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Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval!

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A covered porch with wicker furniture and a view of a swimming pool area with lounge chairs.
A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.
A spacious living area with a kitchen, dining table, and a view of the outdoors.
A modern living room with a glass coffee table, a grey sofa, and a dining area with chairs.
A pool area with lounge chairs and a clear blue pool.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms2 bathroomsSleeps 41564 sq ft

Popular amenities

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

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪2 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪4 min walk‬
  • Place, Southernmost Point
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪9 min drive‬

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  • Pool
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About the neighborhood

Key West

Located in Old Town Key West, this vacation home is within a 5-minute walk of Duval Street and within 15 minutes of other popular attractions like Florida Keys Beaches. The vacation home includes a kitchen, a balcony, and a fenced private yard.
View more Vacation Homes in Key WestOpens in a new window

What's nearby

  • Duval Street - 2 min walk - 0.1 miles
  • Ernest Hemingway Home and Museum - 4 min walk - 0.3 miles
  • Key West Lighthouse and Keeper's Quarters Museum - 4 min walk - 0.3 miles
  • South Beach - 6 min walk - 0.4 miles
  • Southernmost Point - 8 min walk - 0.5 miles

Getting around

  • Key West Intl. Airport (EYW) - 12 min drive

Restaurants

  • ‪Circle K - ‬4 min walk
  • ‪Cuban Coffee Queen (Duval) - ‬5 min walk
  • ‪801 Bourbon Bar - ‬6 min walk
  • ‪Old Town Tavern - ‬4 min walk
  • ‪Rum Bar at the Speakeasy Inn - ‬5 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.

Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval!

The Breezy Retreat is situated in the Windward Park gated community, offering a convenient location within walking distance to the Historic Southernmost Point and one block away from the famous Duval Street, known for its vibrant atmosphere and attractions.

As you enter the gated community, you'll be greeted by a large community pool surrounded by lush tropical plants. It provides a refreshing spot for swimming and relaxation.

The living room space inside the home is cozy and open, seamlessly connecting to the kitchen and dining area. The kitchen is well stocked and equipped with everything you need to prepare meals, including the fresh catch of the day or your favorite dishes. The dining table comfortably seats four, and there are two additional seats at the countertop, offering plenty of space for entertaining.

Through the French doors, you have access to a side porch, providing a pleasant place to spend time during the day or night. It's a great spot to enjoy the tropical surroundings and relax.

The first floor features a guest room with two twin beds that can be converted into a king-size bed upon request. The room is perfect for accommodating guests and visitors. There is also a full shower bathroom on this floor, ensuring convenience and comfort for guests.

The master bedroom, located on the second floor, features a king-size bed and an ensuite bathroom with a full bath/shower combination. It offers a private and comfortable space for relaxation.
Step onto the second floor balcony to enjoy the pleasant evening breezes. This balcony provides a peaceful setting to unwind and savor the end of the day.

With its convenient location, cozy living space, well-stocked kitchen, and relaxing outdoor areas, the Breezy Retreat offers a delightful vacation rental option for guests looking to enjoy the attractions and ambiance of Key West.

Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know.

Guests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check.

7 night minimum stay, maximum stay is 14 days.
This unit does have it's own washer and dryer which are located outside
No pets allowed
Pool is heated during the Winter months
Both Bedrooms have TV's
One assigned Parking Spot
Pool is Heated Seasonally
The vacation home is air-conditioned and features a kitchen, 2 bathrooms, and a balcony, and there's space to spread out with 2 bedrooms. Other standard amenities include a washing machine, a fenced private yard, and a coffee maker. Housekeeping is available on request.

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Interior entrance
Wicker Guesthouse
Old Town Key West
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
8.6 out of 10, Excellent, 1,004 reviews
$199 nightly
The price is $224
Aug 24 - Aug 25
Total with taxes and fees
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Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Communal pool
  • Heated pool

Internet

  • Available in the house: WiFi

Parking and transportation

  • Parking on site

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Concierge services
  • Housekeeping (on request)
  • Iron/ironing board

Location highlights

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

Things to do

  • Heated pool
  • Basketball nearby
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Windsurfing 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

  • Housekeeping (on request)
  • Unit size: 1,564 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

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 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
  • Minimum check-in age: 25

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.
  • 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

2302-240155

Frequently asked questions

What's there to see around this vacation home?

