Book by phone: +1 (305) 296-9292
Private Hot Tub and Deck Area With Patio Furniture

Leeward Isle - Nightly

Guest Rating:

Vacation rental house. Sleeps 6, 2 bedrooms, 1 bathroom. Cats, Dogs allowed.

529 Olivia St Key West, FL 33040 United States

view full size image gallery

  • Private Hot Tub and Deck Area With Patio Furniture
  • This Beautiful Unit and It's 'Sister' - Next Door are part of the Tradewinds Group Unit and are Both 'Shotgun' Style Homes.
  • View of Beautiful Yard Area from Patio Set and Private Jacuzzi
  • Rental of this Property Provides Access to Our Off - Site Family Community Pool and Deck Area
  • Rental of This Unit Grants Access to Our Off - Site Adults Only - 21 Years and Older - Community Pool and Lounger Area
Private Hot Tub and Deck Area With Patio Furniture

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).

Download Vacation Rental Flyer
Rooms and Amenities
Property Type House, 1 story
Unit Code 531Lee
Beds 2 king beds, 1 sleeper sofa
Bathrooms 1 bathroom
Rooms Sleeps 6
Floor Area 810 square feet
Pets Cats, Dogs allowed.
Parking 1 Private Parking Spot
Living Air Conditioning, Ceiling Fans, Linens, Ironing Board, No Phone, Free Wifi
Kitchen Full Kitchen, Refrigerator, Coffee Maker, Microwave, Toaster, Cookware
Outdoor Deck, Patio, Gas Grill, Outdoor Shower, Hot Tub, Outside eating area, Off-Site Shared Pool
Geographic Near Beach, Close to Duval
Entertainment Cable TV
Average Manager Rating (Based on 2854 reviews)
Overall satisfaction: 4.5 stars
Overall satisfaction
Services from rental manager: 4.5 stars
Services from rental manager
Average Vacation Rental Rating (Based on 13 reviews)
Overall satisfaction: 5 stars
Overall satisfaction
Cleanliness: 4.5 stars
Cleanliness
Location: 4.5 stars
Location
Property condition: 4.5 stars
Property condition
100 % of our reviewers would recommend this vacation rental.

Vacation Rental Reviews

  • Nice Place!!!

    Stayed 3 days ending in July, 2015

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 4
    • Location
      Location: 5
    • Property condition
      Property condition: 4

    Overall satisfaction: Overall satisfaction: 4

    Bob S from MacDill AFB, FL recommends this vacation rental

    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!

    Stayed 3 days ending in May, 2015

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 5
    • Location
      Location: 5
    • Property condition
      Property condition: 4

    Overall satisfaction: Overall satisfaction: 5

    a guest recommends this vacation rental

    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

    Stayed 5 days ending in February, 2015

    • Services from rental manager
      Services from rental manager: 4
    • Cleanliness
      Cleanliness: 4
    • Location
      Location: 5
    • Property condition
      Property condition: 4

    Overall satisfaction: Overall satisfaction: 5

    a guest from Kalamazoo, MI recommends this vacation rental

    Nothing fancy, but everything you need and more. Great location at an affordable price.

  •  
  • Amazing !!!

    Stayed 2 days ending in December, 2014

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 5
    • Location
      Location: 5
    • Property condition
      Property condition: 4

    Overall satisfaction: Overall satisfaction: 4

    Chethan J from Philadelphia, PA recommends this vacation rental

    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!

    Stayed 3 days ending in September, 2014

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 5
    • Location
      Location: 5
    • Property condition
      Property condition: 5

    Overall satisfaction: Overall satisfaction: 5

    Heather F from Sterling, MA recommends this vacation rental

    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 !!

    Stayed 4 days ending in May, 2014

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 4
    • Location
      Location: 4
    • Property condition
      Property condition: 4

    Overall satisfaction: Overall satisfaction: 5

    Dianne B from Folsom, PA recommends this vacation rental

    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

    Stayed 4 days ending in May, 2014

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 5
    • Location
      Location: 4
    • Property condition
      Property condition: 5

    Overall satisfaction: Overall satisfaction: 5

    Anthony L from Philadelphia, PA recommends this vacation rental

    Awesome place for 2 couples

  •  
  • Dream house

    Stayed 5 days ending in May, 2014

    • Services from rental manager
      Services from rental manager: 4
    • Cleanliness
      Cleanliness: 5
    • Location
      Location: 4
    • Property condition
      Property condition: 5

    Overall satisfaction: Overall satisfaction: 5

    Julia S from Cincinnati, OH recommends this vacation rental

    It was an incredible stay in super house!

