Parrotville

2 Bedrooms 2 Bathrooms Sleeps 4 Key West 1152 sq. ft.

Parrotville is part of the Windward Park gated community just off Simonton Street. This 2 bedroom, 2 bathroom townhome is surrounded by lush tropical landscaping and views of a sparkling swimming pool.

This spacious vacation home is just a block from downtown Key West's famous Duval Street and has an open floor plan with lots of space on the main level for relaxing and entertaining. The first floor has a comfortable seating area with couch and chairs and a flat screen television for those days you want to get out of the sun and just relax. Completing the first floor is a dining area, a full modern kitchen with a bar and stools, a full bathroom, and a washer and dryer.

The second floor has two bedrooms and a full, shared bath. The front bedroom has a king bed, TV, closet, and opens to a second floor porch with views of the pool area and compound. The rear bedroom has two twin beds, a TV, and a double closet.

Parrotville is located in an ideal area of Old Town Key West. A short stroll to Duval Street offers world-class restaurants, bars, shopping, and galleries. Hop on a bicycle and head down to Mallory Square or the Key West Seaport, just a slightly farther ride. Everything is pretty close on our island. The beaches are also just a short distance from Parrotville. 

We offer all the comforts you need for your stay in paradise including WiFi, flat screen TVs, laundry, a lovely and inviting community pool, and one assigned parking space. There is a 4 person maximum limit to this home. This condo is in a quiet local community and is not recommended for parties or group celebrations.  We ask you to please be respectful of the residents and neighbors and keep the noise level to a minimum.

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
  • Shampoo
  • Wireless Internet
  • Body Wash
  • Air Conditioning
  • Bed Linens
  • Cable
  • Towels
  • Hot Water
  • Dryer
  • Essentials
  • Living Room
  • Parking
  • Iron & Ironing Board
  • Lock on Bedroom Door
  • Private Entrance
  • Private Living Room
  • Washer

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

Kitchen

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

Home Safety

  • Fire Extinguisher
  • Smoke Detector

Family

  • Bathtub

Outdoor

  • BBQ Area
  • Patio or Balcony
  • Balcony
  • Fenced Pool

Entertainment

  • Satellite or Cable
  • Television

Facility

  • Free Parking
  • Pool

Logistics

  • Long Term Stays Allowed

Location

  • Historic District

Pool

  • Communal Pool
LEAVE A REVIEW
June 28, 2026 - Track Survey

by Karen R

We really enjoyed the location and the townhome. It would be nice if the pool was not so hot, but overall we loved the location.

Thank you for your review! We're so glad to hear that you enjoyed the townhome and loved its location. Thank you for staying with us. We hope to welcome you back again soon!

June 19, 2026 - Track Survey

by Delia L

Excellent accommodations and service! The home was comfortable and well-appointed, and thoughtful details were provided (sunscreen, fully stocked kitchen, beach towels, etc). Would 10/10 recommend.

Thank you for your great review! We're glad you enjoyed the comfortable, well-equipped home and thoughtful extras. We hope to welcome you back soon!

April 26, 2026 - Track Survey

by Emma S

Parrotville was a great townhome. Clean, great location, perfect size.

Thank you Emma for the review! This townhome is defintely in a prime location! Close enough to Duval for all the fun yet still quiet and peaceful! We look forward to your next stay with us!

January 4, 2026 - Track Survey

by Sally A

This is the third year my friend and I have re wanted with you - the first two years was in Paradise on Porter in Truman Annex and then this year in Parrotville in Windward. We have enjoyed working with you, you’ve streamlined the system and everyone has been so friendly! We’ve rented from other companies in the past (Last Key, Vacasa and Compass) and your attention to detail and knowledgable team members makes it much easier to work with you! FYI - Conpass is the WORST! We had two concerns in the condo that Kevin addressed immediately and he was awesome, even recommending a great restaurant! The ONLY thing I might comment on in the condo is the poor wifi, which I know you’re aware of already. It not only made communication complicated, but the TVs are basically useless without it. Granted we’re not in Key West to watching, but it’s nice to have the option. I might suggest basic cable in the TVs. Otherwise, the trip was flawless!! Thank you so much for everything!

Thank you so much for your thoughtful review and for choosing to rent with us again for the third year. We truly appreciate your continued trust and are delighted to hear that our streamlined process, friendly team, and attention to detail have made your experience easier and more enjoyable.

We're especially glad Kevin was able to address your concerns right away and provide a great local recommendation. We'll be sure to share your kind words with him.

We also appreciate your feedback regarding the Wi-Fi and TV access. We understand how frustrating unreliable internet can be, especially when it affects communication and the ability to use the TVs. Your suggestion about adding basic cable is helpful and will be shared with our team as we continue evaluating ways to improve the condo experience.

Thank you again for your loyalty and kind words. We're so happy the rest of your trip was flawless, and we look forward to welcoming you back again!