This vacation home is situated in Old Town Key West, just steps from Duval Street, and within a 10-minute walk of Florida Keys Beaches and Ernest Hemingway Home and Museum. You'll also find South Beach and Southernmost Point less than a mile away.

Is there parking available at Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval!?

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, there is no indoor pool at this vacation home.

What do couples enjoy most about Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval!?

Couples staying at this vacation home will appreciate amenities like a kitchen as well as a heated pool and concierge services.

Does Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval! have a hot tub?

No, but this vacation home does have a heated pool.

Does this vacation home offer breakfast?

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.

Does Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval! have connecting rooms available?

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

Where is the closest airport to this vacation home?

The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 3.5 mi away (12 minutes by car).

Are there rooms with balconies at Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval!?

Yes, every house at Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval! comes with a balcony.

Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval! Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 24 out of 26 reviews
Rating 8 - Good. 2 out of 26 reviews
Rating 6 - Okay. 0 out of 26 reviews
Rating 4 - Poor. 0 out of 26 reviews
Rating 2 - Terrible. 0 out of 26 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Daniel S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great time, nice place and will stay there again
Stayed 7 nights in Mar 2026
Verified review

10/10 Excellent

Denise G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We love this little enclave of townhouses situated around the community pool. It's very quiet inside the compound but still so close to everything you want to do in Key West. Breezy Retreat fit our needs 100%.
Stayed 14 nights in Mar 2026
Verified review

10/10 Excellent

Beth P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was perfect; beautiful condo that was clean, quiet and well located.
Stayed 9 nights in Nov 2025
Verified review

10/10 Excellent

Stefani S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Just as described. Conveniently located. Clean and well appointed
Stayed 7 nights in Jan 2026
Verified review

10/10 Excellent

Angela R.

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

Great place

Place was very nice. Would stay there again.
Stayed 7 nights in Mar 2023
Verified review

10/10 Excellent

Belinda S.

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

Nice and Convenient

Enjoyed the quietness of the property. The home had all the amenities we needed. Great location that allowed walking distance to many attractions and restaurants. Very pleasant stay and would recommend this place.
Stayed 7 nights in Apr 2025
Verified review

10/10 Excellent

Laurent C.

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

wonderful residence

Great location, quiet, clean, cozy, and right in the best part of town. You can walk anywhere and also it is on the main road of key west for easy in and out access. I would strongly recommend this place for short or long stay periods.
Stayed 9 nights in Apr 2023
From a partner site

10/10 Excellent

Karen F.

Wonderful!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location and nice accommodations.
Verified review

10/10 Excellent

John R.

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

Family time and fun!

Great location! Can walk to everything. Quiet but close to the hustle and bustle of Duval Street.
Stayed 7 nights in Feb 2023
Verified review

10/10 Excellent

Christopher B.

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

National Park Tour

This rental was in the perfect location for us. Two blocks from Duval and only a 15 minute walk to the Gulf side to catch the Ferry to Dry Tortugas. The place is secluded and the neighbors are really nice. The space had everything we needed and any communication with the property manager was quickly answered....top notch all around!
Stayed 7 nights in Apr 2025
Verified review

10/10 Excellent

Sally F.

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

Amazing Accommodations in Key West!

This was the perfect property for our family spring break. We were close to everything we wanted to be close to while also having privacy from being on the main road. All the other "neighbors" were friendly so sharing a pool with others wasn't a problem at all. I would absolutely rent this property again and will definitely refer!! Thank you!
Stayed 7 nights in Mar 2025
Verified review

10/10 Excellent

Adam S.

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

Perfect place to relax away from the crowds

This was a fantastic place to stay. Beautifully re-done townhome with no interior problems. It was great being able to come back and hang out at the large heated saltwater pool when we didn’t want to be around the massive crowds on Duval street. When we did want to go out, it was only a couple minute walk. Overall great experience and would recommend for all travelers
Stayed 7 nights in Mar 2024
Verified review

10/10 Excellent

Scott S.

