterdeck" Colorful Comfortable 2ba

About the neighborhood

Map
Key West, Florida

What's nearby

  • Ernest Hemingway Home and Museum - 6 min walk - 0.4 miles
  • Duval Street - 6 min walk - 0.4 miles
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.4 miles
  • Mallory Square - 11 min walk - 0.6 miles
  • Southernmost Point - 14 min walk - 0.8 miles

Getting around

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

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Moondog Cafe & Bakery - ‬8 min walk
  • ‪Kaya Island Eats - ‬7 min walk
  • ‪Santiago's Bodega - ‬6 min walk

Frequently asked questions

Does THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard! have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard! pet-friendly?

No, pets are not allowed at this property.

What time is check-in at THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard!?

Check-in begins at 4:00 PM.

What time is check-out at THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard!?

Check-out is at 10:00 AM.

Where is THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard! 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. Mallory Square and Fort Zachary Taylor Historic State Park are also within 15 minutes.

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Reviews

THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard! Reviews

9.4

Exceptional

9.8

Cleanliness

9.8

Location
Rating 10 - Excellent. 65 out of 89 reviews
Rating 8 - Good. 19 out of 89 reviews
Rating 6 - Okay. 3 out of 89 reviews
Rating 4 - Poor. 1 out of 89 reviews
Rating 2 - Terrible. 1 out of 89 reviews

Reviews

10/10 Excellent

Kyle C.

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

Great location

Great property in an awesome location.
Stayed 7 nights in Dec 2021

10/10 Excellent

Peggy W.

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

Get away from the cold

This is our 2nd time staying at this place. We love the location and the size of the units. The 2 balconies are a plus for us. Definitely would book again.
Stayed 12 nights in Dec 2024

10/10 Excellent

Patti O.

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

Keywest Vacation

Everything went smoothly, no problems. We enjoyed our stay.
Stayed 7 nights in Apr 2022

10/10 Excellent

Verified traveler

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

Perfect location

Property nice & clean & location was very well maintained & in the perfect location for what we wanted to do. The steps going up would not be good for everyone, but was fine for us.
Stayed 7 nights in Jan 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Sarah S., Kill Devil Hills

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: This was our 2nd time staying in the Truman Annex Condos. We love this location. Quiet area and walking distance to everything.

10/10 Excellent

Dana G., Tampa, FL

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

Cozy hideaway near the quiet end of Duval.

This property is fantastic. Dedicated parking, 1 minute walk to the Duval Loop free bus. 5 minute walk to all the entertainment of Duval. Attractive, spacious condo. Easy check-in. Very clean and quiet. Large kitchen and living room. The saltwater pool is very private and relaxing. Would love to stay here again!
Stayed 7 nights in Jun 2019

10/10 Excellent

Verified traveler

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

Very nice. Great location.

The property was nice, clean & bright. Just know it’s located at Shipyard condominiums. If you can’t do stairs it’s probably not for you.
Stayed 7 nights in Mar 2023
This review was submitted before 2018 and has not been verified.

10/10 Excellent

John P.

Wonderful Rental

Truman Annex is a great location in Key West. Its a long block away from Duval St, 4-5 blocks from Mallory Square, 8-10 blocks from Southern Most Point. It is very quiet, peaceful, has a nice pool. This unit is a clean, bright 2 bedroom unit. Very well maintained, has an abundance of towels, extra linens, and kitchen needs (plates, utensils, cooking items, etc). The washer/dryer does come in handy to take care of the dirty things from walking about in the heat or going to the beach. WiFi was safe, secured and fast to do on-line work. We were very impressed and had a wonderful stay. A great value.

10/10 Excellent

Shannon C., Woodstock, GA

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

Perfect Peaceful Location

My husband and I were visiting for our second trip to Key West this year and chose this gem! It was perfect for us two and probably could have had another couple join. The condo had two balconies!! The front facing was so awesome for watching the sunrise. The rear balcony was beautiful showing old warehouses with murals and palm trees for scenery. Several times while we were sitting, we saw some of the largest iguanas that were just so cool to look at sitting in the palms. The property is extremely well maintained with a cute little pool area. The condo itself had comfy beds & pillows and the coldest AC I have ever experienced in Florida. All TVs had cable/satellite and the kitchen really made cooking easy with all necessary accoutrements. The location was walking distance to just about anything you want to do in old town Key West and either an Uber ride away (so inexpensive) or golf cart ride to anyplace else. Highly recommend this location.
Stayed 7 nights in Aug 2022
This review comes from a trusted partner site and has not been verified.

8/10 Good

Janet A.

Quarterdeck review

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 nice visit. The onsite parking was definitely a plus. The central location made walking around quite easy. It’s usually nice to have a few things in the cupboards like salt and pepper, garlic salt oil and vinegar, coffee filters......

6/10 Okay

Philip W.

