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Entire condo

2 bedrooms1 bathroomSleeps 4

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About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

Two Bed One Bath Ground Floor End Unit in the Heart of Old Town

TRUMAN ANNEX:

PLEASE NOTE: As Of January 2026, This property is switching to monthly rentals and can be booked here:

https://www.airbnb.com/rooms/1374590031464974940

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, ceiling fan, 55" TV and double french doors that open onto the back deck.
The queen bedroom offers natural light through the front window, ceiling fan and 55" TV.
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 65" 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 art work. 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 are located within the unit for your convenience. The kitchen is fully equipped with pots & pans, dish towels and dish ware. 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.

(Due to fire code ordinance, this condo is unable to have an outdoor grill, much like many other condos on the island.)

Thank you.

2019 New deck and landscaping

2018 and 2017 CONDO UPDATES: New bathroom, All new AC & air handler,

Property amenities

Beach

  • Beach nearby
  • Beach loungers
  • Beach towels

Pool/Spa

  • Communal pool
  • Fenced private pool
  • Outdoor pool

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shampoo
  • Shower
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Fenced yard
  • Garden
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Single level property
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near the marina
  • Near the sea

Things to do

  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Garden

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 21

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the neighborhood

Located near the beach, this condo is in Old Town Key West, a neighborhood in Key West. Fort Zachary Taylor Historic State Park and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. USCGC Ingham Maritime Museum and Florida Keys Eco - Discovery Center are also worth visiting. With jet skiing, scuba diving, and snorkeling nearby, you'll find plenty of adventures in the water. Visit our Key West travel guide
View more Condo Rentals in Key West
Map
FL, Key West

What's nearby

  • Duval Street featuring signage
    Duval Street
    6 min walk - 0.5 km
  • Ernest Hemingway Home and Museum featuring heritage elements and a house
    Ernest Hemingway Home and Museum
    6 min walk - 0.5 km
  • Fort Zachary Taylor Historic State Park showing military items, heritage elements and interior views
    Fort Zachary Taylor Historic State Park
    8 min walk - 0.7 km
  • Mallory Square featuring outdoor art, a square or plaza and signage
    Mallory Square
    11 min walk - 1.0 km
  • Florida Keys National Marine Sanctuary
    5 min walk - 0.4 km

Getting around

  • Key West Intl. Airport (EYW)
    16 min drive

Restaurants

  • Green Parrot Bar
    5 min walk
  • Bourbon Street Pub
    9 min walk
  • Blue Heaven
    9 min walk
  • Mangoes Restaurant
    8 min walk
  • Moondog Cafe & Bakery
    9 min walk

Frequently asked questions

Does Two Bed One Bath Ground Floor End Unit in the Heart of Old Town have a pool?

Yes, this property has an outdoor pool.

Is Two Bed One Bath Ground Floor End Unit in the Heart of Old Town pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Two Bed One Bath Ground Floor End Unit in the Heart of Old Town?

Check-in begins at 4:00 PM.

What time is check-out at Two Bed One Bath Ground Floor End Unit in the Heart of Old Town?

Check-out is at 10:00 AM.

Where is Two Bed One Bath Ground Floor End Unit in the Heart of Old Town located?

Located in Old Town Key West, this condo building is within a 10-minute walk of Florida Keys Eco - Discovery Center, Duval Street, and Florida Keys Beaches. Fort Zachary Taylor Historic State Park and Ernest Hemingway Home and Museum are also within 10 minutes.

Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 131 out of 149 reviews
Rating 8 - Good. 13 out of 149 reviews
Rating 6 - Okay. 5 out of 149 reviews
Rating 4 - Poor. 0 out of 149 reviews
Rating 2 - Terrible. 0 out of 149 reviews

9.8

Cleanliness

9.8

Location

8.0

Property conditions & facilities

Reviews

10/10 Excellent

Michelle B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A great place to get good Key West vibes

Great place and a great location! We were able to walk, rent a golf cart, or catch a ride to the most iconic places in Key West. Would stay here again!
Stayed 6 nights in Jul 2024

10/10 Excellent

David R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Comfortable, friendly, great location

Property was spotless, owner was very responsive, and the location is central to everything Key West has to offer!
Stayed 6 nights in Apr 2024

10/10 Excellent

Geoffrey M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Location

The unit is clean and comfortable. It is close to all the fun and quiet in the evenings.
Stayed 10 nights in Dec 2024

10/10 Excellent

Gina M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location

Really enjoyed staying at this location near Fort Zachary Taylor beach and Duval Street. The place was quiet and simple and served our needs well!
Stayed 6 nights in May 2024

6/10 Okay

James W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Convenient Location

A great location. The unit we stayed in was adequate. It really needs to be updated.
Stayed 7 nights in Dec 2024

8/10 Good

Marilyn M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key west

Great location
Stayed 6 nights in Jul 2024

10/10 Excellent

lisa s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

So comfortable and convenient

We have stayed in several units in Shipyard and this by far is the most comfortable. King size bed in one room , Queen in the other. All tvs were large with great pics. Sofa large and relaxing, two could literally lay down and enjoy your chill time. Kitchen had everything you needed!!! Will return.
Stayed 7 nights in Mar 2025

10/10 Excellent

Rob M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome place to stay

This place is awesome. The guy who runs it is very helpful place was clean. Also has a wash machine and dryer.
Stayed 6 nights in Aug 2023

8/10 Good

Gordon S.

Liked: Cleanliness, check-in, location, listing accuracy

Great location

Clean, comfortable, and simple.
Stayed 6 nights in Aug 2023

10/10 Excellent

Richard K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Shipyard Gem

A very comfortable property with everything we needed for a great stay. A big plus .... great deck furnishings for relaxing outdoor living.
Stayed 7 nights in Dec 2023

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place

It was very convenient to walk to everything. Great place, nice and clean. Good communication with the host. Used the pool one day.
Stayed 9 nights in Mar 2024

10/10 Excellent

Krista H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Key West rental

Clean, comfy, all the details are taken care of! Just as described and host is easy to work with. Rental has everything you need, no need to bring things like towels or dish soap, no extra expenses for toilet paper! Pool is beautiful and a great size. Not usually busy, plenty of seating both in the sun or shade.
Stayed 6 nights in May 2024

10/10 Excellent

sriecke@yahoo.com, Port Crane

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key West Escape

We have been to Key West about 7 times and this property was incredible. Perfect condo, perfect location. We loved it! Enjoyed Fantasy Fest for the first time. Will definitely book again. Also, Tyler was fantastic! Sharon.
Stayed 7 nights in Oct 2023

10/10 Excellent

Kevin S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect place for four, perfect location!

This is a great place to stay, and is EXACTLY where you want to be in Key West. The place was clean, very well kept, and had everything we needed for the four of us to stay a week. Our host was very quick to respond, though we really didn't need him for anything while we were there. A short walk to all the fun stuff, and secure parking if you drive in. Quiet and secure relaxation on the back deck taking in what Key West does best! There is a ton of stuff to do close by, and all of the must visit places and attractions are within walking distance. We will definitely stay here again on out next visit to Key West.
Stayed 7 nights in Jun 2024

10/10 Excellent

valerie m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Met all our expectations

One of the nicest places we have stayed. Liked the privacy of the corner unit. Television and cable worked great. Very comfortable furniture. Back deck and foliage was very nice and we had a cute little lizard we named Runt come visit us every morning. Would love to stay here again!
Stayed 7 nights in Sep 2023

8/10 Good

James W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice Location

We VRBO often and this was our first trip to Key West. The location of this property was great…most things within walking distance including our favorite restaurant Blue Heaven! It’s a must try! We liked that the community was gated and had a dedicated parking spot as parking around town can be challenging. The property manager was very accommodating. We would consider this place again when we come back to Key West for sure.
Stayed 7 nights in Dec 2023

