Osprey @ Colony

0 Bedrooms 1 Bathrooms Sleeps 4 Key West 481 sq. ft. Pet Friendly

Welcome to Osprey—a beautiful studio in the heart of Old Town Key West! Perfectly located at the Colony on Olivia Street, just two blocks from famous Duval Street, this ground-floor studio suite is equipped to make your stay in the islands comfortable and

Studio

1 King

Studio

1 Sofa Bed

Welcome to Osprey—a beautiful studio in the heart of Old Town Key West! Perfectly located at the Colony on Olivia Street, just two blocks from famous Duval Street, this ground-floor studio suite is equipped to make your stay in the islands comfortable and convenient. Osprey is both removed from and integrated into Old Town Key West. It is tucked away in a quiet neighborhood, but close enough to walk to any bar, restaurant, shop, or gallery. This is a non-smoking unit designed to accommodate two people.

This charming suite is comfortably furnished with a King bed, comfortable couch, flat-screen TV, and tropical artwork. An open floor plan creates a breezy atmosphere and the kitchenette features a coffee maker, microwave oven, stovetop, refrigerator, and the accessories to allow for small meal preparation if you aren't up for going out. A spacious bathroom with standing shower and full-length mirror completes this wonderful accommodation. The french doors lead out to an inviting deck close to the shared pool.

Kitchen

  • Stove
  • Coffee Maker - Drip
  • Dishes & Silverware
  • Microwave
  • Refrigerator
  • Toaster
  • Cooking Basics
  • Dishes & utensils for kids
  • Blender

Location

  • Historic District

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
  • Free wifi
  • Body Wash
  • Air Conditioning
  • Bed Linens
  • Cable
  • Towels
  • Hot Water
  • Iron & Ironing Board
  • Private Entrance

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

Home Safety

  • Fire Extinguisher
  • Smoke Detector

Entertainment

  • Satellite or Cable
  • Television

Facility

  • Paid Parking on Premises
  • Pool
  • Street Parking
  • Shared laundry on site

Outdoor

  • Patio or Balcony

Pool

  • Communal Pool
  • Heated Pool
LEAVE A REVIEW
June 20, 2026 - Track Survey

by Richard L

While my second stay at the Colony compound, this was my first at The Osprey #8. It was a great studio, perfect for a single. Already thinking of booking for a stay in 6-months.

We are happy to hear that you enjoyed our cottage!  We hope to have you stay with us again.

April 2, 2026 - Track Survey

by Donald C

The compound and the unit itself were really special. Location is important to me and this was spot on!

March 28, 2026 - Track Survey

by Troy B

Property was very nice and quiet without much street noise. The unit was a good size for our needs. Two tips to the owner - add a lamp or two and consider a new mattress. Otherwise we really enjoyed our stay at the Colony. The location is really ideal and the neighborhood is vintage Key West.

Thank you for your review! We're glad you enjoyed the quiet atmosphere, comfortable space, and ideal location in one of Key West's charming historic neighborhoods.

We appreciate your suggestions about adding more lighting and updating the mattress and will share them with the property owner for consideration.

Thank you for staying with us. We hope to welcome you back to The Colony again soon!

February 12, 2026 - Track Survey

by Walt M

After staying in one of the other units of The Colony, I expected this one (Osprey) to be similar. I was not. I would describe this unit a small efficiency apartment.

Thank you for your review and for choosing to stay with us again. We appreciate your feedback and understand that Osprey did not meet the expectations you had based on your previous stay at another unit within The Colony.

Each unit at The Colony has its own unique layout, size, and features, and we're sorry to hear that this particular property felt smaller than anticipated. We understand how expectations can be shaped by prior experiences, and we appreciate you sharing your perspective.

We're glad you gave Osprey a try, and we'd be happy to help you find a property that better matches your preferences and space requirements for a future stay. Thank you again for your valuable feedback, and we hope to have the opportunity to welcome you back to Key West.

January 3, 2026 - Track Survey

by Morgan M

I enjoy working with this company for rentals. This was our 3rd time to rent with them . However I didn’t care for this unit, it was very small, bed was not comfortable and TV was positioned poorly for watching.

Thank you for your continued trust in our company and for choosing to stay with us for the third time. We truly appreciate your loyalty and are glad to hear you've enjoyed working with our team over the years.

We're sorry to learn that this particular unit did not meet your expectations. We understand that comfort is a key part of any stay, and we're disappointed to hear that you found the space smaller than anticipated, the bed uncomfortable, and the TV placement less than ideal. Your feedback is valuable and will be shared with our team as we continually evaluate ways to improve our properties and the guest experience.

We appreciate your honest comments and hope we'll have the opportunity to welcome you back to a unit that better suits your preferences on your next visit.

September 23, 2025 - Track Survey

by Carolann S

They make it easy and fast so you can start your vacation and hit the ground running!

June 17, 2025 - Track Survey

Easy walk to everything!

by Jen J

We loved this apartment - it had all we needed to rest and relax when we were not exploring the island. The pool was perfect for cooling off from the June heat. Especially loved location for easy walk to everything!

October 15, 2024 - Track Survey

by Amy A

Very nice place and easy to access.

May 25, 2024 - Track Survey

by Eric L

We loved everything about our stay here!

April 11, 2024 - Website

Clean & Quiet

by Patricia R

The location of this property was great and it is a quiet street. The cottage was very clean and the perfect size for the two of us. We also enjoyed use of the shared pool. The bed is very high so I would like to make the suggestion of having a foot stool available for short people like me. We will definitely be back.

