10/10 Excellent
Christopher B.
May 9, 2025
Liked: Cleanliness
National Park Tour
Christopher B.
Stayed 7 nights in Apr 2025
Entire home
Breezy Retreat - New Listing - 2/2 Windward Park - Pool, close to Duval
Choose dates to view prices
Photo gallery for Breezy Retreat - New Listing - 2/2 Windward Park - Pool, close to Duval
Reviews
9.89.8 out of 10
Exceptional
Entire home
2 bedrooms2 bathroomsSleeps 41564 sq ft
Popular amenities
- Dryer
- Washer
- Parking available
- Kitchen
- Outdoor Space
- Air conditioning
Explore the area
Key West, Florida
- Duval Street2 min walk
- Ernest Hemingway Home and Museum4 min walk
- Southernmost Point8 min walk
- Key West, FL (EYW-Key West Intl.)8 min drive
Room options
You may also like
Ad
Hyatt Vacation Club at Beach House, Key West
Key West
- Pool
- Hot Tub
- Parking included
- Free WiFi
9.2 out of 10, Wonderful, 1,002 reviews
9.2
Wonderful
1,002 reviews
$305 nightly
The price is $343
$343 total
Aug 7 - Aug 8
Total includes taxes and fees
Ad
Hyatt Vacation Club at Windward Pointe, Key West
Key West
- Pool
- Hot Tub
- Parking included
- Free WiFi
9.6 out of 10, Exceptional, 1,002 reviews
9.6
Exceptional
1,002 reviews
$309 nightly
The price is $348
$348 total
Aug 6 - Aug 7
Total includes taxes and fees
Ad
La Concha Key West, Autograph Collection
Key West Historic District
- Pool
- Pet friendly
- Free WiFi
- Restaurant
8.8 out of 10, Excellent, 158 reviews
8.8
Excellent
158 reviews
$267 nightly
The price is $300
$300 total
Jul 21 - Jul 22
Total includes taxes and fees
Ad
Santa Maria Suites
Old Town Key West
- Pool
- Free WiFi
- Restaurant
- Air conditioning
9.6 out of 10, Exceptional, 1,000 reviews
9.6
Exceptional
1,000 reviews
$399 nightly
The price is $449
$449 total
Jul 15 - Jul 16
Total includes taxes and fees
Ad
The Key West Hotel
Key West Historic District
- Pool
- Pet friendly
- Free WiFi
- Air conditioning
9.2 out of 10, Wonderful, 487 reviews
9.2
Wonderful
487 reviews
$351 nightly
The price is $389
$389 total
Aug 6 - Aug 7
Total includes taxes and fees
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 Ernest Hemingway Home and Museum. The vacation home includes a kitchen, a balcony, and a fenced private yard.
What's nearby
- Duval Street - 2 min walk - 0.1 miles
- Ernest Hemingway Home and Museum - 4 min walk - 0.3 miles
- South Beach - 6 min walk - 0.4 miles
- Southernmost Point - 8 min walk - 0.5 miles
- Mallory Square - 20 min walk - 1.1 miles
Getting around
- Key West Intl. Airport (EYW) - 12 min drive
Restaurants
- Bourbon Street Pub - 7 min walk
- 801 Bourbon Bar - 5 min walk
- Moondog Cafe & Bakery - 6 min walk
- Old Town Tavern Key West - 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 - New Listing - 2/2 Windward Park - Pool, close 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.
This unit does have it's own washer and dryer which are located outside and locked.
7 night minimum stay
No pets allowed
Pool is heated during the Winter months
Both Bedrooms have TV's
One assigned Parking Spot
Pool is Heated Seasonally
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.
This unit does have it's own washer and dryer which are located outside and locked.
7 night minimum stay
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.
Property manager
The Team at Preferred Properties
Languages
English
Similar properties
Classic Key West living w/ a full kitchen, balcony, & shared pool
Classic Key West living w/ a full kitchen, balcony, & shared pool
Old Town Key West
- Kitchen
- Washer
- Dryer
- Air conditioning
9.6 out of 10, Exceptional, 30 reviews
9.6
Exceptional
30 reviews
**VILLA CUBANA @ OLD TOWN** Comfy Cottage Near Duval + LAST KEY SERVICES...
**VILLA CUBANA @ OLD TOWN** Comfy Cottage Near Duval + LAST KEY SERVICES...
Old Town Key West
- Kitchen
- Washer
- Dryer
- Free WiFi
9.8 out of 10, Exceptional, 75 reviews
9.8
Exceptional
75 reviews
OFF COURSE ~ Adorable 2 BR, 2.5 Ba Townhome in Truman Annex w/ Shared Pool!
OFF COURSE ~ Adorable 2 BR, 2.5 Ba Townhome in Truman Annex w/ Shared Pool!
Old Town Key West
- Kitchen
- Washer
- Dryer
- Free WiFi
9.8 out of 10, Exceptional, 30 reviews
9.8
Exceptional
30 reviews
TROPICAL FRONT ~ Remodeled 2 BR, 2.5 Ba w/ Parking in Perfect Location!
TROPICAL FRONT ~ Remodeled 2 BR, 2.5 Ba w/ Parking in Perfect Location!
