A short walk from Duval Street and Southernmost Point, Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval! provides laundry facilities and more. Stay connected with in-room WiFi.
Reviews
1010 out of 10
Exceptional
Entire home
2 bedrooms2 bathroomsSleeps 41564 sq ft
Popular amenities
Kitchen
Washing machine
Dryer
Air-conditioning
Outdoor space
Parking available
Add dates for prices
About this property
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 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, offering a pleasant place to spend time 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 bathroom with a shower 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 for guests looking to enjoy Key West's attractions and ambiance.
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.
Some booking platforms allow a guest to book a stay longer than 14 days; these reservations will not be honored and will be canceled, with any payments refunded.
Guests are subject to a 2% credit card processing fee. To avoid that fee, we encourage you to pay by check.
7-night minimum stay; maximum stay is 14 days. This unit does have its own washer and dryer, which are located outside No pets allowed Pool is heated during the Winter months Both Bedrooms have TVs One assigned Parking Spot Pool is Heated Seasonally
Property amenities
Beach
Beach nearby
Pool/Spa
Communal pool
Heated pool
Internet
Available in the house: WiFi
Parking and transport
Parking on site
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Hob
Microwave
Oven
Refrigerator
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
Smoke-free property
Services and conveniences
Concierge services
Housekeeping on request
Iron/ironing board
Location highlights
In the city centre
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
Snorkelling 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)
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
Pets not allowed
Children and extra beds
Children are welcome
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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 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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
About the area
Located near the beach, this holiday home is in Old Town Key West, a neighbourhood 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 snorkelling nearby, or enjoy the great outdoors with ecotours. Visit our Key West travel guide
Is Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval! pet-friendly?
No, pets are not allowed at this property.
How much is parking at Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval!?
On-site 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!?
Checkout 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 holiday 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.
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Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval! Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Just as described. Conveniently located. Clean and well appointed
Stayed 7 nights in Jan 2026
From a partner site
10/10 Excellent
Karen F.
5 Mar 2025
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.
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
From a partner site
10/10 Excellent
Brian W.
2 Feb 2024
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.
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
8/10 Good
A guest from Stanwood, WA
3 May 2024
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.
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!
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
Kathryn H.
12 May 2026
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
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.
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.
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!
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!
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.
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.
14 Sept 2025
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.
18 May 2023
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
dona g.
28 Apr 2023
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.