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
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
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April 2026
S M T W T F S
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$534
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$616
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$619
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$533
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$522
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May 2026
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03 04 05 06
$399
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$453
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$501
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$504
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$404
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$388
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$533
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$439
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$439
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$503
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$511
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$468
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$452
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$480
31
$383
           
June 2026
S M T W T F S
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$363
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$350
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$381
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$444
05 06
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$369
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$431
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$479
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$386
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$357
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$446
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$334
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$324
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$419
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$470
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$386
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$338
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$329
       
July 2026
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$361
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$483
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$484
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$485
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$471
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$394
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$380
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$331
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$351
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$425
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$473
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$349
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$371
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$440
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$450
 
August 2026
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$451
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$344
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$391
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$352
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$307
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$299
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$355
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$294
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$410
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$412
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$342
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$289
         
September 2026
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$280
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$306
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$401
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$415
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$456
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$459
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$299
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$353
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$399
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$404
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$328
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$289
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$282
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$312
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$368
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$419
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$431
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$345
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$304
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$297
30
$328
     
October 2026
S M T W T F S
        01
$397
02
$441
03
$447
04
$364
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$320
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$312
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$344
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$405
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$461
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$467
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$539
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$713
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$731
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$751
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$811
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$803
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$812
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$951
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$881
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$858
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$863
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$877
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$950
31
$478
November 2026
S M T W T F S
01
$397
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$344
03
$335
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$446
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$633
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$702
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$699
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$653
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$336
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$412
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$409
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$428
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$478
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$490
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$374
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$309
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$332
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$394
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$444
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$454
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$552
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$348
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$326
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$541
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$504
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$507
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$509
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$512
30
$331
         
December 2026
S M T W T F S
    01
$365
02
$440
03
$532
04
$477
05
$484
06
$394
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$390
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$374
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$368
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$435
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$494
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$501
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$410
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$357
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$351
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$390
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$463
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$530
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$540
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$555
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$469
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$437
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$677
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$764
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$1000
   
January 2027
S M T W T F S
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$1000
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$1000
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$666
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$566
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$552
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$614
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$741
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$820
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$835
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$684
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$603
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$591
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$656
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$900
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$940
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$898
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$693
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$823
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$913
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$735
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$671
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$711
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$713
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$780
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$882
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$889
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$736
           
February 2027
S M T W T F S
  01
$631
02
$615
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$667
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$782
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$885
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$897
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$747
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$632
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$623
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$673
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$1045
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$1047
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$1055
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$714
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$965
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$964
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$843
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$812
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$923
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$916
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$922
           
March 2027
S M T W T F S
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$806
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$786
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$861
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$1003
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$919
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$984
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$744
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$620
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$592
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$656
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$817
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$801
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$795
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$566
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$626
     
April 2027
S M T W T F S
        01
$748
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$803
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$802
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$652
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$601
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$536
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$683
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$814
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$774
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$592
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$540
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$554
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$624
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$729
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$758
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$726
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$530
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$519
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$548
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$780
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$811
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$743
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$699
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$502
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$483
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$523
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$693
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$758
 

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