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Roosters Perch at Truman Annex- LOW SUMMER RATES!!!

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Pool
Exterior
Living area
Private kitchen
Dining

Reviews

9.2 out of 10
Wonderful
2 bedrooms1+ bathroomSleeps 4960 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Key West, FL
  • Place, Harry S. Truman Little White House
    ‪3 min walk‬
  • Place, Duval Street
    ‪5 min walk‬
  • Place, Mallory Square
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪14 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Guest Bedroom

1 Queen Bed

Master Bedroom

1 Queen Bed

Sofa Sleeper

1 Double Bed

1 bathroom, 1 half bathroom

Full Bathroom

Toilet · Shower only

Powder Room

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
Garden

About this property

Roosters Perch at Truman Annex- LOW SUMMER RATES!!!

Welcome to Roosters Perch in Truman Annex, Porter Lane!

This spacious corner duplex is flooded with natural light and boasts abundant windows throughout. The home offers two generous bedrooms, each featuring comfortable queen beds, private balconies, and large closets for your convenience. A shared bathroom with a shower is easily accessible from the hallway, serving both bedrooms.

The main floor showcases an open-concept layout combining the kitchen, dining, and living areas. The living room includes a sofa sleeper for additional guests. Also on this level is a powder room and a roomy rear patio deck, complete with outdoor dining seating for four—perfect for relaxing evenings or meals al fresco.

As an end unit, Roosters Perch offers privacy with neighbors on only one side.

Porter Lane is one of the most sought-after complexes in Truman Annex, providing quick access to Mallory Square where you can experience breathtaking nightly sunsets. You’re just a short walk from Fort Zachary Taylor Beach (with beach chairs and towels provided), and steps away from Mile 0, the iconic Duval Street, and Ernest Hemingway’s historic home.

Guests can enjoy the large, shared pool within the complex, one of the biggest in Truman Annex, complete with loungers for ultimate relaxation.

Roosters Perch is fully furnished and turnkey ready for your stay.

We look forward to hosting you at Roosters Perch @ Truman Annex!


Check-in time is at 4 PM and check-out is at 10 AM. Please plan your travel accordingly or consider booking an extra night if you require more flexible arrival or departure times.
Our prices include all fees. No hidden fees.

Add dates for prices

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Life in the Slow Lane at the Truman Annex in Key West
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  • Washer
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8.8 out of 10, Excellent, (33 reviews)
Life in the Slow Lane at the Truman Annex in Key West

House Rules

Check in after 4:00 PM
Minimum age to rent: 28
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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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 has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Key West

Located near the beach, this vacation home is in Old Town Key West, a neighborhood in Key West. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. USCGC Ingham Maritime Museum and Mel Fisher Maritime Museum are also worth visiting.
View more Vacation Homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Harry S. Truman Little White House - 3 min walk - 0.3 km
  • Duval Street - 5 min walk - 0.4 km
  • Florida Keys National Marine Sanctuary - 6 min walk - 0.6 km
  • Mallory Square - 8 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park - 9 min walk - 0.8 km

Getting around

  • Key West Intl. Airport (EYW) - 14 min drive

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Margaritaville - ‬6 min walk
  • ‪Willie T's - ‬6 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Jack Flats - ‬6 min walk

Frequently asked questions

Does Roosters Perch at Truman Annex- LOW SUMMER RATES!!! have a pool?

Yes, this property has an outdoor pool.

How much does it cost to stay at Roosters Perch at Truman Annex- LOW SUMMER RATES!!!?

As of Apr 5, 2026, prices found for a 1-night stay for 2 adults at Roosters Perch at Truman Annex- LOW SUMMER RATES!!! on Apr 11, 2026 start from $263, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Roosters Perch at Truman Annex- LOW SUMMER RATES!!! 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 Roosters Perch at Truman Annex- LOW SUMMER RATES!!!?

Check-in begins at 4:00 PM.

What time is check-out at Roosters Perch at Truman Annex- LOW SUMMER RATES!!!?

Check-out is at 10:00 AM.

