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Key West Vacation Rentals

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Key West

Foundry on the Waterfront

Private Homes, New Town

1800 Atlantic

Galleria

Private Homes, Old Town

Bahama Village

Key West Cuban Club

Private Homes, Unspecified

Beach House Resort

Key West Golf Club

Private Homes, UpTown

BeachSide

Kings Pointe

Seaside Resort

Casa Marina

La Brisa

Sunrise Suites

Coconut Mallory

Meadows

Sunset Marina

Coral Hammock

Private Homes, DownTown

Truman Annex

Duval Square

Private Homes, Historic Seaport

White St. Gallery

Other Key West Properties

Private Homes, Mid Town

Windward Park

  

Available Dates Credit Cards OK Guest Comments Pet Friendly VRBO Bear stayed here (#) Photos

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Foundry on the Waterfront Vacation Rentals

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Foundry on the Waterfront Foundry on the Waterfront - Exclusive Row House Residence [#139485]3
  2BR/2.5BA (Sleeps 4) $300-$425/nt - $1500-$2500/nt US Dollars

Galleria Vacation Rentals

 Show only: Galleria Vacation Rentals Top
Galleria Quaint, Artistic Key West Guest House [#118363]12
  1BR/1BA (Sleeps 1-2) $89-$98/nt US Dollars
Galleria Caribbean "Styled" Condo in Paradise, Key West Florida [#138036]11
  1BR+/1BA (Sleeps 2-4) $115/nt US Dollars
Galleria Cozy Condo in Key West [#138062]7
  1BR/1BA (Sleeps 2) $120 OR $90 US Dollars
Galleria An Artistic Hideaway in Paradise [#129956]6
  1BR+/1BA (Sleeps 2-4) From $99/nt US Dollars

Key West Cuban Club Vacation Rentals

 Show only: Key West Cuban Club Vacation Rentals Top
Key West Cuban Club Spacious and Comfortable Duval St. Oasis [#178773]9
  2BR+/2BA (Sleeps 4-7) $249-$599/nt US Dollars

Key West Golf Club Vacation Rentals

 Show only: Key West Golf Club Vacation Rentals Top
Key West Golf Club Craig & Cindy's Key West Coral Hammock Rentals [#47580]16
  3BR+/3BA (Sleeps 6-8) $1200-$1900/wk US Dollars
Key West Golf Club "The Spa" @ the Sanctuary: Walled Yard, Spa & 2 Master Suites! [#71542]16
  2BR+/3BA (Sleeps 4-6) $2500-$5500/mo US Dollars
Key West Golf Club "Poolside Retreat": Town Home @ the Pool with 2 Master Suites [#104772]16
  2BR/2.5BA (Sleeps 4) $3000-$5000/mo US Dollars
Key West Golf Club Key West "Coral Hammock" - Poolside [#105427]16
  3BR/3BA (Sleeps 6) $1260-$1750/wk US Dollars
Key West Golf Club "Colorful Conch" @ the Sanctuary: 3 BR, 3 Bath & Private Pool [#115109]16
  3BR+/3BA (Sleeps 6) $4,400-$13,000/mo US Dollars
Key West Golf Club "Paradise Perfected" @ the Sanctuary: a Home You Always Wanted [#118166]16
  3BR/2.5BA (Sleeps 6) $3500-$9900/mo US Dollars
Key West Golf Club "Quiet Conch" @ Kingfisher: 3BR & Private Pool on Cul-De-Sac. [#183386]16
  3BR/2BA (Sleeps 6) $3300-$5500/mo US Dollars
Key West Golf Club Key West - Poolside Conch Paradise at Key West Golf Club [#113115]12
  2BR/1.5BA (Sleeps 4) $2250-$4000/mo US Dollars
Key West Golf Club "Tropic Oasis" @ the Sanctuary: Private Home & Pool, Sleeps 8 [#161495]12
  4BR+/3BA (Sleeps 6-8) $3300-$8800/mo US Dollars
Key West Golf Club "Fairway Villa" Key West Golf Course [#177627]5
  3BR+/2.5BA (Sleeps 6) From $4000/mo US Dollars
Key West Golf Club Key West Homes with Golf - 2 Pools - 5 Minutes to Old Town [#9737]3
  3BR+/2.5BA (Sleeps 6) From $2000/mo US Dollars
Key West Golf Club Beautiful Key West Townhouse on Golf Course/2 Pools [#23242]3
  2BR+/2BA (Sleeps 4-6) $1500-$3500/mo US Dollars
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Key West Golf Club Key West Private Spa Home Paradise [#149891]3
  2BR+/2.5BA (Sleeps 4-6) $2500-$7000/mo US Dollars

