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Classic Key West condo w/ private parking, covered porches, & shared pool

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Outdoor dining
TV
A heated pool
Fridge, microwave, oven, stovetop
2 bedrooms, iron/ironing board, Internet, bed sheets

Reviews

9.4 out of 10
Exceptional

Entire condo

2 bedrooms3 bathroomsSleeps 689 sq m

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Kitchen
  • Outdoor space
  • Air conditioning

About this property

Entire place

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

Classic Key West condo w/ private parking, covered porches, & shared pool

Cool Breeze

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

Enjoy the best location in Key West. You will love this newly renovated, professionally decorated, casual but elegant townhome in the heart of Old Town on President's Walk in the Truman Annex, Key West's most exclusive gated community. Walk to the beach, restaurants, bars, the marina sunset celebration, water park, playground, and the Truman White House.

Enjoy seamless indoor/outdoor living where you can prepare your meal in the newly renovated kitchen, then enjoy dining outdoors under the shade of palm trees. Watch parades from the front porch or have a drink on one of two additional covered terraces. This vacation paradise is just steps away from one of the Annex’s best swimming pools.

What's nearby:
Smathers Beach, Key West's largest public beach, is just three miles away from this condo. Tourist attractions such as the Ernest Hemingway Home and Museum, Mallory Square, and Fort Zachary Taylor State Park are all within one mile of the condo. Guests can tee off at Key West Golf Club just over six miles away. Guests can rent a bike or scooter to see the sights from We Cycle, just one block away.

Things to know:
Free WiFi and cable
Full kitchen
Snowbird friendly
One reserved parking space
*Please note that this home only allows minimum night stays of seven nights or longer. This is enforced by the HOA and we cannot make any exceptions.

This property is managed by Vacasa LLC.

Parking notes: There is free parking available for 1 vehicle.



Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the "Rental Agreement" on the checkout page.

Due to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Property manager

Vacasa of Florida

Languages

English, French, German, Italian, Spanish

Add dates for prices

Property amenities

Pool/Spa

  • Communal pool
  • Heated pool

Internet

  • Available in the condo: Internet access

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Bedrooms

  • 2 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 2.5 bathrooms
  • Free toiletries
  • Hair dryer
  • Towels provided

Living spaces

  • Living room

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property
  • Note from host: Smoking is not permitted anywhere on the premises.

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre
  • Near a hospital
  • Near the sea

Things to do

  • Heated pool
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Swimming nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Unit size: 960 square feet

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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

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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
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

Property is also known as

Vrbo Property
33612

About the area

Map
Key West, FL

What's nearby

  • Duval Street - 5 min walk - 0.4 km
  • Ernest Hemingway Home and Museum - 7 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
  • Mallory Square - 9 min walk - 0.8 km
  • Southernmost Point - 15 min walk - 1.3 km

Getting around

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

Restaurants

  • ‪Margaritaville - ‬7 min walk
  • ‪Blue Heaven - ‬9 min walk
  • ‪Green Parrot Bar - ‬6 min walk
  • ‪Willie T's - ‬7 min walk
  • ‪Mangoes Restaurant & Island Cuisine - ‬7 min walk

Frequently asked questions

Is Classic Key West condo w/ private parking, covered porches, & shared pool pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Classic Key West condo w/ private parking, covered porches, & shared pool?

Check-in begins at 4:00 PM.

What time is check-out at Classic Key West condo w/ private parking, covered porches, & shared pool?

Checkout is at 10:00 AM.

Where is Classic Key West condo w/ private parking, covered porches, & shared pool located?

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

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Classic Key West condo w/ private parking, covered porches, & shared pool Reviews

Reviews

9.4

Exceptional

Rating 10 - Excellent. 22 out of 30 reviews
Rating 8 - Good. 7 out of 30 reviews
Rating 6 - Okay. 1 out of 30 reviews
Rating 4 - Poor. 0 out of 30 reviews
Rating 2 - Terrible. 0 out of 30 reviews

10/10

Cleanliness

Reviews

10/10

Close to every thing
Stayed 12 nights in Jan 2025
This review comes from a trusted partner site and has not been verified.

10/10

Just checked out and loved Cool Breeze. I would definitely stay there again. Cleanliness and location was perfect.
This review comes from a trusted partner site and has not been verified.

10/10

Wonderful amenities, perfect location, and had absolutely everything we needed. We will definitely book here again.

10/10

Had good idea of location we would like to be. Pursued that in search for 2 bedroom, 2 bath & was successful
Stayed 7 nights in Mar 2023

10/10

Property was great, close to everything but quiet and relaxing as well. Our stay was perfect. Easy access to bike& golf cart rentals as well as walking distance to all the entertainment and dining. Pool was perfect everyone was friendly. Well maintained. Can’t wait to stay again
Stayed 7 nights in May 2023

10/10

Location was great. Close to all the action. Condo was clean and had everything we needed. Only issue was construction/renovation of a nearby condo during the day made sitting on the back deck and pool area not enjoyable.
Stayed 7 nights in Mar 2024

10/10

Had a great week with friends at this property. Walking distance to everything or a short bike ride. Fun to sit on the front porch and people watch, or enjoy your morning coffee or evening drink. Patio in the back is also nice. Would not hesitate to return
Stayed 7 nights in Feb 2023

10/10

Clean is most important to me . It was that . Well stocked . No complaints.
Stayed 7 nights in Feb 2023
This review comes from a trusted partner site and has not been verified.

