Vacation Rentals by Owner

Key West Vacation Rentals Show this location only Back to top

•   Pelican Landing Andros Suite 1BR/1BA – Sleeps 4 – Other Key West Properties #3174222ha
  8
  $133 - $300 per night

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•   Finn Key 2BR/1BA – Sleeps 4 – Truman Annex #3245854ha
  0
  $157 - $362 per night

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•   The Victoria House 5BR/5.5BA – Sleeps 12 – Other Key West Properties #3245888ha
  0
  $829 - $1776 per night

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•   Key West Casa 3BR/2BA – Sleeps 6 – Other Key West Properties #3245858ha
  0
  $286 - $725 per night

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•   Leeward Isle Key West Retreat 2BR/2BA – Sleeps 4 – Other Key West Properties #3245882ha
  0
  $225 - $471 per night

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•   4 Palms 2BR/2BA – Sleeps 6 – Other Key West Properties #3245861ha
  0
  $179 - $381 per night

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•   Parrot Perch 2BR/2BA – Sleeps 5 – Other Key West Properties #3245862ha
  0
  $157 - $362 per night

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•   Key West Charming 2BR/1BA – Sleeps 4 – Other Key West Properties #3245859ha
  0
  $157 - $362 per night

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•   Island Spice 2BR/2.5BA – Sleeps 6 – Other Key West Properties #3245852ha
  0
  $229 - $487 per night

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•   Conch Condo 2BR/2BA – Sleeps 4 – Truman Annex #3245865ha
  0
  $186 - $399 per night

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•   A Place in Paradise 2BR/2.5BA – Sleeps 6 – Other Key West Properties #3245878ha
  0
  $214 - $414 per night

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•   A Zen Ocean Garden 2BR/2BA – Sleeps 6 – Other Key West Properties #3245866ha
  0
  $257 - $487 per night

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•   Beach House Condo 2BR/2BA – Sleeps 4 – Other Key West Properties #3245853ha
  0
  $186 - $399 per night

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•   The Hemingway 2BR/2BA – Sleeps 6 – Other Key West Properties #3245860ha
  0
  $186 - $409 per night

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•   Spa on Duval 2BR/2.5BA – Sleeps 6 – Other Key West Properties #3245842ha
  0
  $200 - $456 per night

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•   Conch Wind 2BR/2BA – Sleeps 4 – Other Key West Properties #3245881ha
  0
  $196 - $471 per night

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•   Artist Garden 2BR/2.5BA – Sleeps 6 – Other Key West Properties #3245849ha
  0
  $243 - $489 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488392ha
  30
  $117 - $299 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488394ha
  23
  $117 - $299 per night

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•   Rare 2BR/2BA Shipyard Condo Truman Annex Key West! 2BR+/2BA – Sleeps 4-6 – Truman Annex #57100
  2
  From $900/wk to $2500/wk

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•   Tom's Parrot Perch: Gut Renovation! Pool, Close to Beach 2BR+/2BA – Sleeps 4-6 – 1800 Atlantic #345756
  8
  $270 per night 3 night min stay

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•   Truman Annex: the Plantation, Beautifully Landscaped 3BR/3BA – Sleeps 6 – Truman Annex #194366
  30
  $2500- $3500/wk Some Special Event prici

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•   Truman Annex: Paradise Lost Garden Level Condominium 2BR+/2BA – Sleeps 4-6 – Truman Annex #198738
  32
  $1500- $2200/wk Special event Pricing

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•   Ann's Tropical Paradise in Key West 2BR/1BA – Sleeps 3-4 – Truman Annex #73629
  6
  $225 per night 3 night min stay

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•   Truman Annex, Foundry Townhouse, Free Wifi Internet 2BR/2.5BA – Sleeps 4 – Truman Annex #148626
  9
  From $1350/wk

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•   Beach House Exclusive Private Resort Island 500 Yards from Heart of Key West 3BR/1BA – Sleeps 6 – Other Key West Properties #275026ha
  4
  $667 - $833 per night

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•   Key West Ocean View 3 Bedroom Truman Annex Vacation Condo 3BR/3BA – Sleeps 6 – Truman Annex #223802
  1
  $3300 - $5000 per week 7 night min stay

