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Windward Isle - Nightly Rental

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2 Bedrooms
1 Bathroom

Parking

  • 1 Private Parking Spot
  • Off Street
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Description

One half of the group unit Tradewinds and opposite Leeward Isle The style is common throughout the islands. Our shotgun offers original Dade County pine floors and sandblasted walls that reflect the antiquity of design.

The Webster Dictionary dates windward back to 1549; defined as, the side or direction from which the wind is blowing. Our Windward Isle is to landlubbers what windward gusts are to sea captains: a means to easy travel and safe passage.

Windward Isle is one of the two cottages that are a favorite of our guests who like to relax in the private, quiet, beautiful garden areas with large spas that are behind each house. Your party can book these cottages for a relaxing vacation, just steps from Duval Street.

Key West Vacation Rentals typically releases all minimum night stay requirements within 60 days of the arrival date. Otherwise, our minimum night requirements are as follows:

- January thru April - 5 night minimum
- May thru mid - December - 3 night minimum
- Fantasy Fest Week - (late October) - 7 night minimum
- Christmas & New Years - 7 night minimum
- Special Holidays and Events may have up to 7 night minimums

Our software is designed to fill in small gaps between reservations that are outside of 60 days. Feel free to call our office for more info or special requests.

Individual making the reservation must be 25 years or older with proper identification and be an occupant of the property

Amenities

Living

  • Air Conditioning
  • Ceiling Fans
  • Linens
  • Ironing Board
  • Free Wifi

Outdoor

  • Deck
  • Patio
  • Gas Grill
  • Outdoor Shower

Geographic

  • Near Beach
  • Close to Duval

Availability

Key
#Night Available#Night Unavailable#Arrive Only#Depart Only
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Rates

DatesNightlyWeeklyMonthly
09/24/17 - 09/28/17$198 - $238
10/01/17 - 10/05/17$198 - $238
10/08/17 - 10/12/17$198 - $238
10/15/17 - 10/19/17$198 - $238
09/17/17 - 10/19/17$198 - $478$2,146
10/22/17 - 10/24/17$368
10/20/17 - 10/24/17$368
10/25/17 - 10/28/17$588
10/29/17 - 11/02/17$248
10/29/17 - 11/07/17$248 - $388$2,016
11/05/17 - 11/07/17$248
11/08/17 - 11/12/17$438
11/13/17 - 11/16/17$248
11/13/17 - 11/21/17$248 - $388$2,016
11/19/17 - 11/21/17$248
11/26/17 - 11/30/17$288
12/03/17 - 12/07/17$258
12/10/17 - 12/14/17$258
12/17/17 - 12/21/17$258
12/01/17 - 12/21/17$258 - $378$2,166
12/22/17 - 12/27/17$588
12/28/17 - 01/04/18$4,528
01/05/18 - 04/30/18$438$3,066$13,140
05/01/18 - 05/03/18$288
05/01/18 - 05/24/18$288 - $341$2,176
05/06/18 - 05/10/18$288
05/13/18 - 05/17/18$288
05/20/18 - 05/24/18$288
05/25/18 - 05/27/18$388
05/28/18 - 05/31/18$288
05/28/18 - 06/28/18$288 - $341$2,176$9,280
06/03/18 - 06/07/18$288
06/10/18 - 06/14/18$288
06/17/18 - 06/21/18$288
06/24/18 - 06/28/18$288
07/01/18 - 07/05/18$398
06/29/18 - 07/07/18$398$2,786
07/08/18 - 07/12/18$288
07/08/18 - 08/18/18$288 - $341$2,176$9,280 - $9,440
07/15/18 - 07/19/18$288
07/22/18 - 07/26/18$288
07/29/18 - 08/02/18$288
08/05/18 - 08/09/18$288
08/12/18 - 08/16/18$288

Reviews

AWESOME

Reviewed on 2017-08-05 by Larissa M. of Jacksonville, FL United States
Updated on 2017-08-05
Review of stay from 2017-07-18 to 2017-07-20
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Recommend to Others
This is a very cute and cozy home to stay, great location. Near the beach, you can literally walk there. the pace was very clean and nice. Me and my family had a great time while we were there. Totally recommend this place, very affordable price too.

