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Entire condo·Private host

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

Condo with an outdoor pool, 7-minute walk to Duval Street

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

Outdoor dining
Outdoor pool
Smart TV, books
Smart TV, books
Property grounds
Close to Ernest Hemingway Home and Museum and Duval Street, Two Bed One Bath Ground Floor End Unit in the Heart of Old Town provides a garden, a playground and laundry facilities. Stay connected with free in-room WiFi.

Reviews

9.8 out of 10
Exceptional

Entire condo

2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Dryer
  • Washer
  • Kitchen
  • Outdoor space

Add dates for prices

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 transport

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • 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
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre
  • 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
  • Snorkelling 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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  • Kitchen
  • Washer
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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are 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

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

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
On-site 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 area

Map
Key West, FL

What's nearby

  • Florida Keys National Marine Sanctuary - 5 min walk - 0.4 km
  • Duval Street - 6 min walk - 0.5 km
  • Ernest Hemingway Home and Museum - 6 min walk - 0.5 km
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
  • Mallory Square - 11 min walk - 1.0 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 16 min drive

Restaurants

  • ‪Green Parrot Bar - ‬5 min walk
  • ‪Blue Heaven - ‬9 min walk
  • ‪Moondog Cafe & Bakery - ‬9 min walk
  • ‪Kaya Island Eats - ‬8 min walk
  • ‪Santiago's Bodega - ‬4 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 at Two Bed One Bath Ground Floor End Unit in the Heart of Old Town?

On-site 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?

Checkout 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 Fort Zachary Taylor Historic State Park. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 10 minutes.

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Reviews

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

9.8

Exceptional

9.8

Cleanliness

9.8

Location

8.0

Eco-friendliness

8.0

Property conditions & facilities
Rating 10 - Excellent. 130 out of 147 reviews
Rating 8 - Good. 13 out of 147 reviews
Rating 6 - Okay. 4 out of 147 reviews
Rating 4 - Poor. 0 out of 147 reviews
Rating 2 - Terrible. 0 out of 147 reviews

Reviews

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

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

Todd S.

Tropical getaway

Wonderful stay in Key West.
Stayed 7 nights in Mar 2019

10/10 Excellent

Cindy B.

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

Lovely

We had a lovely time
Stayed 6 nights in May 2024

10/10 Excellent

John H.

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

Great location in Key West !

We have been to key west twice before but this was the best location for us . We walked everywhere and enjoyed local sights . Instacart was a bonus so we could eat breakfast and lunch on the patio
Stayed 7 nights in Apr 2023

10/10 Excellent

Jane N.

Great location

This condo is in a great location. It was close to the beach, shops, and restaurants but far enough from Duval to be nice and quiet. It was clean and comfortable and had all the amenities we needed. Owners Marie and Tom were great and the self check-in was easy.
Stayed 7 nights in Apr 2019

10/10 Excellent

Stacy Y.

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

Perfect little Paradise

What a wonderful place to stay. Centrally located between all of the hot spots and must sees In key west. Will definitely be going back to the Rooster Retreat! Thank you again!
Stayed 7 nights in Sep 2020

10/10 Excellent

JoEllen A.

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

Great location.

I loved that we could walk everywhere. The pool was close and it was a short walk to see the sunset. The owners and the property manager were quick to respond to any questions I had.
Stayed 7 nights in Dec 2021

10/10 Excellent

Daren B.

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

Coming back

My daughter and I loved this place. I think she just wants to live there now!
Stayed 7 nights in Aug 2022

10/10 Excellent

Mary L.

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

Great Location

My husband and I rented this condo for a week. Great location. Walkable to most destinations. Very close to the state park . We had our own private patio. Enjoyed eating breakfast outside in the morning. Would rent again
Stayed 7 nights in Mar 2021

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
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Beautiful 2 bedroom 1 bath condo

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.

10/10 Excellent

Jennifer B., Milwaukee

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

Perfect location

The price was great and the location was absolutely perfect. We were able to walk just about anywhere and rented a golf cart which I highly recommend as it makes it easier to go even further. Marie was very communicative and there was more than enough of everything needed. I have stayed in a VRBO in Ruskin and didn’t have towels as stated and cooking items. At the annex we had EVERYTHING. Thanks for a wonderful stay
Stayed 7 nights in Apr 2022
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Amazing Getaway!

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!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Best Owner on VRBO, Best spot on Key West!

This condo was the absolute perfect location! We were able to be close enough to the action yet we came home to a quiet oasis. We walked everywhere...no need for cabs or cars! Marie is the most kind considerate owner I have ever rented from on VRBO! She went above and beyond to make sure we had everything we needed. Loved having all the beach towels and chairs to use! You will not be disappointed with your stay at rooster retreat! I highly recommend staying here!!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

great location

This was our first trip to Key West we are thrilled with our choice of places to stay. Not only is this condo warm and inviting, but we felt very safe in this gated area. The location is close to all the action, but also close to Zachary Park, swimming in the Gulf, and in the middle of beautiful walking and biking byways. We like the end unit because it has extra light. One thing we do have to mention, we were unaware that the roosters crow throughout the day - it was a blast

6/10 Okay

Tami W.