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

Truly fantastic

Was probably the best VRBO experience I’ve ever had. The house was near everything that you wanted to do in Key West. However, the courtyard set up of these properties with the common pool made you feel like you were not in the middle of a busy area. It is truly an oasis in the middle of paradise. communication was fantastic. The house was spotlessly clean and everything went extremely well. We hope to be back in the near future.
Stayed 7 nights in Feb 2023
Verified review

10/10 Excellent

Jennifer B.

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

Key West 2.0

The home was exactly as described. Very close to Duval street, but not in the middle of chaos. We loved it. The management company was terrific! Communication with them was a breeze and they went above and beyond. (I asked if there was a box fan somewhere in the home and unfortunately there wasn’t, I was going to purchase one. But I didn’t have to; one was delivered the same day! We look forward to returning for future stays!
Stayed 7 nights in Mar 2025
From a partner site

10/10 Excellent

Denise S.

The Breezy Retreat was Easy Breezy!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Everything about our stay was easy Breezy from booking to check out!When we arrived our keys were in a lockbox and when we entered the property it was exactly how the pictures appeared online. The pool was lovely and the property management team were there daily to clean the pool and surrounding area.We had an issue with an emergency light that was buzzing due to an electrical blip and an electrical came within a few hours. Although we didnt take advantage of the service, you can have tours, golf carts, or bicycles booked through Preferred Reality which is very convenient.When you stay you dinner at Duffy's is a must! I had the best surf and turf dinner, the price was reasonable and the service was top notch. Thank you Preferred Reality for making our stay at the Breazy Retreat easy breezy.
From a partner site

8/10 Good

David W.

Private & Quiet Spot

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The unit is very good. Location is outstanding. Really enjoyed the pool. We had TV issues which took several days and multiple visits to fix. Smart thermostat kept pushing the Temps up requiring regular monitoring. Lastly, the outdoor areas need mosquito treatment. All fixable issues.
Stayed 10 nights in May 2023
From a partner site

10/10 Excellent

Brian W.

Outstanding!!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: It looks just like it does on the website! Inside the property was very clean and updated. Brand new kitchen. Outside was just as just as clean. Great porches for sitting. Pool area was very clean and the water temp was just right. Location was good for walking anywhere in town, but bad for noise. You'll hear every Harley, truck, and sports car zooming down Truman. Angela provided great costumer service and answered all questions. We'll probably stay again.
Verified review

10/10 Excellent

Jennifer H.

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

Old Town Key West-heated pool/close to everything

This was a fantastic place. Pool was at perfect temperature the whole time. We were there eight days, and someone there about every third day to clean out pool. Great communication, quick and easy to get questions answered. Condo itself was great. Upstairs bedroom had a nice en suite bathroom that included a bathtub. Downstairs bedroom could be two singles or one king. Full bathroom with shower downstairs. Kitchen had everything we needed. Condo was clean. Full-size washer dryer was in a small room attached to the condo outside. So condo only users of washer/dryer. Actually nice having it outside since Key West can get humid. Would 100% stay again.
Stayed 8 nights in Feb 2024
From a partner site

10/10 Excellent

dona g.

It was better than we expected!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: When we arrived at the home, we were pleasantly surprised because it looked even nicer than the photos. I think some of the furniture and bedding had been replaced, which was quite nice. The beds were comfortable and the kitchen was well-stocked. Everything was lovely. I think the upstairs tv was a little slow due to Wi-Fi connection issues. The central pool was great. The grounds were well kept. This is a great location because within a 10 minute bike ride, you can pretty much get everywhere you’d want to go. They even provide pool towels. One thing to note: it was hard to figure out how to get past the main gate. No one told us that this is unit #11. You need to know this so that you can access the correct lockbox outside the main gate. They did give me a code, but we just kept trying different lockboxes until we happened to open #11. From there, you use one of the keys on the intercom box to open the gate. The rental company should give some more specific directions. I had to call the office when we got there and they walked me through it, but it could have been outlined in a email to save time.
Stayed 10 nights in Mar 2023
From a partner site

8/10 Good

A guest from Stanwood, WA

Family get away

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We enjoyed our stay! Great location and the property was kept up and low key.
Verified review

10/10 Excellent

John B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 6 nights in Sep 2025
Verified review

10/10 Excellent

TIMOTHY H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 8 nights in Sep 2024

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