Weekend Getaway

Reviewed on 2017-07-14 by Unknown of Fort Meade, FL United States
Updated on 2017-07-14
Review of stay from 2017-07-01 to 2017-07-04
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Recommend to Others
Great little place not far from Duval Street and within walking distance to just about anywhere you would want to go. House was clean aside from the hot tub having some dead bugs and leaves in it and the backyard lights not working, however we didn't let that stop us from enjoying our stay.

Wonderful little cottage

Reviewed on 2017-02-21 by Abbey H. of Saint Joseph, MN United States
Updated on 2017-02-21
Review of stay from 2017-02-12 to 2017-02-17
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Recommend to Others
We were very pleased with the Windward Isles cottage. Great location, the house and amenities were exactly what we expected (even better actually). The beds and pillows were comfortable, the house was well equipped and clean. The charming d├ęcor was perfect. The hot tub was clean and ready for us when we arrived. The management and housekeeping were very reliable and obviously thought about everything we would need while we were there. Excellent.

Pleased and Satisfied

Reviewed on 2017-04-14 by Melissa G. of Markesan, WI United States
Updated on 2017-04-14
Review of stay from 2017-04-07 to 2017-04-12
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Recommend to Others
The rental was exactly as I expected very nice and clean with good housekeeping staff. The beds were very comfortable and loved the hot tub. The office staff were very accommodating.

Come back and work with these guys

Reviewed on 2017-03-09 by Unknown of Clive , IOWA United States
Updated on 2017-03-09
Review of stay from 2017-03-05 to 2017-03-07
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Recommend to Others
People were great! Service was incredible!! And we hope to come back.
Hot tub was down, but they overnighted parts and got it working the next morning!

Only small negative was it was right across from a bar that got a little loud into the evenings.

Perfect holiday

Reviewed on 2016-06-28 by Charlotte K. of Halmstad, HA United States
Updated on 2016-06-28
Review of stay from 2016-06-20 to 2016-06-23
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Recommend to Others
We stayed in Key West for a few days, rented this house. 2 families with 2 children, this was perfect for us. The location in the town, nearby where everything happends so we walk around every night. The house was clean and a bath in the tub outside after a long day was very injoyful from the children. We can rekomend it to our friends.

Great Key West Rental!

Reviewed on 2016-07-29 by Jessica F. of Branford, CT United States
Updated on 2016-07-29
Review of stay from 2016-06-23 to 2016-06-27
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Recommend to Others
The house was great! SO clean, super comfortable beds, great (spotless) hot tub, and plenty of room for 4 adults! The kitchen had everything we needed to make breakfast and lunch each day and and outdoor shower was awesome! There were always plenty of towels delivered, however we did have to call and ask for them (not a big deal at all). The pool was right around the corner and was a nice place to hang out. Being one block away from Duval was so great and made getting everywhere super easy, anything you needed was barely a two minute walk away. I would recommend this house to anyone looking for a great place to stay while in Key West :)

Great cottage

Reviewed on 2016-11-08 by Unknown of Clemmons, NC United States
Updated on 2016-11-08
Review of stay from 2016-11-01 to 2016-11-06
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Recommend to Others
Really enjoyed our stay at Windward Isle. Convenient location to walk to all popular places in Key West. Private parking spot was nice. Would be tight with a large vehicle. You will notice noise from the bar across the street if you are using the front bedroom. Beds slept great. They still need to fix the bathroom door (just don't close it all the way or you will get stuck in the bathroom).

Nice Place

Reviewed on 2016-07-30 by Kathryn R. of Buffalo, NY United States
Updated on 2016-07-30
Review of stay from 2016-07-21 to 2016-07-28
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Recommend to Others
My third time renting from this company and it has always been a pleasant experience. This home was clean, bright, and very convenient to all we wanted to do. In addition, it was on a quiet side street that added to the relaxation factor. Two negatives...One, housekeeping was a bit inconsistent; our beds did not get made up a couple of days and nobody came to clean the hot tub later during the week we were there. Also, it was steamy hot, and the AC struggled to keep the place cool. It was not central AC, and two of the units looked very old & were rusty on the outside. It seemed to affect performance. It probably wouldn't cost much to replace them, and it would go a long way toward making the house more comfortable. But, overall, a nice place & we would stay again.

