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Book Online or call HomeAway Booking Assistance 888-640-7927

Beautiful 2BR king/twins, End Unit Truman Annx Ground FL, Pool on property

Bedrooms 2
Space 679 sq. ft.
Property type condo
Minimum Stay 7 nights


About the property

Beautiful 2BR king/twins, End Unit Truman Annx Ground FL, Pool on property

The Rooster Retreat is a lovely 2 bedroom, (king/twins, and queen bed) 1 bathroom end-unit offering a nice kitchen, comfortable leather sectional, LARGE deck and lush landscaping. Due to fire code ordinance, this condo is unable to have an outdoor grill, much like many other condos in the area.

This ground floor condo is very clean, and has well-appointed bedrooms with beautiful linens and art work. 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 quartz 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 2016 CONDO UPDATES: All new AC & air handler, queen bed, king bed, bath fixtures & lighting, and landscaping

More Details


Old Town Condo Accommodation and Amenities

Property Type:
  • condo
  • floor 1
  • Guests provide their own meals
Floor Area:
  • 679 sq. ft.
House Rules:
  • Max. occupancy: 4
  • pets not allowed
  • non smoking only
  • 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 ...
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 -
(45 traveler reviews)

91% Complete
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Beautiful 2BR king/twins, End Unit Truman Annx Ground FL, Pool on property
average rating of 4.911111 based on 46 reviews

Rooster Retreat Rocks!

  • 5 of 5

Perfectly located a couple of blocks from central Duval St. and an easy walk to many of the bars and restaurants. Clean and extremely comfortable for a home away from home and had everything we needed. Grounds are tropical, lush and well cared for. We enjoyed our stay tremendously!

  • Submitted: May 27, 2017
  • Stayed: May 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for the fabulous review. We appreciate your comment about how clean and comfortable the condo was with everything you needed for your stay. The location can't be beat - and at night, it's quiet. We look forward to your next stay. Cheers! Marie
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We had a wonderful time and loved the condo. Definitely will be coming back and staying here again.

  • 5 of 5

Nice, clean, easy to access. Plenty of room

for our family of 4. Upstairs neighbors were basically our alarm clock as they were not the quietest but that is normal anywhere, hotels included. Loved the ability to cook our own meals and also bring home left overs from our evenings eating out. Location was perfect, allowed for us to walk almost everywhere. The worst part about it was that we had to leave. Myself and my daughter have fallin in love with Key West.

  • Submitted: Dec 30, 2017
  • Stayed: December 2017
  • Source: VRBO, from HomeAway
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Great Stay at Rooster Retreat

  • 5 of 5

We stayed at Rooster Retreat for one week and thoroughly enjoyed it. The condominium was equipped with anything you need for a day at the beach or at the pool. The location is within walking distance of downtown and the beach. Marie and Tom were very good communicating with us before and after our stay. Due to the hurricane that occurred prior to our stay, they kept us updated on the condition of the condo and city. Our security deposit was returned very timely. We would definitely consider staying there again.

  • Submitted: Nov 21, 2017
  • Stayed: November 2017
  • Source: VRBO, from HomeAway
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Very clean and very well stocked with all pool, beach and kitchen amenities.

  • 5 of 5

The condo is a great 2 bedroom corner unit, very clean with lots of natural lighting.

It is also very close to everything on the island. We rented bikes for the 7 days we were here and explored the whole island, all the beaches and found some amazing places to eat off the beaten trail. Would highly recommend this property and area of the island.

  • Submitted: Aug 8, 2017
  • Stayed: July 2017
  • Source: VRBO, from HomeAway
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Great place to stay!

  • 5 of 5

Had everything we needed. Marie was awesome to deal with. Loved the back deck for morning mimosas. Would definitely stay there again. First time in Key West - won't be the last. So much fun!

  • Submitted: Apr 8, 2017
  • Stayed: March 2017
  • Source: VRBO, from HomeAway
Owner's Response: Paula, Thank you for the great review. I'm so glad you and your friends had such a fun time and loved the condo. We look forward to hearing from you again! Marie
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Wonderful Stay

  • 4 of 5

My wife and I visited Key West for my retirement celebration and we are very happy that we chose this property.

With the exception of one day, the property was very quiet and relaxing. The city is building a waterfront park behind the Shipyard complex and one morning the workers decided to start at 5:30 am and continued through about 4 in the afternoon. Fortunately this only occurred on one day and was not repeated.

The unit is very clean with all that you need to set up housekeeping with the exception of the food you want.

The lanai is very comfortable and the perfect place for breakfast or just relaxing between sight seeing.

The location is perfect for walking anywhere around Old Town. No car would be necessary but if you bring one there is a reserved parking space available which, if your been to KW before, you know is a major plus.

We will definitely check for availability of Rooster Retreat the next time that we plan a trip to Key West. Thank you Marie and Tom!

  • Submitted: Mar 26, 2017
  • Stayed: March 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you George for taking the time to write a review. I'm glad you chose our place for your retirement celebration and found our place to be clean, comfortable, the perfect place in location, having breakfast on the deck. The city is working on a large waterfront park right out back of the Truman complex, so I'm trying to let renters know of this, and I'm sorry to hear work started at 530 am! I keep in touch with the project managers for the city - they let me know they were warned about this early start - and I presume this is why it was only day. I look forward to when the park is finished as it will be a gem for the community. Thank you for your understanding. Congratulations on your retirement. We look forward to hearing from you as you mentioned you would stay again - please do! Marie and Tom
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Tom and Marie
Member since: 2012
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
February 19, 2018

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 Old Town

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


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

Taxes and fees are additional

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.