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

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms2 bathroomsSleeps 4145 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space
  • Parking available

Explore the area

View 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

Room options

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Blue Flamingo Resort Key West

New Town
  • Pool
  • Pet-friendly
  • Free Wi-Fi
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8.6 out of 10, Excellent, 2,788 reviews
The price is NZ$336
includes taxes & fees
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About the area

Key West

This holiday home puts you in the heart of Key West, within just a 10-minute stroll of popular attractions like Duval Street and Florida Keys Beaches. Highlights at this holiday home include a kitchen, a washing machine and a balcony. .Home features 2 bathrooms, a living room and a fenced private garden. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A TV, a coffee/tea maker and a hairdryer are also available. Housekeeping is available on request. .This smoke-free holiday home offers concierge services and barbecues. Added amenities include laundry facilities. .Attractions within a 10-minute walk of this Old Town Key West holiday home include Ernest Hemingway Home and Museum and South Beach.
View more Holiday homes in Key WestOpens in a new window

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, FL (EYW-Key West Intl.) - 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

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 is cosy 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 favourite dishes. The dining table comfortably seats four, and there are two additional seats at the worktop, 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 ground 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 savour the end of the day.

With its convenient location, cosy living space, well-stocked kitchen, and relaxing outdoor areas, the Breezy Retreat offers a delightful holiday 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 honoured and will be cancelled, 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 washing machine 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

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Southernmost Beach Resort and Guesthouses
Old Town Key West
  • Pool
  • Spa
  • Free Wi-Fi
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4.3 out of 5, Excellent, 3,660 reviews
The price is NZ$564
includes taxes & fees
30 Nov - 1 Dec
Southernmost Beach Resort and Guesthouses

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)

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

  • No pets allowed

Children and extra beds

  • Children are welcome.

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
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. On-site parties or group events are strictly prohibited.

Property is also known as

2302-240155

Frequently asked questions

Are there any beaches close to Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval!?

Yep, Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval! is a short 8-minute walk from Florida Keys Beaches. Fun beach activities include jet skiing, snorkelling and scuba diving.

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

Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval! has a heated pool and a communal pool.

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

You bet! With amenities such as laundry facilities, a BBQ and children's dinnerware, it's no surprise that Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval! is a winner with our family travellers.

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

No, Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval! does not offer an airport shuttle service.

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

Check-in begins at 4:00 PM. Check-out time is 10:00 AM.

Are pets allowed at Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval!?

No, pets are not allowed.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 26 out of 28 reviews
Rating 8 - Good. 2 out of 28 reviews
Rating 6 - Okay. 0 out of 28 reviews
Rating 4 - Poor. 0 out of 28 reviews
Rating 2 - Terrible. 0 out of 28 reviews

10/10

Cleanliness

Reviews

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
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
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
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.
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
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.
Verified review

10/10 Excellent

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