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Leeward Isle - Nightly

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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 Opposite
Windward Isle , the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and walls, which were completely renovated in 1998.

Leeward 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.

Minimum Stay:
Please contact Key West Vacation Rentals regarding minimum stays and special rates. Minimum stay requirements apply on weekends (at least 3 nights), Winter/Spring season (January 2nd - April 30th - 5 night minimum), holidays and special events( Fantasy Fest & Christmas/New Year - 7 night minimum).

Amenities

Living

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

Outdoor

  • Deck
  • Patio
  • Gas Grill
  • Outdoor Shower
  • Off-Site Shared Pool

Geographic

  • Near Beach
  • Close to Duval

Availability

Key
#Night Available#Night Unavailable#Arrive Only#Depart Only
February 2016
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June 2016
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February 2017
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April 2017
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May 2017
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Rates

DatesNightlyWeeklyMonthly
02/07/16 - 02/11/16$378 - $398
02/14/16 - 02/18/16$378 - $398
02/21/16 - 02/25/16$378 - $398
02/28/16 - 03/03/16$378 - $398
03/06/16 - 03/10/16$378 - $398
03/13/16 - 03/17/16$378 - $398
03/20/16 - 03/24/16$378 - $398
03/27/16 - 03/31/16$378 - $398
04/03/16 - 04/07/16$378 - $398
04/10/16 - 04/14/16$378 - $398
04/17/16 - 04/21/16$378 - $398
04/24/16 - 04/28/16$378 - $398
01/02/16 - 04/30/16$378 - $438$2,646 - $3,066$11,340 - $11,940
05/01/16 - 05/26/16$298$2,086
05/08/16 - 05/12/16$298
05/15/16 - 05/19/16$298
05/22/16 - 05/26/16$298
05/27/16 - 05/29/16$398
05/30/16 - 06/30/16$298$2,086$8,940
06/05/16 - 06/09/16$298
06/12/16 - 06/16/16$298
06/19/16 - 06/23/16$298
06/26/16 - 06/30/16$298
07/03/16 - 07/04/16$368
07/01/16 - 07/04/16$368
07/05/16 - 07/31/16$298$2,086
07/10/16 - 07/14/16$298
07/17/16 - 07/21/16$298
07/24/16 - 07/28/16$298
07/31/16 - 07/31/16$298
08/01/16 - 09/01/16$258$1,806$7,740
08/07/16 - 08/11/16$258
08/14/16 - 08/18/16$258
08/21/16 - 08/25/16$258
08/28/16 - 09/01/16$258
09/02/16 - 09/04/16$298
09/05/16 - 09/15/16$258$1,806
09/11/16 - 09/15/16$258
09/16/16 - 09/18/16$298
09/19/16 - 10/20/16$258$1,806$7,740
09/25/16 - 09/29/16$258
10/02/16 - 10/06/16$258
10/09/16 - 10/13/16$258
10/16/16 - 10/20/16$258
10/21/16 - 10/29/16$3,346
10/30/16 - 11/05/16$258$1,806
11/06/16 - 11/13/16$378$2,646
11/14/16 - 11/22/16$298$2,086
11/20/16 - 11/22/16$298
11/23/16 - 11/27/16$378
11/28/16 - 12/15/16$258$1,806
12/04/16 - 12/08/16$258
12/11/16 - 12/15/16$258
12/16/16 - 12/23/16$378$2,646
12/24/16 - 01/01/17$3,346
01/02/17 - 04/30/17$378$2,646$11,340

Reviews

Good time in Key West

Reviewed on 2016-01-30 by Unknown of Boca Raton, FL United States
Updated on 2016-01-30
Review of stay from 2016-01-10 to 2016-01-14
Overall satisfaction
Services from rental manager
Cleanliness
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Recommend to Others
This is a great location for prowling Duval St. It was very rainy and cool while we were there, that had nothing to do with the accommodation which were comfortable. The cool weather necessitate a call for space heaters and they were provided in a timely manner and definitely took the chill out of the air.

Perfect location and not loud!

Reviewed on 2016-01-17 by nicole p. of sears port, ME United States
Updated on 2016-01-17
Review of stay from 2015-12-20 to 2015-12-27
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Recommend to Others
This was the perfect location. We loved our little house! It was a great size for the 4 of us, was right off of Duval but still private! People aren't kidding, the beds are SUPER comfortable and we loved having the front porch and back sitting area! The little bamboo shower outside is cool too - I showered outside every day! They come in everyday to give you clean towels etc. but it would be nice if they actually cleaned during your stay. Overall, we would totally stay here again!

Great House, Great Location

Reviewed on 2016-01-13 by Nicholas P. of Absecon, NJ United States
Updated on 2016-01-13
Review of stay from 2016-01-05 to 2016-01-10
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Recommend to Others
Myself and 4 others stayed at Leeward Isle for 5 nights. The house was great, very comfortable for the 5 of us and very clean throughout. The backyard was great to sit back and relax with the hot tub and outside shower. Being just one block from Duval Street, the house had an ideal location. The windows were older and couldn't quite fully shut in some of the rooms, which made it a little difficult to block out the roosters early in the morning. Overall we had a great stay at this house and would definitely stay there again!

