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Isle Be Back at The Truman Annex in Key West

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A water park with a slide, a water fountain, and palm trees at sunset.
A gated community entrance with a sign for Shipyard Condominiums, surrounded by palm trees and a clear blue sky.
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.
A residential street with a white picket fence, a sidewalk, and lush green bushes with red flowers.
A house with a white front door, a porch, and a white picket fence.

Reviews

9.6 out of 10
Exceptional

Entire condo

2 bedrooms2 bathroomsSleeps 4

Popular amenities

  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space
  • Parking available

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, Ernest Hemingway Home and Museum
    ‪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 patio, a refrigerator, and a microwave.
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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) - 15 min drive

Restaurants

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

Isle Be Back at The Truman Annex in Key West

Thank you for considering Isle Be Back for your escape to the tropical paradise of Key West. Here you will enjoy the lap of luxury with this two-bed & two-bath upstairs unit located in the highly desirable Shipyard section of the Truman Annex. Paradise awaits you just two blocks from the sights and sounds of Duval Street. A short walk or bike ride to Ft. Zachary State beach for sunbathing and snorkeling, Mallory Square to catch a spectacular sunset and the Ernest Hemingway House where the six-toed cats call home. Fine dining is an easy walk in any direction from this perfectly located condo where you get to live the laid-back tropical lifestyle of Key West.
Please note: This property is monthly rental - the minimum rental period is 28 nights
The condo is air-conditioned and features a patio and 2 bathrooms, and there's space to spread out with 2 bedrooms. Guests can expect to find free WiFi. Other standard amenities include a washing machine, a microwave, and a refrigerator.

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Property amenities

Pool/Spa

  • Communal pool

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Parking on site

Food and drink

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

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

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

Living spaces

  • Living room

Outdoor areas

  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center

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

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 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

Gracie Bay's Hideaway in The Truman Annex
Gracie Bay's Hideaway @ The Truman Annex Key West
Gracie Bay's Hideaway @ The Truman Annex Private vacation home
20% Off Summer Special Gracie Bay's Hideaway @ The Truman Annex
2698-193295

Frequently asked questions

What can I see within easy reach of 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 parking available on site at Isle Be Back at The Truman Annex in Key West?

No, this condo doesn't offer parking.

Is this condo next to a casino?

No, this condo is not connected to a casino.

Is there an indoor pool at this condo?

No, there is no indoor pool at this condo.

Are there hot tubs at Isle Be Back at The Truman Annex in Key West?

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

Does this condo include breakfast service?

No, this condo doesn't offer breakfast.

Does this condo allow pets to stay for free?

No, pets aren't allowed at this condo.

Are there connecting rooms at Isle Be Back at The Truman Annex in Key West?

No, this condo doesn't feature connecting guestrooms.

Where is the closest airport to this condo?

The closest major airport to this condo is Key West Intl. Airport (EYW), which is 4.1 mi away (15 minutes by car).

Are there rooms with balconies that I can book at Isle Be Back at The Truman Annex in Key West?

Yes, every condo at Isle Be Back at The Truman Annex in Key West comes with a patio.

Isle Be Back at The Truman Annex in Key West Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 35 out of 44 reviews
Rating 8 - Good. 7 out of 44 reviews
Rating 6 - Okay. 1 out of 44 reviews
Rating 4 - Poor. 0 out of 44 reviews
Rating 2 - Terrible. 1 out of 44 reviews

9.8/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Stefanie S.

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

Best of Key West

This property was fantastic! Easy access to all the great places you want to see in Key West.
Stayed 7 nights in Jun 2025
Verified review

10/10 Excellent

Dan N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Property was beautiful and well stocked. Would definitely recommend.
Stayed 7 nights in Jul 2025
Verified review

8/10 Good

Darlene P.

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

Truman annex is a great location

In Key West for a wedding and this was a great location for us. Walking distance to historic areas and restaurants. We had a parking place for our car which was convenient
Stayed 7 nights in Apr 2025
Verified review

10/10 Excellent

Jason B.

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

Perfect

Amazing property ..and a great company to deal with
Stayed 10 nights in May 2025
Verified review

10/10 Excellent

Laura-Anne C.

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

Key West

Perfect location! We had a great stay in this beautiful, bright, super clean, comfortable condo! It is well kept and well stocked. The grounds and pool are lovely!
Stayed 7 nights in Mar 2024
Verified review

10/10 Excellent

TIM T.

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

MAY TRIP

Been coming to key west for the last 11 years and this is the first time we stayed at the trumans annex The place was very clean and had plenty of room would not hesitate to come back.
Stayed 7 nights in May 2023
Verified review

10/10 Excellent

Jean A.

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

Beautiful space

Thoughtfully decorated, furnished and plenty of space for a family of 4. Thank you for sharing your place!
Stayed 7 nights in Feb 2025
Verified review

10/10 Excellent

Robin M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Check in/out was a little inconvenient as it was half mile from the unit. However, the place was clean, close to most everything and felt very safe!
Stayed 7 nights in Oct 2025
From a partner site

10/10 Excellent

brenda o.

