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MARCH OPENINGS: Beautiful 2BR (king or twin bed), END-UNIT Truman Annx 1st FL

Bedrooms 2
Property type condo
Minimum Stay 7 - 8 nights


Minimum Stay
7 - 8 nights

About the property

MARCH OPENINGS: Beautiful 2BR (king or twin bed), END-UNIT Truman Annx 1st FL

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.

LIKE WHAT YOU SEE HERE & NEED MORE SPACE or EXTRA CONDO for additional guests? Visit VRBO #595903 to see more photos and description of the large and 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 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 a day
Response rate:
Calendar last updated:
20 January, 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
  • 1 of 1


Wonderful! 4.9/5 -
(35 traveller reviews)

MARCH OPENINGS: Beautiful 2BR (king or twin bed), END-UNIT Truman Annx 1st FL
average rating of 4.9428573 based on 36 reviews
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!!!

  • Review Submitted: Dec 15, 2016
  • Date of Stay: 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.

  • Review Submitted: Jul 15, 2016
  • Date of Stay: 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!

  • Review Submitted: Nov 19, 2015
  • Date of Stay: 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!!!!!

  • Review Submitted: Aug 18, 2015
  • Date of Stay: 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.

  • Review Submitted: Jul 17, 2015
  • Date of Stay: 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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Great Time

  • 5 of 5

After 18 years we returned to key west with the kids and couldn't have picked a better place. Close to the park beach with great snorkeling. Close to the Green Parent for drinks at night. Everything was in good shape and clean. Would recommend!

  • Review Submitted: Jul 1, 2015
  • Date of Stay: Jun 2015
  • Source: VRBO, from HomeAway
Owner's Response: Bill, I'm so glad you found our place perfect and could share it with your kids. Key West is a special place and our condo is right in the heart of it all (close to the beach, sunsets, restaurants, entertainment, of course the landmark Green Parrot), all of which can make for wonderful family memories.
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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.


Prices & Availability

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Additional pricing information

Refundable Damage Deposit £162
Card Processing £53
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 for cancellations more than 60 days before check-in date.
Available arrival


Accommodation and facilities for this holiday condo in Truman Annex in Lower Florida Keys

Property Type:
  • condo
  • floor 1
  • Self-catering
  • 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 ...
  • Terrace ...
  • Barbecue ...
  • Veranda ...
  • non smoking only
  • pets not allowed
Pool / Spa:
  • Communal Pool
  • cinemas
  • library
  • live theatre
  • marina
  • museums
  • restaurants
Leisure Activities:
  • antique hunting
  • beachcombing
  • Boating
  • Shopping
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • laundrette - serviced
  • medical services
Sports & Adventure Activities:
  • deepsea fishing
  • fishing
  • golf
  • jet skiing
  • Kayaking
  • Parasailing
  • pier fishing
  • sailing
  • diving
  • snorkelling
  • Snorkeling/Diving
  • swimming
  • water skiing

Partner Offers

Portable wifi hotspot

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