  •  
  • Great place! Awesome location

    Stayed 5 days ending in April, 2014

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 5
    • Location
      Location: 5
    • Property condition
      Property condition: 5

    Overall satisfaction: Overall satisfaction: 5

    Colin C from aldie, VA recommends this vacation rental

    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

    Stayed 10 days ending in March, 2014

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 5
    • Location
      Location: 5
    • Property condition
      Property condition: 5

    Overall satisfaction: Overall satisfaction: 5

    Rigney C from E. Orleans, MA recommends this vacation rental

    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.

  •  
  • Amazing weekend getaway!!

    Stayed 2 days ending in February, 2014

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 4
    • Location
      Location: 5
    • Property condition
      Property condition: 5

    Overall satisfaction: Overall satisfaction: 5

    Janet M from Kissimee, `FL recommends this vacation rental

    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!

  •  
  • Key West Vacation

    Stayed 5 days ending in February, 2014

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 5
    • Location
      Location: 5
    • Property condition
      Property condition: 5

    Overall satisfaction: Overall satisfaction: 5

    Paula A from Berkley, MA recommends this vacation rental

    We had a wonderful stay!!!!

  •  
  • A little bit of Paradise

    Stayed 4 days ending in January, 2014

    • Services from rental manager
      Services from rental manager: 5
    • Cleanliness
      Cleanliness: 4
    • Location
      Location: 4
    • Property condition
      Property condition: 4

    Overall satisfaction: Overall satisfaction: 5

    Susan M from Easy Hanover, NJ recommends this vacation rental

    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!

  •  
Getting your rate Getting your rate...
1. Select Your Dates to Check Availability

Click calendar to set checkin/checkout dates. clear calendar

 Unavailable  Selected  Available  Checkin only  Checkout only
2. Review Dates and Rates

Select/Confirm the number of travelers to get a rate quote.

: :
Base Rent:
Promo Savings: Remove
Discounted Rent:
Fees & Taxes:*
Total Price:
:
:

What's this?

A promo code is for special discounts and may have been provided to you in either a newsletter, email or other correspondence from the manager or owner of this property.

*Click 'Continue Booking' to view details of fees & taxes

Seasonal Rental Rates for this Vacation Rental

Dates Daily Weekly Monthly Minimum Stay Checkin Restrictions
Sep 4, 2015-Sep 6, 2015 $298 na na 1 No restrictions
Sep 7, 2015-Sep 17, 2015 $258 $1,806 na 1 No restrictions
Sep 18, 2015-Sep 20, 2015 $298 na na 1 No restrictions
Sep 21, 2015-Oct 21, 2015 $258 $1,806 $7,740 1 No restrictions
Oct 22, 2015-Oct 24, 2015 $368 na na 3 No restrictions
Oct 25, 2015-Oct 31, 2015 $456-$478 $3,236 na 5 No restrictions
Nov 1, 2015-Nov 14, 2015 $368 $2,576 na 1 No restrictions
Nov 15, 2015-Nov 24, 2015 $298 $2,086 na 1 No restrictions
Nov 25, 2015-Nov 28, 2015 $368 na na 4 No restrictions
Nov 29, 2015-Dec 10, 2015 $258 $1,806 na 1 No restrictions
Dec 11, 2015-Dec 23, 2015 $368 $2,576 na 5 No restrictions
Dec 24, 2015-Jan 1, 2016 na $3,346 na 7 No restrictions
Jan 2, 2016-Apr 30, 2016 $368 $2,576 $11,040 5 No restrictions
May 1, 2016-Jun 30, 2016 $298-$345 $2,086-$2,296 $8,940-$9,150 3 No restrictions
May 20, 2016-May 22, 2016 $368 na na 3 No restrictions
Jul 1, 2016-Jul 4, 2016 $368 na na 3 No restrictions
Jul 5, 2016-Jul 31, 2016 $298 $2,086 na 3 No restrictions
Aug 1, 2016-Sep 1, 2016 $258 $1,806 $7,740 3 No restrictions
Sep 2, 2016-Sep 4, 2016 $298 na na 3 No restrictions

*Seasonal rates are estimates only. Actual rates may differ. Seasonal rates do not include fees or taxes.

To request information about booking this vacation rental, please fill out the form below.


Sorry, we encountered the following error(s):

  • Unable to process request.
loading Sending Email...
Your email has been sent successfully!

Sorry, we encountered the following error(s):

  • Unable to process request.
loading Sending Email...
Your email has been sent successfully!
24.552814,-81.798945
CALL US 1-(800) 797-8787

Key West Vacation Rentals 1075 Duval St Suite C22 Key West, Florida 33040 +1 (305) 296-9292 rick@hgakwvr.com

© 1999 - 2015 | Powered By Escapia Vacation Rental Software | Terms of Use

Logon