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•   Relax Getaway - Oceanfront Fishing, Dock, Quiet Neighborhood 3BR+/2BA – Sleeps 6-8 – Private Homes, Unspecified #19593
  2
  $3500/mo

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•   Beautiful Duval St. Condo, Location, Location!!!! 2BR/1BA – Sleeps 4 – Other Key West Properties #156723ha
  24
  $150 - $300 per night

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•   Architect's Personal Residence, Private Pool, 1 Blk. to Duval 2BR+/2.5BA – Sleeps 4-6 – Private Homes, Old Town #105102
  30
  $368- $468/nt

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•   Tom's Courtyard / Ocean View: Heated Pool, Close to Beach 2BR+/2BA – Sleeps 4-6 – 1800 Atlantic #404725
  3
  $270 per night 3 night min stay

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•   Truman Annex - Beautiful Townhome - President's Lane 2BR+/1.5BA – Sleeps 4-6 – Truman Annex #55160
  0
  $1300/wk - $4300/mo

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•   Island Escape Condo in Beautiful Truman Annex 1BR/1BA – Sleeps 3 – Truman Annex #383457
  14
  $171 per night

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•   Anderson's Key West Home 4BR/3.5BA – Sleeps 10 – Truman Annex #30934
  3
  $900 per night 2 night min stay

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•   Affordable Waterfront Luxury Condo Sleeps 4-6 Daily/Weekly! 2BR+/2BA – Sleeps 6 – 1800 Atlantic #318919
  6
  $180-$295/nt - $1100-$1900/wk

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•   Luxury Island Mansion 5BR/4BA – Sleeps 10 – Private Homes, Unspecified #264164
  11
  $3500- $8000

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•   Key West Vacation Townhouse Rental in the Truman Annex 2BR/2.5BA – Sleeps 6 – Truman Annex #226962
  5
  $183 - $393 per night

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•   Villa Fleur, Elegant Truman Annex Condo in Old Town 2BR/1BA – Sleeps 4 – Other Key West Properties #207098ha
  1
  $214 - $257 per night

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•   Charming Home with Great Old Town Flair! 3BR+/2BA – Sleeps 6-8 – Private Homes, Old Town #35288
  11
  $4000 - $7000/mo

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•   Beautiful Key West Townhouse on Golf Course/2 Pools 2BR+/2BA – Sleeps 4-6 – Key West Golf Club #23242
  1
  $1650- $3600/mo

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•   Shipyard at Truman Annex "Where the Sun Sets in Old Key West" 2BR/1BA – Sleeps 4 – Truman Annex #103761
  7
  $975- $1200/wk

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•   Casa De Suenos (House of Dreams) Monthly Rental 1BR/1BA – Sleeps 4 – Private Homes, Old Town #147469ha
  1
  $83 - $150 per night

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•   Sunrise South 2BR+/2BA – Sleeps 4-6 – Sunrise Suites #28444
  0
  From $150/nt

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•   Pelican Landing Harbor Island Retreat 2BR/2BA – Sleeps 6 – Other Key West Properties #3175768ha
  20
  $167 - $350 per night

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•   Pelican Landing St. Kitts Retreat 3BR/4BA – Sleeps 10 – Other Key West Properties #3174204ha
  19
  $200 - $450 per night

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•   Pelican Landing St.Croix Retreat 4BR/4BA – Sleeps 12 – Other Key West Properties #3174230ha
  24
  $233 - $550 per night

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•   Pelican Landing St.John Retreat 3BR/3BA – Sleeps 10 – Other Key West Properties #3174206ha
  25
  $200 - $450 per night

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•   Pelican Landing St. Thomas Retreat 4BR/4BA – Sleeps 14 – Other Key West Properties #3174201ha
  22
  $233 - $550 per night

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•   Pelican Landing Aruba Retreat 2BR/2BA – Sleeps 8 – Other Key West Properties #3174199ha
  35
  $167 - $350 per night

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•   Pelican Landing Antigua Retreat 2BR/2BA – Sleeps 8 – Other Key West Properties #3174207ha
  22
  $167 - $350 per night

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•   Pelican Landing Bermuda Retreat 2BR/2BA – Sleeps 8 – Other Key West Properties #3174209ha
  20
  $167 - $350 per night

