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!

Available
Unavailable
Check-In Only
Check-Out Only


September 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
$248
19
$261
20 21 22 23 24 25 26
$248
27
$248
28
$248
29
$248
30
$248
     
October 2026
S M T W T F S
        01 02 03
04 05 06
$270
07
$281
08
$328
09
$358
10
$365
11
$321
12
$310
13
$308
14
$285
15
$335
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
$613
06
$671
07
$673
08
$557
09
$434
10
$466
11
$471
12
$521
13
$516
14
$494
15 16 17 18 19 20 21
22 23 24 25 26 27 28
$447
29
$415
30
$346
         
December 2026
S M T W T F S
    01
$353
02
$371
03
$428
04
$481
05
$483
06 07 08 09 10 11 12
13 14 15 16 17 18 19
20 21 22
$484
23
$508
24
$610
25
$709
26
$829
27 28 29 30 31    
January 2027
S M T W T F S
          01 02
$868
03
$736
04
$642
05
$619
06
$625
07
$681
08
$688
09
$682
10
$601
11
$575
12
$572
13
$592
14
$648
15
$761
16
$802
17
$741
18
$646
19
$654
20
$620
21
$702
22
$716
23
$719
24
$642
25
$636
26
$704
27
$707
28
$741
29
$781
30
$810
31
$651
           
February 2027
S M T W T F S
  01
$620
02
$628
03
$652
04
$735
05
$800
06
$819
07
$734
08
$692
09
$696
10
$709
11
$789
12
$857
13
$923
14
$843
15
$835
16
$839
17
$812
18
$899
19
$923
20
21 22 23 24 25 26
$877
27
$867
28
$768
           
March 2027
S M T W T F S
  01
$726
02
$712
03
$721
04
$803
05
$839
06
$857
07
$780
08
$785
09
$782
10
$786
11
$837
12
$863
13
$886
14
$809
15
$809
16
$810
17
$805
18
$847
19
$854
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
$668
11
$592
12
$561
13
$554
14
$566
15
$622
16
$648
17
$746
18
$646
19
$564
20
$547
21
$597
22
$672
23
$722
24
$629
25
$566
26
$532
27
$525
28
$601
29
$643
30
$688
 
May 2027
S M T W T F S
            01
$694
02
$565
03
$491
04
$482
05
$490
06
$532
07
$555
08
$555
09
$484
10
$457
11
$473
12
$464
13
$556
14
$603
15
$620
16
$474
17
$480
18
$446
19
$484
20
$530
21
$532
22
$535
23
$501
24
$511
25
$506
26
$506
27
$502
28
$517
29
$517
30
$490
31
$484
         
June 2027
S M T W T F S
    01
$479
02
$421
03
$458
04
$487
05
$490
06
$439
07
$412
08
$407
09
$420
10
$464
11
$494
12
$503
13
$449
14
$419
15
$419
16
$429
17
$471
18
$501
19
$538
20
$457
21
$421
22
$411
23
$421
24
$482
25
$517
26
$492
27
$457
28
$423
29
$420
30
$438
     
July 2027
S M T W T F S
        01
$513
02
$517
03
$543
04
$520
05
$458
06
$454
07
$461
08
$501
09
$513
10
$496
11
$453
12
$416
13
$439
14
$468
15
$497
16
$525
17
$531
18
$457
19
$426
20
$423
21
$432
22
$480
23
$527
24
$593
25
$523
26
$526
27
$530
28
$523
29
$541
30
$537
31
$495
August 2027
S M T W T F S
01
$440
02
$396
03
$392
04
$393
05
$442
06
$465
07
$471
08
$404
09
$434
10
$456
11
$461
12
$455
13
$420
14
$547
15
$354
16
$314
17
$305
18
$314
19
$360
20
$385
21
$384
22
$325
23
$285
24
$277
25
$289
26
$340
27
$364
28
$369
29
$315
30
$277
31
$273
       
September 2027
S M T W T F S
      01
$256
02
$324
03
$381
04
$410
05
$380
06
$335
07
$313
08
$255
09
$287
10
$308
11
$310
12
$265
13
$248
14
$248
15
$248
16
$281
17
$304
18
$305
19
$274
20
$248
21
$248
22
$248
23
$264
24
$316
25
$316
26
$276
27
$248
28
$248
29
$248
30
$261
   

Book Now

Detailed Quote
Add to Favorites
Inquire
Share
Print