Kings Pointe Vacation Rentals

 Show only: Kings Pointe Vacation Rentals Top
Kings Pointe "Oceanside Oasis" @ Kings Pointe: Direct Ocean Views & 3 BR'S [#129405]16
  3BR/2BA (Sleeps 4-6) $1700-$3000/wk US Dollars
Kings Pointe King's Pointe Marina "Oceanfront" Key West's Luxury 3BR Rental [#154578]16
  3BR+/2BA (Sleeps 2-8) $1600-$2600/wk - $6000-$8500/mo US Dollars
Kings Pointe Kings Point Key West Vacation Rental [#170889]16
  3BR+/2BA (Sleeps 2-8) $1500-$2500/wk - $6000-$8000/mo US Dollars
Kings Pointe “Azure Afternoon” at Kings Pointe: 3BR/2BA on the Atlantic [#199426]16
  3BR+/2BA (Sleeps 6-8) $1500-$3600/wk - $4400-8800/mo US Dollars
Kings Pointe Kings Pointe Ocean-Side Luxury 3 BR Condo [#138365]10
  3BR/2BA (Sleeps 6) $1600-$2900/wk US Dollars

La Brisa Vacation Rentals

 Show only: La Brisa Vacation Rentals Top
La Brisa Deluxe 3 BR Oceanfront Condo [#57418]12
  3BR+/2BA (Sleeps 6-8) From $1200/wk US Dollars
La Brisa Luxury Beachfront Condo [#133090]12
  2BR+/2BA (Sleeps 8) From $1200/wk US Dollars
La Brisa Serenity at La Brisa [#148855]10
  2BR+/2BA (Sleeps 4-6) $3000-$5000/mo US Dollars
La Brisa Tropical Breeze- Two Bedroom, Two Bath, Oceanfront Condominium [#92450]6
  2BR+/2BA (Sleeps 6) $1300-$1905/wk US Dollars
La Brisa Key West Oceanfront Condominium [#64489]3
  2BR+/2BA (Sleeps 6) $1175-$1675/wk US Dollars

Meadows Vacation Rentals

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Meadows Key West Rental (Casa De Suenos) House of Dreams! and a Pool!! [#171894]9
  1BR+/1BA (Sleeps 2-4) $1700-$3500/mo US Dollars
Meadows Elegant and Luxurious New Home in Historic Key West [#192314]7
  2BR/2.5BA (Sleeps 4) $8,500-$10,500/mo US Dollars
Meadows Key West Conch House [#174300]5
  3BR/2.75BA (Sleeps 6) $4000/mo US Dollars
Meadows Old Town - Cottage, Free Wireless, Near Marina [#168348]3
  1BR+/2BA (Sleeps 4) $2000-$4000/mo US Dollars

Private Homes, DownTown Vacation Rentals

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Private Homes, DownTown "Duval Street Condo" Brand New & Best Location Key West [#166862]12
  2BR/1BA (Sleeps 4) From $1200/wk US Dollars
Private Homes, DownTown Key West Oasis [#168182]12
  3BR/3BA (Sleeps 6) $7000/mo US Dollars
Private Homes, DownTown Down Island Digs - Ideal Location Downtown, Private Pool. [#184018]10
  2BR+/2BA (Sleeps 4-6) $375-$450/nt - $2050-$2700/wk US Dollars
Private Homes, DownTown Secret Courtyard Cottage - Downtown with Privacy! [#184021]8
  2BR+/1BA (Sleeps 4-5) $275-$350/nt - $1400-$1750/wk US Dollars
Private Homes, DownTown Key West Dreamin' - Downtown Location with a Private Pool [#184033]6
  2BR+/2BA (Sleeps 4-6) $425-$500/nt - $2350-$2975/wk US Dollars
Private Homes, DownTown Downtown Key West 5 BR House [#119766]3
  5BR/4BA (Sleeps 10) $5000-$8000/wk US Dollars

