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 A PRIVATE POOL ON SITE!

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

  • Hangers
  • Kitchen
  • Wireless Internet
  • 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
  • Shampoo
  • 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 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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November 2025
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December 2025
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January 2026
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$518
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$642
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$661
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$482
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$477
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$663
February 2026
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March 2026
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$596
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$469
       
April 2026
S M T W T F S
      01
$494
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$608
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$650
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$639
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$593
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$427
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$466
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$482
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$453
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$395
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$382
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$445
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$448
   
May 2026
S M T W T F S
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$519
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$498
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$438
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$381
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$368
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$402
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$473
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$523
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$524
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$421
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$367
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$355
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$389
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$481
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$511
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$415
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$361
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$349
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$382
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$475
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$500
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$502
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$471
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$470
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$469
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$380
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$447
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$491
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$490
31
$393
           
June 2026
S M T W T F S
  01
$343
02
$332
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$363
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$428
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$488
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$492
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$385
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$338
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$327
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$358
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$423
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$476
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$499
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$400
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$416
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$364
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$401
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$464
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$473
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$476
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$374
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$361
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$316
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$347
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$414
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$473
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$476
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$380
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$332
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$322
       
July 2026
S M T W T F S
      01
$354
02
$499
03
$500
04
$500
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$501
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$339
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$329
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$361
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$430
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$477
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$480
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$378
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$329
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$319
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$351
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$421
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$476
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$478
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$387
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$335
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$324
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$479
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$520
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$614
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$655
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$520
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$445
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$447
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$499
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$582
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$581
 
August 2026
S M T W T F S
            01
$461
02
$357
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$311
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$300
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$329
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$395
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$455
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$453
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$347
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$302
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$292
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$319
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$382
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$484
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$469
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$337
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$294
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$284
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$311
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$371
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$434
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$434
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$332
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$288
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$279
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$305
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$367
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$503
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$541
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$344
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$294
         
September 2026
S M T W T F S
    01
$275
02
$301
03
$405
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$422
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$425
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$401
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$399
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$293
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$346
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$388
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$388
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$315
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$268
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$262
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$289
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$348
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$401
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$408
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$328
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$280
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$274
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$302
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$368
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$427
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$438
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$346
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$296
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$288
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$318
     
October 2026
S M T W T F S
        01
$390
02
$444
03
$453
04
$363
05
$312
06
$303
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$334
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$406
09
$462
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$472
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$383
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$327
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$316
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$347
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$406
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$605
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$710
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$592
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$517
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$503
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$556
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$660
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$753
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$762
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$508
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$321
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$305
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$338
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$406
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$449
31
$461
November 2026
S M T W T F S
01
$408
02
$354
03
$344
04
$387
05
$488
06
$551
07
$593
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$531
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$349
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$408
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$400
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$400
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$435
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$469
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$363
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$298
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$291
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$321
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$388
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$496
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$433
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$362
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$312
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$309
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$512
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$519
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$622
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$631
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$515
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$399
         

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