Fleming-O

2 Bedrooms 1 Bathrooms Sleeps 6 Key West 792 sq. ft.

Fleming-O (pronounced “flamingo”) is located on one-way Fleming Street in the middle of historic Old Town Key West and only two blocks from world famous Duval Street and its restaurants, bars, art galleries, and shops.

First Bedroom

1 King

Second Bedroom

2 Twin

Living Room Sofa Bed

1 Sofa Bed

This conch cottage has all the modern amenities you would need.

The contemporary kitchen with a cathedral ceiling is equipped with a full-size refrigerator, stove/oven, all cookware, utensils and dishes. The kitchen has a dining table and seating for four in addition to two stools at the breakfast bar. Glass sliding doors open to a fenced, private deck that includes a gas grill, two chaise lounges, built-in benches, an outdoor dining table, and an outdoor shower. The living room contains a queen convertible sofa. All linens and towels, including beach towels, are supplied. The home is equipped with a washer and dryer located in a bathroom closet. The owners have installed a central air system, which is a luxury that few Old Town rental properties possess.

Both bedrooms share the common area bath, with double-basin pedestal sink and beautifully tiled walk-in shower. One bedroom has a king bed and the other has two twin beds. Both bedrooms and the living room contain flat-screen TVs. The large front porch is a few steps above the street, making it the perfect place to sit on the wicker chairs and relax with your morning coffee.

The location is ideal—just blocks from Blue Heaven and Pepe’s, the best breakfast spots in town. We also highly reccomend the following nearby spots: Mangia Mangia Pasta Café, Michaels Restaurant, Sarabeth’s Kitchen, Seven Fish, Conch Republic, The Boat House Bar and Grill, Alonzo’s, BO’s, and many more. The nightlife venues located within a short walking distance include Margaritaville, Willie T’s, The Green Parrot, Schooner Wharf, Rick’s & Durty Harry’s, The Hog’s Breath Saloon, Sloppy Joe’s, Irish Kevin’s, and Captain Tony’s.

PLEASE NOTE THAT THIS PROPERTY DOES NOT HAVE ACCESS TO A POOL.

You may use the pool at Dante’s if you utilize their food and beverage services or you may purchase a day pass using the link below at any of the hotels located near your rental.

https://www.resortpass.com/s/us/fl/key-west/pool?search_term=Key+West%2C+Florida&city_alias_id=26

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
  • Extra Pillows & Blankets
  • Living Room
  • 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
  • Dishes & utensils for kids
  • Kitchen Island
  • Dining table
  • Coffee Maker - Kcup
  • Coffee Maker - Kcup and Drip
  • Blender

Home Safety

  • Fire Extinguisher
  • Smoke Detector
  • First Aid Kit

Outdoor

  • BBQ Area
  • Patio or Balcony
  • Deck Patio Uncovered
  • Grill
  • Fenced Yard
  • Outdoor

Entertainment

  • Satellite or Cable
  • Television

Facility

  • Single Level Home
  • Street Parking

Location

  • Historic District
LEAVE A REVIEW
May 21, 2026 - Track Survey

by Justin B

Great stay. Cottage was clean and is in walking distance to Duval st. Overall satisfied with our stay

Thank you for your review! We're so glad to hear that you enjoyed your stay and found the cottage clean and conveniently located within walking distance of Duval Street. We hope to welcome you back again soon!

May 11, 2026 - Track Survey

by Aj R

Great place, convenient location, would definitely stay again.

Thank you AJ for the review! We are so happy to hear you enjoyed your stay. We look forward to having you as a guest again soon!

April 22, 2026 - Track Survey

by Charlene C

Great location! Quiet street, but close to everything. The house was perfect!

Thank you Charlene. This house truly is the perfect location. We enjoyed having you as our guest and look forward to your return stay!

April 9, 2026 - Track Survey

by Christine W

The home was very cute, clean and the outside shower was great!

So glad you enjoyed your stay! We can't wait for you to return!

February 23, 2026 - Track Survey

by Lisa H

Fleming-O is such a hidden gem! As soon as you walk through the front door, you are immersed in the island vibe that is Key West! Everything in the house was immaculate. The bathroom and kitchen had all amenities that you could possibly need while away from home. I highly recommend this property and would definitely stay again.

January 25, 2026 - Track Survey

by Monika S

Lovely house, perfect neighbourhood, easy access,

May 16, 2025 - Track Survey

by Ann P

This trip was our second time staying at the Fleming-O. Great place, location and it's like coming home. Can't wait for our next visit. Thank you!!

May 5, 2025 - Track Survey

by Paul F

Ideal location for places we like to go in old town. Also on a 1 way street so less traffic noise than typical. Will utilize again.

March 10, 2025 - Track Survey

by Melissa H

The house was very clean. Check-in and check-out were made simple by a guest portal. Gracious staff who had a suitcase storage facility when we arrived earlier than check-in. Recommend going directly through Rent Key West as you avoid online app fees.