Private Homes, Historic Seaport Vacation Rentals

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Private Homes, Historic Seaport Tropical Tranquility - 5 Star Caribbean Resort-Style Villa [#173086]14
  4BR/3.5BA (Sleeps 8) $950-$1250/nt - $4500-$6000/wk US Dollars
Private Homes, Historic Seaport Experience Key West Like a Local [#55262]12
  1BR/1BA (Sleeps 2) $2000-$3500/mo US Dollars
Private Homes, Historic Seaport Historic Seaport Home [#120234]12
  4BR+/4.75BA (Sleeps 10) $9,000-$15,000/mo US Dollars
Private Homes, Historic Seaport Island Village Cottage-Historic Seaport of Key West [#183984]7
  2BR+/2BA (Sleeps 4-6) $325-$400/nt - $1850-$2550/wk US Dollars
Private Homes, Historic Seaport Darling Old Town Cottage for Single or Couple [#31609]6
  1BR/1BA (Sleeps 2) $2000-$3500/mo US Dollars
Private Homes, Historic Seaport Key West 'S Finest Historic Harbor Monthly Rental Cottage! [#54945]5
  3BR+/2BA (Sleeps 6-8) $4000-$7000/mo US Dollars
Private Homes, Historic Seaport Key West Boat & Breakfast, Reef Sailing Trips, Island Hopping [#169864]5
  2BR+/2BA (Sleeps 2-4) $295/nt US Dollars
Private Homes, Historic Seaport Exquisite 3BR/3BA Historic Villa on Quiet Lane Near Seaport [#185319]5
  3BR+/3BA (Sleeps 6-7) $6000-$9000/mo US Dollars
Private Homes, Historic Seaport Spectacular Turn-of-the-Century - Classic Key West Estate [#138048]3
  5BR+/4BA (Sleeps 6-14) $1050-$1375/nt - $5000-$6900/wk US Dollars
Private Homes, Historic Seaport The Grand Marshall Key West - a Rare One-of-a-Kind Estate Home [#139521]3
  5BR+/4BA (Sleeps 10-14) $1050-$1375/nt - $5000-$6900/wk US Dollars
Private Homes, Historic Seaport Key West Classic Revival (Renovated) [#206911]
  3BR/3.5BA (Sleeps 6) $7500-$9000/mo US Dollars

Private Homes, Mid Town Vacation Rentals

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Private Homes, Mid Town Amanda's Dream Suites-Good Value with Giant Pool in Key West [#183990]10
  4BR+/3BA (Sleeps 8-10) $500-$700/nt - $2900-$4100/wk US Dollars
Private Homes, Mid Town Coco's Poolside Retreat - Three Story Town Home by Giant Pool. [#183994]7
  3BR+/2.5BA (Sleeps 6-8) From $300/nt - $1600/wk US Dollars
Private Homes, Mid Town House in Key West [#172857]5
  2BR/2.5BA (Sleeps 4) $5000-$7000/mo US Dollars
Private Homes, Mid Town Charming 1/1 in Historic District. Large Tropical Garden [#184514]5
  1BR+/1BA (Sleeps 2-4) $900/wk US Dollars
Private Homes, Mid Town 4 Bedroom 3 Bath Key West Heated Pool Home [#201807]5
  3BR+/3BA (Sleeps 8) $6000-$6500/mo US Dollars
Private Homes, Mid Town Paradise Manor with Private Pool and Patio [#201847]5
  4BR/2BA (Sleeps 9) From $300/nt US Dollars