6/10

The home was lovely but had no instructions as to how to use television remotes. Also the overhead fans speed could not be lowered and either was off or on high. The stair case is very steep and hand rail not adequate.
Stayed 7 nights in Apr 2024

8/10

Need to supply salt, pepper, sugar, etc. All others have basic spices. Took 3 days to get a package out of mailbox. Vacasa never followed up. Numerous calls, went to 3 different offices, no one had a clue. Vacasa never called me back as promised. Sent me on a wild goose chase, I finally went to post office. They helped me. Very poor communication.
Stayed 10 nights in Mar 2021

10/10

Stayed 21 nights in Feb 2025

8/10

The property was perfectly located. We were within walking distance to everything. The Truman Annex was gated so felt very secure. Construction was going on in front off the unit but we didn’t have issues getting in and out since there were multiple entrances. The bedrooms were upstairs and fairly small but beds were very comfortable. The unit could have been stocked better with coffee filters, salt/pepper, paper towels and other basics. Otherwise it was perfect!
Stayed 7 nights in Dec 2024

10/10

We have stayed in 5 of the townhouses in Presidents Walk over 7 years and Cool Breeze was the best. Comfortable furniture and bed, beautiful decor and a deck area that we lived on to read and dine! We stayed a month and cook in many nights so found a few things missing in the kitchen. Vascasa was very prompt in sending over whatever we requested. FYI The parking spot is difficult to find but for future renters it is the 3rd space in from the corner on the curb of Porter Lane. Enjoyed our stay and Truman Annex is the best area to stay in Key West.
Stayed 28 nights in Feb 2023
This review comes from a trusted partner site and has not been verified.

8/10

The house was pretty, well maintained and a great location. Enjoyed the backyard deck and front porch. Had an unexpected maintenance issue and Vacasa handled it quickly and did the right thing for our inconvenience. We would rent there again.
Stayed 7 nights in Feb 2023

10/10

Go directly to VACASA and save money.
Stayed 7 nights in Jan 2023

10/10

This was a lovely apartment centrally located in Key West. We spent a lot of time outside in the patio garden at the back of the property, and visited the shared pool often.
Stayed 14 nights in Mar 2022

8/10

Overall, the property was nice. However, I called twice about the tub not getting hot water out of the tub spout (it was fine/hot coming out of the shower spout). No one ever came to address the issue or if they came while we were gone it wasn't fixed.
Stayed 7 nights in Feb 2022

10/10

Really nice place close to everything we wanted. Everything went smooth.
Stayed 7 nights in Jan 2022

8/10

First, the good, and there was a lot! The location can't be beat. Close to Duval, Fausto's, Cuban coffee, the Farmers Market, and a liquor store. Everything you need is within biking distance, if not walking. Firefly and Santiago's are both great restaurants within walking distance! The pool was great (heated, which in December was important.) Beds were very comfortable. The best part was our outdoor space in the back, with a sofa and dining table...we LIVED out there all week. The uplighting on the tropical foliage at night was absolutely gorgeous. The outdoor space absolutely makes the unit. Also, when our garbage disposal backed up (totally our fault, one of the men decided it should be fine to put a bunch of raw broccoli through there), we called Vacasa who said they would send out a repairman in the morning. But then he showed up anyway to fix it right on the spot, at about 9:00 at night on a holiday weekend! We were so impressed and grateful. There were a few things that were less than perfect, so I'll be honest about those, too. The kitchen lacked even the most very basic, standard things that most places make sure are stocked at least for your first night, such as salt and pepper, a couple coffee filters, oven mitts, etc. While it did sleep six of us as advertised, it was a really tight fit. Not a lot of space to park six bikes, either, which meant we had to give up our front porch space (but we preferred the back anyway.) The very nice gentleman next door, who is a full-time resident, smokes several cigars every day out on his back deck, so if you are sensitive to that smell, you will probably be happier in another location. All in all, it was a very good stay in Key West, which is always fabulous.
Stayed 7 nights in Dec 2021
This review comes from a trusted partner site and has not been verified.

10/10

Couldn't ask for a better location. Everything we needed was in walking distance. Avoid the crowds of Mallory Square and enjoy a breathtaking sunset from Truman Annex. The shared salt water pool was only steps aways and wonderful. The kitchen had everything we needed except oven mitts. The crock pot was a nice surprise. 2.5 bathrooms was a nice perk. The master bath is tiny but small tradeoff for such a nice home. There were ample bathroom and beach towels. The home was very clean and nicely decorated. The beds were very comfortable. We were so thrilled to have a parking spot, but please repaint over the 231 with a fresh coat of white and spray paint new numbers. As first time visitors it took us 30 minutes to realize the spot because 231 was painted over old numbers that were still visible, so it's very hard to see #231. Vacasa seemed unaware of this issue and relied on the cleaners to assist. We had to contact Vacasa for extra keys as advertised. Maintenance promptly dropped them off. We would love to stay at this house again. Thank you for sharing your home!

10/10

Had never stayed in Truman Annex sea & we were pleasantly surprised & really enjoyed our trip!
Stayed 7 nights in Oct 2021

10/10

It was great
Stayed 7 nights in Oct 2021
This review comes from a trusted partner site and has not been verified.

10/10

Perfect Location…..close to Duval St (few blocks) but also far enough away to be able to relax without the foot/car/scooter traffic. Cool Breeze was clean, appeared to be well maintained and had everything that we needed for the week we were there.
This review comes from a trusted partner site and has not been verified.

10/10

Very nice condo and nicely decorated
This review comes from a trusted partner site and has not been verified.

10/10

The location was perfect, near everything yet still quiet and serene surroundings. Very clean and comfortable. Had a great time spent here with family.