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•   Pelican Landing Curacao Retreat 2BR/2BA – Sleeps 8 – Other Key West Properties #3174203ha
  24
  $167 - $350 per night

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•   Pelican Landing Bonaire Retreat 2BR/2BA – Sleeps 8 – Other Key West Properties #3175767ha
  20
  $167 - $350 per night

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•   Relax in Paradise 1BR+/1BA – Sleeps 2-4 – Truman Annex #151616
  0
  $175 - $215 per night 2-7 night min stay

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•   Pelican Landing Dominica Retreat 2BR/2BA – Sleeps 8 – Other Key West Properties #3174200ha
  15
  $167 - $350 per night

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•   Shipyard 253 2BR/1BA – Sleeps 6 – Other Key West Properties #3174183ha
  39
  $117 - $300 per night

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•   Garden Oasis Has a Large Tranquil Garden for Outside Enjoyment. 2BR/1BA – Sleeps 4 – Truman Annex #3510442ha
  0
  $200 - $225 per night 3 night min stay

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•   205e La Brisa 2BR/2BA – Sleeps 4 – Other Key West Properties #3174194ha
  12
  $133 - $300 per night

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•   Peaceful 2 BR Condo with All Amenities 2BR+/2BA – Sleeps 4-6 – Sunrise Suites #164954
  100
  $175 - $250 per night 1 night min stay

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•   Paradise Found 2BR/1BA – Sleeps 4 – Other Key West Properties #3170337ha
  49
  $117 - $300 per night

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•   Isla Bella-Serene and "Green" Just Blocks from Duval Street 2BR+/2BA – Sleeps 4-6 – Private Homes, Old Town #287243
  2
  $348- $428/nt

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•   Charming Conch Cottage One Block Frorm Duval 2BR/2BA – Sleeps 4 – Private Homes, Old Town #163420ha
  0
  $133 - $283 per night

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•   Key West Truman Annex Town Home 2BR/1.5BA – Sleeps 4 – Truman Annex #216176
  2
  $1500-$2400/wk - $4500-$7200/mo

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•   Pelican Landing Florida Suite 1BR/1BA – Sleeps 4 – Other Key West Properties #3174228ha
  8
  $133 - $300 per night

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•   Idyllic Conch House in Quiet Meadows Neighborhood 2BR/2BA – Sleeps 4 – Meadows #208842
  2
  $4200 - $6450 per month 30 night min stay

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•   Single-Family Home for Rent on Key Haven 3BR/2.5BA – Sleeps 6-8 – Key Haven #467834
  0
  $1995 - $2450 per week 7 night min stay

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•   Pelican Landing Harbor Island Room 1BR/1BA – Sleeps 4 – Other Key West Properties #3174218ha
  8
  $100 - $200 per night

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•   Shipyard 106-2 1BR/1BA – Sleeps 4 – Other Key West Properties #3174185ha
  31
  $100 - $250 per night

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•   Enjoy More Privacy in a Truman Annex End Unit Townhome 2BR/1.5BA – Sleeps 4-5 – Other Key West Properties #3552474ha
  0
  $250 - $500 per night 3 night min stay

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•   Paradise Manor with Private Pool is Available June 2013 4BR/2BA – Sleeps 9 – Private Homes, Mid Town #363366
  3
  $500 per night 3 night min stay

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•   Foundry on the Waterfront - Island Brownstone Residence 2BR/2.5BA – Sleeps 4 – Truman Annex #139485
  0
  $300-$425/nt - $1500-$2500/nt

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•   Eaton Manor 2BR/2BA – Sleeps 6 – Other Key West Properties #3174191ha
  10
  $108 - $250 per night

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•   Villa Paradiso a Peaceful Private Retreat 3BR/1BA – Sleeps 6 – Other Key West Properties #489605ha
  14
  $430 - $510 per night

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•   Sunrise Hideaway #407 2BR/2BA – Sleeps 6 – Other Key West Properties #3002900ha
  3
  $190 - $210 per night 2 night min stay

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•   Pelican Landing Andros Room 1BR/1BA – Sleeps 4 – Other Key West Properties #3174223ha
  8
  $100 - $200 per night