Private Homes, New Town Vacation Rentals

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Private Homes, New Town Relax and Get Away in This Completely Refinished Quiet Home [#143190]5
  3BR+/2BA (Sleeps 6-8) $1000-$1500/wk - $3500/mo US Dollars
Private Homes, New Town Private Estate 4 Bed/4 Bath with Dock [#185966]5
  4BR/4BA (Sleeps 9) $6000-$12,000/mo US Dollars

Private Homes, Old Town Vacation Rentals

 Show only: Private Homes, Old Town Vacation Rentals Top
Private Homes, Old Town Walk Everywhere... One Block to Harbor... Three to Duval [#89834]16
  3BR+/2BA (Sleeps 6) From $4500/mo US Dollars
Private Homes, Old Town Casa De Cuba a Beach House - Cuban Flair Steps from Duval [#98473]16
  3BR/2BA (Sleeps 6) $458-$620/nt - $3000-$4200/wk US Dollars
Private Homes, Old Town Captains Mansion - Fantasy Fest Avail. [#99427]16
  3BR/3BA (Sleeps 6) $8000-$14,000/mo US Dollars
Private Homes, Old Town "The Real Deal" Key West, Only 1 Block Off Duval on Southard [#117148]16
  1BR/1BA (Sleeps 2-4) $160-$248/nt - $997-$1597/wk US Dollars
Private Homes, Old Town "Old Town" Key West Charmer [#118424]16
  1BR+/1BA (Sleeps 2-14) From $99/nt - $895/wk US Dollars
Private Homes, Old Town "Southard Comfort" @ Old Town: a Dazzling Key West Conch House [#122535]16
  3BR/2BA (Sleeps 6) From $500/nt - $2500/wk - $4500/mo US Dollars
Private Homes, Old Town Villa Tropicale - Secluded Tropical Villa [#125695]16
  4BR+/5BA (Sleeps 8-9) $4600-$7900/wk US Dollars
Private Homes, Old Town The Mermaids House - Old Town, Historic Bahama Conch House [#129511]16
  2BR+/1.25BA (Sleeps 3-6) $2000-$6000-mo US Dollars
Private Homes, Old Town The "Hollinsed House" "Big House" Condos #1, 2, 3, 5 Guesthous [#144522]16
  3BR/3BA (Sleeps 2-12) From $99/nt - $937/wk - $3,400/mo US Dollars
Private Homes, Old Town "The Secret Garden" Very Private & Classic Key West [#153214]16
  2BR/1.75BA (Sleeps 2-6) $2,900-$6400/mo US Dollars
Private Homes, Old Town "Falling Water” @ Old Town: Breathtaking Residential Compound [#168095]16
  5BR+/4.5BA (Sleeps 10-12) $8000-$24,000/mo US Dollars
Private Homes, Old Town "Bimini" Luxurious Townhome Villa in the Heart of Old Key West [#168724]16
  2BR+/3.5BA (Sleeps 6) From $428/nt - $2700/wk US Dollars
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Private Homes, Old Town **Fantasy Fest $400discount** Supermodel Vacation Rental [#185246]16
  2BR/2BA (Sleeps 4-5) From $2,600/wk - $1200/wkd - $4800/mo US Dollars
Private Homes, Old Town Luxury House,Old Town Lane, Pool - Free Wireless- Monthly Only [#123424]14
  2BR/2BA (Sleeps 4) $4000-$7500/mo US Dollars
Private Homes, Old Town Private Gated Escape...Heart of Old Town [#194278]14
  3BR+/2.25BA (Sleeps 2-8) $895/wk - $1895-$8500/mo US Dollars
Private Homes, Old Town Dos Casas-4 BR Compound in Beautiful Old Town Key West [#76082]13
  4BR/2BA (Sleeps 8) $5500-$8500/mo US Dollars
Private Homes, Old Town Sophisticated Elegance on Fleming Street (Pool, Parking) [#128058]13
  3BR/2.75BA (Sleeps 6) $8000-$14,000/mo US Dollars
Private Homes, Old Town 200 Yards from Beach! [#170598]13