Overall a wonderful stay

Reviewed on 2016-08-01 by Chris B. of , United States
Updated on 2016-08-01
Review of stay from 2016-07-28 to 2016-07-30
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Recommend to Others
Loved staying here.

Overall great location with minor caveat. The property is right off of Duval St. but Duval is pretty long so it's important to add some context to that. This property is off of the mid-section of Duval, but most of the tourist stuff (Sunset Pier, Mallory Square, bars etc) is about a 15-20 minute walk away. If it's hot, you can always take a taxi or pedi-cab to save some steps. There are, however, some good, small restaurants nearby (we ate at Deuce's Off the Hook Grill; make reservations, you won't be disappointed).

This place is fully equipped with most of what you need for a long stay. Refrigerator, microwave, coffee maker, kitchen sink, etc. We only stayed a few days so we didn't really need to make use of these, but for a longer stay these would be much appreciated.

The general condition of the property was fair. Renovated nice on the inside but older windows & doors, and hardwood floors had a big crack in one of the bedrooms (I could see sunlight through the crack). This is somewhat expected in Key West, as most of the properties are old and rustic.

Cleanliness - the property was almost spotless when we arrived. We were very impressed with the inside of the house and the bedroom cleanliness. The only problem I had was that the hot tub was pretty nasty when we went to use it; there were dead bugs and leaves in it. The cover was on so the only thing I can think of was that it just wasn't cleaned. Wife was pretty grossed out until I fished everything out. Dear KWVR, please make sure the hot tub is spotless before your guests arrive.

Parking - There is room in the back of the property for one car. Any more than that will have to park somewhere else. I would not advise bringing multiple cars.

Nice place

Reviewed on 2017-01-11 by Unknown of , United States
Updated on 2017-01-11
Review of stay from 2017-01-03 to 2017-01-08
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Recommend to Others
Good location. Backyard was nice.

Short stay in Key West

Reviewed on 2016-12-28 by Adam L. of Columbus, OH United States
Updated on 2016-12-28
Review of stay from 2016-12-09 to 2016-12-12
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Recommend to Others
Great stay in Key West. Place was perfect for a long weekend. Both bedrooms were nicely sized with king beds. Kitchen and bath were very accommodating. The hot tub was nice and the off street parking was definitely a plus. There is a bar close by (a couple buildings down) and 1 of the 3 nights we stayed there (Friday-Saturday-Sunday), their music was extremely loud. We understood this going in but it was a little extreme on the one night; the other nights we didn't even hear it. Given that, the location was great for Old town Key West.

HoneyMoon Starts Here

Reviewed on 2016-12-25 by Paivi N. of Mantsala, ES Finland
Updated on 2016-12-25
Review of stay from 2016-12-06 to 2016-12-09
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Recommend to Others
House was exactly like we wanted, old style KW house. Location was perfect. Close to everything. Jacuzzi in back was nice, a little bit too hot, but nice. Will come back one day.

Best Vacation Ever!

Reviewed on 2015-04-04 by John P. of Lee'summit, MIssouri United States
Updated on 2015-04-04
Review of stay from 2015-03-28 to 2015-04-02
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Recommend to Others
This was exactly what I expected. The pictures described it well.

Love Key West

Reviewed on 2015-01-30 by Darlene S. of , United States
Updated on 2015-01-30
Review of stay from 2015-01-11 to 2015-01-14
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Recommend to Others
TheThe home we stayed on was fantastic. It was walking distance to ever thing Duval St. A clean laundry mat around the corner, a hot tub in the back for resting the sore muscles from walking all day. Easy ck in/ck out.

President's Day 2015

Reviewed on 2015-02-17 by Franz Z. of Tampa, FL United States
Updated on 2015-02-18
Review of stay from 2015-02-13 to 2015-02-15
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Recommend to Others
Very easy to book, check-in and check-out.
Cottage location is excellent.
The inside was comfortable from a space perspective.
Room temperature was very comfortable.
Beds, living room and kitchen were all clean.
We slept soundly.

Only two complaints are:
1) the TV Cable reception cuts in and out from time to time and the equipment is relatively old. Wouldn't take too much to get newer TVS.
2) the bathroom door needs a new doorknob or lock. It wasn't a big deal with 2 people in the house but I can imagine it would become an issue with more.