March 2, 2025 - Track Survey

by Cathy S

After several stays at Fleming-O over the last 12+ years, I’m pleased to say it’s as delightful and well-maintained as on day one. Spotless. Well-equipped. Optimal location. All dealings with the rental staff were efficient, helpful and friendly. All around 100% satisfied.

August 6, 2024 - Track Survey

by Susan S

It was the best rental in Key West!!!

We are glad you had a great time!  We hope too see you again!

July 22, 2024 - Track Survey

by Eva W

Perfect location & had everything we needed for a family vacation. We will be back!

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September 2026
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$263
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$241
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$238
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$238
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$238
     
October 2026
S M T W T F S
        01
$267
02
$362
03
$366
04
$316
05
$365
06
$364
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$377
08
$434
09 10
11
$422
12
$409
13
$407
14
$377
15
$440
16
$535
17
$590
18
$585
19
$614
20
$629
21
$661
22
$724
23
$767
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$723
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$444
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$384
27
$377
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$382
29
$514
30
$546
31
$562
November 2026
S M T W T F S
01
$506
02
$480
03
$412
04 05 06 07
08 09 10
$521
11
$446
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$537
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$435
20 21
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$461
30
$388
         
December 2026
S M T W T F S
    01
$402
02
$425
03
$490
04
$550
05
$553
06
$479
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$443
08
$435
09
$449
10
$534
11
$557
12
$551
13
$489
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$459
15
$459
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$482
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$544
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$594
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$607
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$555
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$545
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$552
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$677
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$674
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$739
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$831
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$756
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January 2027
S M T W T F S
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$774
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$712
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$713
06
$744
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$828
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$840
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$841
10
$748
11
$723
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$722
13
$752
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$824
15 16
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$645
19
$805
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24 25 26 27
$699
28
$919
29 30
31            
February 2027
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$877
13
$936
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$846
15
$831
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$827
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$795
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$875
19
$898
20
21 22
$739
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$744
24
$772
25
$863
26
$887
27
$875
28
$780
           
March 2027
S M T W T F S
  01
$734
02
$723
03
$741
04
$827
05
$872
06
$889
07
$811
08
$804
09
$804
10
$804
11
$851
12
$873
13
$888
14
$809
15
$805
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$805
17
$802
18
$846
19
$856
20
$852
21
$747
22
$700
23
$688
24
$712
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$776
26
$812
27
$817
28
$728
29
$724
30
$666
31
$683
     
April 2027
S M T W T F S
        01
$738
02
$779
03
$774
04
$680
05
$641
06
$631
07
$649
08
$708
09
$740
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$732
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$646
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$609
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$604
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$615
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$676
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$705
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$710
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$634
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$588
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$581
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$598
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$659
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$685
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$689
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$621
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$584
27
$582
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$667
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$717
30
$743
 
May 2027
S M T W T F S
            01
$779
02
$635
03
$554
04
$551
05
$562
06
$618
07
$646
08
$649
09
$567
10
$536
11
$555
12
$544
13
$598
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$622
15
$620
16
$550
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$560
18
$520
19
$561
20
$618
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$611
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$610
23
$547
24
$584
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$582
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$580
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$578
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$598
29
$601
30
$573
31
$571
         
June 2027
S M T W T F S
    01
$569
02
$502
03
$547
04
$581
05
$583
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$515
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$480
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$473
09
$486
10
$538
11
$564
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$572
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$509
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$473
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$472
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$483
17
$529
18
$557
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$567
20
$508
21
$469
22
$459
23
$472
24
$524
25
$550
26
$556
27
$516
28
$477
29
$469
30
$486
     
July 2027
S M T W T F S
        01
$570
02
$571
03
$598
04
$573
05
$508
06
$506
07
$519
08
$570
09
$582
10
$565
11
$510
12
$469
13
$495
14
$534
15
$564
16
$591
17
$578
18
$505
19
$471
20
$465
21
$476
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$526
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$574
24
$636
25
$559
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$562
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$572
28
$565
29
$586
30
$585
31
$542
August 2027
S M T W T F S
01
$484
02
$437
03
$439
04
$447
05
$502
06
$527
07
$550
08
$472
09
$515
10
$548
11
$563
12
$563
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$527
14
$697
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$454
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$406
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$396
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$419
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$484
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$521
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$519
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$442
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$396
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$386
25
$405
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$485
27
$519
28
$524
29
$445
30
$390
31
$381
       
September 2027
S M T W T F S
      01
$353
02
$443
03
$520
04
$561
05
$521
06
$464
07
$439
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$353
09
$403
10
$434
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$440
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$376
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$332
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$322
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$342
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$401
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$436
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$439
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$394
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$346
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$340
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$356
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$420
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$453
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$458
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$399
27
$360
28
$358
29
$376
30
$432
   

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