  1BR+/1BA (Sleeps 2) $2500-$3000/mo US Dollars
Private Homes, Old Town Sophisticated Southard Street Charmer [#176314]13
  2BR/2BA (Sleeps 4) $4500-$8000/mo US Dollars
Private Homes, Old Town The White House Key West's Finest Monthly Rental/4 BR [#177512]13
  4BR/3BA (Sleeps 8) $5000-$9000/mo US Dollars
Private Homes, Old Town Contemporary Gem [#177596]13
  3BR/2.5BA (Sleeps 6) $4500-$7500/mo US Dollars
Private Homes, Old Town Family Reunion - 3 Homes and a Cottage in Pool Garden Compound [#202539]13
  12BR+/10BA (Sleeps 22-28) From $1,350/nt - $7,500/wk US Dollars
Private Homes, Old Town Key West Lazy Lane Vacation Rental Accommodations & Cottages [#6429]12
  1BR+/1BA (Sleeps 1-6) $75-$260/nt - $700-$1600/wk US Dollars
Private Homes, Old Town Private Place- 2 BR ~ 1400 Sf ~ Key West Vacation Rental [#23531]12
  2BR+/2BA (Sleeps 4-6) $295/nt - $2000/wk US Dollars
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Private Homes, Old Town "Coconut Cabana" Old Town Tropical Bungalow [#72848]12
  3BR/2BA (Sleeps 4-6) $398-$498/nt - $2200-$3360/wk US Dollars
Private Homes, Old Town Old Town Bali Hideaway for 2, Just Steps from Duval [#82634]12
  Studio/1BA (Sleeps 2) $168-$230/nt - $1100-$1540/wk US Dollars
Private Homes, Old Town Harbor Inn Condominium [#82650]12
  2BR+/2BA (Sleeps 6) $1400-$1750/wk US Dollars
Private Homes, Old Town Historic Conch Cottage 1/2 Block Off Duval -- "Casa Louisa" [#88122]12
  3BR/2BA (Sleeps 6) $2695-$3325/wk US Dollars
Private Homes, Old Town Key West * Laid-Back Sophistication and Understated Glamour * [#89318]12
  3BR/2BA (Sleeps 4-6) $6000-$9000/mo US Dollars
Private Homes, Old Town "Tranquility " at Ann Street Gardens Steps from Duval [#98557]12
  1BR/1BA (Sleeps 2) $188-$260/nt - $1400-$1750/wk US Dollars
Private Homes, Old Town Old Town Historic Eyebrow House (3 BR/2 BA) [#108861]12
  3BR/2BA (Sleeps 5-6) $7,500-8,500/mo US Dollars
Private Homes, Old Town Historic 4 BR/3 BA Luxury Home in Key West [#116745]12
  4BR/3BA (Sleeps 4-8) $2200-$5600/wk US Dollars
Private Homes, Old Town Precious Pink Cottage with Private Pool & 4 Blocks from Duval [#129563]12
  2BR+/1BA (Sleeps 4-5) $1500-$1700/wk US Dollars
Private Homes, Old Town Secret Villa - Hidden Gem in a Heart of Old Town Key West [#137683]12
  3BR/3BA (Sleeps 6) $458-$620/nt - $2900-$4200/wk US Dollars
Private Homes, Old Town Colony Cabanas - Tropical Bungalow in the Heart of Old Town [#137869]12
  1BR+/1.5BA (Sleeps 2-4) $158-$240/nt - $1150-$1610/wk US Dollars
Private Homes, Old Town Historic Restored "Eyebrow" Home [#139799]12
  3BR/3BA (Sleeps 6) $6000-$8500/mo US Dollars
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Private Homes, Old Town "Harvey's Haven" Vintage Charm in the Perfect Location [#154275]12
  Studio+/1BA (Sleeps 2-4) From $99/nt - $938/wk US Dollars
Private Homes, Old Town Key West Cottage (Roxies Hide-a-Way) [#188966]12
  1BR+/1BA (Sleeps 2-3) $4,000/mo U S Dollars
Private Homes, Old Town A Royal Home with 4 Master Suites and Style [#123121]11