Liked: Check-in, communication, location
Disliked: Cleanliness

Needs some TLC

Due to A/C issues the unit was very musky smelling. Mold around the window in the living room, in the shower and in the washer. Unit definitely needs a little TLC. A/C issues was resolved the day before we departed.
Stayed 6 nights in Nov 2024
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Rooster Retreat

The Rooster Retreat accomodations were clean and appropriately furnished for our needs. All but one of our activities was within walking distance of the condo including Fort Zachary Beach. The owners of the condo provided chairs and beach towels which was a huge savings on rental of these items. If your a nature lover I would recommend the Botonical gardens and the Butterfly Conservatory. Like to cook? Get your fresh seafood and grill it on the deck of the condo.

10/10 Excellent

Thomas T.

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

EXCELLENT STAY

This was our first time to Key West and we could not of picked a better place to stay. The place was amazing!!! Perfect location near the beach and Duval Street. The owners our the unit were amazing. They made sure we had all our information and confirmed with us times and how to access the property. The place was VERY clean and well maintained and stocked with all the kitchen stuff you need. Was nice because they allow guests to leave stuff for other guests. We meet some people at our layover airport that were staying five doors down in the same complex and they loved our place. WE spent each morning on the patio just enjoying our time.
Stayed 7 nights in May 2019
This review was submitted before 2018 and has not been verified.

10/10 Excellent

O S., Newtown, PA

Great location; awesome time!

This was our first time using Homeaway so we were a little bit anxious about the process in general. Could not have been easier getting into the unit (even more hassle-free than staying at a hotel). We were with a group where the rest were staying a few blocks away at La Concha; every single one of them was jealous. Quiet but centrally located (two blocks away from Green Parrott)...it was definitely the best of both worlds. The patio in the back was a great place to relax before and after days and nights spent on Duval Street, fishing, jet skiis, etc. If you are considering the option of staying in a hotel near Duval vs. this unit, it is a no brainer. Stay here.
This review was submitted before 2018 and has not been verified.

8/10 Good

Barry W., Fort Worth

Very Nice and Up to Date

Marie and Tom were really great to work with. First time to use VRBO. Marie e-mailed us while we were there just to make sure we had everything we needed. Super nice. I told her when we left that the pillows were flat and she e-mailed me back that the cleaning lady would replace them. The beds were alittle firm for me. I like my beds softer. The condo is at the very end of the annex. We rented scooters. My wife loved them. The Truman Anex is a wonderful place to stay. The grounds are first class.

10/10 Excellent

Nicole W.

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

Fantastic Unit

We had the pleasure of staying at this lovely end unit. We have never stayed in New Town. This unit is in the heart of the downtown area. Walking distance to Duval Street. The owner and property manager were both very helpful. We spent most of our time in the back patio area. The back area is very private unlike most of the end units in Truman Annex. It backs up against the waterfront park so there are no neighbors behind the unit. This unit is also on an end next to a street that is not part of Truman Annex so there are no units on one side at all. I especially liked being so close to the Truman Waterfront Park. The unit has everything that is needed for eating in. We are looking forward to staying again next year.
Stayed 7 nights in Mar 2023
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Nicely appointed condo!

We stayed in Marie and Tom's condo the first week of December. Marie was very accommodating, easy to communicate with, and very helpful in recommending restaurants, etc. The condo is central located, a few blocks off Duval. We didn't rent a car, or bikes, so did a lot of walking! The best restaurants are just blocks away - Blue Heaven for the all around best dining experience, La Creperie for breakfast/lunch, Santiago Bodega for tapas, and Kelly's for happy hour and a beautiful dining garden (food good too!) The condo is immaculately kept, very nice furnishings - nice shower, comfortable beds, great ceiling fans. Although we didn't use it, the kitchen is nicely equipped. Being an artist, I appreciated a couple of pieces of original art on the walls - especially the roosters watercolor. BTW, there are lots of roosters running around this island - entertaining and beautiful. Can't wait to get to my easel! This is a great unit, great value, and great owners. Thank you, Marie and Tom!!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Victoria M., Ohio

Great stay at Rooster Retreat!

Are you looking for a quiet retreat that's affordable and located in a walking distance of the popular Duval St., Mallory Square, or a beach? This retreat provides it all and is located within the heart of Key West. The couple that owns this wonderful condo really tries to ensure that you have a wonderful stay. The greatest thing for us besides the roosters was the grill. Key West isn't affordable when it comes to eating out, so we went out and bought groceries for the week to save money. While we were unsure of what was included in the condo, we were able to cook every meal without worrying about not having the proper supplies. It's also on a corner lot, which makes it more private because you don't have constant people walking by the condo (we walked by a lot of porches on our way). The condo also provides bikes which would be useful by we actually didn't use the bikes at all because we were able to walk everywhere within 5 minutes. We also drove to Ft. Zachary beach because it was cheaper and located right behind the condo. Overall, if you want an affordable condo with a peaceful stay located in the heart of Key West, then you found the right place. Don't forget to read the review book because it provides a lot of ideas of things to do. Blue heaven is right down the street but be prepared to pay a hefty price!