Windsor Townhomes #5

3 Bedrooms 3.5 Bathrooms Sleeps 6 Key West 1541 sq. ft. Pet Friendly

Elegance and modern sophistication are apparent as you enter any one of these six conveniently located townhomes in a quiet Old Town Key West neighborhood just three blocks from Duval Street.

Main Bedroom

1 King

Bedroom 2

1 Queen

Bedroom 3

2 Twin

These beautiful villas boast over 1700 sq ft. on two levels for your vacation destination, with it’s own private garden with heated pool. The open living/dining area features comfortable sofas and chairs, and a dining table to seat six. Just off the living room is your complete and fully-equipped modern kitchen with top-of-the-line appliances and a center island/bar. The half-bath is situated in the hall between the foyer and kitchen. Sliding doors open from the living area to a deck and the pool edged by variety of tropical plants. An inviting deck surrounding the pool provides atmosphere for peaceful conversation and relaxation after a day of sightseeing. One bedroom is on the first level with a queen bed and en-suite bath with shower only. The second level of the house offers two bedroom suites with en-suite bathrooms. The bedrooms are expertly decorated to offer luxury without being overbearing. Spacious and plush, the main suite has an elegant king bed and a grand tiled bath with his-and-hers sink and large shower. The second bedroom has two twin beds with luxurious linens and an en-suite bathroom with tub.

The villas are equipped with central air-conditioning system, flat-screen TVs, security system, and fully-equipped kitchen. These elegant villas are a destination for those expecting a special and exclusive holiday with the warm atmosphere of your own home! Located across the street from the Basilica of St. Mary Star of the Sea, it is the perfect spot for destination wedding parties.

Bedding: 1 king, 1 queen, 2 twins
Parking: One off-street parking space

Kitchen

  • Stove
  • Dishes & Silverware
  • Microwave
  • Refrigerator
  • Toaster
  • Cooking Basics
  • Dishwasher
  • Oven
  • Dining table
  • Coffee Maker - Kcup
  • Coffee Maker - Kcup and Drip
  • Blender

Location

  • Historic District
  • Village

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
  • Cable
  • Towels
  • Hot Water
  • Dryer
  • Essentials
  • Ethernet Connection
  • Living Room
  • Parking
  • Iron & Ironing Board
  • Private Entrance
  • Private Living Room
  • Shampoo
  • Washer
  • Body Wash

Sports

  • Paddle Boarding
  • Fishing - Surf
  • Hiking
  • 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
  • Cycling
  • DeepSea Fishing
  • Fishing - Backcountry
  • Jet Skiing
  • Para-sailing
  • Fishing - Pier
  • Sailing
  • Snorkeling
  • Swimming

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

Local

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

Home Safety

  • Fire Extinguisher
  • Smoke Detector

Outdoor

  • BBQ Area
  • Garden or Backyard
  • Patio or Balcony
  • Balcony
  • Deck Patio Uncovered
  • Grill
  • Fenced Pool
  • Fenced Yard

Car

  • Not Necessary

Entertainment

  • DVD Player
  • Satellite or Cable
  • Television

Facility

  • Free Parking
  • Pool

Pool

  • Heated Pool
  • Private Pool

Themes

  • Family
  • Historic
  • Romantic
  • Tourist Attractions
LEAVE A REVIEW
May 21, 2025 - Track Survey

by Laurie S

We had a great time. It was exactly like the photos. Location was good. Parking lot was a huge plus

January 4, 2025 - Track Survey

Highly recommended

by Stephen G

Had a great time everything was great.highly recommended

December 28, 2024 - Airbnb

Pool was the best!

by Peter B

We loved walking to attractions from the home. But the best part for us was soaking in the hot pool after a long day of walking.

May 30, 2024 - Airbnb

Amazing location

by Logan

Amazing location, and comfortable for a family trip. We loved our time at appreciated the quick response of management! Thank you, will definitely be back!

June 1, 2022 - Website

Keywest

by Recent Guest
The rental was amazing! The location was close but during pick up and drop off uber had a hard time finding where we were located. Other then that Jann was very helpful through out the entire process and the house was perfect for what we needed. Manager's ResponseThank you for your review of unit 5 at Windsor Town Homes. We are happy that you found the unit amazing and perfect for what you needed. We look forward to welcoming you back soon!
Thank you for your review of unit 5 at Windsor Town Homes. We are happy that you found the unit amazing and perfect for what you needed. We look forward to welcoming you back soon!
October 1, 2021 - Website

50th Birthday Celebration

by Recent Guest
Celebrated a 50th birthday and the home met every need for our group. It is beautifully decorated, spacious and had all the amenities we needed. It is walking distance to Duval Street, Southernmost point and beaches. All in all it is a perfect home to vacation in!
June 1, 2021 - Website