  4BR/4.75BA (Sleeps 6-8) $10,000-$15,000/no US Dollars
Private Homes, Old Town Duncan Island Home, Private Pool, Easy Walk to Duval [#164094]11
  3BR+/2BA (Sleeps 6) $3000-$7000/mo US Dollars
Private Homes, Old Town Stop Looking Now! Historic Old Town [#166113]11
  1BR/1BA (Sleeps 2) $3000-$5000/mo US Dollars
Private Homes, Old Town Old Town Cottage Home with Tropical Decor & Pool [#30517]10
  2BR/2BA (Sleeps 4) $3500-$6600/mo US Dollars
Private Homes, Old Town Southern Most City Historic Vacation Home [#148393]10
  3BR/3BA (Sleeps 6-8) $4000-$10,000/mo US Dollars
Private Homes, Old Town Designer Dream 2BR/2BA with Heated Pool and Concierge [#190172]10
  2BR/2BA (Sleeps 2-4) $4000-$7000/mo US Dollars
Private Homes, Old Town A Hop, Skip and Jump to Duval Street (1 1/2 Blocks) 3bd/2.5BA [#100392]9
  3BR+/2.5BA (Sleeps 6-8) $3000-$6500/mo US Dollars
Private Homes, Old Town Fabulous Key West Retreat [#150680]9
  2BR/2BA (Sleeps 4) From $5000/mo US Dollars
Private Homes, Old Town Ashe Splash--Award-Winning Classic Home in Old Key West [#177438]9
  3BR/3BA (Sleeps 6-7) $3950--$7500/mo US Dollars
Private Homes, Old Town Heart of Old Town - Nightly 1 BR - Upscale, Pool, & Breakfast! [#89723]8
  1BR+/1BA (Sleeps 2-4) $215-$335/nt US Dollars
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Private Homes, Old Town Exclusive "Old Town" Cottage [#156551]8
  1BR/1BA (Sleeps 2) $3300/mo US Dollars
Private Homes, Old Town Bella Grande Premier - 5 Star Quality Victorian Estate [#157257]8
  5BR/5.5BA (Sleeps 10) $9000-$14,500/mo US Dollars
Private Homes, Old Town Private Tropical Pool Courtyard Completely Hidden from View [#201627]8
  3BR/3BA (Sleeps 6-8) $600-$750/nt - $3500-$4500/wk US Dollars
Private Homes, Old Town Spectacular Spanish Style Show Piece - One of a Kind Villa [#201647]8
  2BR/2BA (Sleeps 4-6) $5000-$7500/mo US Dollars
Private Homes, Old Town Babalu Cottage - a Colorful Vacation Rental Home in Key West [#6735]7
  3BR/1.5BA (Sleeps 6) From $302-$377/nt - $1800-$2300/wk US Dollars
Private Homes, Old Town Summer Rates from $3000/Month - Louisa Bella [#101530]7
  2BR+/1BA (Sleeps 4-6) $3000-$6500/mo US Dollars
Private Homes, Old Town Key West Charmer Offers Serenity, Simplicity & Close to Beach [#114836]7
  1BR/1BA (Sleeps 2-3) $90-$180/nt - $645-$1395/wk US Dollars
Private Homes, Old Town Abaco Dreams 3BR/2BA Old Town Private Paradise Key West [#151361]7
  3BR+/2BA (Sleeps 5-6) From $550/nt - $3850/wk US Dollars
Private Homes, Old Town Royal Street Gardens ---Welcome to Key West! [#159307]7
  1BR/1BA (Sleeps 1-2) $2000-$3500/mo US Dollars
Private Homes, Old Town Charming 100+-Year-Old Conch Cottage in the Heart of Old Town [#37855]6
  1BR/1BA (Sleeps 1-2) $1800-$3500/mo US Dollars
Private Homes, Old Town Key West Vacation Condo - Island Retreat Condo [#62097]6
  2BR+/2BA (Sleeps 4) $140-$300/nt - $980-$1800/wk US Dollars
Private Homes, Old Town Egret Cottage: One Bedroom Cottage - Available Nightly/Weekly [#92567]6
  1BR+/1BA (Sleeps 4) $1050-$1550/wk US Dollars
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