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!

Available
Unavailable
Check-In Only
Check-Out Only


August 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
$238
19 20 21 22
23 24
$238
25
$238
26
$238
27
$251
28
$272
29
$276
30
$250
31
$246
         
September 2026
S M T W T F S
    01
$245
02
$260
03
$340
04
$338
05
$345
06
$314
07
$287
08
$263
09
$268
10
$378
11 12
13 14 15 16 17
$257
18
$281
19
$285
20
$276
21
$255
22
$247
23
$269
24
$243
25 26
27 28
$257
29
$252
30
$265
     
October 2026
S M T W T F S
        01
$292
02
$370
03
$378
04
$322
05
$375
06
$370
07
$393
08
$443
09
$481
10
$483
11
$432
12
$423
13
$421
14
$426
15
$494
16
$548
17
$624
18
$539
19
$569
20
$596
21
$642
22
$705
23
$772
24
25 26 27 28 29
$458
30
$490
31
$495
November 2026
S M T W T F S
01
$440
02
$416
03
$406
04 05 06 07
08 09 10
$334
11
$421
12 13 14
15 16 17 18
$393
19
$436
20
$472
21
$475
22
$431
23
$407
24
$413
25
$484
26
$478
27
$490
28
$492
29
$476
30
$403
         
December 2026
S M T W T F S
    01
$405
02
$420
03
$469
04
$530
05
$537
06
$479
07
$449
08
$445
09
$465
10
$509
11
$517
12
$521
13
$466
14
$434
15
$437
16
$456
17
$506
18
$554
19
$563
20
$506
21
$471
22
$475
23
$617
24
$618
25
$660
26
$792
27
$749
28 29 30 31    
January 2027
S M T W T F S
          01 02
03
$654
04
$629
05
$657
06
$695
07
$784
08
$697
09
$725
10
$695
11
$610
12
$611
13
$637
14
$694
15 16
17 18
$670
19
$823
20 21 22 23
24 25 26 27
$878
28
$948
29
$982
30
$1025
31
$831
           
February 2027
S M T W T F S
  01
$789
02
$716
03
$729
04
$797
05
$855
06
$863
07
$764
08
$721
09
$702
10
$719
11
$811
12
$857
13
$920
14
$817
15
$800
16
$795
17
$750
18
$843
19
$874
20
$875
21
$769
22
$714
23
$704
24
$735
25
$837
26
$879
27
$870
28
$805
           
March 2027
S M T W T F S
  01
$735
02
$708
03
$751
04
$876
05
$883
06
$933
07
$892
08
$814
09
$817
10
$820
11
$893
12
$908
13
$930
14
$848
15
$832
16
$827
17
$825
18
$882
19
$887
20
$834
21
$778
22
$731
23
$668
24
$759
25
$837
26
$810
27
$805
28
$760
29
$732
30
$650
31
$743
     
April 2027
S M T W T F S
        01
$801
02
$772
03
$765
04
$662
05
$629
06
$766
07
$783
08
$849
09
$724
10
$725
11
$629
12
$590
13
$585
14
$729
15
$701
16
$728
17
$723
18
$697
19
$573
20
$565
21
$576
22
$681
23
$707
24
$681
25
$612
26
$576
27
$578
28
$595
29
$692
30
$718
 
May 2027
S M T W T F S
            01
$757
02
$655
03
$543
04
$537
05
$547
06
$598
07
$639
08
$631
09
$553
10
$520
11
$517
12
$528
13
$591
14
$615
15
$621
16
$546
17
$507
18
$502
19
$519
20
$578
21
$599
22
$613
23
$546
24
$572
25
$568
26
$566
27
$565
28
$588
29
$591
30
$559
31
$557
         
June 2027
S M T W T F S
    01
$483
02
$450
03
$490
04
$549
05
$549
06
$441
07
$408
08
$405
09
$415
10
$461
11
$524
12
$525
13
$452
14
$435
15
$430
16
$405
17
$460
18
$492
19
$502
20
$432
21
$405
22
$390
23
$404
24
$467
25
$488
26
$490
27
$445
28
$408
29
$402
30
$410
     
July 2027
S M T W T F S
        01
$484
02
$492
03
$526
04
$486
05
$422
06
$410
07
$422
08
$480
09
$497
10
$500
11
$437
12
$398
13
$392
14
$406
15
$468
16
$491
17
$497
18
$436
19
$404
20
$393
21
$397
22
$462
23
$503
24
$533
25
$456
26
$427
27
$417
28
$426
29
$486
30
$501
31
$480
August 2027
S M T W T F S
01
$411
02
$374
03
$383
04
$376
05
$433
06
$460
07
$488
08
$489
09
$483
10
$486
11
$367
12
$418
13
$442
14
$446
15
$394
16
$351
17
$344
18
$363
19
$411
20
$442
21
$440
22
$393
23
$340
24
$330
25
$333
26
$414
27
$451
28
$451
29
$354
30
$304
31
$288
       

Book Now

Detailed Quote
Add to Favorites
Inquire
Share
Print