Great Location and Great Service

Reviewed on 2015-03-30 by Emily T. of MOuntain View, CA United States
Updated on 2015-03-30
Review of stay from 2015-03-23 to 2015-03-28
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Recommend to Others
We had a great experience at this rental. The location was close to Higgs and Fort Zachary. The concierge service was excellent, we highly recommend using it. The house was located two blocks from Duval St., and using the rental bikes was the best way to get around.
The house was clean and the kitchen was well stocked if you are interested in making a few of your own meals.
We enjoyed the restaurants close by such as Duffy's and Deuces off the hook(small place make reservations for dinner).
I would definitely recommend this place to friends and family.

Getaway in the keys

Reviewed on 2015-07-16 by Nick M. of Bluffton, SC United States
Updated on 2015-07-16
Review of stay from 2015-07-08 to 2015-07-14
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Recommend to Others
A nice little house right off duval. Close to everything. The hot tub and grill we're nice to have. Only complaint is that the mattresses are due to be replaced.

spring break with teens

Reviewed on 2015-04-24 by Cynthia V. of Key West, FL United States
Updated on 2015-04-24
Review of stay from 2015-04-05 to 2015-04-08
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Recommend to Others
I loved the location of our house. It was perfect for what we wanted. We could walk downtown - almost everywhere we wanted to go, which was good. It has off street parking - which is a huge plus - but a very narrow driveway - so if you are planning on getting a rental car - pick a smaller one - we had a huge one and that is my only complaint.

Windward Isle Review

Reviewed on 2015-06-26 by Unknown of Plantation, FL United States
Updated on 2015-06-26
Review of stay from 2015-06-22 to 2015-06-24
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Recommend to Others
We stayed about a block away from Duval Street. You couldn't beat the location. Everything was in walking distance. The house had plenty of space and a full kitchen. The only bummer was the tv's didn't work in the bedrooms and the tv in the family room was sketchy. Also on the last day the door knob came off of the bathroom and one of us was locked in. Other than that the rental worked great for a family of 6. The hot tub was a fun bonus!

Super fun stay

Reviewed on 2015-08-20 by Unknown of San Ramon, CA United States
Updated on 2015-08-20
Review of stay from 2015-08-16 to 2015-08-18
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Recommend to Others
It was great experience staying in this jewel home right at the rival street. We had a family of 3 adults and two kids and we all had great time. Home has. Jacuzzi in the backyard as well which was cherry on the cake. Having a parking at the property was also plus. I will definitely give it 5 star to the property. It is not super big home but you won't feel it.

Keys

Reviewed on 2016-01-28 by Mary P. of Stoughton, WI United States
Updated on 2016-01-28
Review of stay from 2016-01-20 to 2016-01-26
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Recommend to Others
Family vacation

Windward Isle is a great stay!!

Reviewed on 2016-03-03 by Steve B. of Watertown, WI United States
Updated on 2016-03-03
Review of stay from 2016-02-23 to 2016-02-25
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Recommend to Others
More than we expected. Very clean and maintained. King size beds very comfortable. Cleaning service daily. Wonderful private patio and off street parking. Location was the best, within walking distance of everything. I would recommend key west rentals.

Amazing location

Reviewed on 2016-01-01 by Unknown of Port Hope, ON Canada
Updated on 2016-01-01
Review of stay from 2015-12-26 to 2015-12-28
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Recommend to Others
This rental unit was very clean, and perfectly located for access to everything. The hot tub was a nice feature. The managing staff were extremely friendly and helpful. Overall, I would highly recommend this unit.

Awesome stay with Key West Vacation Rentals!

Reviewed on 2016-04-03 by Craig H. of Mukwonago, WI United States
Updated on 2016-04-03
Review of stay from 2016-03-27 to 2016-03-29
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Recommend to Others
First of all, the communication and professionalism from the Key West Vacation Rental staff is second to none. The accommodations were excellent and the process was extremely convenient. We were running late in our arrival and they had everything we needed to get into our rental after office hours. On our last day we booked a snorkel trip after the check out time and we were able to leave our luggage with them at their office. On top of that, after we finished our snorkel trip they scheduled a free shuttle to take us to the Key West Express Ferry. This really shows how much they care. I would highly recommend this company to anyone!
I would also highly recommend to download their app. It had our contract details, check-in instructions, directions, GPS location service, etc...