October 29, 2025 - Track Survey

by Kevin P

House was as advertised! We had a great time and definitely will be staying again. From check in to check out the process worked seamlessly. House was stocked with anything we needed to make for a comfortable stay.

November 17, 2024 - Track Survey

Great location

by Megan O

Really enjoyed the place. Great location. Beach towels were a great addition. Pool was clean. Would have loved a cooler to be able to use and another fan but otherwise we enjoyed our stay greatly! Thank you!

July 7, 2024 - Airbnb

Highly recommend

by Teresa

The Pictures properly represented the townhouse. The kitchen was well appointed with modern appliances & well stocked for cooking. In was a very clean townhouse. Very nice sized TV in the family room as well as TV’s in both bedrooms. The shared pool was a good size & right outside our door. It was in a super convenient location to Duval Street, but still a quiet community to come home to. I highly recommend this rental property & can’t wait to come back & stay here again!

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July 2026
S M T W T F S
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05 06 07 08 09 10 11
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$347
17 18
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$269
22
$278
23
$384
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August 2026
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02 03 04 05 06 07 08
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30 31          
September 2026
S M T W T F S
    01 02 03 04 05
06 07 08 09 10 11
$283
12
$321
13 14 15 16 17 18
$271
19
$305
20 21 22 23 24 25 26
$335
27
$277
28
$310
29
$313
30
$360
     
October 2026
S M T W T F S
        01
$366
02
$382
03
$387
04
$388
05
$394
06
$402
07
$410
08
$420
09
$439
10
$447
11
$451
12
$459
13
$468
14
$477
15
$359
16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
November 2026
S M T W T F S
01 02 03 04 05
$616
06
$669
07
$680
08
$566
09
$535
10
$504
11
$502
12
$508
13
$533
14
$516
15 16 17 18 19 20 21
22 23 24 25 26 27 28
$458
29
$445
30
$370
         
December 2026
S M T W T F S
    01
$365
02
$375
03
$421
04
$464
05
$485
06 07 08 09 10 11 12
13 14 15 16 17 18 19
20 21 22
$736
23
$739
24
$731
25
$747
26
$838
27 28 29 30 31    
January 2027
S M T W T F S
          01 02
$862
03
$733
04
$657
05
$651
06
$673
07
$753
08
$684
09
$691
10
$613
11
$585
12
$614
13
$613
14
$657
15
$710
16
$805
17
$742
18
$703
19
$703
20
$672
21
$763
22
$724
23
$726
24
$688
25
$612
26
$657
27
$659
28
$696
29
$735
30
$769
31
$709
           
February 2027
S M T W T F S
  01
$673
02
$644
03
$668
04
$753
05
$819
06
$835
07
$738
08
$712
09
$709
10
$729
11
$822
12
$878
13
$908
14
$835
15
$831
16
$835
17
$788
18
$905
19
$934
20
21 22 23 24 25 26
$891
27
$892
28
$784
           
March 2027
S M T W T F S
  01
$736
02
$729
03
$752
04
$845
05
$860
06
$885
07
$809
08
$807
09
$803
10
$806
11
$868
12
$886
13
$892
14
$820
15
$819
16
$816
17
$814
18
$859
19
$881
20
$856
21
$765
22
$719
23
$691
24
$731
25
$832
26
$812
27
$809
28
$749
29
$709
30
$651
31
$723
     
April 2027
S M T W T F S
        01
$788
02
$741
03
$742
04
$647
05
$602
06
$684
07
$686
08
$763
09
$682
10
$685
11
$689
12
$572
13
$563
14
$672
15
$748
16
$658
17
$783
18
$684
19
$592
20
$574
21
$627
22
$706
23
$758
24
$704
25
$580
26
$534
27
$532
28
$594
29
$686
30
$788
 
May 2027
S M T W T F S
            01
$760
02
$633
03
$502
04
$493
05
$500
06
$543
07
$566
08
$566
09
$498
10
$463
11
$460
12
$478
13
$584
14
$633
15
$651
16
$496
17
$453
18
$454
19
$458
20
$508
21
$530
22
$556
23
$506
24
$518
25
$517
26
$516
27
$507
28
$522
29
$522
30
$497
31
$492
         
June 2027
S M T W T F S
    01
$423
02
$420
03
$420
04
$433
05
$507
06
$476
07
$453
08
$466
09
$485
10
$490
11
$548
12
$479
13
$429
14
$425
15
$421
16
$441
17
$423
18
$449
19
$565
20
$442
21
$412
22
$378
23
$413
24
$506
25
$543
26
$436
27
$453
28
$437
29
$433
30
$486
     
July 2027
S M T W T F S
        01
$554
02
$568
03
$507
04
$523
05
$383
06
$420
07
$426
08
$478
09
$496
10
$496
11
$438
12
$412
13
$481
14
$525
15
$618
16
$689
17
$697
18
$570
19
$498
20
$371
21
$383
22
$429
23
$488
24
$494
25
$423
26
$385
27
$388
28
$404
29
$439
30
$445
31
$440

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