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
July 19, 2026 - Track Survey

by Diane W

We had a lovely stay in Parrotville. We arrived very late in the evening, the check-in and key collection went smoothly and the property was well lighted and cool when we arrived. Everything we needed was provided, the property was very comfortable and the outside and pool areas well tended. I would recommend Parrotville to friends/family.

We are so happy that your late check in whent smoothly.  After a day of travel, nobody wants to enounter problems getting into their rental.  Thank you for the wonderful review and we hope to have you stay with us again!

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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November 2026
S M T W T F S
01 02 03
$320
04 05
$463
06
$490
07
$497
08
$440
09
$309
10
$333
11
$372
12
$368
13
$394
14
$429
15 16 17 18 19 20 21
22 23 24 25 26 27 28
$408
29
$352
30
$294
         
December 2026
S M T W T F S
    01
$303
02
$331
03
$449
04
$552
05
$555
06 07 08 09 10 11 12
13 14 15 16 17 18 19
20 21 22
$575
23
$592
24
$681
25
$737
26
$859
27 28 29 30 31    
January 2027
S M T W T F S
          01 02
$764
03
$631
04
$581
05
$557
06
$582
07
$642
08
$660
09
$670
10
$597
11
$565
12
$558
13
$576
14
$640
15
$769
16
$796
17
$749
18
$636
19
$634
20
$590
21
$669
22
$702
23
$700
24
$605
25
$579
26
$676
27
$712
28
$757
29
$771
30
31            
February 2027
S M T W T F S
  01 02 03 04 05
$760
06
$786
07
$697
08
$656
09
$651
10
$682
11
$770
12
$823
13
$856
14
$838
15
$815
16
$830
17
$809
18
$901
19
$897
20
21 22 23 24 25 26
$841
27
$841
28
$751
           
March 2027
S M T W T F S
  01
$702
02
$694
03
$709
04
$788
05
$827
06
$829
07
$765
08
$770
09
$774
10
$778
11
$829
12
$854
13
$865
14
$809
15
$803
16
$802
17
$800
18
$844
19
$923
20
21 22 23 24 25 26 27
28 29 30 31      
April 2027
S M T W T F S
        01 02 03
04 05 06 07 08 09 10
$676
11
$593
12
$557
13
$551
14
$560
15
$681
16
$720
17
$821
18
$711
19
$620
20
$602
21
$657
22
$739
23
$794
24
$677
25
$567
26
$532
27
$528
28
$543
29
$659
30
$757
 
May 2027
S M T W T F S
            01
$696
02
$526
03
$484
04
$470
05
$478
06
$551
07
$564
08
$564
09
$489
10
$448
11
$440
12
$464
13
$612
14
$663
15
$682
16
$542
17
$486
18
$430
19
$450
20
$553
21
$585
22
$589
23
$551
24
$551
25
$504
26
$497
27
$499
28
$520
29
$520
30
$482
31
$475
         
June 2027
S M T W T F S
    01
$467
02
$407
03
$452
04
$486
05
$490
06
$424
07
$430
08
$396
09
$408
10
$456
11
$495
12
$495
13
$479
14
$474
15
$438
16
$424
17
$467
18
$498
19
$592
20
$463
21
$431
22
$403
23
$432
24
$530
25
$569
26
$545
27
$473
28
$412
29
$410
30
$437
     
July 2027
S M T W T F S
        01
$511
02
$520
03
$531
04
$518
05
$455
06
$444
07
$449
08
$495
09
$498
10
$494
11
$431
12
$407
13
$403
14
$440
15
$518
16
$578
17
$584
18
$477
19
$418
20
$413
21
$427
22
$481
23
$518
24
$606
25
$535
26
$545
27
$554
28
$531
29
$563
30
$557
31
$488
August 2027
S M T W T F S
01
$419
02
$379
03
$373
04
$384
05
$436
06
$463
07
$471
08
$399
09
$351
10
$344
11
$348
12
$396
13
$423
14
$420
15
$351
16
$317
17
$307
18
$315
19
$358
20
$387
21
$385
22
$323
23
$281
24
$273
25
$284
26
$341
27
$367
28
$367
29
$322
30
$293
31
$283
       
September 2027
S M T W T F S
      01
$259
02
$362
03
$327
04
$422
05
$381
06
$366
07
$308
08
$254
09
$295
10
$300
11
$301
12
$281
13
$273
14
$261
15
$248
16
$270
17
$293
18
$297
19
$260
20
$248
21
$290
22
$309
23
$358
24
$382
25
$309
26
$267
27
$248
28
$248
29
$252
30
$293
   
October 2027
S M T W T F S
          01
$374
02
$382
03
$344
04
$312
05
$310
06
$327
07
$377
08
$420
09
$427
10
$389
11
$392
12
$393
13
$353
14
$407
15
$476
16
$532
17
$517
18
$538
19
$609
20
$715
21
$823
22
$1193
23
$1209
24
$682
25
$668
26
$591
27
$506
28
$518
29
$533
30
$544
31
$495
           
November 2027
S M T W T F S
  01
$451
02
$595
03
$590
04
$591
05
$709
06
$704
07
$595
08
$559
09
$480
10
$542
11
$625
12
$610
13
$598
14
$517
15
$453
16
$433
17
$435
18
$480
19
$526
20
$532
21
$483
22
$460
23
$463
24
$550
25
$624
26
$616
27
$614
28
$516
29
$410
30
$408
       

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