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Beautiful 2BR king or twins, END-UNIT Truman Annx Ground FL, Pool on Grounds

Bedrooms 2
Property type condo
Minimum Stay 7 - 8 nights


Minimum Stay
7 - 8 nights

About the property

Beautiful 2BR king or twins, END-UNIT Truman Annx Ground FL, Pool on Grounds

Rooster Retreat is a lovely 2 BR / 1 BA end-unit offering a LARGE deck with a Weber gas grill and lush landscaping.

This ground floor condo with King (or two separated twins) and Queen bed is very clean, and has well-appointed bedrooms which have been recently updated with beautiful linens, art work and comfortable beds. The extra large window in the living room floods the condo with lots of natural light not found in many other units. The new and open kitchen with quartzite countertops, beautiful lighting and seating for four is stylish and functional. A washer/dryer are located within the unit for your convenience. The fully equipped kitchen, pots & pans, towels & linens and central air conditioning provide all the amenities you want for long- and short-term stays.

Relax at the Truman Annex Shipyard Pool - which is a minute walk from the condo.

NEED MORE SPACE or EXTRA CONDO for additional guests? Visit VRBO #595903 to see photos & description of the large & proud SHABBY CHICKEN!!

At the Rooster Retreat, you'll also enjoy a comfortable leather couch in the living room with a 32' flat screen TV, secure wireless Wi-Fi and Bluetooth speaker for your device to connect to for music.

Rooster Retreat is within easy walking and biking distance to everything Old Town Key West has to offer, including Fort Zachary Beach and a one minute walk to the Truman Annex Shipyard pool. Our condo is outfitted with beach towels, beach chairs, a cooler, etc. We also have designated on-site parking, although it's likely you will not need (or want) to get in your car while you're here. We request a 7 night minimum, and try for a Saturday to Saturday schedule. Thank you.

FALL 2015 & 2016 CONDO UPDATES: All new AC & air handler, queen bed, king bed, bath fixtures & lighting, and landscaping

More Details

Tom and Marie
Member since: 2012
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
February 21, 2017

About Tom and Marie

We both grew up in Ohio, met at Ohio State University, married and moved to Charlotte, NC. Ten years ago we relocated to Chicago. Living in Chicago is great, but the winters are long and the city is hectic. Visiting Key West allows us to slow down and really enjoy a different pace of life.

Tom and Marie purchased this condo in 2012

Why Tom and Marie chose Key West

We purchased this property, and named it The Rooster Retreat, as a sanctuary from when life has you running around like a chicken, or in this case a 'rooster'. The lifestyle in Key West and amazing sunsets can all teach us to keep life simple and take pause when you can. The only rush hour here is the walk to your favorite happy hour. We retreat to the keys to unwind and relax, hear live music, eat great local seafood.

What makes this condo unique

Our ground floor end unit condo offers more light, privacy and island breezes than others because there are no buildings to the left of us or behind us. In addition, our assigned parking spot is close to our front door, which makes for easy loading and unloading of suit cases, groceries, etc.

Guestbook comments from the owner

As new owners of the Rooster Retreat (formerly Holiday Dance), we keep the well-appointed two bedroom place clean and comfortable for your stay. Read up past reviews on the Holiday Dance to find out more.
May 2012
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Truman Annex Condo Accommodation and Amenities

Property Type:
  • condo
  • floor 1
  • Guests provide their own meals
  • Air Conditioning ...
  • Clothes Dryer ...
  • Internet ...
  • Linens Provided ...
  • Living Room ...
  • Parking ...
  • Parking Off Street ...
  • Telephone
  • Washing Machine ...
  • Wireless Internet
  • Cooking Utensils
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Refrigerator
  • Dining Area
  • 1 Bathroom
  • Bathroom 1 -
  • 1
  • 2 Bedrooms, Sleeps 4
  • King size beds (1) Two twins in the one bedroom that have the flexiblity to be converted into one king bed or remain as two separate twins., Queen size Beds (1)
  • CD Player
  • DVD Player
  • Satellite / Cable ...
  • Stereo ...
  • Television ...
  • Deck / Patio ...
  • Outdoor Grill ...
  • Porch / Veranda ...
  • non smoking only
  • pets not allowed
Pool / Spa:
  • Communal Pool
  • cinemas
  • library
  • live theater
  • marina
  • museums
  • restaurants
Leisure Activities:
  • antiquing
  • beachcombing
  • boating
  • shopping
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • laundromat
  • medical services
Sports & Adventure Activities:
  • deepsea fishing
  • fishing
  • golf
  • jet skiing
  • kayaking
  • parasailing
  • pier fishing
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • swimming
  • water skiing


Wonderful! 4.9/5 -
(36 traveler reviews)

Beautiful 2BR king or twins, END-UNIT Truman Annx Ground FL, Pool on Grounds
average rating of 4.9444447 based on 37 reviews

Very good

  • 5 of 5

Very clean, surroundings were beautiful, grounds well kept, temp. excellent

Some of pool furniture is not appropriate for the and didn't function very well.

