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

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

A covered porch with wicker furniture and a view of a swimming pool area with lounge chairs.
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.
A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Dive into relaxation
    Unwind in the top-rated pool, your perfect spot for relaxation.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Duval Street

Popular amenities

  • Balcony
  • Shared communal pool
  • Barbecue grill
  • Air conditioning
  • Refrigerator
  • Washer

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, South Beach
    ‪6 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪9 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Balcony
Dining area

Add dates for prices

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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 Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. Discover the area's water adventures with jet skiing, scuba diving, and snorkeling nearby, or enjoy the great outdoors with ecotours.
View more Vacation Homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Duval Street - 2 min walk - 0.2 km
  • Ernest Hemingway Home and Museum - 4 min walk - 0.4 km
  • South Beach - 6 min walk - 0.6 km
  • Key West Butterfly and Nature Conservatory - 6 min walk - 0.6 km
  • Southernmost Point - 8 min walk - 0.7 km

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
  • ‪Banana Cafe - ‬6 min walk

Frequently asked questions

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

No, pets are not allowed at this property.

How much does it cost to stay at Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval!?

As of Oct 31, 2026, prices found for a 1-night stay for 2 adults at Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval! on Nov 9, 2026 start from $639, 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.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval!?

Check-in begins at 4:00 PM.

What time is check-out at Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval!?

Check-out is at 10:00 AM.

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

Located in Old Town Key West, this vacation home is within a 5-minute walk of Tennessee Williams Key West Exhibit and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 10 minutes.

Reviews

10

Exceptional

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. 25 out of 27 reviews
Rating 8 - Good. 2 out of 27 reviews
Rating 6 - Okay. 0 out of 27 reviews
Rating 4 - Poor. 0 out of 27 reviews
Rating 2 - Terrible. 0 out of 27 reviews

10/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Second time renting this unit. It's clean,well maintained and close to all the Key West action.
Stayed 7 nights in Oct 2026
Verified review

10/10 Excellent

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

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful house . Home from home . Loved it so close to everything.
Stayed 10 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything we had hoped for and more! Beautiful interior, adorable front porch with rocking chairs, cute little deck, and a beautiful and clean pool right outside our front door! Complex was quiet but that was part of its charm and was just perfect. Would definitely recommend and hope to return!
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

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
From a partner site

10/10 Excellent

Key west condo

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: Wonderful! Great property, perfect location. Great amenities and furnishings
Verified review

10/10 Excellent

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

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

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

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

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
Response from VrboOwner on Jul 26, 2023
Laurent, Thank you for your review! Breezy Retreat is a great retreat and we are glad you reccomend it!
Verified review

10/10 Excellent

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
From a partner site

10/10 Excellent

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

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

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

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

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
Response from VrboOwner on Mar 13, 2023
Thank you for taking the time to write such a wonderful review of Breezy Retreat. We are thrilled to hear that it was the best VRBO experience you've ever had and that you enjoyed the convenient location of the house. Love how you described it as being an oasis in the middle of paradise. Hope to be able to host you again in the future!
Verified review

10/10 Excellent

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

8/10 Good

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
Response from VrboOwner on Jul 26, 2023
David thanks for your feedback! We are glad to say the issues with the TV should remain fixed with the new internet modom. With your feedback we were able to get the smart thermostat off the cooling schedule it was on, so now a guest can have it set at the temp they want during their whole stay. Thanks!
From a partner site

10/10 Excellent

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

10/10 Excellent

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.
Response from VrboOwner on Feb 10, 2024
Brian. Thank you for the great review and for staying with us at Breezy Retreat. Sorry about the noise level of Truman Avenue. Perhaps earplugs in the bedside tables are in order from now on! We do hope that you will return and look forward to seeing you in Key West soon. Please let us know if we can be of help with future vacation rentals. All the best! The Preferred Properties Team
Verified review

10/10 Excellent

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

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
Response from VrboOwner on Jul 26, 2023
Thank you for your kind words! 🌟 We're thrilled you enjoyed your stay and found the home even better than the photos! Since your stay the WiFi modom has been upgraded so there should be no more connection issues. With your feedback we have provided more detailed instructions in our Guest Hopsitiality app/website that can also be sent via email. Thanks again for your feedback!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely property - clean and conveniently located in town. Lush gardens with small pool. Very comfortable.Check in instructions could have been slightly more clear regarding where to open the main gate. Enjoyed our stay!
Stayed 7 nights in Jun 2026
From a partner site

8/10 Good

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.
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