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

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

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

Outdoor dining - "A Captain's Quarters at the Truman Annex in Key West" (Key West)
Exterior - "A Captain's Quarters at the Truman Annex in Key West" (Key West)
Fridge, microwave, oven, stovetop - "A Captain's Quarters at the Truman Annex in Key West" (Key West)
Fridge, microwave, oven, stovetop - "A Captain's Quarters at the Truman Annex in Key West" (Key West)
Terrace/patio - "A Captain's Quarters at the Truman Annex in Key West" (Key West)
Nestled in a palm tree-lined residential community, A Captain's Quarters offers the epitome of island living with its own private pool and tasteful decor. Just two blocks from Duval Street and the nightly sunset celebration at Mallory Square, this 4-bedroom townhome is perfect for those seeking a memorable Key West vacation.

Reviews

9.8 out of 10
Exceptional

Entire home

4 bedrooms3 bathroomsSleeps 8178 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space

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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 is monthly rental - This property has a 28 night minimum stay

Property amenities

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: WiFi

Parking and transport

  • Parking on site

Kitchen

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

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre

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

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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

Pets not 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
On-site 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 that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
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

Property is also known as

2698-250428

About the area

Located in Key West, this holiday home is in the city centre. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. USCGC Ingham Maritime Museum and Florida Keys Eco - Discovery Center are also worth visiting. Visit our Key West travel guide
View more Holiday homes in Key West
Map
Key West, FL

What's nearby

  • Harry S. Truman Little White House which includes signage
    Harry S. Truman Little White House
    3 min walk - 0.3 km
  • Duval Street featuring signage
    Duval Street
    5 min walk - 0.4 km
  • Mallory Square featuring outdoor art, a square or plaza and signage
    Mallory Square
    8 min walk - 0.7 km
  • Ernest Hemingway Home and Museum featuring heritage elements and a house
    Ernest Hemingway Home and Museum
    9 min walk - 0.8 km
  • Fort Zachary Taylor Historic State Park showing military items, heritage elements and interior views
    Fort Zachary Taylor Historic State Park
    9 min walk - 0.8 km

Getting around

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

Restaurants

  • Green Parrot Bar
    5 min walk
  • Margaritaville
    4 min walk
  • Willie T's
    5 min walk
  • Blue Heaven
    9 min walk
  • First Flight Island Restaurant & Brewery
    6 min walk

Frequently asked questions

Does "A Captain's Quarters at the Truman Annex in Key West" have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is "A Captain's Quarters at the Truman Annex in Key West" pet-friendly?

No, pets are not allowed at this property.

How much is parking at "A Captain's Quarters at the Truman Annex in Key West"?

On-site parking is available at the property.

What time is check-in at "A Captain's Quarters at the Truman Annex in Key West"?

Check-in begins at 4:00 PM.

What time is check-out at "A Captain's Quarters at the Truman Annex in Key West"?

Checkout is at 10:00 AM.

Where is "A Captain's Quarters at the Truman Annex in Key West" located?

Located in Old Town Key West, this holiday home is within a 5-minute walk of Jackson Square and Duval Street. Mallory Square and Ernest Hemingway Home and Museum are also within 10 minutes.

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

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers 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.
More informationOpens in a new window
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

Cleanliness

9.8

Location

Reviews

10/10 Excellent

Ronald P.

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

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, check-in, communication, location, listing accuracy

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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Beth

Perfect vacation

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: New years eve week stay. Perfect location. Beautiful home with all amenities. Will recommend to friends
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Joe G.

500 Porter

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: Outstanding location, clean, comfortable and very responsive management company. We would love to stay or any other properties they host.

10/10 Excellent

Kimbrly B.

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

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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Jennifer M.

We found paradise in Key West!

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: Traveled with 4 couples (50's) to Key West in late January. Paradise Found checked all the boxes! Great location! The house is located in a very serene neighborhood but only steps away from Duvall and great bars, restaurants and live music. Also - walkable to beach and boardwalk. The house had plenty of room for 8 of us -- great kitchen, living space, bedrooms & pool. We loved our stay and highly recommend! Compass Realty was very easy to work with and accomodating!
This review comes from a trusted partner site and has not been verified.

8/10 Good

Anonymous B.

Pros and Cons

Rating Details: The property manager was very unhelpful. The vacation rental was very 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: This house is located in a great location! Walking distance to everything. Cozy house w/ private heated pool. But, Compass Realty is not opened on weekends, although Saturday is very busy turnover day for rentals. They provide an "after hours" number to call for "emergencies," but NOBODY answered the phone NOR returned our calls when we experienced a major leak within 13 hours of checking into house. While our nanny were bathing our young children in the only bathtub available on the 2nd floor, it caused a major leak to the 1st floor w/ water running down the ceiling into kitchen bar, dining room, and part of living room. We spent the entire morning cleaning and mopping water w/ bath towels provided for us to use. Rental company told us to wash/reuse the towels used to clean the dirty floors and water. They did not respond to the emergency until 30 minutes after we called and texted multiple times. Instead of calling us back to get information, apologize, and update us on the process, the rental company only texted us and NEVER apologized NOR called us at all. The plumber arrived 1.50 hours later and housekeeping arrived 1.75 hours later. As soon as plumber arrived, he said he was in a rush to leave because "it's a Sunday." Leak was NEVER fixed. Couldn't use bathtub for entire stay. By the time housekeepers arrived, we had already finished cleaning and mopping the water to mitigate damages for owner. Instead of calling us and offering to compensate us for the problem, we received an e-mail from rental company within 30 minutes after the housekeepers left charging us $300 which we found out was for our 25 lb. dog which an employee of this rental company allowed us to bring off the record. Pool heater broke during our stay. Fridge does NOT get cold during the day and only gets cold while everyone is sleeping. Hot water does NOT last long. NO locks for balconies. Cannot open windows. Rental company NEVER cleaned iguana poop and poop stains before our arrival.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Mark D.

Paradise Found again!

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: 500 Porter Lane is the perfect vacation house! 4 comfy bedrooms and an updated kitchen and private pool/patio were perfect. We were able to walk to our favorite restaurants and downtown venues. This was our second stay at this house.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Mark M.

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: Great property for our 6 adults and 4 children. Pool in the backyard is a real plus.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

robert m.

Paradies 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: very accurate description of Property, which met and exceeded or expectations
Stayed 7 nights in Mar 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Nancy S.

Key west adventure

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: My girlfriends and I totally enjoyed our stay! Thank you for being so accommodating on our arrival and departure times. We will be coming back!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Patti G.

Great Home in Key West

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 is the second time staying in this lovely home, but the new owner has done a beautiful job of updating. The house is in a great location - easy to walk everywhere. The renovations turned a nice place to stay into a great place to stay! Compass Realty made the process of checking in/out quite simple. Completely enjoy our stay in Key West!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Joe G.

500 Porter

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: Outstanding location, clean, comfortable and very responsive management company. We would love to stay or any other properties they host.

10/10 Excellent

Brian K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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, check-in, communication, location, listing accuracy
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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Scott M.

Great place!

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: The place was in a nice gated community. Close to shopping, dining and other attractions that we had scheduled! Having our own private pool was a bonus!

8/10 Good

Alan W.

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

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