Very Good

5 reviews

1 / 14 Private ground floor end-unit beautiful decor, nice beds, great location



Pets allowed:
Wi-Fi available:

1 Full bath

Description from owner

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TripAdvisor Property ID: 7178382

About the area

PROXIMITY TO PLACES... The 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. Duval Street, music, bars, restaurants are within 2 blocks of the condo. Walk or bike through the gorgeous Truman Annex over to happening Mallory Square for shops, museums, and special events.

Owner profile

Marie T.
Years listed:

Languages spoken: English

About the owner

My husband and I fell in love with Key West after visiting and spending a fun week with some locals we befriended on that trip - we looked at some properties, and as karma would have it - we brought our first property. We love the collection of history, humanity from all walks of life living harmon...

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To be covered by Payment Protection this rental needs to be paid for online through Vacation Home Rentals using your credit/debit card or PayPal. Never pay for your holiday rental by wire transfer (such as Western Union or Moneygram) as this type of payment is untraceable.
No smoking at this property
Cancellation policy
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  • Bedroom 1: King bed 2 Twin beds
    Bedroom 2: Queen Bed


  • Air conditioning
  • Heating
  • Shared outdoor pool (heated)
  • Balcony/Terrace
  • Private garden
  • High Speed Internet
  • Linen provided
  • Parking Included
  • Secure parking
  • Balcony/Terrace
  • Towels provided
  • Wi-Fi available


  • Ceiling Fans
  • Clothes dryer
  • Dishwasher
  • DVD player
  • Freezer
  • Hair dryer
  • Iron
  • CD player
  • Refrigerator
  • Satellite TV
  • Microwave
  • Stove
  • Telephone
  • Toaster
  • TV
  • Washing machine


  • Cycling Trips
  • Fishing
  • Golf
  • Water sports


  • 1 Full bath

Reviews (5)

Very Good – based on 5 reviews Very Good
5 reviews

“A Lovely Place!”

Reviewed 12 Mar 2017

We (2 retired couples) enjoyed our stay at Rooster Retreat. What you see in the pictures is true to what you get, but I will add that the "twins to king conversion" is probably the best I have ever experienced. It just did not "feel" like twins -- the infamous "crack" was non-existent! All in all a wonderful time! We would definitely rent this unit again.

“Cozy comfy condo = Rooster Retreat!”

Reviewed 22 Nov 2016

Location, location, location...Rooster Retreat is part of the Shipyard condos in the Truman Annex complex and is so conveniently located to the action on Duval Street. One can walk to the familiar attractions that made Key West Green Parrot Bar, Sloppy Joe's, Captain Tony's Saloon, Blue Heaven and Mallory Square Sunset Celebration just to name a few. Rooster Retreat had everything we needed to make our stay the king bed in the front bedroom and a queen in the back bedroom providing restful sleep, modern washer/dryer, big "L" shaped sofa was set up perfectly for watching the flat-screen TV, ceiling fans in every room, plenty of towels – both bath and beach, plenty of kitchen utensils, plates, glassware and cookware. The deck can be seen/accessed through the French doors and provides a nice view of the outside with its lush green tropical plants. It's also equipped with a nice grill and plenty of private seating. Last, but not least, Rooster Retreat is affordably priced which combined with everything else makes for a pleasant Key West vacation!

Owner's reply: Thank you Donna for writing a lovely and lively review of the Rooster Retreat! We're so glad you and your husband chose our place for your stay. Looking forward to hearing from you again, Marie

“After Sunset, the Sun Still Shines in Key West”

Reviewed 20 Sep 2016

Our stay in Rooster's Retreat was lovely. The condo is clean and supplied well. It worked well for us especially since it's a walk out unit, so struggling to climb a stair case with luggage after a long flight is a non-issue. If you're a veteran, the people of Key West will honor you perhaps in a way you've never experienced. We felt like we were home when we returned to the condo after our adventures. The bed we slept in was more comfortable then the one we have at home! The owners are quick to respond to inquiries about their property. All in all, if you're considering a stay in Key West, I strongly recommend Rooster's Retreat, you will not be disappointed!

Owner's reply: Tami, Thank you and to your family for your service to our country. I'm so glad you loved the condo and felt it was like home. So glad you thought the bed was comfortable - we try to make our place as comfortable and welcoming for our guests. Thank you and we look forward to hearing when you'll be coming back again. Marie

“Beautiful 2 bedroom condo”

Reviewed 15 Jul 2016

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.

Owner's reply: 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

“Rooster's Retreat”

Reviewed 30 May 2016

Rooster's Retreat was the perfect spot for my family's first stay at Key West. The location was fabulous, close to all the fun but also quiet and very secure. The unit was super clean and well furnished and equipped. The owners were wonderful to work with, providing great recommendations for activities and dining!!! Such a fun time for all of us!! I highly recommend and would love to return.

Owner's reply: Renee, I'm so glad you chose the Rooster Retreat for your family's first stay in Key West and found the location and condo to be fabulous, super clean, and well furnished. It's great to hear you liked the recommendations, and I truly appreciate your comment about us as owners. I'm always thrilled to hear when we meet and exceed our guest's expectations as this is your vacation and we want it to be best for you! We hope you'll be able to return again in the future - Key West is so special.