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•   Key West Condo - One and Two Bedrooms Studio/0BA – Sleeps 4-6 – Sunrise Suites #446852
  1
  $195 per night 2 night min stay

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•   On the Beach at Beautiful 1800 Atlantic Blvd Condo. Huge Pool! 2BR+/2BA – Sleeps 4-6 – 1800 Atlantic #72157
  0
  $1595- $2595/wk

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•   Our Place in Key West 1BR+/1BA – Sleeps 2-4 – Truman Annex #31180
  0
  $1300- $1900/Wk

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•   Awesome Truman Annex Shipyard with Tropical Garden 2BR+/1BA – Sleeps 4 – Truman Annex #20158
  4
  From $850/wk - $2800/mo

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•   Our Sunrise Condo in Key West, Florida 2BR+/2BA – Sleeps 4-6 – Sunrise Suites #285022
  11
  $100- $175/nt

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•   Deluxe 3 BR Villa at Fort Zach Beach in Historic Old Town Key West Sleeps 1 - 16 3BR/2BA – Sleeps 8 – Other Key West Properties #336442ha
  1
  $2975 - $3800 per week 7 night min stay

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•   The Palms 3BR/2BA – Sleeps 8 – Other Key West Properties #3174189ha
  7
  $183 - $231 per night

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•   The Loft at Echo Gardens 1BR/1BA – Sleeps 4 – Other Key West Properties #3499642ha
  6
  $100 - $124 per night

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•   Pelican Landing Bermuda Room 1BR/1BA – Sleeps 4 – Other Key West Properties #3174227ha
  7
  $100 - $200 per night

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•   Pelican Landing Eleuthera Suite 1BR/1BA – Sleeps 4 – Other Key West Properties #3174221ha
  5
  $133 - $300 per night

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•   Charming "Conch Cottage" on Oceanfront Property Near Key West 2BR+/1BA – Sleeps 4-6 – Private Homes, Unspecified #46442
  17
  $695-$2150/wk - $2800-$6000/mo

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•   Pelican Landing Antigua Suite 1BR/1BA – Sleeps 4 – Other Key West Properties #3174210ha
  5
  $133 - $300 per night

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•   Southernmost Belle a Grand Home in Historic Old Town Key West 5BR/3BA – Sleeps 10 – Other Key West Properties #387301ha
  2
  $750 - $950 per night 2-3 night min stay

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•   Pelican Landing Dominica Suite 1BR/1BA – Sleeps 4 – Other Key West Properties #3174219ha
  5
  $133 - $300 per night

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•   Pelican Landing Bonaire Suite 1BR/1BA – Sleeps 4 – Other Key West Properties #3174197ha
  4
  $133 - $300 per night

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•   Pelican Landing Curacao Room 1BR/1BA – Sleeps 4 – Other Key West Properties #3174215ha
  6
  $100 - $200 per night

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•   Pelican Landing Curacao Suite 1BR/1BA – Sleeps 4 – Other Key West Properties #3174214ha
  3
  $133 - $300 per night

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•   Pelican Landing Bermuda Suite 1BR/1BA – Sleeps 4 – Other Key West Properties #3174226ha
  3
  $133 - $300 per night

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•   The Pirate's Quarter 1BR/1BA – Sleeps 2 – Bahama Village #388207
  11
  $3,000 - $3,500/mo

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•   Pelican Landing Aruba Suite 1BR/1BA – Sleeps 4 – Other Key West Properties #3174212ha
  3
  $133 - $300 per night

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•   Classic Key West Charm and Location Too! 3BR/3BA – Sleeps 6 – Truman Annex #309835
  32
  $1,989 to $3,849/wk!

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•   The Sanctuary House Summer $2500 Too!!! Best Boating Time! 4BR/2.75BA – Sleeps 4-9 – Key West Golf Club #216626
  2
  $2800 per week 7 night min stay

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•   Seaport House 2BR/2BA – Sleeps 6 – Other Key West Properties #3174184ha
  3
  $133 - $178 per night

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•   Pelican Landing Florida Room 1BR/1BA – Sleeps 4 – Other Key West Properties #3174229ha
  4
  $100 - $200 per night

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•   Southard Square 2BR/2BA – Sleeps 6 – Other Key West Properties #3174233ha
  1
  $117 - $160 per night

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