Great time in key west

Reviewed on 2016-04-08 by Kim R. of Grand island, NY United States
Updated on 2016-04-08
Review of stay from 2016-04-03 to 2016-04-05
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Recommend to Others
Our experience was very positive. The cottage was clean, well stocked, plenty of space, and had a private hot tub out back. 4 adults stayed with plenty of room. Location was incredible. We rented a golf cart and it was the best thing we did. Covered a lot of miles. Saw beautiful beaches that we would not have seen without the gulf cart. Tour of hemingways house was very informative. Must eat at blue heaven and salute's. Only thing I have to say that was not perfect was the doorknob fell off the bathroom door. I think that's a small price to pay for an incredible vacation.

Our first trip to Key West

Reviewed on 2016-05-12 by Unknown of Brunswick, OH United States
Updated on 2016-05-12
Review of stay from 2016-05-07 to 2016-05-10
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Recommend to Others
I would definately stay at the house again for the price. It was within walking distance to Duval Street, however, the neighborhood could have been better. There were several run down houses across the street.

great house and location is perfect to Duval

Reviewed on 2014-02-03 by Unknown of New York, NY United States
Updated on 2014-02-03
Review of stay from 2014-01-29 to 2014-01-31
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Recommend to Others
The property was so much better than I expected and very clean! The private backyard and jacuzzi really made the place, although the bathroom really needs to be updated, if you're charging this much. The property management was fine, but they didn't greet me or explain anything, they just gave me my keys and hurried me out the door. I had to keep stopping them from rushing me out, so I could ask questions.

All the rooms were great, except the bathroom. i.e. shower head was outdated, the tub was chipped and rusted, and the shower curtain was too long, so it draped inside of the bath tub

Key West annual trip

Reviewed on 2014-05-22 by Rich S. of Racine, WI United States
Updated on 2014-05-22
Review of stay from 2014-05-02 to 2014-05-06
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Recommend to Others
Have used KWVR for several years . Most years we try a different property , and have never been disappointed . This years stay at Windward Isle was among the best . Great location - very secluded yard space , and a comfortable home with old towne charm .

Can't wait to come back!

Reviewed on 2014-05-14 by Cristina P. of Miami, FL United States
Updated on 2014-05-14
Review of stay from 2014-04-26 to 2014-04-27
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Recommend to Others
The property was super clean and spacious. 6 of us stayed comfortably in the unit and the location could not have been more perfect. We can't wait to visit again!

Will do again

Reviewed on 2014-12-10 by Unknown of Lanford, PA United States
Updated on 2014-12-10
Review of stay from 2014-12-04 to 2014-12-08
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Recommend to Others
It was a great expierence. loved the location. nice neighbors. didnt like the ants,bathroom doorknow didnt stay on. water heater broke,took 3 hrs to get fixed.

Better than expected!!!

Reviewed on 2014-10-09 by Brandon B. of Lawton, Oklahoma United States
Updated on 2014-10-09
Review of stay from 2014-10-01 to 2014-10-07
Overall satisfaction
Cleanliness
Location
Property condition
Recommend to Others
We knew we were not walking into a 5 star hotel or residence, but what we walked into, for the price, was fantastic!!!
One block from Duval St and right in the middle of all the amenities Key West had to offer.
Even the neighbors were welcoming, helpful and a pleasure to talk with.
We will be back and will look to Key West Vacation Rentals for our next location

Cute little, private place. Recommend!

Reviewed on 2014-08-16 by Unknown of Lexington, KY United States
Updated on 2014-08-16
Review of stay from 2014-07-29 to 2014-07-31
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Was a nice place. Comfortable, large beds. Cable didn't work first night, didn't really matter that much because we stayed outside. Best hot tub I have ever been in. Large, clean and strong jets in every seat! Private driveway was a major plus! Have to share it with neighbor which would be interesting cause it is extremely narrow! Lucky for us, no one was staying next door. Absolutely love the back patio, privacy fence, and safe in room. Only upgrade that would be nice is more living room furniture. Overall great stay! Great location. Can walk to a lot of sights. Recommended and will definitely be back! First stay in key west and this place was great :)

Windward Isle house

Reviewed on 2014-10-08 by tim h. of dunedin, FL United States
Updated on 2014-10-08
Review of stay from 2014-09-19 to 2014-09-22
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
great time, would stay there again

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