Top Vacation Rental in Key West



The Rooster Retreat

4.9 ⭐️ (107 Reviews)

The Rooster Retreat is a lovely 2 bedroom, (1 king/2 twins, and queen bed) with one remodeled bathroom located in Truman Annex in Old Town Key West. It is a bright, end unit with a great deck, private yard, and access to the pool.

Over 100 5 Star Reviews

Minutes from the beach

Private & Very Clean

2 Bedrooms, sleeps 4

The Rooster Retreat is a lovely two-bedroom, one-bathroom ground-floor end unit with a spacious backyard deck.

The master bedroom offers one king-size bed, a ceiling fan, a 43" TV, and double french doors that open onto the back deck.

The queen bedroom offers natural light through the front window, ceiling fan, and small Television.

The bathroom, located in the common area between the two bedrooms, offers a recently updated vanity and walk-in shower.

This unit is cleaned regularly by our local cleaning service and we are following CDC guidelines for cleaning/disinfectants. Read our reviews, we have always been known to have a spotless, clean place - and we've increased our care. Stay with us!

Being at the far-end corner of the property, unit #175 boasts added privacy compared to neighboring units. Unique to this floor plan is the added natural light from the extra exterior wall and window. Enjoy the open kitchen to living room layout, large leather sectional, and newly added 55" Sony TV. You will be just a short walk from Truman Water Front park and Coffee Butler Amphitheater. Pack a picnic and take a short bike ride to nearby Fort Zachary Beach.

This sunny ground-floor condo is clean with well-appointed bedrooms, beautiful linens, and artwork. Enjoy the breeze on a cool night with open double french doors in the master bedroom. The newly remodeled kitchen with quartz countertops thoughtfully placed lighting, and seating for four is both stylish and functional. A washer/dryer is located within the unit for your convenience. The kitchen is fully equipped with pots & pans, dish towels, and dishware. Enjoy central air conditioning, on-site laundry, and all the necessities for both long and short-term stays.

Relax at the Truman Annex Shipyard Pool - located within the property grounds.

Our condo is outfitted with beach towels, beach chairs, coolers, 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.

The Best Experience

Stayed 09-22

Communication with the owner Nick, and property manager, Marie was beyond phenomenal. They were very responsive to all my questions. The property is beautiful, clean, and perfect! We will forever stay at the Rooster Retreat. Can't say enough great things about the property and the management and owners!!! So extremely happy we chose to stay here!!! ❤️❤️❤️

- Connie K.

Coming Back

Stayed 09-22

My daughter and I loved this place. I think she just wants to live there now!

- Darren B. 


Stayed 09-22

Wow! That was the first word out of our mouths upon entering. The rooms were spacious and well-decorated. The beds are comfortable and we loved the walk-in shower. The back deck had good sunshine and privacy to lounge upon. We definitely will look at re-booking upon our return.

- Santa Lance M.