Working with the owners was a pleasant experience.....

  • Submitted: Feb 13, 2017
  • Stayed: Jan 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for staying at the Rooster Retreat. It was so nice to meet you and your wife the other week. I'm glad you found the condo to be very clean and you liked the location & surroundings, along with my customer service. There are a lot lounge chairs at the Shipyard pool and the association replaced about half of them with some really nice ones, and hopefully more will be arriving soon.
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Roanoke, VA

What a FANTASTIC place to stay!

  • 5 of 5

This place was perfect for me and my husband. All the amenities and more. Marie was so helpful throughout our stay. I would give 10 Stars!!!

  • Submitted: Dec 15, 2016
  • Stayed: Oct 2016
  • Source: HomeAway
Owner's Response: Thank you Erika for the fantastic review. I'm so glad you loved the place. We often get repeat guests and hope to hear from you again when you travel down to Key West. Marie
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Gainesville, Fl

Beautiful 2 bedroom 1 bath condo

  • 5 of 5

This 2 bedroom 1 bath condo was beautiful, homey, small, yet extremely cozy. The condo was stocked with many things to fit our needs from towels, sunscreen, and beach chairs to books and board games. This location is also very central to many places and just a few blocks from Duvall street. It was a delight to spend the week at the Truman Annex in this condo and I will definitely book again when I return to keywest in the future.

  • Submitted: Jul 15, 2016
  • Stayed: Jun 2016
  • Source: VRBO, from HomeAway
Owner's Response: Ashley, Thank you for your review. We are so glad that you and your girlfriends had a wonderful time. The photo you sent was just beautiful - you're a great photographer. I look forward to hearing when you'll be back again. Thank you, Marie
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Amazing Getaway!

  • 5 of 5

Just got back from an amazing vacation at The Rooster Retreat. The attention to detail and cleanliness in the condo was refreshing to see! Centrally located just off Duval so you're still close enough if you wanted to walk. The condo has literally everything that you need and then some! Very impressing in working with Marie, providing any and all the information that you will need for your stay. Will definitely be returning next year!

  • Submitted: Nov 19, 2015
  • Stayed: Nov 2015
  • Source: VRBO, from HomeAway
Owner's Response: Thank you so much for the review. I'm so glad you had a fantastic week, loved the place and location of the Rooster Retreat. I look forward to hearing from you again when you have your dates set for next year. Cheers! Marie
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Shabby Chicken & Rooster Retreat

  • 5 of 5

This past June we, 3 separate families, rented 3 condos in the Truman Annex. The Shabby Chicken & The Rooster Retreat were absolutely amazing. Both condos were impeccably decorated, cleanly kept, and spacious enough for family meals. Both condos came with parking spaces which was a plus as we rented cars for the drive from Miami airport to Key West. Marie was great to work with as she provided a list of all that there is to do in Key West and the surrounding Key's. Marie also provided great suggestions on where to eat in Key West - all of which were fabulous. The 3rd condo we rented which was not one of Marie's but was located near The Rooster Retreat. This "other condo" located in Truman Annex was not nearly as clean nor were the owners/operators of the this unit as accommodating as Marie. I would most definitely return to either the Shabby Chicken or the Rooster Retreat again. It was a great value for all the amenities and location. We were able to walk to the beach and Duval Street within 5 minutes. I would also recommend doing a Fury boating trip as we had children with us age ranges from 8 - 20. Everyone in our group loved the 1/2 day Fury boat trip it included jet skis, para sailing and tubing in the Gulf...great time had by adults and children. The Rooster Retreat & The Shabby Chicken are most definitely a GEM of the Truman Annex!!!!!

