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"A Captain's Quarters at the Truman Annex in Key West"

Vacation home with private pool, 4-minute walk to Duval Street

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Photo gallery for "A Captain's Quarters at the Truman Annex in Key West"

Outdoor dining
Exterior
Terrace/patio
Fridge, microwave, oven, stovetop
Fridge, microwave, oven, stovetop

Reviews

9.8 out of 10
Exceptional

Entire home

4 bedrooms3 bathroomsSleeps 81920 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Key West, FL
  • Place, Harry S. Truman Little White House
    ‪3 min walk‬
  • Place, Duval Street
    ‪5 min walk‬
  • Place, Mallory Square
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪9 min drive‬

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About the neighborhood

Key West

Located in Old Town Key West, this vacation home is within a 5-minute walk of Duval Street and within 15 minutes of other popular attractions like Mallory Square. The vacation home includes a private pool, a kitchen, and a balcony.
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What's nearby

  • Harry S. Truman Little White House - 3 min walk - 0.2 miles
  • Duval Street - 5 min walk - 0.3 miles
  • Mallory Square - 8 min walk - 0.5 miles
  • Ernest Hemingway Home and Museum - 9 min walk - 0.5 miles
  • Fort Zachary Taylor Historic State Park - 9 min walk - 0.5 miles

Getting around

  • Key West Intl. Airport (EYW) - 13 min drive

Restaurants

  • ‪Green Parrot Bar - ‬5 min walk
  • ‪Margaritaville - ‬4 min walk
  • ‪Willie T's - ‬5 min walk
  • ‪First Flight Island Restaurant & Brewery - ‬6 min walk
  • ‪Jack Flats - ‬5 min walk

About this property

Entire place

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

"A Captain's Quarters at the Truman Annex in Key West"

Searching for the perfect vacation home away from it all? Your hunt ends in here! A Captain's Quarters is an updated and tastefully decorated LARGE 2-story townhome with its own private pool that epitomizes island living at its finest while offering all the comforts of home. This recently updated 4 bedroom, 3 bath home is 1920 SF and features its own private heated (12/15-4/15) pool and separate carport. First floor has a bedroom with full bath, dining, living areas and kitchen. French doors open to the private pool and rear deck. Second floor has the primary suite, two guest bedrooms and two full baths.
Best of all, this home is nestled in a palm tree lined award-winning residential community with many historic buildings including the Truman Little Whitehouse. This beauty is walking distance to many of Key West’s finest dining establishments, two blocks from the world-famous Duval Street, two blocks from the nightly sunset celebration at Mallory Square, and less than a half mile from the beach at Fort Zachary Taylor State Park. Break away from the ‘high seas’ of everyday life while you settle into for what’s sure to be a memorable Key West vacation!

Please note: This property will require a minimum of a 28 night stay.
The vacation home is air-conditioned and features a kitchen, 3 bathrooms, and a balcony, and there's space to spread out with 4 bedrooms. Other standard amenities include a private pool, a washing machine, and a fenced private yard.

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Property amenities

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: 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

  • 4 bedrooms
  • Bedsheets provided

Bathroom

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

Living spaces

  • Dining table
  • Living room

Entertainment

  • Cable/satellite channels

Outdoor areas

  • Balcony
  • Fenced yard

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

Things to do

  • Heated pool

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

  • Unit size: 1,920 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
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

2698-250428

Frequently asked questions

What can I see around this vacation home?

This vacation home is situated in Old Town Key West within a 10-minute walk of Duval Street, Mallory Square, and Ernest Hemingway Home and Museum. You'll also find Fort Zachary Taylor Historic State Park and Florida Keys Beaches less than a mile away.

Is there parking available at this vacation home?

No, there isn't parking at this vacation home.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home; however, the accommodation features a private pool.

Is "A Captain's Quarters at the Truman Annex in Key West" a good place to stay for couples?

Couples staying at this vacation home will appreciate amenities like a private pool and a kitchen as well as a heated pool.

Are there hot tubs at "A Captain's Quarters at the Truman Annex in Key West"?

No, but guests can enjoy a heated pool at this vacation home.

Does this vacation home offer breakfast?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

Are there connecting rooms at this vacation home?

No, there aren't connecting rooms at this vacation home.

What is the closest airport to this vacation home?

The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 4.1 mi away (13 minutes by car).

Are there rooms with balconies that I can book at "A Captain's Quarters at the Truman Annex in Key West"?

Yes, every accommodation at "A Captain's Quarters at the Truman Annex in Key West" comes with a balcony.

"A Captain's Quarters at the Truman Annex in Key West" Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 17 out of 19 reviews
Rating 8 - Good. 2 out of 19 reviews
Rating 6 - Okay. 0 out of 19 reviews
Rating 4 - Poor. 0 out of 19 reviews
Rating 2 - Terrible. 0 out of 19 reviews

9.8/10

Cleanliness

Reviews

10/10 Excellent

Sue D.

Liked: Cleanliness
All bedrooms were large very nice. The pool was wonderful. Location was the best. House had everything you could need.
Stayed 7 nights in Dec 2025

10/10 Excellent

Christopher S.

Liked: Cleanliness
The house is beautiful and very well appointed with everything you need. Kitchen had plenty of everything. The beds are super comfortable and everything is brand new. Our small issue with the air conditioning was fixed right away. Plenty of room for extended family. The outdoor space is wonderful and we really enjoyed the pool. We had a wonderful vacation. Great location!
Stayed 8 nights in Nov 2025

10/10 Excellent

Brian K.

Liked: Cleanliness
Captains Quarters was a fantastic house set in a great location. Beautifully furnished and well maintained, it was a short walk to Duval and close to so many restaurants, stores and other activities. It was pretty warm and humid during our stay so the pool was a welcome respite. We spent hours in that great backyard! Check-in was relatively easy and check-out, a breeze! My family had such a great time here!
Stayed 7 nights in Jul 2025

10/10 Excellent

Jonathan R.

Liked: Cleanliness
Awesome property in a awesome location. Close to everything you want to do. Everything was thought of. Pool was a perfect way to end a hot day!!!
Stayed 7 nights in Jul 2025

10/10 Excellent

Ronald P.

Liked: Cleanliness

Great home, Great location

While I have been to Key West before, this was a first for my family. We stayed a week and had a blast! The home fit all of our needs - including the relaxing time by the pool!!
Stayed 7 nights in Apr 2025

10/10 Excellent

Edward O.

Liked: Cleanliness

Great week at Captains Quarters

We had plenty of room for 5 adults. Loved spending time by the pool. It’s an easy walk to all of our favorite spots. House is beautifully decorated. Would definitely return if available.
Stayed 7 nights in Mar 2025

10/10 Excellent

Kimbrly B.

Liked: Cleanliness

Beautiful home for a family vacation

This home was perfect for our family of 7! The house is exactly as described but even better in person. We had plenty of family time around the pool during those hot afternoons and game nights around the dining table after evenings in town. It’s an easy walk to Duval St and Mallory Square so there is plenty to see and do. Even though you’re close to the action, the neighborhood is very quiet. The kitchen is well equipped with anything you need for dinners in. Beds are super comfy! The management team was so accommodating for our early arrival and even brought us a bag of ice since the freezer had been emptied. We loved it and will not hesitate to come back next time we visit the Keys!
Stayed 7 nights in Jul 2024

8/10 Good

Alan W.

Liked: Cleanliness

Not paradise found.

Lots of minor upkeep and cleaning issues and had to get an electrician the first day do to a short circuit and blown circuit breaker.
Stayed 7 nights in Jan 2024