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
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!

Available
Unavailable
Check-In Only
Check-Out Only


January 2026
S M T W T F S
        01 02 03
04 05 06 07 08 09 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
$380
February 2026
S M T W T F S
01
$412
02 03 04 05 06 07
08 09 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
March 2026
S M T W T F S
01
$417
02
$407
03
$410
04
$411
05
$424
06
$431
07
$432
08
$426
09
$429
10
$430
11
$427
12
$425
13
$428
14
$430
15
$425
16
$422
17
$427
18
$415
19
$411
20
$409
21
$403
22
$384
23
$379
24
$379
25
$379
26
$379
27
$381
28
$379
29
$379
30
$379
31
$379
       
April 2026
S M T W T F S
      01
$345
02 03 04
05 06 07 08 09 10 11
12 13 14 15 16 17 18
19 20 21 22 23 24 25
26 27 28 29 30
$259
   
May 2026
S M T W T F S
          01
$259
02
$257
03
$239
04
$228
05
$224
06
$225
07
$229
08
$231
09
$228
10
$216
11
$208
12
$204
13
$204
14
$208
15
$212
16
$214
17
$203
18
$197
19
$196
20
$199
21
$206
22
$208
23
$208
24
$207
25
$204
26
$204
27
$196
28
$202
29
$205
30
$205
31
$195
           
June 2026
S M T W T F S
  01
$190
02
$189
03
$191
04
$197
05
$201
06
$201
07
$191
08
$187
09
$185
10
$188
11
$193
12
$197
13
$197
14
$188
15
$186
16
$182
17
$187
18
$191
19
$196
20
$196
21
$187
22
$183
23
$182
24
$185
25
$191
26
$196
27
$196
28
$187
29
$183
30
$182
       
July 2026
S M T W T F S
      01
$185
02
$198
03
$198
04
$198
05
$198
06
$184
07
$183
08
$186
09
$192
10
$196
11
$196
12
$187
13
$183
14
$182
15
$184
16
$190
17
$195
18
$194
19
$186
20
$181
21
$180
22
$189
23
$191
24
$195
25
$195
26
$186
27
$179
28
$185
29
$188
30
$190
31
$188
 
August 2026
S M T W T F S
            01
$187
02
$177
03
$173
04
$171
05
$173
06
$179
07
$183
08
$189
09
$176
10
$168
11
$167
12
$169
13
$174
14
$183
15
$177
16
$169
17
$164
18
$163
19
$165
20
$170
21
$174
22
$174
23
$165
24
$161
25
$160
26
$161
27
$167
28
$172
29
$171
30
$161
31
$157
         
September 2026
S M T W T F S
    01
$156
02
$158
03
$166
04
$167
05
$167
06
$164
07
$164
08
$163
09
$153
10
$157
11
$164
12
$165
13
$156
14
$153
15
$154
16
$153
17
$160
18
$166
19
$168
20
$161
21
$159
22
$160
23
$164
24
$171
25
$178
26
$181
27
$173
28
$170
29
$171
30
$175
     
October 2026
S M T W T F S
        01
$184
02
$191
03
$193
04
$186
05
$183
06
$184
07
$188
08
$196
09
$204
10
$207
11
$199
12
$195
13
$196
14
$201
15
$208
16
$235
17
$246
18
$234
19
$228
20
$229
21
$238
22
$251
23
$259
24
$259
25
$228
26
$221
27
$222
28
$227
29
$236
30
$244
31
$248
November 2026
S M T W T F S
01
$259
02
$259
03
$259
04
$259
05
$281
06
$293
07
$297
08
$285
09
$259
10
$267
11
$268
12
$271
13
$279
14
$287
15
$272
16
$268
17
$267
18
$274
19
$285
20
$294
21
$297
22
$290
23
$284
24
$285
25
$313
26
$315
27
$318
28
$319
29
$322
30
$296
         
December 2026
S M T W T F S
    01
$297
02
$305
03
$318
04
$328
05
$333
06
$323
07
$328
08
$328
09
$338
10
$357
11
$354
12
$351
13
$340
14
$330
15
$330
16
$337
17
$349
18
$360
19
$364
20
$356
21
$347
22
$349
23
$357
24
$379
25
$379
26
$379
27
$379
28
$379
29
$379
30
$379
31
$379
   
January 2027
S M T W T F S
          01
$434
02
$426
03
$386
04
$379
05
$379
06
$384
07
$401
08
$411
09
$425
10
$418
11
$390
12
$391
13
$401
14
$430
15
$432
16
$437
17
$438
18
$423
19
$423
20
$425
21
$436
22
$444
23
$441
24
$435
25
$420
26
$431
27
$446
28
$454
29
$462
30
$457
31
$447
           

Book Now

Detailed Quote
Add to Favorites
Inquire
Share
Print