KW SY

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: Awesome time at a really nice place.
Verified review

10/10 Excellent

Alvin B.

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

Beautiful and well maintained

We loved our stay at Isle be Back! It felt like it was actually built and maintained with quality materials unlike most nightly rentals. Communication with the property manager was excellent. She actually contacted me and made sure that I knew all of the important information about the unit and the area.
Stayed 7 nights in Mar 2025
From a partner site

10/10 Excellent

Cynthia P.

A Favorite

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 love this property! Everything inside is upgraded and beautiful! Great location for easy walks everywhere.
Verified review

10/10 Excellent

Doris J K.

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

Perfect Location

What a perfect location to stay. Close to Duval. Close to Fort Zachary Beach which in my option is the best. Each there. At the Truman annex is a much better place to see the sunset then Malloy square. It was in walking distance from the place. The place was clean and updated. I will be booking again.
Stayed 7 nights in Apr 2025
Verified review

2/10 Terrible

Donna K.

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

Vacation

Very nice. Good porch. Door knob on porch needs to be fixed.
Stayed 7 nights in May 2024
From a partner site

10/10 Excellent

Paula F.

Isle Be Back

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: The property was very clean and the kitchen well stocked with appliances and tools. It is centrally located in a very quiet, well groomed community.
From a partner site

10/10 Excellent

Sara P.

Awesome stay!

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 condo, close to everything. Very clean, well equipped. This place is updated and bright. The bed was very comfortable. 11/10 would recommend and would absolutely love to stay here again.
Stayed 8 nights in Jun 2023
Verified review

8/10 Good

Walt K.

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

A Very Merry Christmas in Key West

Overall, we enjoyed our stay in Key West at a compass realty property. The description is accurate and the location is great! We requested service for a tv in one of the bedrooms which was provided promptly. We also requested dish towels and they were also delivered promptly. We suggest attention to the patio doorknob.
Stayed 7 nights in Dec 2024
Verified review

8/10 Good

Jason B.

Liked: Cleanliness, communication, location, listing accuracy
The pickup and drop off of the key was relatively easy, but the doors should be switched to the digital/electric locks.
Stayed 7 nights in Oct 2025
Verified review

10/10 Excellent

janet m.

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

Love Truman annex

Truman annex is the best place to stay for fantasy fest week. You can walk anywhere or take the bus, no need for a rental car. The pools are great. Love having a balcony with our room. The rental was lovely and very clean. The only problem was the closet door in one bedroom was broken. Other than that it was great. All amenities provided in kitchen and bath. This place was great.
Stayed 7 nights in Oct 2022
Verified review

8/10 Good

Laura K.

Liked: Cleanliness, communication, location, listing accuracy

Parking??

Real small parking spots and you only get one!! Don’t bring friends, no place to park!
From a partner site

10/10 Excellent

Natalie T.

Truman annex perfect accomodatioms

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: Brand new condo CLEAN and BEAUTIFULLY decorated. Needed ice cube tray. Also would like to see kitchen towels and cleaning spray for counter top and glass tabletop and toilet bowl cleaner. Truman annex is a convenient wonderful place to stay in Key West.
Verified review

10/10 Excellent

Allison H.

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

The condo is beautifully modern and clean.

We loved the location of the complex. We rented bikes for the week and rode them everywhere. We took advantage of the pool as well which was nice to have in case of a chance of rain. My only complaint was that we did not have full control of the a/c so we had to sleep with the bedroom door open at night until it cooled down enough. It just wouldn’t get as cool as we liked.
Stayed 7 nights in Jul 2020
From a partner site

10/10 Excellent

brandy g.

Our stay at Isle Be Back rental!

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 rental was in a great location, we could have walked anywhere we wanted. The condo was decently priced for our stay. It is very cute and had a lot of amenities and very clean. Compass Reality were very helpful with whatever questions we had. The only downside was the mattresses were pretty firm but a lot of people prefer that. I would definitely recommend this property!
Stayed 7 nights in Jul 2024
Verified review

10/10 Excellent

Lorrie N.

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

Girls Trip

Location is perfect. The condo was just right for the two of us. There were a few things we did expect (because we’ve stayed in other VRBO condos) a cooler would have been nice [we left you a styrofoam one] dish towels and maybe better stocked salt/pepper/sugar - kitchen essentials. The parking is a little confusing-if it wasn’t for someone in the complex we might not have found the right spot. We would definitely consider coming back. Thank you!
Stayed 9 nights in May 2024
From a partner site

10/10 Excellent

You better believe "Isle Be Back"

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: Unit appeared to be recently updated. Very nicely appointed. Close to everything within Old Town. Definitely would stay again.
From a partner site

8/10 Good

KEITH B.

I'll be back

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: very pleasant and clean. One of the nicer units that we have stayed in Key WEst. Good location

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