Where is Roosters Perch at Truman Annex- LOW SUMMER RATES!!! located?

Located in Old Town Key West, this vacation home is within a 10-minute walk of We Cycle Key West, Duval Street, and Ernest Hemingway Home and Museum. Florida Keys Beaches and Fort Zachary Taylor Historic State Park are also within 15 minutes.

Reviews

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 37 out of 50 reviews
Rating 8 - Good. 8 out of 50 reviews
Rating 6 - Okay. 3 out of 50 reviews
Rating 4 - Poor. 1 out of 50 reviews
Rating 2 - Terrible. 1 out of 50 reviews

9.6/10

Cleanliness

10/10

Check-in

9.4/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

8/10 Good

Melinda D.

Liked: Check-in, communication, location, listing accuracy
We had a wonderful time. The location and property were amazing
Stayed 7 nights in Oct 2025
Verified

10/10 Excellent

Justin V.

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

Amazing location

Amazing location. Great property.
Stayed 7 nights in Dec 2022
Verified

10/10 Excellent

John S.

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

Convenient to Old Town attractions & restaurants

The property was spacious
Stayed 10 nights in Dec 2023
Verified

10/10 Excellent

Jeremy D.

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

Great property

This property had everything we needed and was so convenient to everything we wanted to do. Thank you so much for allowing us to rent your little house in paradise.
Stayed 9 nights in May 2024
Verified

10/10 Excellent

Tom V.

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

we had a great stay ...would love to come back.

could use a little bit of updating.
Stayed 7 nights in Feb 2023
Verified

10/10 Excellent

Ed P.

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

Would definitely stay again

Excellent. property.
Stayed 7 nights in Nov 2023
Verified

10/10 Excellent

Sarah K.

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

Great family vacation

We loved our stay here. Very easy check in and out. We loved the location. Easy walk to Truman park, beach, fishing, shopping, dining out! We would have loved to rent a golf cart for our entire stay, but we didn’t want to pay to park our vehicle somewhere else. We love Key West so much, and this house was perfect for our family!
Stayed 7 nights in Mar 2024
Verified

10/10 Excellent

jo p.

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

Great place, a bit noisy on weekend nights due to proximity to the public parking lot

Very nice
Stayed 12 nights in Jan 2023
Verified

10/10 Excellent

Kelaine H.

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

Great location

We had a great stay! The location was ideal for walking and it was an amazing place with clean, quiet grounds! Air conditioning was phenomenal. Could use a grill and maybe a new fridge but it worked and served its purpose! Absolutely would give your place 5 stars!!!!!! We’d stay again, for sure! Thank you for a great stay!
Stayed 7 nights in Oct 2024
Verified

10/10 Excellent

Rachel A.

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

Just as expected

I spent a lot of time researching the area and deciding what would be most convenient, then looked for the perfect place in that area. This really fit all of our requirements and more. The location was great, easy to walk anywhere we wanted to go. The room was really nice and spacious. Having the outdoor space was really nice, and the washer and dryer was also very nice. We would definitely stay here again if we come back.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Sheila G.

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

Week Away

We were pleasantly surprised with how nice Roosters Perch was. We would rent again. One negative, the public parking lot can be loud but mostly on the weekends
Stayed 7 nights in Jan 2025
Verified

10/10 Excellent

Kim W.

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

Our family vacation

We have stayed in the Truman Annex before, but we were in the condos. The townhome was much roomier and allowed for more privacy. We enjoyed our stay and were pleased with our accommodations. The owners responded quickly to all our questions during our stay. We would definitely stay again.
Stayed 7 nights in Dec 2022
Verified

4/10 Poor

7 S.

Liked: Communication, location
Disliked: Cleanliness, listing accuracy
The first problem was the tile floors (up and down stairs) were filthy enough to turn your feet black. No TV's in bedrooms. And cockroaches in kitchen. The manager was very helpful when called, but definetly not worth 6,000. We've stayed in Key West for many years and this was not one we'd pay that price for again.
Stayed 7 nights in Jan 2026
Verified

8/10 Good

April M.

