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Poolside Hangover at The Truman Annex in Key West

Condo near Duval Street in Key West

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

Pool
Living area
Property grounds
Interior
Outdoor dining

Reviews

9.2 out of 10
Wonderful

Entire condo

2 bedrooms2 bathroomsSleeps 4780 sq ft

Popular amenities

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

Explore the area

View in a map
Key West, FL
  • Place, Florida Keys National Marine Sanctuary
    ‪5 min walk‬
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Fort Zachary Taylor Historic State Park
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪15 min drive‬

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About the neighborhood

Key West

City center stay.Within a 10-minute walk of this Old Town Key West condo, you'll find Duval Street and Ernest Hemingway Home and Museum. Florida Keys Beaches and Southernmost Point are also within 2 miles (3 km).
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What's nearby

  • Florida Keys Eco - Discovery Center - 3 min walk - 0.2 miles
  • 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

Getting around

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

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Moondog Cafe & Bakery - ‬8 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

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Holly's Hideaway - Truman @ Duval | Charming Hideaway Near Duval!
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  • Air conditioning
  • Microwave
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Total with taxes and fees
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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

  • No pets 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 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
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. 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. 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

How close is Poolside Hangover at The Truman Annex in Key West to the airport?

This condo is 4.1 mi (19-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does Poolside Hangover at The Truman Annex in Key West have an airport shuttle?

Airport shuttle services are not available at this condo.

How close is Poolside Hangover at The Truman Annex in Key West to the beach?

This condo is a short 14-minute walk from Florida Keys Beaches and 0.8 mi (8-min drive) from South Beach. Don't forget your sunscreen!

Does Poolside Hangover at The Truman Annex in Key West offer free breakfast?

This condo does not offer free breakfast.

Is there a casino at Poolside Hangover at The Truman Annex in Key West?

No, there is no casino at this condo.

What time is check-in at Poolside Hangover at The Truman Annex in Key West?

Check-in begins at 4:00 PM.

Is there free parking at Poolside Hangover at The Truman Annex in Key West?

Free parking is not available at this condo.

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

Yes, there's a pool.

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

There are no spa services available at this condo.

How close is Poolside Hangover at The Truman Annex in Key West to downtown Key West?

This condo is 0.2 mi away from Key West.

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

8/10 Good

Gordon E.

Liked: Cleanliness
comfortable and clean.disappointed the pool closed for two days, this is only reason not 5 star.
Stayed 7 nights in Dec 2025

10/10 Excellent

TJ L., Waterford

Liked: Cleanliness

Key west truman annex

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

10/10 Excellent

Sheila D.

Liked: Cleanliness
Stayed 7 nights in Mar 2025

6/10 Okay

Nancy R.

Liked: Cleanliness

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

10/10 Excellent

Michaelanne R.

Liked: Cleanliness

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

10/10 Excellent

Chris V.

Liked: Cleanliness

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

10/10 Excellent

Jean R.

Liked: Cleanliness

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

8/10 Good

Jeff B.

Adequate and Comfortable

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

10/10 Excellent

Gina P.

Liked: Cleanliness

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

10/10 Excellent

Teresa W.

Liked: Cleanliness

Great except for getting the keys at a different location

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

10/10 Excellent

Natalie K.

Liked: Cleanliness

Perfect

Perfect everything!
Stayed 7 nights in Sep 2022

10/10 Excellent

John H.

Liked: Cleanliness

Nice condo

really liked the location
Stayed 7 nights in Jul 2022

10/10 Excellent

Regina H.

Liked: Cleanliness

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

10/10 Excellent

Lisa U., Nanticoke

Liked: Cleanliness

Beautiful!

The property is gorgeous! The room was very clean and cozy. It has all the amenities of home! The location is awesome, close to Duval. The only negative for me is getting the keys at check-in. I thought it was an inconvenience for me to have to pick them up a few blocks away. Perhaps a key pad lock would be easier for the renter? However, the cab driver was very nice. a He took us to the office to pick them up at check-in and drop them off at checkout. :)
Stayed 7 nights in Apr 2022

10/10 Excellent

Robert M.

Liked: Cleanliness

Great time

Great place and great location. Any issues were handled promptly. Would stay again.
Stayed 7 nights in Oct 2021

10/10 Excellent

Eileen R.

Liked: Cleanliness

Poolside Hangover Review

Location was great. A short walk to Duval Street and other restaurants near Truman Annex. Condo was clean and had everything we needed. We were surprised to find towels for the pool and foldable chairs we could take to the beach. Great place! The owner should add a grab bar in peach bathroom—I nearly went down in the tub.
Stayed 7 nights in Jul 2021

10/10 Excellent

Cindy R.

Liked: Cleanliness

Great Condo

We loved our condo, the balcony was great, clean, comfortable beds. Great location, easy to walk everywhere. Kitchen had everything we needed. We would stay there again
Stayed 8 nights in Jun 2021

10/10 Excellent

DAVE W.

Liked: Cleanliness

Simple but good

This is a second-floor condo. Easy in, clean, not fancy, a little dated furnishings but had everything we needed. Loved the balcony for morning coffee. Pool is right below you through the greenery. Would rent this unit again.
Stayed 7 nights in May 2021

10/10 Excellent

Gerilee D.

Liked: Cleanliness

Truman Annex Shipyard Commons 287

Great location. We walked everywhere to eat and shop. Many conveniences provided such as beach chairs and beach towels. The only thing that I would suggest is to have TV's in both bedrooms. And a bar to hold onto in the small shower. Everything else was great. The washer and dryer was also a real convenience.
Stayed 7 nights in Feb 2020

6/10 Okay

Verified traveler

Disliked: Cleanliness

Disappointed guests

We found this condo to be marginally clean. The bathroom rugs appeared dirty so I washed them immediately. The floors and baseboards appeared not to have been washed, and the shower curtains were moldy. There was also a deck chair that was torn. The property manager was alerted and shown pictures of our concerns, and she immediately contacted the cleaning person to come to the unit to address these issues. She cloroxed one of the shower curtains and replaced the liner and appeared to have wash the floor in one of the bathrooms. Given what it costs to rent this unit, this condo is in need of some upgrades and better quality mattresses and bed linens.
Stayed 11 nights in Nov 2019

8/10 Good

Mary Dianne S.

Liked: Cleanliness

Great location!

Mix up getting correct keys when we arrived! No hot water in Master shower! Enjoyed our stay overall!
Stayed 7 nights in Jun 2019