8/10 Good

Ray C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Location Location Location

This was an older not totally updated unit that was clean and comfortable. Everything worked but the best part was the location ideal for Fantasy Fest. It's not a large unit so we used the second bedroom for our luggage and dressing room. There was not enough room in the bedroom with a king to put luggage except in the closet. Not sure how comfortable it would be for two couples.
Stayed 8 nights in Oct 2024

8/10 Good

Clifford M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Concert getaway

The location was great. We were a reasonable distance from everything in old town. We rarely had to drive unless we were going to grocery store or it was too hot to walk. We went to a concert at the amphitheater which was about a 10 minute walk away. Beaches at fort Zachary were about a 15-20 minute walk. We had a two year old and the house provided beach toys, cabana, chairs and all the beach essentials. We’d stay here again if ever in key west.
Stayed 6 nights in Aug 2024

8/10 Good

Stacy H.

Liked: Cleanliness, location, listing accuracy
Disliked: Check-in

Great location

This sits in the middle area of Duval street which was nice. You could do one side of Duval One day and walk the other half on another day. For the most part the condo was great. We didn’t get our code to check in until 5 after 4, the cleaning crew took 6 hours for a tiny two bedroom 1 bath. They also had their 2 year old daughter in there while cleaning. The queen bed wasn’t attached to the headboard so the bed laid out from the wall. There is no ice machine so you have to walk to buy bagged ice. Only one ice tray. The kitchen was well stocked with anything you should need. Bathroom is tiny…..for two teen girls, myself and my husband. NO plug ins or space to put clothes basically living out of your suitcase. Would be nice to have something to put clothes. We stayed a week had a great time, pool was very nice, fort Zachary was a perfect beach and the condo had beach chairs, umbrella snorkeling. We left a few things as well when we left. Pay it forward.
Stayed 6 nights in Jun 2024

6/10 Okay

Stuart M.

Liked: Communication, location, listing accuracy

Nice property …but with some dislikes

Good location, great pool, decent facilities within the unit. Animal hair on sofas on arrival, dirt in cupboards & under beds and in kitchen drawers. We had to wash everything including towels on arrival. I disliked the fact I did not get details on how I could access the unit until 4pm on arrival day. I don’t like traveling half way across the world without knowing for sure how I will access a property. Appreciate this could just be personal preference. We also had noisy neighbours who shouted and played music at 4am after coming back from a night out. There was route to resolve this I was told which I appreciated but didn’t make for a great stay. Not ideal when staying with kids. Overall the unit is well equipped but felt neglected in terms of cleaning and a few changes needed IMO. We had an ok stay but probably wouldn’t come back being honest.
Stayed 7 nights in Aug 2023

10/10 Excellent

Douglas K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, onsite pool, and nice two bedroom condo.
Stayed 7 nights in Sep 2025

10/10 Excellent

Deb

Liked: Cleanliness, amenities, property conditions & facilities, communication
Safe, clean & quiet & lovely!
Stayed 6 nights in Aug 2025

10/10 Excellent

Mercedes P.

Always a great stay when I stay here. Always very accommodating and pleasant.
Stayed 7 nights in Jul 2025

10/10 Excellent

Lori S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great home base for exploring Key West! It had everything we needed, from beach chairs, beach toys, beach towels to all the kitchen needs. It was very clean and comfortable. We got quick replies for our questions. Location can’t be beat and the swimming pool is wonderful.
Stayed 6 nights in Jul 2025

10/10 Excellent

Cheryl S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing again!

This was our second stay here. We had a slight hiccup with the internet but communication was great and it was fixed promptly. Super clean unit in a quiet neighborhood. Looking forward to staying again.
Stayed 9 nights in Jun 2025