Island Wind Tropical Old Town Hideaway

Island WindLiving Dining RoomPool View
“ Excellent ”
9 Reviews
606 Truman Ave, Key West, FL 33040


Bedrooms: 2
Bathrooms: 2
Sleeps: 4
Type: Townhouse
Per night: $205 - $300
Per week: $1,390 - $1,800
Pets allowed: No
Internet: Yes
Description of the Key West vacation townhouse rental
"Island Wind" welcomes you to a sun drenched oasis in the heart of Old Town. Charming Bahamian style townhome with tin roof and white spindled porches reminiscent of Old Key West Just a block off Duval Street at the corner of Truman & Simonton in Windward Park a gated community consisting of 13 privately owned homes around a 20 x 60 ft. pool. Within walking distance of all the attractions and nightlife that Key West has to offer including Mallory Square, Historic Seaport, Land's End Village, Southernmost Point, Hemingway House, museums, art galleries, shops, restaurants, Atlantic beaches and gulf water activities.

The two-story vaulted living room has TV (with cable),stereo, and DVD player. Wireless Internet is available.The adjoining kitchen with breakfast bar, (and dining area) is equipped with all appliances and every utensil and accessory required for snacking, baking, grilling, or gourmet cooking. Gas BBQ on back deck.

The main floor bedroom has twin beds, private bath with shower, and double french doors leading to a large private furnished deck.

The second floor master suite has a king size bed and private bath with tub and shower. French doors lead to a balcony overlooking the living room and to a furnished covered balcony overlooking the pool. Both bedrooms have flat screen TV's. Central air/heat and all rooms have ceiling fans.

Renovated in September 2011, new kitchen and bathrooms. Decorated in tropical blues and greens with white trim, rattan & wicker, wrought iron and glass, painted wood, hardwood and ceramic floors and local artwork. Island Wind offers guests modern accommodations with a tropical flare.

Paradise is closer than you think! Please join us.

For longer term rentals please ask about "Lone Palm" our other Key West vacation Home located just across the pool.

Maximum 4 guests - Strictly Enforced!

Availability Calendar


Begins Ends Week
Weekly Monthly Min
Dec 12 2014 Apr 30 2015 $300 $300 $1,800 - -
May 01 2015 May 28 2015 $235 $235 $1,550 - -
Jun 01 2015 Dec 11 2015 $205 $205 $1,390 - -
Check In: 4 p.m. Check Out: 10 a.m.
Lodging tax: 12.5%
Deposits: 20%
Payment Options: Cashier's Check, Money Order, PayPal, Personal Check
Other Fees: Cleaning charge of $125 for stays of less than a week


  • Beds

  • 1 King Bed
  • 2 Twin Beds
  • Features

  • Air Conditioning
  • Full Kitchen
  • Linens Provided
  • Patio
  • Balcony
  • Hardwood Floors
  • Outdoor Shower
  • Porch
  • Beach Towels
  • Heating
  • Parking Included
  • Private Pool
  • Deck
  • High Speed Internet
  • Appliances

  • Alarm Clock
  • Dishwasher
  • Oven
  • TV (Cable/Satellite)
  • Blender
  • Gas Grill
  • Radio
  • Telephone
  • CD Player
  • Hair Dryer
  • Refrigerator (Full)
  • Toaster
  • Ceiling Fan
  • Ice Maker
  • Stereo
  • VCR
  • Coffee Maker
  • Iron
  • Stove
  • Washer/Dryer
  • DVD Player
  • Microwave
  • Activities

  • Pool
  • Grocery Store
    (<1 mile)
  • Park
    (<1 mile)
  • Surfing
    (<1 mile)
  • Aquarium
    (<1 mile)
  • Jet Skiing
    (<1 mile)
  • Playground
    (<1 mile)
  • Tennis
    (<1 mile)
  • Beach
    (<1 mile)
  • Kayaking
    (<1 mile)
  • Restaurant
    (<1 mile)
  • Windsurfing
    (<1 mile)
  • Bicycling
    (<1 mile)
  • Live Entertainment
    (<1 mile)
  • Sailing
    (<1 mile)
  • Casino
    (1 mile)
  • Boating
    (<1 mile)
  • Movie Theater
    (<1 mile)
  • Scuba Diving
    (<1 mile)
  • Winery
    (1 mile)
  • Deep Sea Fishing
    (<1 mile)
  • Ocean
    (<1 mile)
  • Shopping Area
    (<1 mile)
  • Golf
    (3 miles)
  • Fishing
    (<1 mile)
  • Parasailing
    (<1 mile)
  • Snorkeling
    (<1 mile)

Other Vacation Rental Amenities
Located in the heart of Old Town and within walking distance of shops, restaurants, bars, art galleries, museums, Atlantic beaches, the Key West Aquarium, Butterfly Conservatory, Hemingway House, Fort Zachary State Park, Southernmost Point, Mallory Square, Historic Seaport, Harry S Truman Little White House etc. All watersports available as well as deep sea, flats fishing etc., tours offered by Historical Tours of America, boat, bike & scooter rentals, sunset cruises etc.

Reviews for this vacation townhouse rental in Key West, Florida

Have you been a guest of this property? Write a review!
James Edwards

James Edwards

Charlotte NC

Amazing place

July 28, 2014

Amazing place just like we thought. Close to everything and beautiful. We will deffinatly be staying here again!!!!

