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Chilmark South Tropical Key West Waterfront Condo

Bedrooms 2
Property type condo
Minimum Stay 5 nights


About the property

Condo, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 6)

From the minute you walk through the front door, you'll feel like you're in paradise. The view is spectacular day and night. Located 2 blocks from Duval Street where all the action happens, this waterfront condo at Harbour Place in the private gated community of Truman Annex is a great place to escape to in tropical Key West. A number of restaurants and bars are an easy walk away, as you are located right on the harbor where the cruise ships come in.

Enjoy sunsets from your private balcony or at Mallory Pier's sunset celebration, just a few steps from your door. You can either partake in all the craziness or simply enjoy the solitude of your private residence. The pool has a great view, as it is located on the harbor as well.

The airport is a quick 10 minute drive, and everything else is within walking distance. You will feel like you are in the Caribbean with the nearly perfect weather year round, with out the hassle of traveling further, or dealing with another currency or language. If you want to feel far removed from everyday life, this is the place for you.

See details below regarding the amenities this condo has to offer.....

Keywords: Condo

More Details

Member since: 2008
Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
March 10, 2017


Truman Annex Condo Accommodation and Amenities

Property Type:
  • condo
  • floor 2
  • Guests provide their own meals
  • Housekeeper Included
House Rules:
  • Max. occupancy: 6
  • non smoking only
  • pets not allowed
  • children welcome
Location Type:
  • Ocean View
  • Oceanfront
  • Water View
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning
  • Clothes Dryer
  • Covered Parking
  • Elevator
  • Hair Dryer
  • Internet
  • Linens Provided
  • Living Room
  • Parking
  • Parking Off Street
  • Telephone
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Refrigerator
  • Stove
  • Toaster
  • Dining Area
  • seating for 6 people
  • 2 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
  • 2 Bedrooms, Sleeps 6
  • King size beds (1), Queen size Beds (1), Sleep Sofa or Futons (1)
  • Books
  • CD Player
  • DVD Player
  • Satellite / Cable
  • Television
  • Deck / Patio
  • Outdoor Grill
  • Long-term Renters Welcome
  • wheelchair accessible
Pool / Spa:
  • Communal Pool
  • jetted tub
  • cinemas
  • live theater
  • museums
  • restaurants
Leisure Activities:
  • boating
  • shopping
  • sight seeing
  • walking
Sports & Adventure Activities:
  • cycling
  • fishing
  • jet skiing
  • parasailing
  • sailing
  • snorkeling
  • snorkeling/diving
  • swimming
24-hour security in private gated community


Exceptional! 5/5 -
(8 traveler reviews)

Chilmark South Tropical Key West Waterfront Condo
average rating of 5.0 based on 8 reviews

Simply Amazing Vacation

  • 5 of 5

Get ready for postcard views everyday from your balcony. You can not beat this location, quiet, clean, perfect. I will be a future guest here, we can't wait to get back.

  • Submitted: Nov 2, 2014
  • Stayed: Oct 2014
  • Source: VRBO, from HomeAway
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2 0
Jacksonville, FL

30th Anniversary Trip

  • 5 of 5

This is the second time we have stayed at this property and have never been disappointed! Close to everything yet feels so secluded. Easy stroll to Mallory Square and Duval Street. The condo is clean, spacious and has everything you could possibly need. The view is incredible and perfect for watching the sunset each evening.

  • Submitted: Oct 6, 2014
  • Stayed: Sep 2014
  • Source: VRBO, from HomeAway
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3 0

Excellent location and well appointed condo

  • 5 of 5

My husband and I stayed here for a week with my elderly parents and we all loved it! Fantastic location, comfortable furnishings and decently equipped kitchen. Quiet, safe area but just a couple of blocks from Duval Street. We enjoyed watching the regatta teams and cruise ships in the morning and evening - great to just sit on the porch and watch all the activity below. Lindsay was very helpful and the rental process was a breeze.

