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.
Ernest Hemingway Home and Museum - 9 min walk - 0.5 miles
Fort Zachary Taylor Historic State Park - 9 min walk - 0.5 miles
Southernmost Point - 17 min walk - 0.9 miles
Getting around
Key West Intl. Airport (EYW) - 13 min drive
Restaurants
Margaritaville - 5 min walk
Blue Heaven - 9 min walk
Green Parrot Bar - 6 min walk
Willie T's - 5 min walk
Caroline's Cafe - 7 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!
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.
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
Pets
This property doesn't allow pets
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, this vacation home doesn't offer parking.
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.
What amenities will couples enjoy at "A Captain's Quarters at the Truman Annex in Key West"?
Couples staying at this vacation home will appreciate amenities like a private pool and a kitchen as well as a heated pool.
Does "A Captain's Quarters at the Truman Annex in Key West" have a hot tub?
No, but this vacation home does have a heated pool.
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
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 13 out of 15 reviews
10 - Excellent
13
Rating 8 - Good. 2 out of 15 reviews
8 - Good
2
Rating 6 - Okay. 0 out of 15 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 15 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 15 reviews
2 - Terrible
0
9.6/10
Cleanliness
Reviews
10/10 Excellent
Ronald P.
May 7, 2025
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!!
Ronald P.
Stayed 7 nights in Apr 2025
10/10 Excellent
Edward O.
Mar 19, 2025
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.
Edward O.
Stayed 7 nights in Mar 2025
10/10 Excellent
Kimbrly B.
Jul 14, 2024
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!
Kimbrly B.
Stayed 7 nights in Jul 2024
8/10 Good
Alan W.
Jan 27, 2024
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.