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Poolside Hangover at The Truman Annex in Key West

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Photo gallery for Poolside Hangover at The Truman Annex in Key West

A water park with a slide, a water fountain, and palm trees at sunset.
A two-story house with a white picket fence, a front porch, and a small garden.
A gated community entrance with a sign for Shipyard Condominiums, surrounded by palm trees and a clear blue sky.
A deck with a table and chairs, surrounded by a white picket fence, overlooking a lush garden with palm trees and other greenery.
A living room with a television, sofa, armchair, and a dining area with a table and chairs.

Reviews

9.2 out of 10
Wonderful

Entire condo

2 bedrooms2 bathroomsSleeps 6780 sq ft

Popular amenities

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

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪8 min walk‬
  • Place, Fort Zachary Taylor Historic State Park
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪11 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 Ernest Hemingway Home and Museum. The condo includes a kitchen, a balcony, and a refrigerator.
View more Condo Rentals in Key WestOpens in a new window

What's nearby

  • Florida Keys National Marine Sanctuary - 5 min walk - 0.3 miles
  • Duval Street - 6 min walk - 0.4 miles
  • Ernest Hemingway Home and Museum - 8 min walk - 0.4 miles
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.4 miles
  • Mallory Square - 12 min walk - 0.7 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
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Rams Head Southernmost - ‬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.

Poolside Hangover at The Truman Annex in Key West

This is an amazing second floor two bedroom TWO BATH condo over by the gorgeous pool. Fully equipped for you to enjoy your time away from it all. Enjoy mornings out on the rear deck overlooking the refreshing community pool. Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and close to all of the Old Town Key West attractions. The properties are also located 1/4 mile from one of the best beaches on the island. All properties are outfitted with washer/dryer, pots & pans, towels & linens, condo has central air conditioning, off street parking and community pool access.
Please note: This property is monthly rental - the minimum rental period is 28 nights
The condo is air-conditioned and features a kitchen, 2 bathrooms, and a balcony, and there's space to spread out with 2 bedrooms. Guests can expect to find free WiFi. Other standard amenities include a washer/dryer, a coffee maker, and an ironing board.

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Property amenities

Pool/Spa

  • Communal pool

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Onsite parking includes off-street options

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Outdoor areas

  • Balcony

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center

Things to do

  • Ecotours 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 not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Unit size: 780 square feet

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 not indicated whether there is a smoke detector on the property
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
  • 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.
  • 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.
  • 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.

Property is also known as

Poolside Hangover in the Truman Annex
Poolside Hangover @ the Truman Annex Key West
Poolside Hangover @ the Truman Annex Private vacation home
SIZZLING SUMMER DEAL!! Poolside Hangover @ the Truman Annex
20% Off Summer Special Poolside Hangover @ the Truman Annex
2698-193322

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 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 Poolside Hangover at The Truman Annex in Key West?

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.

What do couples enjoy most about Poolside Hangover at The Truman Annex in Key West?

Couples will appreciate amenities at this condo, including a kitchen in each condo plus a kitchen and free WiFi in some.

Does Poolside Hangover at The Truman Annex in Key West have a hot tub?

No, there isn't a spa tub at this condo.

Does this condo include breakfast service?

No, this condo doesn't offer breakfast.

Will this condo allow pets to stay free of charge?

No, pets aren't allowed at this condo.

Does Poolside Hangover at The Truman Annex in Key West 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 4.1 mi away (19 minutes by car).

Are there rooms with balconies at Poolside Hangover at The Truman Annex in Key West?

Yes, every condo at Poolside Hangover at The Truman Annex in Key West comes with a balcony.

Poolside Hangover at The Truman Annex in Key West Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 23 out of 36 reviews
Rating 8 - Good. 9 out of 36 reviews
Rating 6 - Okay. 4 out of 36 reviews
Rating 4 - Poor. 0 out of 36 reviews
Rating 2 - Terrible. 0 out of 36 reviews

9.4/10

Cleanliness

Reviews

Verified review

8/10 Good

Gordon E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
comfortable and clean.disappointed the pool closed for two days, this is only reason not 5 star.
Stayed 7 nights in Dec 2025
Verified review

10/10 Excellent

TJ L.

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

Key west truman annex

Check in and checkout were super smooth.
Stayed 7 nights in Apr 2025
Verified review

10/10 Excellent

Chris V.

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

Great place to stay

Had a wonderful vacation, third time at Truman Annex. Can’t wait for the fourth!
Stayed 7 nights in Mar 2024
Verified review

8/10 Good

Jeff B.