The only thing that could have made our stay even better would have been a higher toilet seat for my 90 year-old folks - they had a little difficulty with the low toilet in the master bathroom. (If I'd known earlier in our stay, we could have looked for a portable toilet seat riser for the week - I'm sure the medical supply store there would have them, and I think you can get one for under $50. Helpful for anyone with mobility issues.)

  • Submitted: Feb 15, 2014
  • Stayed: Jan 2014
  • Source: VRBO, from HomeAway
Owner's Response: Glad you enjoyed it! Just to clarify, there are 2 toilets in the master bathroom, a standard one and a bidet which I believe may be the lower one. Hope you make it back there in the future!
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2 0

William M.

  • 5 of 5

My wife and I just spent Christmas down at Key West with our four girls(ages 17-22). We had read the glowing reviews on VRBO and this property exceeded our expectations.

The condo has a stunning view and was very clean and nicely decorated. We had six of us staying there(all my girls are over 6 feet, playing volleyball in college) and we never felt crowded. Sitting out on the porch and watching the sunset or the cruise ships come and go was such a bonus. The proximity to anything you want to do in Key West was a huge plus. We walked everywhere. Anything you want to do in Key West is within 10-15 blocks. We didn't use our car and didn't need bikes. You're right next to Mallory Pier and access to all manner of water activity.

Lindsey provided us with a summary of some awesome restaurants close by(Blue Heaven is not to be missed--breakfast, lunch, dinner, drinks, etc, Kelly's is one block away and wonderful). There is just something about eating dinner at night in late December on a patio covered in tropical trees and vines in your shorts and a Tommy Bahaman shirt.

The facility is gated and very secure. There are many pedestrian entrances and all require a key after 6pm. The surrounding, homes and condos are well kept and nicely landscaped, many on the National Historic Register. Its been a while since I'd been in Key West. It was clean, safe and very festive with wonderful places to eat, drink, listen to music and people watch.

I went all over the key and couldn't imagine a more strategic home base for exploring. I promise, you couldn't find a place any better situated than this.

  • Submitted: Jan 3, 2013
  • Stayed: Dec 2012
  • Source: VRBO, from HomeAway
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3 0

Key West Perfection

  • 5 of 5

We are global, discerning, upscale travellers. Chilmark exceeded ALL of our expectations. It is impeccable. Located in the picturesque, gated, secure, Truman Annex, on the water, right behind the Truman White House. Everything is in short walking distance. The sunset views from the large double balcony were breathtaking. The unit is spacious, and gorgeously decorated.

There is not a thing about this spotless, spacious, fully appointed unit that could have been improved upon.

Thank you Linsay, for sharing this little piece of heaven with us.

Bob & Glory

P.S. Please feel free to use us as references for prospective renters. We would be happy to talk their ears off about how ideal Chilmark is.

  • Submitted: Oct 18, 2011
  • Stayed: Oct 2011
  • Source: VRBO, from HomeAway
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3 1
Warsaw, IN


  • 5 of 5

Pictures don't do this condo & the location justice! The interior is clean, & upscale with gorgeous decor. The ocean couldn't have been closer & how fun to watch the cruise ships come & go! Plus "Truman's Little White House" is out the opposite side of the condo! Just pinch me!!! Very quiet yet so very close to Duval & all the activity. We rented bikes but everything is in walking distance. We took a "Danger Charter" half day sailing/snorkeling/kayaking trip, straight out from the condo. Fun, fun time & great crew!

This condo is absolutely beautiful & Lindsay was great to work with.

Icing on the cake was when the midwest was hit by a winter storm, airports were closed, & we were "stranded" here for an extra 2 days! Life doesn't get any better than this :-)

One of the very best vacations we've ever had!!!

  • Submitted: Feb 5, 2011
  • Stayed: Jan 2011
  • Source: VRBO, from HomeAway
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3 0



Rates & Availability

Truman Annex Condo Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly * Event
Dec 15 2016 - Apr 30 2017
5 night minimum stay
May 1 2017 - Dec 14 2017
5 night minimum stay
My Standard Rate
5 night minimum stay

Additional information about rental rates

Tax Rate 5.0%

- NEW YEARS $4920/WK

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.

Enter dates for accurate pricing


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