Liked: Cleanliness

Roosters perch

Condo was great if I had one complaint it would be beds were not very comfortable otherwise great experience thank you
Stayed 7 nights in Apr 2025
Verified

10/10 Excellent

michael i.

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

Location location location

Wonderful condo in the heart of Key West. No car needed, you can walk to the famous Mallory square to watch the sun set. Or walk to any of the fine restaurants KW has to offer. The condo was exceptionally clean and comfortable. Beach chairs are available ( short walk to Fort Zack beach). Highly recommended this wonderful condo.
Stayed 7 nights in Nov 2024
Verified

10/10 Excellent

Theresa H.

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

Love Key West but Too Expensive

Loved the location and the property was great. Short walk to everything. Truman Annex is very quiet with lush tropical plants. Unfortunately, this is probably our last visit to Key West because everything has become incredibly expensive. There are so many other cities that are more affordable to visit.
Stayed 13 nights in Jun 2024
Verified

8/10 Good

Mary Jane G.

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication
More information should be given upon check-in. We couldn't locate the keys for the pool and the gate when we arrived. Also, there were no instructions for the TV - just 3 remotes! Very confusing!We had a problem with the Keurig - reported it with no response from the property manager.But, all in all, we enjoyed our stay there. No place is ever perfect!
Stayed 10 nights in Oct 2025
Verified

8/10 Good

SUSAN B.

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

Loved the property/ location

Some glitches w/ the television/live streaming first few days, but property mgmt made it good. Wish it had been ready at start. Very responsive to requests for help.
Stayed 7 nights in Apr 2023
Verified

10/10 Excellent

Matt T.

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

Almost perfect

Great location, comfortable accommodations. Great deck in back, access to the pool; terrific. 1 little thing. You’re renting to adults. To pay $4G’s for a weekly rental and have a cheap 4 cup coffee maker is silly.
Stayed 7 nights in Feb 2023
Verified

8/10 Good

Karen K.

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

Reprive from the doldrums

It was nice and mostly as advertised. It definitely needed work in the bathroom, showers needed mat to prevent sliding, should have been instruction books for all the remotes that operate the TV's. Comfortable ,centrally located, and good for 2 people. Overall a nice place to stay, needs some updates.
Stayed 7 nights in May 2023
Verified

8/10 Good

Deborah M.

Liked: Check-in, communication, location

Great location

We had several issues that arose during our stay and the property manager addressed them quickly. The location was perfect but the unit needs updating inside and out. A rusted bench and weeds at the front door do not promote a great first impression.
Stayed 14 nights in May 2023
Verified

10/10 Excellent

Carol B.

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

Rooster’s Perch

The condo is perfect for a couple or a small family. My husband is 90 and has Alzheimer’s. It is not an ideal location for someone with mobility issues, but it is a perfect spot for people who have no trouble with stairs and low toilets. It’s very “key west.” Very close to duval and all the fun.
Stayed 7 nights in Feb 2024
Verified

10/10 Excellent

Wayne C.

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

Excellent Service

Property was as advertised. We did have a few issues during our stay. We contacted the property manager, Theresa, who was very responsive. The problems were dealt with in a timely manner allowing us to enjoy our getaway. Highly recommend The Conch Collection and especially Theresa for excellent service.
Stayed 28 nights in Feb 2024
Verified

6/10 Okay

Jacque M.

Liked: Check-in, location, listing accuracy

Birthday trip

Condo is in need of TLC inside & out. Information on back gate would have been very helpful. Checking out was confusing. Location was perfect except for parking lot next door.
Stayed 7 nights in Aug 2022
Verified

10/10 Excellent

Bob B.

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

Conch get enough vacation

We had a great time in our unit and in Key West.We tried to rent for next year but the unit was taken, which we were very disappointed to hear. Surprised that we were not given first choice. Great location and set up. Very quiet and private too.Could use a new refrigerator and silverware set too.Frying pans were not usable. Purchased our own for the weeks we were there.Cabinets in upstairs bath were pretty bad as was the shower. All in all, very nice unit to rent.Bob
Stayed 35 nights in Feb 2025

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