Liked: Check-in, location, listing accuracy

Adequate and Comfortable

Comfortable beds. Great location.
Stayed 7 nights in Nov 2023
Verified review

10/10 Excellent

Teresa W.

Liked: Cleanliness, communication, location, listing accuracy

Great except for getting the keys at a different location

Very nice, clean great location
Stayed 14 nights in Jan 2023
Verified review

10/10 Excellent

Michaelanne R.

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

Wonderful condo

Exactly as advertised - very easy checkin and even graciously accommodated a late check out due to a late flight. Location is phenomenal. Gated access appreciated. Condo unit itself very well stocked. We felt right at home for the week. Would definitely rent again!
Stayed 7 nights in Dec 2024
Verified review

10/10 Excellent

Jean R.

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

Lovely stay in Key West

Had a delightful time in Key West. The condo was perfect for 4 women and clean as a whistle. It was easy walking distance to most attractions and Duval Street. Close to the swimming pool if you are willing to take a break. We would definitely recommend this condo and realty company.
Stayed 7 nights in Jan 2024
From a partner site

10/10 Excellent

Julia L.

Beautiful condo in Shipyards

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: Very nice unit. Comfortable, clean, nice decor. Had everything needed for a great stay.
From a partner site

8/10 Good

harry c.

February in Paradise

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We've stayed at many condos in Shipyard, this one was 'typical'. The only real negative was the furniture (old, used and uncomfortable)
Verified review

6/10 Okay

Nancy R.

Liked: Cleanliness, check-in, communication, location

Great location

Great location & good bones, but getting a bit worn & dated. The unit is 2 bedroom & 2 bath, but it was not ‘equipped’ for 4. Only 2 porch chairs, 3 beach chairs, only 1 tiny towel bar in hall bath and minimal eating utensils. It was very clean overall (one shower needs attention) & the furnishings were quality @ one time.
Stayed 7 nights in Jan 2025
Verified review

10/10 Excellent

Regina H.

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

Great location!

For our 3rd trip to Key West, we wanted to be close to swimming & snorkeling at Ft Zach Taylor and all that Old Town has to offer. A couple family members were joining us so 2BR & 2baths were essential. We didn't mind the stairs & appreciated that while the pool was nearby, being upstairs still provides plenty of privacy on the back patio. Decor is beachy & charming. Ceiling fan in 2nd bedroom is noisy & pillows were flat but otherwise, had everything we needed, including beach towels, folding chairs & a great blender ;-)
Stayed 7 nights in Jun 2022
From a partner site

6/10 Okay

Sherry D.

Great location

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 have rented from Compass many times and always have had a good experience.This home was well stocked, close to the community pool, and in a quiet area. While this home was clean and within walking distance to most that Key West has to offer, it could use some updates. The cushions on the living room furniture were dingy, the fan in the second bedroom was so noisy that you could not use it. The towels in both bathrooms were worn and the pillows were flat and uncomfortable. I have rented from Compass in the past and had a great experiences, from the initial booking to departure. This location is not up to par with their other locations. With some updates, I would most certainly recommend Poolside Hangout and would definitely recommend Compass for all of your Key West rental needs.
Verified review

10/10 Excellent

Gina P.

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

Spring Break in Key West

This was the first time my family has been to Key West and we had a fantastic time! Our condo in The Truman Annex was the perfect space for my family. I have 2 very tall teenage sons and having 2 bedrooms and 2 bathrooms was perfect. It would have been nice to have bigger beds in the 2nd bedroom than twins, but the boys managed since there was no footboards on the bed. The condo was well stocked with dishes and other essentials such as a hairdryer, towels, and beach chairs/snorkeling masks. The condo was nicely located just steps away from the pool. The deck off the living room and master bedroom had at least some sun all day and was a nice place to rest and relax before leaving for the day or at night for a drink and snacks. We were centrally located and it was an easy walk to Duvall Street and other attractions. The one major problem that I had was the queen bed in the master was absolutely the most uncomfortable bed I have slept on in years. I have chronic back pain and within 10 minutes of just lying down, my back was in serious pain. Much more pain than any daytime activity caused. And it wasn’t just me. My husband had a difficult time sleeping as well. If I was the owner I would take steps to replace that bed ASAP. I would definitely stay in the Truman Annex again with its central location and quiet neighborhood. However, I would look at other units because of the uncomfortable master bed.
Stayed 7 nights in Apr 2023
From a partner site

8/10 Good

morgan h.