Old Town Key West
- Kitchen
- Washer
- Dryer
- Free WiFi
9.4 out of 10, Exceptional, 40 reviews
9.4
Exceptional
40 reviews
Tranquil tropical retreat with pool, private deck, & W/D - walk to bars/dining
Tranquil tropical retreat with pool, private deck, & W/D - walk to bars/dining
Old Town Key West
- Pool
- Kitchen
- Washer
- Dryer
10.0 out of 10, Exceptional, 2 reviews
10.0
Exceptional
2 reviews
Roosters Perch at Truman Annex- LOW SUMMER RATES!!!
Roosters Perch at Truman Annex- LOW SUMMER RATES!!!
Old Town Key West
- Pool
- Kitchen
- Washer
- Dryer
9.6 out of 10, Exceptional, 44 reviews
9.6
Exceptional
44 reviews
Key West Caribbean Cottage - On Duval St w Private Pool
Key West Caribbean Cottage - On Duval St w Private Pool
Old Town Key West
- Pool
- Kitchen
- Washer
- Dryer
9.2 out of 10, Wonderful, 62 reviews
9.2
Wonderful
62 reviews
Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool
Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool
Old Town Key West
- Pool
- Kitchen
- Washer
- Dryer
9.4 out of 10, Exceptional, 33 reviews
9.4
Exceptional
33 reviews
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
Old Town Key West
- Kitchen
- Washer
- Dryer
- Pet friendly
9.8 out of 10, Exceptional, 136 reviews
9.8
Exceptional
136 reviews
PALMS AWAY ~ Truman Annex Townhome with Outdoor Patio and Community Pool!
PALMS AWAY ~ Truman Annex Townhome with Outdoor Patio and Community Pool!
Old Town Key West
- Kitchen
- Washer
- Dryer
- Free WiFi
10.0 out of 10, Exceptional, 76 reviews
10.0
Exceptional
76 reviews
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
- 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
- Golf
- Heated pool
- Tennis
- 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
Pets
- This property doesn't allow pets
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
Parties and events are allowed on site
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.
- Parties and events are allowed on site.
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 Ernest Hemingway Home and Museum and Florida Keys Beaches. You'll also find South Beach and Southernmost Point less than a mile away.
Is parking available on site at this vacation home?
No, this vacation home doesn't offer parking.
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.
Is Breezy Retreat - New Listing - 2/2 Windward Park - Pool, close to Duval a good place to stay for couples?
Couples staying at this vacation home will appreciate amenities like a kitchen as well as tennis and a heated pool.
Are there hot tubs at Breezy Retreat - New Listing - 2/2 Windward Park - Pool, close to Duval?
No, but guests can enjoy a heated pool at this vacation home.
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 this vacation home have connecting rooms?
No, there aren't connecting rooms at this vacation home.
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 that I can book at Breezy Retreat - New Listing - 2/2 Windward Park - Pool, close to Duval?
Yes, every accommodation at Breezy Retreat - New Listing - 2/2 Windward Park - Pool, close to Duval comes with a balcony.
Breezy Retreat - New Listing - 2/2 Windward Park - Pool, close to Duval Reviews
Reviews
9.8
Exceptional
All reviews shown are from real guest experiences. Only travelers 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.
Rating 10 - Excellent. 14 out of 16 reviews
10 - Excellent
14
Rating 8 - Good. 2 out of 16 reviews
8 - Good
2
Rating 6 - Okay. 0 out of 16 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 16 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 16 reviews
2 - Terrible
0
10/10
Cleanliness
Reviews
10/10 Excellent
Belinda S.
Apr 21, 2025
Liked: Cleanliness
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.
Belinda S.
Stayed 7 nights in Apr 2025
10/10 Excellent
Sally F.
Apr 14, 2025
Liked: Cleanliness
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!
Sally F.
Stayed 7 nights in Mar 2025
10/10 Excellent
Jennifer B.
Mar 16, 2025
Liked: Cleanliness
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!
Jennifer B.
Stayed 7 nights in Mar 2025
10/10 Excellent
TIMOTHY H.
Oct 23, 2024
Liked: Cleanliness
TIMOTHY H.
Stayed 8 nights in Sep 2024
10/10 Excellent
Adam S.
Mar 9, 2024
Liked: Cleanliness
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
Adam S.
Stayed 7 nights in Mar 2024
10/10 Excellent
Jennifer H.
Mar 3, 2024
Liked: Cleanliness
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.
Jennifer H.
Stayed 8 nights in Feb 2024
10/10 Excellent
Laurent C.
May 9, 2023
Liked: Cleanliness
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.
Laurent C.
Stayed 9 nights in Apr 2023
10/10 Excellent
Angela R.
Mar 18, 2023
Liked: Cleanliness
Great place
Place was very nice. Would stay there again.
Angela R.
Stayed 7 nights in Mar 2023
10/10 Excellent
John R.
Feb 25, 2023
Liked: Cleanliness
Family time and fun!
Great location! Can walk to everything. Quiet but close to the hustle and bustle of Duval Street.
John R.
Stayed 7 nights in Feb 2023
10/10 Excellent
Scott S.
Feb 20, 2023
Liked: Cleanliness
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.
Scott S.
Stayed 7 nights in Feb 2023