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Leeward 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, 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.

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
  • Outdoor Shower

Geographic

  • Near Beach
  • Close to Duval

Availability

Key
#Night Available#Night Unavailable#Arrive Only#Depart Only
October 2017
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Rates

DatesNightlyWeeklyMonthly
10/15/17 - 10/19/17$238
09/17/17 - 10/21/17$238 - $478$2,146
10/22/17 - 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$248
12/03/17 - 12/07/17$228 - $258
12/10/17 - 12/14/17$228 - $258
12/17/17 - 12/21/17$228 - $258
12/01/17 - 12/21/17$228 - $478$2,096
12/24/17 - 12/27/17$588
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
08/19/18 - 08/23/18$258
08/19/18 - 08/30/18$258 - $378$2,166
08/26/18 - 08/30/18$258
09/03/18 - 09/06/18$258
09/03/18 - 10/18/18$258 - $378$2,166$9,180 - $9,540
09/09/18 - 09/13/18$258
09/16/18 - 09/20/18$258
09/23/18 - 09/27/18$258
09/30/18 - 10/04/18$258
10/07/18 - 10/11/18$258
10/14/18 - 10/18/18$258

Reviews

2 thumbs up!

Reviewed on 2017-07-20 by Unknown of Ste-Therese, QC United States
Updated on 2017-07-20
Review of stay from 2017-07-01 to 2017-07-04
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Recommend to Others
Nice house, very clean and comfortable. Right in thé middle of the action ( 1 corner from Duval street) My husband and I LOVED our stay,would absolutly recommand To anyone and hopping To have a chance To go back.
Only negative point, we could not use the spa in the backyard as it was broken .. .

Prima Aufenthalt in historischem Key West Holzhaus

Reviewed on 2017-05-20 by Christoph T. of Hamburg, XX United States
Updated on 2017-05-20
Review of stay from 2017-05-16 to 2017-05-18
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Recommend to Others
Wunderschönes altes, aber top renoviertes traditionelles Key West Häuschen mit einem hübschen kleinen Garten. Viel geräumiger und geschmackvoller, als es die Fotos vermuten lassen. Top Ausstattung: Gute Betten, komplette Küche, Klima, Wlan, Handtücher, es fehlt an gar nichts. Spitzenlage: Man ist mitten drin und trotzdem abseits vom Rummel. Im Garten wimmeln Eidechsen und Geckos, was wir klasse fanden. Gefährliche oder eklige Viecher haben wir nicht gesehen, auch mit Moskitos gab es keine Probleme. Einziger Haken: Die Schlafzimmer haben so komische Glasklappfenster, die nicht geräuschdicht sind. Man hört die Klimaanlagen und alles, was draußen vor sich geht. Nachts ist da kaum Verkehr und mit Ohrpröppeln konnten wir gut schlafen. Für Lärmallergiker ist das eher nicht geeignet. Insgesamt hatten wir einen tollen Aufenthalt!

Leeward isle

Reviewed on 2017-03-29 by George S. of North Providence, RI United States
Updated on 2017-03-31
Review of stay from 2017-03-05 to 2017-03-09
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Recommend to Others
We needed an overnight that fit the schedule so leeward worked,
However beware, bar on corner plays til 4 am every night and the windows st leeward are shuttered panes so all noise comes through, even people talking.

wonderful location

Reviewed on 2017-03-13 by Unknown of Miramichi, NB United States
Updated on 2017-03-13
Review of stay from 2017-02-14 to 2017-02-25
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Recommend to Others
The house was perfect for 4 adults. I think 6 would have been tight. We were about 1/2 block to mid Duval ST. We enjoyed our stay and had no problems whatsoever. Tanner at KW Vacation Rentals went above and beyond to accommodate us.

Nice stay!

Reviewed on 2017-02-07 by Kathy S. of Washington, PA United States
Updated on 2017-02-07
Review of stay from 2017-02-02 to 2017-02-05
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Recommend to Others
Nice 2-bedroom (both King beds) cottage one half-block from the middle of Duval. Hot tub and outdoor shower a nice amenity. Didn't use the kitchen, but is stocked with housewares you'd need during your stay (as well as towels, pillows, sheets, etc). A bar at the end of the block can get loud late at night, but the white noise from the a/c pretty much blocked out the south be (light sleepers bring earplugs and eyeshades!)

Perfect vacation home

Reviewed on 2016-07-11 by deb h. of Clinton, CT United States
Updated on 2016-07-11
Review of stay from 2016-06-23 to 2016-06-26
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Recommend to Others
You want comfort? You want clean?You want the best bed I ever slept in? You want convenience to the main stream of Key West yet quiet. This is the place to stay.

What a charming place!

Reviewed on 2016-06-05 by Sandra P. of , United States
Updated on 2016-06-05
Review of stay from 2016-05-28 to 2016-06-01
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Recommend to Others
Leeward Isles was an absolutely charming place to stay. The location was great...mid island, and close enough to Duval to be able to easily walk everywhere, but far enough away to get away from the hustle and bustle when you wanted. The house was cool, cutely furnished, comfortable and welcoming.

Private parking - squeezing into the space with the next door car

Reviewed on 2016-05-28 by Unknown of South River, NJ United States
Updated on 2016-05-28
Review of stay from 2016-05-21 to 2016-05-24
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Recommend to Others
a nice cottage to stay, the location is off of duval street, so you can get plenty of sidestreet road noise,(mopeds etc.) However there is a corner bar at the end of oliva street, a very noisy at night, yelling, screaming, etc. the neighbor across the street has their dog barking at the middle of the night. Rooms are spacious, but with the flood lights on at night, the bedrooms are not dark and it feels like daylight, need to have blinds at the back kitchen door (missing)and the doorgate fencing would not close, it was warped. The floor needs to be cleaned, don't walk barefoot, they will turn black.

Nice getaway

Reviewed on 2016-03-02 by Unknown of Campton, NH United States
Updated on 2016-03-02
Review of stay from 2016-02-26 to 2016-02-27
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Recommend to Others
Great little getaway. We had 5 people in our party and all had a good time. One bathroom is challenging but as long as your all friends or family it's doable.

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
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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.

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 !!!

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!!

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.

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

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!

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!

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.

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!!!!

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!

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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