Dave Brown

Dave Brown

Deland, FL

Summer Vacation

July 28, 2014

This place was fantastic. The owner has equipped the place with just about anything you need. Also the location is fantastic, anyplace we went in the old town area was on foot or bicycle, great to not have to worry about parking.

Marla Bennett

Marla Bennett

Bella Vista, AR

Great place to stay

May 23, 2014

Rented Island Wind for 5 days for our family vacation. Everything was provided for us. The only thing we bought was food. This property is beautifully decorated. It is in a great location to local events, and in the heart of Key West. Would stay here again, it is paradise!!

Debbie Gray

Owner's reply:

Marla thank you so much for your review and for choosing our home for your family's Key West vacation. Our location is hard to beat; we are close to the action but slightly removed from the craziness that makes this island so unique. Our little piece of paradise is an oasis to come home to after a hectic and sometimes really hot day exploring this wonderful town. We hope you will visit us again...

Nancy Infantino

Nancy Infantino

Palm City, Fl. My grandson was visiting from Md.


July 26, 2013

This rental far exceeded my expectations. It was stocked with just about everything one could ask for. It was nicely furnished, and very clean. I loved the security of the complex, and the tranquil surroundings.

Debbie Gray

Owner's reply:

Nancy, thank you so much for taking the time to write this review and for choosing us for your Key West vacation. We sincerely appreciate your comments and hope you had a wonderful time with your grandson and sister. We strive to ensure that our home is clean, well maintained and well stocked. If something was missing please let us know. Our complex is secure and an oasis close to but slightly removed from the craziness of Duval. Island Wind is truly a little bit of paradise and we love KW!

Eve German

Eve German

Fredericksburg VA

Best vacation get away ever

July 4, 2013

We were in Key West for the first time and brought our two teenage daughters. The home is beautiful -- inside it's quiet and relaxing, the pool area is private and quiet, a nice rest from the hubbub of Key West, even the parking was behind a gate and secure. Great location, we walked to everything. Went snorkeling over the coral reef (Fury Adventures). Great fun. If I had to say something could be improved upon, and it's really a tiny thing -- a little shy on kitchen gear -- no coffee grinder, skillets could use updating, etc. But in the big picture that is a very minor thing and manageable, everything else was beautifully decorated, great supply of towels, washer/dryer, conveniently located to groceries and Duval and the wonders of Key West. When we left our hotel in St. Augustine, I forgot the house keys in the hotel room, and the owner of the home made immediate arrangements to provide a set through her management company. The owner was very helpful and understanding. We had so much fun doing all the touristy things one does in Key West, finding all the hangouts of Hemingway, Silverstein, Stevens, hearing the roosters and finding them in odd spots around town. I was very sad to mail thehouse keys back to the owner. I hope we are able to return again soon, and I wholeheartedly recommend this rental home and Key West.

Debbie Gray

Owner's reply:

Thank you so much for taking the time to review Island Wind. We sincerely appreciate your comments and are glad that you enjoyed your KW vacation. Our location is great; close to everything yet slightly removed from the craziness of Duval. We strive to ensure our home is clean, well maintained and has all the amenities that our guests could possibly want in their "home away from home". We look forward to seeing you again soon. P.S. Missing coffee grinder and warped frying pan have been replaced

Rob Hardin

Rob Hardin

Bellevue, Kentucky

Awesome place to stay

August 31, 2012

The Island Wind was a super place to stay. It was clean, amenities were great and friendly neighbors. We weathered Tropical Storm Isaac and never lost power, just a day of sunshine. We enjoyed the quiet setting a few blocks off Duval St. and had the pool to ourselves during our stay. My wife and I highly recommend the Island Wind.

Nancy Scott

Nancy Scott

Reading, MA


March 27, 2012

Traveling Buddies (3) rented this beautiful, recently renovated single-family townhouse in February, 2012 for two weeks. The house is so perfect in everyway-fully equipped...close to Duval St yet behind the gate and setback from busy Truman, its paradise...quiet and serene...the pool was clean, it felt like "our" private heaven. Debby, the owner was so accommodating with booking and any thing we needed she was there. Within a day, we decided we needed to book this paradise for Feb, 2013...glad we did. You will not be disappointed! I gave this a 5-star rating, because it deserves it...

Sam Lappano

Sam Lappano

Mechanicsburg, PA USA

Perfect in every way!

April 25, 2011

Our 12th vacation in Key West and this property was the best we've ever rented. The location on Southard Street was perfect for our lazy days at Fort Zachary Taylor Park. The home was spotless and had every amenity possible. Each bedroom having its own bathroom and balcony made it perfect for 2 couples traveling together. We also loved the fenced-in backyard with perfect sun exposure for every meal eaten outside. The pool down the back alley was close and very peaceful for those few times we decided to take a quick swim. Thank you for such a wonderful stay!



Arlington, VA USA

Hot, hot, hot

September 1, 2009

I did rent this quiet little townhouse at the very last minute in August. The owner was very nice and booking the room was a snap. The house was exceptionally clean and had a TV in each room. The A/C rocked! We didn't use the grill or the hot tub because it was so hot outside. My brother did use the pool once, but was grossed out by the little dead frogs or lizards that stuck in the corners of the pool. The master suite had a great comfy king size bed and a spacious bathroom and closet. Overall a great house. I just wish it had a third bedroom! I would rent this house again.

Interested in Renting this Property?

Page Views This month: 400 This year: 981 Since listed: 38,603
Last updated: March 18, 2015

Contact Owner

First Name *
Last Name *
Email *
Check In *
Check Out *

Owner Profile