Nice Place!!!

Reviewed on 2015-07-21 by Bob S. of MacDill AFB, FL United States
Updated on 2015-07-21
Review of stay from 2015-07-13 to 2015-07-16
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Recommend to Others
This was a nice place ... close to the action on Duval Street, but quiet at night. The house is small, and well used, but was clean and the beds were very comfortable. Ants were a problem, so keep any open food in the refrigerator. I think this is just a problem with the area, not due to neglect or bad pest control. Staff was nice and helpful.

Great experience!

Reviewed on 2015-05-03 by Unknown of , United States
Updated on 2015-05-03
Review of stay from 2015-04-28 to 2015-05-01
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Recommend to Others
The place was clean and the perfect location! The rental company was so accommodating. It was pouring rain one day durning our stay and we didn't bring umbrella's, they dropped off umbrellas for our use and we went on our way. Will definitely rent from them again!

I would rent again

Reviewed on 2015-02-05 by Unknown of Kalamazoo, MI United States
Updated on 2015-02-05
Review of stay from 2015-01-29 to 2015-02-03
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Recommend to Others
Nothing fancy, but everything you need and more. Great location at an affordable price.

Key West Vacation

Reviewed on 2014-02-20 by Paula A. of Berkley, MA United States
Updated on 2014-02-20
Review of stay from 2014-01-29 to 2014-02-03
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Recommend to Others
We had a wonderful stay!!!!

Great place

Reviewed on 2014-05-24 by Anthony L. of Philadelphia, PA United States
Updated on 2014-05-24
Review of stay from 2014-05-18 to 2014-05-22
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Recommend to Others
Awesome place for 2 couples

Sweet Historic Key West Cottage

Reviewed on 2014-03-06 by Rigney C. of E. Orleans, MA United States
Updated on 2014-03-06
Review of stay from 2014-02-19 to 2014-03-01
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Recommend to Others
Everything about this little historic "shotgun: cottage was perfect and in keeping with everything we wanted from Key West. KW Vacation Rentals,
particularly Craig, was efficient and cordial. We could not have asked for a better first time experience.

Great place! Awesome location

Reviewed on 2014-04-20 by Colin C. of aldie, VA United States
Updated on 2014-04-20
Review of stay from 2014-04-12 to 2014-04-17
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Recommend to Others
Loved the property, the management was great! Check in was a breeze. The hot tub was serviced half way through the stay. Which I though was above and beyond.

All in all I would recommend to anyone. We will be back that's for sure!

Can't wait to come back !!

Reviewed on 2014-05-28 by Dianne B. of Folsom, PA United States
Updated on 2014-05-28
Review of stay from 2014-05-22 to 2014-05-26
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Recommend to Others
We were very happy with the house and the location. Never made it to the pool locations. The manager was very helpful there was a small disturbance the one night and the manager was there at a moments notice. And when I checked out the next day he came out to make sure we were ok. I would use Key West Vacation Rentals for my next visit and will suggest them to friends and family.

Amazing weekend getaway!!

Reviewed on 2014-02-10 by Janet M. of Kissimee, `FL United States
Updated on 2014-02-10
Review of stay from 2014-02-06 to 2014-02-08
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Recommend to Others
We had a fabulous time in this house - the beds were soooo comfortable and the pillows too. It was perfectly situated just off Duval and close to everything else we wanted to do. Thanks again guys for your great service. The staff are excellent!! The only reason I gave a 4 for cleanliness was for the floors apart from that..... perfect!

Dream house

Reviewed on 2014-05-11 by Julia S. of Cincinnati, OH United States
Updated on 2014-05-11
Review of stay from 2014-05-04 to 2014-05-09
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Recommend to Others
It was an incredible stay in super house!

Didn't want to leave ever!

Reviewed on 2014-09-24 by Heather F. of Sterling, MA United States
Updated on 2014-09-24
Review of stay from 2014-09-18 to 2014-09-21
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Recommend to Others
My guests and I were very pleasantly surprised with this place! It had everything we needed to have a great time and the location was prime! Loved the outdoor shower and hot tub! The beds were SO comfortable and I slept like a baby. I will definitely be renting this place again!!! Thank you!!

Amazing !!!

Reviewed on 2014-12-09 by Chethan J. of Philadelphia, PA United States
Updated on 2014-12-09
Review of stay from 2014-12-06 to 2014-12-08
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Recommend to Others
The house was very clean and well maintained, the hot tub was cool.. location is walkable to duval and all other attractions !!!

A little bit of Paradise

Reviewed on 2014-01-29 by Susan M. of Easy Hanover, NJ United States
Updated on 2014-01-29
Review of stay from 2014-01-23 to 2014-01-27
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Recommend to Others
We loved our stay at Leeward Isle. The beds were the most comfortable we've ever slept on. Things at night are a little noisy, keep the AC running it helps muffle the noise. The water in the bathroom sink is reversed hot on right -that took a while to get use to. Loved the fact you could walk everywhere. We hated to leave our little paradise house!

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