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
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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April 2026
S M T W T F S
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$480
28
$522
29 30    
May 2026
S M T W T F S
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03 04 05 06 07 08 09
$476
10
$418
11
$406
12
$437
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$352
22
$487
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$345
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$428
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$461
31
$409
           
June 2026
S M T W T F S
  01
$410
02
$405
03
$413
04
$448
05 06
07 08
$388
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$372
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$388
11
$424
12
$462
13
14 15 16 17
$407
18
$441
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$459
20
$461
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$404
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$386
23
$382
24
$389
25
$428
26
$456
27
$460
28
$411
29
$392
30
$393
       
July 2026
S M T W T F S
      01
$392
02
$445
03
$455
04
$461
05
$441
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$382
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$382
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$393
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$445
10
$462
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$462
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$409
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$409
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$378
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$372
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$392
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$431
24
$469
25
$485
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$420
27
$406
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$427
29
$414
30
$431
31
$443
 
August 2026
S M T W T F S
            01
$441
02
$385
03
$359
04
$361
05
$370
06
$411
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$442
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$445
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$376
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$354
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$347
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$359
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$402
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$463
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$440
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$367
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$346
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$340
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$351
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$413
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$465
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$470
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$362
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$335
25
$335
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$344
27
$404
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$419
29
$423
30
$357
31
$329
         
September 2026
S M T W T F S
    01
$328
02
$339
03
$402
04
$424
05
$453
06
$416
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$398
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$397
09
$330
10
$369
11 12
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$403
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$440
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$425
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$357
21
$330
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$333
23
$345
24
$389
25
$432
26
$463
27
$370
28
$347
29
$343
30
$364
     
October 2026
S M T W T F S
        01
$407
02
$446
03
$464
04
$408
05
$365
06
$368
07
$383
08
$428
09
$467
10
$470
11
$513
12
$679
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$696
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$682
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$715
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$841
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$864
18
$772
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$765
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$773
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$790
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$826
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$951
24
$951
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$881
26
$863
27
$858
28
$863
29
$877
30
$950
31
$482
November 2026
S M T W T F S
01
$438
02
$405
03
$411
04
$483
05
$633
06
$653
07
$681
08
$653
09
$397
10
$419
11
$418
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$439
13
$478
14
$479
15
$402
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$368
17
$366
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$381
19
$417
20
$447
21
$455
22
$552
23
$400
24
$406
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$541
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$470
27
$489
28
$472
29
$474
30
$392
         
December 2026
S M T W T F S
    01
$393
02
$440
03
$532
04
$477
05
$484
06
$435
07
$409
08
$411
09
$425
10
$467
11
$496
12
$499
13
$446
14
$419
15
$419
16
$440
17
$484
18
$535
19
$547
20
$555
21
$469
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$465
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$677
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$674
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$1000
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$1000
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$1000
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$1000
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$1000
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$1000
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$1000
   
January 2027
S M T W T F S
          01
$944
02
$792
03
$698
04
$660
05
$694
06
$737
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$835
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$781
09
$800
10
$771
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$683
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$692
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$712
14
$830
15 16
17 18
$665
19
$810
20 21 22 23
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$721
28
$776
29
$839
30
$837
31
$798
           
February 2027
S M T W T F S
  01
$746
02
$745
03
$708
04
$765
05
$830
06
$840
07
$772
08
$699
09
$695
10
$713
11
$805
12
$828
13
$858
14
$790
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$773
16
$766
17
$720
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$807
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$965
20
$964
21
$843
22
$812
23
$720
24
$739
25
$797
26
$886
27
$837
28
$922
           
March 2027
S M T W T F S
  01
$806
02
$786
03
$861
04
$1003
05
$837
06
$881
07
$1022
08
$897
09
$903
10
$907
11
$893
12
$1000
13
$1003
14
$798
15
$881
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$899
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$873
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$867
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$885
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$904
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$755
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$683
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$655
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$725
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$824
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$843
27
$778
28
$761
29
$761
30
$663
31
$735
     
April 2027
S M T W T F S
        01
$798
02
$744
03
$746
04
$725
05
$604
06
$602
07
$751
08
$845
09
$714
10
$709
11
$752
12
$701
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$573
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$793
15
$991
16
$1178
17
$1174
18
$1063
19
$939
20
$988
21
$563
22
$780
23
$811
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$743
25
$699
26
$550
27
$537
28
$549
29
$643
30
$684
 

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