Key West Townhomes of Windsor #5

by Coleen B.
Townhome Windsor #5- Pros- very clean, well maintained & equipped home. The location was excellent, close to most attractions. Parking was adequate for one car/SUV. Beautifully decorated & very spacious for 2 families. Pool is small, but nicely refreshing in the shaded yard. Cons- first level queen bedroom mattress should be replaced (V shaped, you fall into the middle when you lay down). Both upstairs twin beds are on wheels, so when you turn over in bed, the beds roll across the floor. Both beds should be replaced, very unstable. Front door key needed to be manipulated to work- needs work. The neighboring home (On Windsor -911 #2) had very loud young rentors that partied very loudly outside with foul language until 4am each night. Was not appreciated, esp in this higher rent home. Should contact that Realty Company and establish better consistent, agreeable contracts for all rentors within the townhome community. Overall, a very beautiful home with a just a few issues that can easily be remedied.
February 1, 2019 - Website

Great stay.

by Recent Guest
3 couples on vacation, house was perfect.
December 1, 2017 - Website

GREAT FAMILY TRIP

by Recent Guest
We had a great time.The property was very nice, very clean. The heated pool was great, since we came when it was cold and windy. The kids swam everyday and evening. Off street parking was a plus. Definitely planning on staying here again.
December 1, 2017 - Website

Great location and quiet retreat

by Ronald S.
This is a beautiful townhouse with close proximity to all that old town key west and Duval street has to offer. We biked everywhere and loved the close proximity to Ft Zachary Beach, downtown and other attractions, yet secluded and private hideaway. The decor is beautiful. The only negative would be the uncomfortable mattresses in this unit.
April 1, 2016 - Website

Town homes on Windsor #5

by Davy C.
We had a fabulous week! This town home a great! Upon our arrival, everything was spotless and it looked like a model home. Having our on rivaled pool was a bonus. There is a lot of vegetation and privacy. We will definitely rent this unit again! It is decorated beautifully and less, than 10 years old, a rare find in Key West. Great location!
April 1, 2016 - Website

Town homes on Windsor #5

by Davy & Sandra C.
We had a fabulous week! This town home a great! Upon our arrival, everything was spotless and it looked like a model home. Having our on rivaled pool was a bonus. There is a lot of vegetation and privacy. We will definitely rent this unit again! It is decorated beautifully and less, than 10 years old, a rare find in Key West. Great location!
December 1, 2015 - Website

Family05XMAS

by Recent Guest
My family stayed here for Christmas 2015 for 6 nights and our townhouse we rented truly made us feel like we had a home away from home. I would recommend this place to anyone. The owners of this unit have really thought of everything that could be needed to make your stay comfortable. The keys to the front door were a little tough since they seemed to be copies of the original but once you got the right touch it worked every time. In addition to our unit there were 5 others and I would bet it would be a great place for multiple families wanting their own space but having other families close enough to enjoy their company. This vacation was everything i wanted it to be and the place being as nice and comfortable as it was made it everything plus more. This was truly a good find and a great place to stay. I hope to return someday in the future.
October 1, 2015 - Website

806 Johnson Lane

by Travis R.
the place was awesome. super updated, very clean and really comfortable for three guys. the only issue was check in. although i did arrive a couple of hours early, i was not given a key due to work that was being done outside of the home (fixing a gate-and then the gate wasn't even fixed when i did gain entry. small issue in the end though.
June 1, 2015 - Website

#5 Windsor Townhomes Key West

by Recent Guest
This was our families first stay at #5. The location was perfect for our time in Key West. There were a couple of maitanance issues with the property that were quickly resolved by the on site manager.
February 1, 2015 - Website

Fun in the sun!

by Donald W.
We had a great time in Key West. In fact we would love to come back soon. And we would stay at Town homes on windsor again. The town home proved to be the perfect location. Upon arrival we parked our car at the unit and never needed it again. We spent our days at the beach, the harbour walking Duval street and going to all the historical attractions. Key West is busy place (which is good) so it was always nice to get back to the unit to relax and visit or read pool side. Once we were recharged we would go out for a great dinner and listen to music.
November 1, 2014 - Website

A Family Thanksgiving retreat

by Maxie W.
This was a very nice surprise as it was so peaceful, convenient, and a modern beauty in Key West. It was near everything, clean, and a very friendly management company (rentkw). Couldn't ask for more. recommend highly!
September 1, 2014 - Website

Windsor #5

by Recent Guest
Everything was excellent. The property size, layout, cleanliness, amenities, and location were worth the $. This unit will be our 1st choice every time!
April 1, 2013 - Website