February 7, 2024 - Website

Great Location!

by John D

Great location! The pool was amazing! I met some wonderful friends while staying. I re-booked for next year!!!

We are excited that you have already reserved for next year. 

July 30, 2023 - Website

Great Experience

by Jenny B

I'll never stay at a hotel in Key West again after experiencing Key West Hideaways! 10x better than any crappy hotel experience on that island

March 8, 2023 - Website

Beautiful, Clean property

by DZ

Beautiful, Clean property with awesome landscapes and pool. Staff was excellent. Will be returning next year!!

Thank you!  We look forward to your return

February 25, 2023 - Website

by DQ

I use a wheelchair. Although the property is not billed as wheelchair accessible, my companion and I were able to thoroughly enjoy our stay.

We are so glad the property worked for you.  We have several properties that are close, but not totally handicap accesible, so it is nice to hear you were able to make it work.

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November 2026
S M T W T F S
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$210
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$150
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$162
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$277
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$210
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$169
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$164
         
December 2026
S M T W T F S
    01
$170
02
$186
03
$204
04
$249
05
$249
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$216
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$190
08 09 10 11
$260
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$259
13
$218
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$231
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$230
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$224
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$243
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$264
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$279
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$247
21
$263
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$352
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$345
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$380
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$430
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$443
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$427
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$403
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January 2027
S M T W T F S
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$353
07
$403
08
$450
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$419
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$375
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$357
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$354
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$372
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$416
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$518
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$569
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$470
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$400
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$427
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$372
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$420
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$447
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$391
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$374
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$441
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31
$526
           
February 2027
S M T W T F S
  01
$461
02
$385
03
$413
04
$474
05
$540
06
$553
07
$449
08
$401
09
$397
10
$416
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$465
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$497
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$525
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$527
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$534
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$478
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$462
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$511
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$508
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$500
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$458
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$430
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$465
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$532
26
$553
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$529
28
$442
           
March 2027
S M T W T F S
  01
$415
02
$411
03
$421
04
$468
05
$504
06
$514
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$492
08
$454
09
$455
10
$471
11
$481
12
$494
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$519
14
$462
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$514
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$543
17
$521
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$488
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$508
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$493
21
$431
22
$404
23
$402
24
$416
25
$461
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$483
27
$504
28
$439
29
$431
30
$390
31
$405
     
April 2027
S M T W T F S
        01
$448
02
$474
03
$473
04
$415
05
$430
06
$386
07
$396
08
$446
09
$466
10
$465
11
$408
12
$383
13
$378
14
$389
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$473
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$499
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$500
18
$393
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$373
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$367
21
$372
22
$424
23
$472
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$465
25
$380
26
$358
27
$353
28
$366
29
$442
30
$531
 
May 2027
S M T W T F S
            01
$509
02
$365
03
$324
04
$315
05
$325
06
$361
07
$384
08
$380
09
$329
10
$301
11
$298
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$302
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$363
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$383
15
$360
16
$358
17
$323
18
$285
19
$291
20
$327
21
$351
22
$348
23
$307
24
$323
25
$322
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$320
27
$323
28
$338
29
$340
30
$313
31
$312
         
June 2027
S M T W T F S
    01
$310
02
$271
03
$300
04
$323
05
$320
06
$293
07
$277
08
$255
09
$278
10
$325
11
$361
12
$361
13
$294
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$288
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$267
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$300
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$336
18
$297
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$356
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$287
21
$252
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$244
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$249
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$281
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$301
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$329
27
$285
28
$247
29
$246
30
$255
     
July 2027
S M T W T F S
        01
$299
02
$318
03
$329
04
$299
05
$265
06
$261
07
$268
08
$299
09
$304
10
$303
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$296
12
$253
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$248
14
$268
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$314
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$353
17
$304
18
$268
19
$249
20
$246
21
$252
22
$283
23
$302
24
$352
25
$310
26
$315
27
$324
28
$316
29
$336
30
$336
31
$296
August 2027
S M T W T F S
01
$232
02
$210
03
$207
04
$215
05
$244
06
$259
07
$271
08
$229
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$205
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$204
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$210
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$239
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$260
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$259
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$218
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$198
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$197
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$204
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$237
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$258
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$257
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$217
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$192
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$187
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$199
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$239
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$258
28
$257
29
$224
30
$202
31
$192
       
September 2027
S M T W T F S
      01
$163
02
$284
03
$256
04
$326
05
$297
06
$230
07
$185
08
$155
09
$181
10
$222
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$237
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$175
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$180
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$172
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$154
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$181
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$224
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$230
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$169
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$161
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$177
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$191
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$223
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$308
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$246
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$178
27
$168
28
$166
29
$178
30
$232
   
October 2027
S M T W T F S
          01
$313
02
$320
03
$287
04
$255
05
$253
06
$320
07
$359
08
$393
09
$397
10
$363
11
$366
12
$317
13
$286
14
$331
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$365
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$365
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$378
18
$338
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$543
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$627
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$660
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$724
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$726
24
$405
25
$406
26
$371
27
$330
28
$346
29
$361
30
$369
31
$331
           
November 2027
S M T W T F S
  01
$287
02
$375
03
$405
04
$491
05
$515
06
$509
07
$425
08
$346
09
$298
10
$343
11
$396
12
$390
13
$391
14
$344
15
$306
16
$297
17
$299
18
$331
19
$362
20
$363
21
$325
22
$312
23
$312
24
$363
25
$419
26
$419
27
$428
28
$363
29
$290
30
$289
       

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