A Windsong Delight

2 Bedrooms 2.5 Bathrooms Sleeps 4 Key West 1073 sq. ft. Pet Friendly

Great proximity to everything in old town Key West, but with an abundance of privacy, this two story townhome features 2 bedrooms with ensuite bathrooms and a 1/2 bath downstairs. Relax by the private pool or stroll down to Duval Street to enjoy Key West

Main Bedroom

1 King

Bedroom 2

1 Queen

This two story townhome has both location and amenities for a wonderful month long visit to Key West. Secluded at the rear of a three unit compound, Windsong Delight has two bedrooms, two and a half baths, a private deck and its own private pool.

Access to Windsong Delight is via a pathway from Windsor Lane to the front porch of the townhome. A keyless entry will allow you contact-less check-in.

Step into your first floor living area with open plan kitchen and living areas. The kitchen has everything necessary to prepare meals in the convenience of your home away from home. The ample kitchen island serves as extra counter space and has seating for indoor dining. You can lounge on the comfortable sofa while watching television or enjoy the view of the back yard pool area. While outdoors enjoy the pool and deck space which also offers the perfect escape for relaxing or dining al fresco. The deck and pool is private to Windsong Delight.

On the second floor are both bedrooms with ensuite baths. One bedroom has a king bed and built-in wardrobe. The second bedroom features a queen bed, built-in wardrobe and access to the second floor balcony. Both baths have walk-in showers with glass enclosures.

Please note, parking is on-street. There is NO off-street, reserved parking spot for this property. Parking is available on Windsor Lane on both sides of the street for easy on street parking. This central location is easy to walk to the historic seaport, the beach side of the island or everything on Duval Street!

Please note: This is a Monthly vacation rental with a minimum stay of 30 days, excluding February.

Tourist Attractions

  • Health Beauty Spa
  • Marinas, Boat Rentals & Excursions
  • Museums
  • Key West Aquarium
  • Public Parks & Beaches
  • Key West Historic Seaport
  • Key West Tropical Forest & Tropical Garden
  • Southernmost Point Buoy
  • Dry Tortugas National Park & Fort Jefferson
  • Fort Zachary Taylor State Park & Beach
  • Sunset Celebration at Mallory Square
  • History Tours - Motorized, Walking & Biking
  • The Florida Reef - N. America’s only living coral barrier reef
  • Key West Marine Park stretching from Higgs Beach to South Beach
  • The Key West Butterfly & Nature Conservatory
  • Food Tours
  • Ghost Tours
  • Pub Crawls
  • Your reservation guest portal will provide details

Accommodation Essentials

  • Hair Dryer
  • Hangers
  • Kitchen
  • Wireless Internet
  • Free wifi
  • Air Conditioning
  • Bed Linens
  • Towels
  • Hot Water
  • Dryer
  • Essentials
  • Living Room
  • Iron & Ironing Board
  • Washer

Leisure

  • Dolphin Watching
  • Dining Out
  • Live Theater, Concerts & Entertainment
  • Your reservation guest portal will provide details
  • Paint & Sip Art Classes
  • Bird Watching
  • Boating
  • Eco Tourism
  • Shopping

Kitchen

  • Stove
  • Coffee Maker - Drip
  • Dishes & Silverware
  • Microwave
  • Refrigerator
  • Toaster

Sports

  • Banana Boat Riding & Water Tubing
  • Wind Surfing
  • Ocean Waterpark & Challenge Course
  • Kayaking
  • Kite Boarding
  • Pickleball
  • Tennis
  • Golfing
  • Scuba Diving
  • Skydiving
  • Your reservation guest portal will provide details
  • Paddle Boarding
  • Cycling
  • DeepSea Fishing
  • Fishing - Backcountry
  • Jet Skiing
  • Para-sailing
  • Fishing - Pier
  • Sailing
  • Snorkeling
  • Swimming
  • Fishing - Surf
  • Hiking

Local

  • Banks
  • Grocery Stores
  • Fitness Centers
  • Hospital
  • Laundromats

Home Safety

  • Fire Extinguisher
  • Smoke Detector

Car

  • Not Necessary

Facility

  • Pool
  • Street Parking

Location

  • Historic District
  • Near Ocean
  • Village

Entertainment

  • Television

Outdoor

  • Deck Patio Uncovered
  • Fenced Pool

Pool

  • Private Pool

Themes

  • Historic
  • Tourist Attractions
LEAVE A REVIEW
May 2, 2026 - Track Survey

by Pattie H

We arrived to a clean lovely place and when we left we still loved it!! The staff was friendly and responsive. We will return next year

Thank you for staying with us! We are so happy you loved the property and look forward to your return next year!

February 2, 2025 - Track Survey

by Jeanne Marie K

Everyone we talked to was helpful and kind - thanks so much!!

June 4, 2024 - Website

Return to Wonderful Paradise!!!

by Otto

Fabulous time in paradise! We enjoyed our stay last year at Windsong so much that we decided to return. Our stay was just as delightful this year!!! The unit was just as clean as last year. This place has all the conveniences of home: appliances, comfy couch, extra towels, etc... The pool is warm and wonderful, and the neighborhood is peaceful and quiet. The little balcony off the 2nd bedroom makes an excellent \"quiet space\" to make a few office phone calls - shaded and secluded. There\'s a grocery a few blocks away and some terrific ice cream, brunch cafes, and of course Duval street restaurants, all within walking distance. Fort Zachary beach is the best, well worth the walk. We will hopefully be back again! It\'s so nice to return to a place and know what to expect. Highly recommended!

December 16, 2023 - Track Survey

by Don Maher
November 21, 2023 - Website

Awesome Experience in Windsong!! We\'ll be Baaaack....

by Tim Dunne

We had an incredible time at Windsong Everything was essentially brand new and the layout was fantastic, with two bedrooms upstairs, each with a private bath and a large living room downstairs with a half bath and a beautiful little courtyard with a pool. The location is Stellar, as it\'s a few minutes walk to Duval Street, Hemingway House, Lighthouse; along with lots of great restaurants and of course, most importantly- directly across the street from a magnificent Catholic Basilica. With new appliances including a washer and dryer which was a great benefit, it was just like home. We also found the unit to be impeccably clean which is always a plus. We thoroughly enjoyed our visit and would highly recommend this magnificent rental unit to any and all. We plan on coming back for sure. Tim and Renni PS- The weather was mid 80s each and every day, sunny and no rain whatsoever.

August 10, 2023 - Website

Peaceful Quiet Delight!

by Otto

Well appointed unit. Clean and close to beaches, Duval, fantastic restaurants. Nice quiet area. Pool was great to cool off in. Hosts are easy to work with. We will hopefully, happily be back!

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July 2026
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August 2026
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$158
         
September 2026
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$141
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$178
     
October 2026
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$176
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$182
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$250
November 2026
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$271
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$306
         
December 2026
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$307
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$311
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$330
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$335
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$341
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$346
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$346
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$354
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$378
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$379
   
January 2027
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February 2027
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April 2027
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May 2027
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$238
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$223
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$217
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$208
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$202
         
June 2027
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$201
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$195
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$209
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July 2027
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$191
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$192
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$191
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$198
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$189
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$197
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$198
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$196

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