  • Submitted: Aug 18, 2015
  • Stayed: Jun 2015
  • Source: VRBO, from HomeAway
Owner's Response: Lisa, What an absolutely awesome review. I'm so glad we could accommodate your family and your friend's family at both our condos (Rooster Retreat #420646, and Shabby Chicken #595903). Thank you for your comments about how clean, impeccably decorated, and spacious our places were. It sounds like you all had a wonderful time - between going to the beaches, Duval Street, the Fury excursions, and out to many of the places to eat and drink in Key West. I hope to hear you'll be coming back again next year for your annual outing.
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This Place was Key

  • 4 of 5

We enjoyed our recent stay at the Rooster Retreat (6/27-7/7). The unit was large enough for our family of four, and it was clean and well appointed. The unit was stocked with some cleaning supplies, paper towels, spices and condiments left over from earlier tenants. This was a welcome change from our experiencing renting houses in the Outer Banks where you must bring/remove everything you need, except linens, pots, pans, and dishes. The outside deck provides a nice place in which to relax after a long day of activities. The unit also provides a few beach chairs so you don’t have to bring them with you.

The Shipyard Condominiums are conveniently located to Duval Street, nearby restaurants, Fort Zachary Taylor State Park, and the NOA’s Eco-Discovery Center. The mile walk to Mallory Square can be made along the quiet streets of the Truman Complex. The Shipyard’s pool while not very large is more than sufficient for everyone to enjoy.

Our only complaint is that the walls of Shipyard condos are very thin so noise could be an issue. However, a pleasant chat with neighbors will take care of that problem.

If we return to the Keys, we would consider staying at the Rooster Retreat again.

  • Submitted: Jul 17, 2015
  • Stayed: Jun 2015
  • Source: VRBO, from HomeAway
Owner's Response: John, I'm glad our place out-shined compared to your other renting experiences in NC. We try to make it a home-away-from-home experience. From making the deck a relaxing place - along with a great Weber grill, to providing most all kitchen needs to cook and quickly clean-up, to comfortable beds. The pool is especially nice in the mornings and late afternoon when less people are there. The location is very convenient to main attractions on the island. Your mention of the walls are thin - yes, I understand that is a comment heard throughout the complex. A couple of reasons we chose an end unit is both the additional light from windows, but also only having one shared wall. Thank you for chatting with your neighbors - everyone is there to enjoy themselves and can be very respectful once made aware.
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Our condo is in the heart of old town Key West. Enjoy a three minute walk to Blue Heaven Restaurant, La Creperie, Green Parrot, along with taking in the sights, sounds, and characters on Duval Street. You are a short walk or bike ride from exciting Mallory Square where sunset is celebrated every evening, or walk out behind our complex to appreciate a low-key, quiet sunset from the Coast Guard pier. You are also minutes from Fort Zachary beach.


Rates & Availability

Truman Annex Condo Rental Rates

Rental Basis:
per property
Owner accepts payment in:
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Rate Period Nightly Weekend Night Weekly Monthly Event
Jan 7 2017 - Mar 31 2017
Changeover Day: Saturday
7 night minimum stay
Apr 1 2017 - Apr 30 2017
7 night minimum stay
May 1 2017 - May 31 2017
7 night minimum stay
Jun 1 2017 - Aug 31 2017
7 night minimum stay
Sept Special
Sep 1 2017 - Sep 30 2017
7 night minimum stay
Oct 1 2017 - Oct 19 2017
7 night minimum stay
Fantasy Fest Week
Oct 20 2017 - Oct 29 2017
7 night minimum stay
Power Boat Race Week 2017
Nov 6 2017 - Nov 13 2017
7 night minimum stay
Thanksgiving week
Nov 18 2017 - Nov 25 2017
8 night minimum stay
Flat fee
November - December
Nov 25 2017 - Dec 22 2017
7 night minimum stay
Christmas Week
Dec 23 2017 - Dec 29 2017
7 night minimum stay
New Years Eve week
Dec 30 2017 - Jan 6 2018
7 night minimum stay
Jan 7 2018 - Mar 31 2018
7 night minimum stay
My Standard Rate
7 night minimum stay

Additional information about rental rates

Card Processing $65
Refundable damage deposit $200
Tax Rate 12.5%

Thank you for considering our place for your stay:
We kindly request a $200.00 security deposit, refundable to guest if all is in good order
PayPal will have an additional 3.0% charge to total amount
VRBO Book It or credit card processing is $50.00, along with their (VRBO) service fee
Rates are subject to change until reservation is confirmed
Refer to the rental agreement from the owner for specifics on cancellation policy

Owner's Cancellation Policy

100% refund if canceled at least 60 days before arrival date.
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