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 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
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May 2026
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$458
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$405
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$391
31
$367
           
June 2026
S M T W T F S
  01
$386
02
$379
03
$374
04
$427
05 06
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$346
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$350
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$371
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$441
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14 15 16 17
$397
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$417
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$438
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$438
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$401
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$390
23
$382
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$377
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$422
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$437
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$437
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$397
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$376
30
$371
       
July 2026
S M T W T F S
      01
$391
02
$445
03
$461
04
$461
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$435
06
$386
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$378
08
$403
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$440
10
$458
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$477
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$411
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$407
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$382
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$381
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$385
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$430
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$466
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$414
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$390
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$407
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$402
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$433
31
$439
 
August 2026
S M T W T F S
            01
$431
02
$371
03
$354
04
$355
05
$364
06
$416
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$442
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$455
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$378
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$355
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$353
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$361
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$418
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$475
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$446
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$369
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$342
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$336
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$352
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$412
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$443
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$447
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$359
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$340
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$331
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$342
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$389
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$423
29
$422
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$357
31
$325
         
September 2026
S M T W T F S
    01
$325
02
$331
03
$402
04
$429
05
$453
06
$413
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$399
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09
$326
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$374
11 12
13 14 15 16 17
$382
18
$426
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$423
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$358
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$337
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$328
23
$341
24
$397
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$436
26
$454
27
$377
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$347
29
$343
30
$365
     
October 2026
S M T W T F S
        01
$414
02
$457
03
$456
04
$394
05
$366
06
$369
07
$396
08
$431
09
$468
10
$477
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$513
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$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
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$772
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$765
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$773
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$789
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$815
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$906
24
$906
25
$839
26
$822
27
$817
28
$822
29
$835
30
$905
31
$485
November 2026
S M T W T F S
01
$443
02
$405
03
$397
04 05 06 07
08 09 10
$422
11
$417
12
$441
13
$478
14
$479
15
$417
16
$379
17
$371
18
$383
19
$427
20
$452
21
$464
22
$552
23
$406
24
$409
25
$541
26
$469
27
$476
28
$476
29
$475
30
$398
         
December 2026
S M T W T F S
    01
$394
02
$440
03
$532
04
$488
05
$518
06
$471
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$454
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$412
09
$426
10
$479
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$502
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$508
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$450
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$425
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$420
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$437
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$492
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$531
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$544
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$555
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$469
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$469
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$677
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$674
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$1000
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$1000
27
$1000
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$1000
29
$1000
30
$1000
31
$1000
   
January 2027
S M T W T F S
          01
$917
02
$791
03
$712
04
$663
05
$690
06
$738
07
$837
08
$857
09
$800
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$712
11
$684
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$684
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$704
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$850
15 16
17 18
$658
19
$812
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24 25 26 27
$715
28
$782
29
$839
30
$839
31
$788
           
February 2027
S M T W T F S
  01
$736
02
$732
03
$711
04
$776
05
$833
06
$833
07
$750
08
$697
09
$689
10
$710
11
$793
12
$835
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$849
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$787
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$774
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$768
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$717
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$808
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$965
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$964
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$843
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$812
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$715
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$729
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$807
26
$848
27
$835
28
$922
           
March 2027
S M T W T F S
  01
$806
02
$786
03
$861
04
$1003
05
$824
06
$886
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$1022
08
$897
09
$903
10
$907
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$893
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$1000
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$1003
14
$795
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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$751
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$689
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$653
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$720
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$805
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$782
27
$776
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$753
29
$699
30
$664
31
$715
     
April 2027
S M T W T F S
        01
$795
02
$743
03
$744
04
$719
05
$608
06
$597
07
$722
08
$838
09
$714
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$709
11
$732
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$667
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$576
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$697
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$783
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$791
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$785
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$726
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$645
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$625
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$561
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$780
23
$811
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$743
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$699
26
$551
27
$551
28
$574
29
$642
30
$787
 
May 2027
S M T W T F S
            01
$814
02
$572
03
$526
04
$520
05
$532
06
$595
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$609
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$612
09
$552
10
$508
11
$505
12
$511
13
$583
14
$639
15
$607
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$573
17
$500
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$492
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$527
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$524
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$741
22
$764
23
$709
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$581
25
$550
26
$520
27
$568
28
$606
29
$603
30
$535
31
$511
         

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