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Island Wind Old Town Tropical Hideaway in Key West

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  • bedrooms 2
  • baths 2
  • sleeps 4
  • pool yes
  • hot tub yes
  • pets allowed no
  • type Townhome
  • community Windward Park
  • rates (USD) $ 1,390 - $ 2,500 / week

vacation rental description

Island Wind welcomes you to a tropical sun drenched oasis in the
heart of Old Town. This charming Bahamian style conch home with tin
roof and white spindled decks reminiscent of old Key West is located
a block off Duval Street in award winning Windward Park, a gated and
secure community consisting of 13 privately owned homes clustered
around a 50 foot pool.Decorated in shades of blue and green with
crisp white trim, new hardwood floors, and furnished with white
wicker and glass, painted wood, rattan and wrought iron, plus
tropical prints, island accessories and local art, Island Wind is
the ideal Key West hideaway. Totally renovated in September 2011, new pictures coming soon.

Do you have a Vacation Home/timeshare? Ask us about trading!
We are interested in beachfront properties in Florida, California,
the eastern seaboard, Caribbean, Mexico, French Riviera; and the
Napa Valley, Boston/Cape Cod, New York City, Long Island, San
Francisco, England, France, Greece and any other interesting or
exotic destination.

vacation rental location

property availability

  • dates with deals
  • unavailable dates

Last modified on 05-26-2014 at 3:34 PM.

email owner view full calendar

Debbie Gray 519-862-2122

townhome rental amenities

The two-story vaulted living room has cable TV, stereo, and DVD player. The fully equipped new kitchen with breakfast bar, (and dining area) is equipped with every
appliance, utensil and accessory required for snacking, baking,
grilling or gourmet cooking. The main floor bedroom has twin beds
that convert to king, private bath with shower, and double French
doors leading to a large furnished private deck with gas barbecue
and 5 person hot tub/spa. A great place to enjoy cocktails and relax.
The second floor master suite has a king size bed and private bath
with tub and shower. Other amenities include a washer and dryer,
ironing board and iron, bedroom flat screen tv's, two hairdryers and off street
parking for one car. 20 x 50 foot pool.  Wireless internet available.

activities and attractions in Key West The Florida Keys

Within walking distance of all the attractions and nightlife of Old
Town. Visit the Hemingway House, Fort Zachary Taylor State Park &
Beach, Southernmost Point, Harry S. Truman Little White House,
Mallory Square's Sunset Celebration, Historic Seaport, Flagler
Museum, Key West Aquarium etc. Take the "Historical Tours of
America" Conch Train or Old Town Trolley tour, or walking tour.
Rent scooters, bicycles, boats, wave runners or sign up for
parasailing, snorkeling, diving, or fishing charters/trips. Take a
sunset cruise, visit the shops, boutiques, museums, art galleries,
restaurants, cafes and bars along Duval Street, listen to the music
or just relax on the beach.

vacation rental rates

from $1750/week (Winter - Dec. 15 - May 1)
from $1550/week (Shoulder - May 1 to June 1)
from $1390/week (Summer - June 1 - Dec. 15) 12.5% tax
Higher rates apply for special weeks and Holidays.


 Maximum 4 Adults - STRICLY ENFORCED!

We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.

Key West is Waiting for You!
Monthly rates on Request
This is a non smoking home.

Also available "Lone Palm"
our other vacation home located right next door!
Great for longer term rentals.
"Paradise is closer than you think!"

email owner

Debbie Gray 519-862-2122

contact owner

please fill in the form below to inquire about this rental.


  • owner Debbie Gray
  • phone 519-862-2122

When you book a vacation rental on any of our websites, we want you to experience a carefree vacation. Learn More

accepted payment methods


Prior to paying a reservation deposit, always verify payment instructions by calling the phone number displayed on this listing page. By contacting the owner directly and paying by an approved method - credit card, paypal, check or bank transfer - your reservation payment will be protected up to $1,000.

Learn more in our Security Center
Top things to do in Key West
  • Historical Sites/Tours
  • snorkel/dive/parasail
  • Sunset Sail/Celebration
  • Fishing charters
  • Galleries/Shops/Pub Crawl
Top things to do on a budget
  • Trip to Beach
  • Explore
  • Walk
  • Live Entertainment
  • Happy Hour
Top things to do with a family
  • Beach/water activities
  • Butterfly Conservatory
  • Glass Bottom Boat
  • Aquarium
  • Sunset Celebration/Sail

Debbie Gray , owner

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email owner

Debbie Gray 519-862-2122

traveler reviews for this key west townhome rental

Wonderful in every way!

Review submitted: July 6, 2013   Date of arrival: June 22, 2013

The Island Wind townhome was perfect for our vacation needs. We were visiting Key West for the first time with our two teenaged daughters. The interior of the home is beautifully decorated, with a bedroom and private bath on the first floor (our girls felt right at home) and a king master suite upstairs for us. We loved the privacy of the home, the swimming pool, and even the parking space for our car was behind a gate and very secure -- and yet the home is only about a block or so from Duval, and we had great fun walking all over the island from this convenient central starting point. The air conditioning felt wonderful after a day about town. The owner was super helpful, swift in coming to our rescue when we left our set of house keys at a hotel en route. We absolutely adored this vacation, snorkeling over the coral reef, roaming about town and relaxing in this beautiful quiet home. Highly recommend this experience to all!

Recommended for: age 55+, families with young children, families with teenagers, girls getaway, sight seeing, tourists without a car, romantic getaway

Helpful votes: 2 / 2


I hope to rent again in the future

Review submitted: May 27, 2011   Date of arrival: May 13, 2011

This property is a wonderful and relaxing townhome located in the center of Old Town Key West 1 1/2 blocks from the center of Duval Street within walking distance of all the drinking establishments that Key West is known for. The two story two bedroom/two bath townhome came with a personal hot tub and BBQ on the rear deck, three TVs with the main/living room TV having a DVD player and 5 disc CD player with both a growning DVD movie and CD collection. The gated community is a thirteen townhome campus that share a up to 6' pool with parking for one vehicle per townhome and is clean and well maintained. The owner is a wonderful lady who was friendly both on the phone and by e-mail. We did not have a bad meal during the stay whether we enjoyed only appetizers or a full meal. We took advantage of the 1/2 prices appetizers for dinner at several of the restaurant/bars during the 4pm to 7pm daily happy hour. There is plenty of entertainment both day and night with fishing, parasailing, snorkaling, jetskiing or a nice sunset boat ride. We would recommend this location to friends, family and people we haven't even met yet. There is rumors of renovations to this townhome's two bathrooms and the kitchen area and also the pool to be completed by the end of this year.

Recommended for: adventure seekers, sight seeing, romantic getaway

Helpful votes: 3 / 3


Island Wind

Review submitted: March 9, 2011   Date of arrival: February 26, 2011

This was a lovely townhouse that we rented for a week. It had everything you could possible want. The unit was very comfortable and clean and tastefully decorated. It truly was a home away from home. I would highly recommend this townhome to everyone. The location was great. It was close enough to Duval Street yet far enough away from any noise.

Recommended for: age 55+, people with disabilities, families with teenagers, girls getaway, sight seeing, tourists without a car

Helpful votes: 4 / 4


Reviews are the subjective opinions of travelers and not of, Inc.

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Debbie Gray 519-862-2122

Key West vacation rental

This vacation rental has been listed since 08/20/2003.

Page views: 221 this month – 2554 this year – 70022 since listed

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