See all properties
Entire home

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

Choose dates to view prices

Photo gallery for Roosters Perch at Truman Annex- LOW SUMMER RATES!!!

A covered patio with outdoor furniture, a ceiling fan, and a white fence.
A beach with clear turquoise waters, a sandy shore, and rocky outcrops.
A living room with a ceiling fan, a television, a sofa, and a dining area.
A hotel with a white facade, a red-tiled roof, and a flagpole with an American flag.
A swimming pool with lounge chairs, palm trees, and a large building in the background.

Reviews

9.2 out of 10
Wonderful

Entire home

2 bedrooms2 bathroomsSleeps 4960 sq ft

Popular amenities

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

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪5 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪9 min walk‬
  • Place, Mallory Square
    ‪9 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪11 min drive‬

Room options

You may also like

Ad
Pool

Blue Flamingo Resort Key West

New Town
  • Pool
  • Pet friendly
  • Free WiFi
  • Restaurant
8.6 out of 10, Excellent, 2,757 reviews
$175 nightly
The price is $197
Nov 1 - Nov 2
Total with taxes and fees
Blue Flamingo Resort Key West

About the neighborhood

Key West

Located in Old Town Key West, this vacation home is within a 10-minute walk of popular sights such as Duval Street and Ernest Hemingway Home and Museum. The vacation home includes a kitchen, a balcony, and a refrigerator.
View more Vacation Homes in Key WestOpens in a new window

What's nearby

  • Duval Street - 5 min walk - 0.3 miles
  • Harry S. Truman Little White House - 5 min walk - 0.3 miles
  • Ernest Hemingway Home and Museum - 9 min walk - 0.5 miles
  • Mallory Square - 9 min walk - 0.5 miles
  • Fort Zachary Taylor Historic State Park - 11 min walk - 0.6 miles

Getting around

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

Restaurants

  • ‪Margaritaville - ‬6 min walk
  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Wendy's - ‬7 min walk
  • ‪Jack Flats - ‬6 min walk

About this property

Entire place

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

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.
The vacation home is air-conditioned and features a kitchen, 1.5 bathrooms, and a balcony, and there's space to spread out with 2 bedrooms. Guests can enjoy a TV and stay connected with free WiFi. Other standard amenities include a washing machine, a coffee maker, and a dining table.

Similar properties

A brick building with a number 21 sign, a staircase leading to a porch with blue chairs, and a view into the interior with a sofa and lamp.
Hemingway Hideaway in the Truman Annex
Old Town Key West
  • Pool
  • Kitchen
  • Washer
  • Dryer
9.8 out of 10, Exceptional, 68 reviews
Hemingway Hideaway in the Truman Annex

Property amenities

Beach

  • Beach nearby
  • Beach loungers
  • Beach towels

Pool/Spa

  • Communal pool
  • Outdoor pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bed sheets provided

Bathroom

  • 1.5 bathrooms
  • Hair dryer
  • Shower
  • Soap
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Books
  • TV

Outdoor areas

  • Balcony
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Location highlights

  • In a village
  • In the city center

Things to do

  • Golf

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
  • Unit size: 960 square feet

Policies

Check-in

Check-in time starts at 4:00 PM

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

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

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 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
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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • 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.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.

Property is also known as

Vrbo Property
Roosters Perch
Roosters Perch at Truman Annex Key West
Roosters Perch at Truman Annex Private vacation home
Roosters Perch at Truman Annex Private vacation home Key West

Frequently asked questions

What's there to see within easy reach of this vacation home?

This vacation home is situated in Old Town Key West within a 10-minute walk of Duval Street and Ernest Hemingway Home and Museum. You'll also find Mallory Square and Florida Keys Beaches less than a mile away.

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

No, there isn't parking at this vacation home.

Is this vacation home associated with a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, this vacation home doesn't have an indoor pool; however, there is an outdoor pool.

Is Roosters Perch at Truman Annex- LOW SUMMER RATES!!! a good place to stay for couples?

Amenities that appeal to couples at this historic vacation home include a kitchen as well as an outdoor pool and a garden.

Are there hot tubs at Roosters Perch at Truman Annex- LOW SUMMER RATES!!!?

No, this vacation home doesn't have a spa tub.

Does this vacation home include breakfast service?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay free of charge?

No, pets aren't allowed at this vacation home.

Are there connecting rooms at Roosters Perch at Truman Annex- LOW SUMMER RATES!!!?

No, this vacation home doesn't feature connecting guestrooms.

What is the closest airport to this vacation home?

The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 4.2 mi away (14 minutes by car).

Are there rooms with balconies at Roosters Perch at Truman Annex- LOW SUMMER RATES!!!?

Yes, every house at Roosters Perch at Truman Annex- LOW SUMMER RATES!!! comes with a balcony.

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

Reviews

9.2

Wonderful

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

Reviews

Verified review

8/10 Good

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 review

10/10 Excellent

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

Amazing location

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

Would definitely stay again

Excellent. property.
Stayed 7 nights in Nov 2023
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

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 review

8/10 Good

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 review

10/10 Excellent

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 review

8/10 Good

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 review

8/10 Good

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

6/10 Okay

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 review

4/10 Poor

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 review

8/10 Good

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 review

10/10 Excellent

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

More to Explore