Vacation

by Recent Guest
We had a wonderful time
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September 2025
S M T W T F S
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$500
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$500
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$500
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$500
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28 29
$500
30
$500
       
October 2025
S M T W T F S
      01
$500
02
$500
03
$500
04
$500
05
$500
06 07 08 09 10 11
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$650
18
$641
19
$695
20
$978
21
$916
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$917
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$920
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$930
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26 27 28 29
$672
30
$672
31
$673
 
November 2025
S M T W T F S
            01
$678
02
$684
03
$790
04
$797
05
$798
06
$997
07 08
09 10
$924
11
$918
12
$919
13
$919
14
$920
15
$912
16
$869
17
$764
18
$763
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$764
20
$764
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$766
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$768
23 24 25 26 27 28
$870
29
$840
30
$820
           
December 2025
S M T W T F S
  01
$717
02
$717
03
$723
04 05 06
07 08
$790
09
$776
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$777
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$777
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$748
13
$757
14
$751
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$754
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$753
17
$754
18 19 20
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28 29 30 31
$1401
     
January 2026
S M T W T F S
        01
$2009
02
$2012
03
$1997
04
$1555
05
$1408
06
$1409
07
$1357
08
$1357
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$1360
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$1363
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$1337
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$1338
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$1339
14
$1290
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$1290
16 17
18 19 20
$1469
21
$1481
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$1468
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$1377
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$1455
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$1461
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$1475
27
$1476
28
$1476
29
$1467
30
$1470
31
$1469
February 2026
S M T W T F S
01
$1381
02
$1354
03
$1353
04
$1353
05
$1353
06
$1357
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$1366
08
$1396
09
$1436
10
$1437
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$1419
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$1419
13 14
15 16 17 18 19 20 21
22 23
$1524
24
$1522
25
$1523
26
$1523
27
$1529
28
$1485
March 2026
S M T W T F S
01
$1497
02
$1508
03
$1511
04
$1511
05
$1511
06
$1512
07
$1580
08
$1637
09
$1638
10
$1627
11
$1626
12
$1626
13
$1632
14
$1573
15
$1515
16
$1506
17
$1514
18
$1514
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$1514
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$1522
21
$1479
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$1426
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$1428
24
$1422
25
$1422
26
$1422
27
$1430
28
$1408
29
$1414
30
$1415
31
$1425
       
April 2026
S M T W T F S
      01
$1425
02
$1425
03
$1433
04
$1381
05
$1310
06
$1118
07
$1120
08
$1122
09
$1122
10
$1129
11
$1124
12
$1061
13
$1063
14
$1061
15
$1062
16
$1059
17
$1066
18
$1061
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$1057
20
$1081
21
$1058
22
$1062
23
$1062
24
$1069
25
$1084
26
$1136
27
$1130
28
$1110
29
$1110
30
$1110
   
May 2026
S M T W T F S
          01
$1048
02
$1046
03
$1019
04
$1011
05
$1011
06
$1011
07
$1011
08
$1017
09
$1000
10
$968
11
$956
12
$956
13
$957
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$957
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$963
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$960
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$990
18
$1016
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$1016
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$1016
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$1016
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$1009
23
$1006
24
$970
25
$953
26
$951
27
$952
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$952
29
$959
30
$945
31
$890
           
June 2026
S M T W T F S
  01
$882
02
$882
03
$880
04
$880
05
$885
06
$886
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$902
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$894
09
$894
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$895
11
$914
12
$917
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$913
14
$903
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$909
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$909
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$909
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$891
19
$896
20
$891
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$893
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$889
23
$890
24
$890
25
$870
26
$875
27
$868
28
$888
29
$884
30
$914
       
July 2026
S M T W T F S
      01
$913
02
$913
03
$917
04
$907
05
$912
06
$923
07
$915
08
$949
09
$967
10
$973
11
$942
12
$886
13
$884
14
$884
15
$891
16
$909
17
$915
18
$908
19
$916
20
$934
21
$930
22
$910
23
$891
24
$898
25
$935
26
$928
27
$930
28
$934
29
$935
30
$935
31
$925
 
August 2026
S M T W T F S
            01
$923
02
$818
03
$820
04
$799
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$798
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$798
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$804
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$792
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$858
10
$861
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$861
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$847
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$847
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$854
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$862
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$856
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$801
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$752
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$741
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$741
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$747
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$745
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$742
24
$746
25
$734
26
$735
27
$735
28
$742
29
$716
30
$706
31
$742
         
September 2026
S M T W T F S
    01
$744
02
$745
03
$745
04
$736
05
$754
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$746
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$707
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$700
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$700
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$700
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$700
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$700
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$700
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$700
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$700
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$700
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$700
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$700
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$700
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$700
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$700
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$700
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$700
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$700
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$700
     

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