Vacation Rentals by Owner

Key West Vacation Rentals Show this location only Back to top

•   Beautiful Key West Townhome 2BR+/3BA – Sleeps 4-8 – Seaside Resort #331134
  7
  $3500- $6000/mo

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•   Poolside Paradise - 2 BR Town Home. Spring & Summer Specials 2BR+/1.5BA – Sleeps 4-6 – Key West Golf Club #224670
  3
  From $2500/mo

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•   Shipyard/Truman Annex - Private Tropical Retreat in Key West 1BR/1BA – Sleeps 2 – Truman Annex #84372
  0
  From $1100/wk - $3000/mo

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•   Key West Charming - Two Bedroom Condo in Truman Annex 2BR+/1BA – Sleeps 4 – Truman Annex #93294
  0
  $1100- $1750/wk

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•   Key West Rental (Casa De Suenos) House of Dreams! and a Pool!! 1BR+/1BA – Sleeps 2-4 – Meadows #171894
  11
  $2200- $4800/mo

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•   Charming 100+-Year-Old Conch Cottage in the Heart of Old Town 1BR/1BA – Sleeps 1-2 – Private Homes, Old Town #37855
  1
  $1800- $3500/mo

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•   Lovely 'Old Town' Key West Townhouse on Duval St. 2BR+/2.5BA – Sleeps 4-6 – Duval Square #330409
  6
  $1300- $1800/wk

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•   Beautiful Key West Golf Club -- Paradise Found ! 3BR+/3BA – Sleeps 5-7 – Key West Golf Club #264152
  3
  $3400 - $4300/mo

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•   Serenity at La Brisa 2BR+/2BA – Sleeps 4-6 – La Brisa #148855
  2
  $3000- $5000/mo

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•   Key West... America's Caribbean Island 2BR/2BA – Sleeps 4-6 – Seaside Resort #111817
  1
  $1050 - $1275.00 Per Week

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•   Margaux's Hideaway - Two Story Luxury Home with Private Pool 3BR/3BA – Sleeps 6 – Private Homes, Old Town #386583
  1
  $5300- $8200/mth

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•   Coco's Poolside Retreat - Three Story Town Home by Giant Pool. 3BR+/2.5BA – Sleeps 6-8 – Private Homes, Mid Town #183994
  0
  From $325/nt - $11700/wk

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•   Oceanfront Condo with Beautiful Sunset Views 2 Blocks from Duval St. 2BR+/2.5BA – Sleeps 4-6 – Harbour Place #457386
  0
  $2660 - $3850 per week 7 night min stay

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•   Oceanfront Condominium-You Can Pay More But You Can't Get More 2BR/2BA – Sleeps 6 – 1800 Atlantic #76399
  0
  $5000- $6,500/mo

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•   Penthouse on Duval Street 4BR/4.5BA – Sleeps 8 – Private Homes, DownTown #248958
  0
  $600-$775/nt - $3500-$4300/wk

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•   Private Home in Old Town, Key West Hideaway 2BR+/2BA – Sleeps 4-6 – Private Homes, Old Town #281185
  6
  $300

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•   Key West, Gated Truman Annex Condo, Partial Ocean View, Beach 2BR/1BA – Sleeps 4 – Truman Annex #328241
  0
  from $1100- 1800

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•   Island Village Cottage-Historic Seaport of Key West 2BR+/2BA – Sleeps 4-6 – Private Homes, Historic Seaport #183984
  0
  $325-$400/nt - $1850-$2550/wk

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•   Charming Bahamian Cottage 3bed/ 2.5 Pool, Easy Walk to Town 3BR/2.5BA – Sleeps 5 – Private Homes, Old Town #390616
  6
  From $1600 - $7000.00

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•   Three Bedroom Shipyard Townhome 3BR/2BA – Sleeps 6 – Truman Annex #236720
  0
  $2000 per week 7 night min stay

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•   Spacious Key West Vacation Retreat 2BR+/2BA – Sleeps 6 – 1800 Atlantic #298292
  2
  From $3000/mo

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•   Fantasy Resort Villa - One-of-a-Kind Courtyard Villa 3BR+/3BA – Sleeps 6-8 – Private Homes, Old Town #333274
  0
  From $3800. to $4300./wk

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•   Two Bedroom Oceanfront Condo on Smathers Beach in Key West 2BR/1BA – Sleeps 4 – Other Key West Properties #374440
  2
  $2,190 to $4,290 per mo.