A definite hangover

Rating Details: The property manager was more than helpful. The vacation rental was very clean. 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: We've stayed In shipyard for 4 yrs now with no complaints. Great location, walking distance to Duval.
From a partner site

8/10 Good

Joseph M.

Poolside Hangover Condo at Truman Annex

Rating Details: The property manager was very helpful. The vacation rental was clean. 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: Couldn't be happier with our Compass Realty experience, outstanding customer service. Our condo location was great! The condo itself could definitely use some updating. Probably the biggest issue was the floor, needs a professional cleaning, walking barefoot was not an option, even after we mopped the floor ourselves. We dine out so no issues with the kitchen. I would suggest looking at some newer furniture options, chairs for the deck too. Overall, a pleasant experience
From a partner site

10/10 Excellent

Paige O.

Poolside Hangover Spring Break

Rating Details: The property manager was very helpful. The vacation rental was very clean. 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: This is my 4th time staying in Shipyard Condos which I like for location and decent pricing. Entry was same, wish there were another way to get keys, but since I know it is fine. Condo dated but clean. Several broken items, chair on deck, blow dryer in master. Appreciate condiments in cabinet. Appreciate late checkout.
From a partner site

10/10 Excellent

Rosemary R.

Paradise Found🌴

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 will be returning .... Lovely condo...!
From a partner site

8/10 Good

Amazing & wonderful

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: Fabulous location the place was clean. The area around us was peaceful and wonderful!!!
From a partner site

6/10 Okay

Sheri B.

Don’t use Compass!!!

Rating Details: The property manager was very unhelpful. The vacation rental was clean. 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: Very dissatisfied with service from rental company, request for made, and confirmed on the contract and with three different phone calls as to queen bid instead of twins TVs in the bedroom to arrive, and it was not done and was told it could not be done until four days later. The smoke detector was missing in the living room, which kind of looks bad in an expensive rental house but I was told that they were up to code so it didn’t matter, the ventilation fan in the primary bathroom did not work, which they tried to tell me that I was complaining about the AC, I made no complaints about the AC. Both of the bathrooms, the shower curtains all along the bottom have black mold my contract on the first page stated that I had an early check-in a late check out. . I made no complaints about the AC. Both of the bathrooms, the shower curtains, all along the bottom, have black mold my contract on the first page stated that I had a early check in a late check out and that the bids were to be put into a queen. I have never had issues with any other company that I have used when coming to Key West like I did with compass , when I questioned that being on the contract I was told that’s just customer comments well don’t put it on the contract if you’re not gonna honor it and don’t tell your clients that you will when you book it when you call and talk to three different people that work for the company!!!!!
From a partner site

8/10 Good

Barbara P.

Needs updates

Rating Details: The property manager was more than helpful. The vacation rental was clean. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: The kitchen had small bugs. The primary bedrooms bath Matt’s we filthy. The internet was not working, we tried unplugging like suggested and it still was not working. The towels in the second bedroom should be replaced as they are all shrunk at the band on the ends.
Verified review

10/10 Excellent

Natalie K.

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

Perfect

Perfect everything!
Stayed 7 nights in Sep 2022
Verified review

10/10 Excellent

John H.

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

Nice condo

really liked the location
Stayed 7 nights in Jul 2022
From a partner site

10/10 Excellent

Keebler K.

Just a small bug :)

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 always enjoy staying in the ship yard and other condos/townhomes in the area. We are repeat offenders when it comes to vacationing in Key West. The only complaint I have is that I believe the unit we stayed in may have had bed bugs when we arrived. My entire family has the bites on various parts of our bodies. I'm only telling you so that you take a good look at the unit in case it is bed bugs so you can mediate the issue. Have a great day! Karen.
From a partner site

10/10 Excellent

Robert C.

Very Nice Week

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: The place was clean, a/c worked and had everything you need. My only complaints - they are minor - are that we could not use one of the showers for a day while we were there because the condo below us had a leak. Compass Realty did provide us with a credit for this inconvenience, which was very nice. Secondly, it would be much better if dropping off the keys were not as far away or as laborious as it was. We had trouble finding the place to drop the keys off and it was not close by. Lastly, the WiFi service was a challenge and the cable TV seemed to clip out very regularly. Thankfully, we were not there to watch TV. Aside from those minor issues, it was terrific: the location is ideal, the place is nice. the pool is nice also and the ceiling fans are plentiful.
From a partner site

10/10 Excellent

Damon s.

Key West 2021

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: Basically perfect. No complaints. Would certainly stay here again.

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