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Owner Supplied Testimonials

June 2015
Loved staying in this place!! It had everything we needed and more! Clean, quiet and very pretty! Will definitely recommend it to friends and family!

Dec 2014
Rooster Retreat is clean, well maintained and in a great location. We've stayed in a few different Shipyard condos and after this stay we're definitely hooked on this one. Since it's an end unit there's less noise from neighbors and the fact that we could see the sun coming up each morning, from the back porch, was a lovely morning treat. The photos accurately represent the unit. The beds and pillows were comfortable, towels plentiful and the kitchen had everything we needed for the week. We didn't use the grill on the back porch but it looked to be in working order.

This condo has the best bathroom storage of any Shipyard condo I've seen. Between the medicine cabinet and a shelving unit on the wall, four of us could store all of our daily toiletries without a problem. We stayed in one unit where the only place to put things was the back of the toilet (that place clearly had an owner who didn't spend any time in the unit).

Marie was prompt , clear and friendly in all of her communications. I talked briefly with Karen, the owners' local manager, and she was also personable and professional.

We rented bikes from Eaton Bikes. Eaton delivered them to the unit and sent me a txt with the location of the keys so that we could hop right on the bikes after our arrival. Perfect! We always go to Faustos grocery on Fleming for our weekly breakfast and beach food needs and then eat out each evening. I left other recommendations in the guest book at the Rooster Retreat. We had a great week and hope to return soon - maybe we'll bring more friends next time and stay at the bigger place!

Nov 2014
Rooster Retreat was a wonderful vacation experience! And yes I too will begin with clean...unit is very clean and well maintained. Loved the location, from the perspective of the Truman Annex itself, and from the logistics of being centrally located in Key West. My husband and I use to have a season rental home in California and in my ad I use to say, "just bring a few cookbooks and your spices, everything else is there". The owners could say the same thing, everything you need is there...umbrellas, beach chairs, tons of pots and pans, glasses, dishes, silverware, towels, beach and get the idea! Furniture is very comfortable, king bed is restful, and parking is just a few feet from the front door(great with groceries). Me with a new fitbit we logged in 4-6 miles of walking a day(even with rain) and my husband loved the private garden (no foot traffic) for reading. Having been a Key West visitor for more years than I will mention, we are always looking for new eateries, as well as our favorites...Half Shell Raw Bar for great boiled shrimp, Blue Heaven for breakfast(go early on Sunday), Kelly's for dinner or bar snacks, Santiago Bodega for dinner and Aqua for a fun drag show~
Owners are wonderful to work with, very detailed and timely in the their replies. There is also a wonderful grill to use in the yard, and it is fun to enjoy a private meal in the garden, which is lush with palm trees. The deck in the yard is large enough to spread out a yoga mat and do a few downward dogs, such an added perk!
We did so love our visit and look forward to a return stay at the Rooster Retreat or perhaps the new Shabby Chicken. Both are lovely units!

Aug 2014
Just back from a great week in Key West with my husband and 2 young teenagers (girls 12 and 14). This unit was everything we were looking for. 2 bedrooms worked well for us. The bedroom with the king bed was converted for our use into 2 twin beds. Kitchen was well appointed with everything that we needed. Even had a pitcher of water in a filtered container waiting for us in the fridge. This unit is extremely clean and does not show much wear.

The pros: Clean, end unit, large outside area in the back, well appointed kitchen, brand new washer & dryer (loved the stackable, better than what I have a home), and extremely attentive unit owner. This owner exchanged many emails with my husband, promptly answering questions, making suggestions for dining and activities, etc.

The cons: I'll have to dig deep for a con. The worse I can say is that the walls are thin. This isn't a problem inside the unit, but rather with the neighboring units (upstairs and next door). Likely it is prevalent thru-out the Truman Annex.

Recommendations: While you are there we'd recommend renting bikes from Eaton Bikes (1 1/2 blocks away). We rented 2 tandem bikes for $85/ week each. Great way to get around Key West. For dining, you must try Blue Heaven, La Creperie, Santiago Bodega and Salute on the Beach. For sites, you must go to Mallory Square and Truman's Little White House (tour with Jimmy was amazing). For activities, we liked the jet ski tour with Island Safari Tours on Stock Island (only $99 each for am rental and 1 1/2 hour tour).

Nov 2015:
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!

June 2015:
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!!!!!

June 2015
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 Parrot for drinks at night. Everything was in good shape and clean. Would recommend!

April 2015
I've stayed in Key West over the past 25 years and Rooster Retreat was the best! I appreciated it was clean, well equipped and in a convenient location. Being able to walk to the Green Parrot to hear music is always a perk! As an end unit it is quiet and private. Every aspect of the condo showed caring attentive owners. Marie added small touches such as a filtered water pitcher and a tub mat. Being an older woman I worry about slippery tubs and often travel with my own mat. I liked this one so much that I may purchase one for myself! The weather was very hot so we hung out in the AC and pool a lot. I was there with my daughter and her friend who walked to Fort Zackery beach. Thank you again for a wonderful week hope to visit again soon.