Liked: Cleanliness, check-in, communication, location

Tired

We rented this unit for the month of January in 2025. In a word, the unit is tired. The living room couch is totally beat and should have been replaced years ago. The tile floor is badly scratched and stained. The kitchen is dark as only one of three lights was working. There was an odd assortment of mismatched water glasses, one of which was cracked. There were five totally gross plastic wine glasses. The bathroom is tight with the top of the toilet tank the only place to put your toiletries, a couple of shelves above would be a big help. The entry foyer on the first floor is tight and leads to a difficult stair to the second floor. This is not a unit for anyone with mobility issues. We loved the location, an easy walk to Duval Street and 15 minutes to the beach. We would stay at the Truman Annex again, just not this unit.
Stayed 30 nights in Jan 2025
This review comes from a trusted partner site and has not been verified.

8/10 Good

Michael V.

Great Key West Location

Rating Details: The property manager was very helpful. The vacation rental was spotless. 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: Nice quiet condo just a few blocks off Duval and from the waterfront. Plenty of space for a couple or family with one child. Best of Key West Rentals was great in setting up excursions and tours.

10/10 Excellent

Autumn C.

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

Cute little getaway

My fiancé and I had a great time at this cute little apartment! The 2 decks were great to hang out on, lots of space, and the community had beautiful walkways and pools. We will absolutely stay here again. The property managers were helpful and helped us arrange a lot of our activities, and gave us advice about the best times to do so with the weather.
Stayed 10 nights in Aug 2024
This review comes from a trusted partner site and has not been verified.

8/10 Good

A guest from Key West, FL

Super Clean Rental in Truman Annex

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: This was in a great location - simple accommodations with excellent location. The only negative was not about this particular condo - just the overall complex - the pool is super small and basic for the number of condos in the Shipyard. We were here during a slow time of year and the pool was super crowded with no chairs available - says only 25 person capacity...the overall occupancy of the complex is in the hundreds at least. I recommend this property for the cleanliness and the location, not for the amenities of the overall complex.
This review comes from a trusted partner site and has not been verified.

8/10 Good

A guest from Key West, FL

Super Clean Rental in Truman Annex

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: This was in a great location - simple accommodations with excellent location. The only negative was not about this particular condo - just the overall complex - the pool is super small and basic for the number of condos in the Shipyard. We were here during a slow time of year and the pool was super crowded with no chairs available - says only 25 person capacity...the overall occupancy of the complex is in the hundreds at least. I recommend this property for the cleanliness and the location, not for the amenities of the overall complex.

10/10 Excellent

jessica p.

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

Loved it, great space

This was perfect for our girls trip. We stayed 7 days. The unit was spacious and very bright. The neighborhood was great, everything was mins away. Duval st was just around the corner, we walked every where the first few days and rode bikes the last couple. It was a great experience. Definitely recommend renting bikes or mopeds to explore the island. It was so much fun. Beaches are between 7 and 10 min away, enjoyed both smathers and ft Zachary beach. The property manager Whitney was super responsive, very friendly and helped with a minor issue fast. Definitely appreciated. Would definitely book this exact location again. Highly recommend 😊
Stayed 7 nights in Jul 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Robert T.

Always a NiceStay at the Shipyard

Rating Details: The property manager was very helpful. The vacation rental was spotless. 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: Very clean and nicely renovated. Pleased with the property manager. She was very helpful throughout our stay .
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Crystal A.

Good Stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: It was a great stay. I would have loved it way more if some of trees were cut back just a little. It was very clean.
Stayed 9 nights in Mar 2024
This review comes from a trusted partner site and has not been verified.

8/10 Good

John D.

Reasonably priced unit in Truman Annex

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: We stayed in the Quarterdeck for a month. We had two issues when we arrived that Truman & Company responded to immediately; the plumbing issue was resolved in less than 24 hours while the cable box issue took 3 days but that was because we had to wait for an appointment with the cable company. We loved the location, however, the rental unit needs some updating. The living room sofa needs to be replaced. The mattresses in both bedrooms are beginning to sag in the middle. The bathroom lacks counterspace and storage; the faucet in the shower was the plumbing issue and had to be replaced. The kitchen was adequate. The vacuum didn't pick up the dirt on the floor. All in all we enjoyed our stay and Truman & Company was wonderful to work with.
Stayed 28 nights in Jan 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

A guest from Scarborough, ME

Great stay!

Rating Details: 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 loved the location!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Michele Y.

Quarterdeck was awesome

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: Everything was wonderful! Place was super clean, cozy and perfect!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

brigette

Great stay in Truman!

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: Perfect for our winter stay in beautiful Key West! Location and condo were ideal for our party of 3.
Stayed 7 nights in Dec 2023

10/10 Excellent

Jim J.

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

Would Stay Again

Love being in the Truman Annex.
Stayed 29 nights in Nov 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Patricia A., Noblesville

Private and Secure

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: My husband and I stayed in the Quarterdeck for 2 weeks beginning August 19th. We like this unit because it is an end unit and seems very quiet. Also, there is a secure place to park your car and the parking lot is gated. Just a couple of blocks away and you are walking distance to restaurants and things to do in Old Town. The condo has an excellent kitchen area and a very good washer/dryer. It is a second floor unit so only downside is if you can’t climb stairs. I would rent this unit again when coming back to Key West.

10/10 Excellent

Dale H.

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

Nice Place - Convenient to Duval

We found the Quarterdeck to be clean and exactly as advertised. It is close to Duval and within walking distance of most major Key West attractions.
Stayed 7 nights in Jun 2023