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•   Spectacular Spanish Style Show Piece - One of a Kind Villa 2BR/2BA – Sleeps 4-6 – Private Homes, Old Town #201647
  0
  $5000- $7500/mo

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•   Rent a Piece of Paradise! 2BR/1BA – Sleeps 4 – Truman Annex #201892
  5
  From $1000/wk

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•   Affordable Fun!!- for 2 Adults-5 Min Walk to Ocean or Duval St 1BR/1BA – Sleeps 2 – Casa Marina #377353
  1
  From $129.00 nt or $700.wk

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•   Key West Quarter House ~ Steps from Mallory Square Sunset 4BR+/4BA – Sleeps 8-12 – Private Homes, DownTown #364128
  0
  From $3800- $4800/wk

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•   Duval Street Private Compound 4BR+/4BA – Sleeps 8-12 – Private Homes, DownTown #438179
  1
  $700 per night 4 night min stay

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•   Perfect Cottage with Private Pool and Garden-2bed/2bath 2BR+/2BA – Sleeps 6-8 – Private Homes, Old Town #323986
  2
  $3500- $6500/mo +12.5% tax

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•   Top of Duval ~ Incognito 6BR+/6BA – Sleeps 10-16 – Private Homes, DownTown #379980
  0
  From $1000/nt - $4900/wk

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•   Sunset Key Home W/ Pool on Private Island Off of Key West, Fl 4BR/4BA – Sleeps 6-8 – Other Key West Properties #403618
  0
  $8,000.00/MO

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•   Unique Cottage in Truman Annex Shipyard Free Wifi 2BR/2BA – Sleeps 4 – Truman Annex #246337
  0
  $1700 - $2400/wk

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•   3 Bedroom Plus Waterfront Town Home Boat Slip 3BR+/1BA – Sleeps 16-18 – Geiger Key #327691
  0
  $1200/wk

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•   Calico Cove -- Charming, Key West Apartment Nestled in Old Town. 2BR/1BA – Sleeps 4 – Other Key West Properties #3006638ha
  0
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•   Private Historical Conch House with Pool 3 BR/2 BA, Old Town 3BR/2BA – Sleeps 6 – Private Homes, Old Town #290390
  0
  $4000- $7500/mo

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•   Canal Home in Key West 3BR/2BA – Sleeps 6 – Other Key West Properties #315015
  2
  $1800- $6500/mo

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•   Gulfview Oasis 4BR/2.5BA – Sleeps 10 – Private Homes, Mid Town #433291
  0
  $7,000/mo - $10,000/mo

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•   Old Town Key West - Banyan Resort up to 4 Wks in a 1 BR Apt. 1BR+/1BA – Sleeps 4 – Private Homes, Old Town #379877
  0
  $1200/wk - $2000/wk

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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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•   Key West Casa 3BR/2BA – Sleeps 6 – Truman Annex #3245858ha
  0
  $286 - $725 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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•   Conch Condo 2BR/2BA – Sleeps 4 – Other Key West Properties #3245865ha
  0
  $186 - $399 per night

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•   Island Spice 2BR/2.5BA – Sleeps 6 – Truman Annex #3245852ha
  0
  $229 - $487 per night

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

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

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•   A Place in Paradise 2BR/2.5BA – Sleeps 6 – Truman Annex #3245878ha
  0
  $214 - $414 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 – Truman Annex #3245862ha
  0
  $157 - $362 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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•   Spa on Duval 2BR/2.5BA – Sleeps 6 – Other Key West Properties #3245842ha
  0
  $200 - $456 per night

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•   The Hemingway 2BR/2BA – Sleeps 6 – Truman Annex #3245860ha
  0
  $186 - $409 per night

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•   Artist Garden 2BR/2.5BA – Sleeps 6 – Truman Annex #3245849ha
  0
  $243 - $489 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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•   Paradise Found 2BR/1BA – Sleeps 4 – Truman Annex #3170337ha
  49
  $117 - $300 per night

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

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•   Shipyard 106-2 1BR/1BA – Sleeps 4 – Truman Annex #3174185ha
  31
  $100 - $250 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488370ha
  32
  $117 - $299 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488378ha
  45
  $117 - $299 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488373ha
  40
  $117 - $299 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488359ha
  20
  $117 - $299 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488394ha
  24
  $117 - $299 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488367ha
  24
  $117 - $299 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488384ha
  20
  $117 - $299 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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•   Pelican Landing Bermuda Room 1BR/1BA – Sleeps 4 – Other Key West Properties #3174227ha
  7
  $100 - $200 per night

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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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•   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 Curacao Retreat 2BR/2BA – Sleeps 8 – Other Key West Properties #3174203ha
  24
  $167 - $350 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 Andros Suite 1BR/1BA – Sleeps 4 – Other Key West Properties #3174222ha
  8
  $133 - $300 per night

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•   Pelican Landing Eleuthera Room 1BR/1BA – Sleeps 4 – Other Key West Properties #3175769ha
  3
  $100 - $200 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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•   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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•   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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•   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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•   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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•   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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•   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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•   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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•   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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•   Villa Fleur, Elegant Truman Annex Condo in Old Town 2BR/1BA – Sleeps 4 – Truman Annex #207098ha
  1
  $214 - $257 per night

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

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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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•   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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•   Tropical Paradise on the Atlantic Ocean 2BR+/2BA – Sleeps 4-6 – 1800 Atlantic #144747
  3
  $285- $360

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

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