Vacation Rentals by Owner

Key West Vacation Rentals Show this location only Back to top

•   Oceanfront View Large Expansive Deck Great Sunsets 2wk-Monthly 2BR/2BA – Sleeps 4 – Truman Annex #337229
  0
  $6,500 - $8,000 mo. US

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•   'Amberjack' a Little Slice of Key West Heaven 2BR/1BA – Sleeps 4-6 – Truman Annex #3486581ha
  0
  $175 - $393 per night

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•   Monthly Rental: Historic Oasis Steps from Key West's Best Attractions 3BR/2BA – Sleeps 6 – Private Homes, Historic Seaport #449146
  0
  monthly rental 7,000.00-10,000.00

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•   On the Ocean 2BR+/2BA – Sleeps 2-5 – La Brisa #322566
  4
  From $1400/wk - $4000/mo

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•   Luxury Truman Annex Condo - Walk to Beach/Duval St. 2BR/1BA – Sleeps 4-5 – Truman Annex #200351
  32
  $1300- $1925/wk, discounted monthly rates

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•   Spacious Ocean Front Resort - 3 Bedroom Condo 3BR+/3BA – Sleeps 6-8 – 1800 Atlantic #256294
  25
  $325-$500/nt - $2,275-$3,150/wk

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•   Gated Private Luxurious Getaway-Truman Annex (Private Pool) 3BR/3.5BA – Sleeps 7 – Truman Annex #99722
  2
  $4500- $6500/wk

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•   Enjoy Ocean Views and Breezes.(Handicap Accessible) 2BR/2BA – Sleeps 4 – 1800 Atlantic #256053
  0
  From $200/nt - $380/nt

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•   Island Oasis Garden Home - Hidden in the Heart of Old Town 2BR/2BA – Sleeps 4 – Windward Park #184037
  0
  $300-$400/nt - $1500-$2100/wk

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•   Amanda's Dream Suites-Good Value with Giant Pool in Key West 4BR+/3BA – Sleeps 8-10 – Private Homes, Mid Town #183990
  0
  $3275/wk - $4550/wk or $550/nt - $750/nt

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•   Casa Marina Elegance 3BR/3.5BA – Sleeps 6 – Casa Marina #401222
  1
  $29200 per month 28 night min stay

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•   Oceanside Marina - Luxury 3 BR Condo 3BR/2BA – Sleeps 6 – Oceanside Marina (formerly Kings Pointe) #138365
  1
  $225- $275//nt

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•   Cute, Clean, Cozy and Close to All 1BR/1BA – Sleeps 2-3 – Private Homes, Old Town #250411
  30
  $135-$225/nt - $895- $1500/wk

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•   Tropical Dreaming - 2 Bedroom Home - Private Pool 2BR/2.5BA – Sleeps 4-6 – Private Homes, Old Town #251642
  0
  $340-$470/nt - $2100-$3000/wk

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•   The Kingfisher - Historic Old Town Luxury Home (Monthly Only) 3BR/2.5BA – Sleeps 6 – Private Homes, Old Town #430740
  0
  $6000- $10000/mo

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•   Enjoy Your Own Sunset Escape & Private Pool! 3BR/3BA – Sleeps 6 – Key West Golf Club #429182
  0
  $4,500- $6,500/month

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•   Quiet Lane Retreat in the Heart of Old Town 2BR+/1.5BA – Sleeps 6 – Private Homes, Old Town #425235
  0
  $2500- $6000/mo.

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•   4 Palms Two Bedroom 1800 Atlantic Condo 2BR+/2BA – Sleeps 6 – 1800 Atlantic #93287
  0
  From $1250/wk

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•   Oceanfront Views of Key West's Atlantic Shore 2BR/2BA – Sleeps 6 – 1800 Atlantic #23443
  0
  From $1200/wk

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•   Egret Cottage: 1 Bedroom Cottage Old Town Key West 1BR+/1BA – Sleeps 4 – Private Homes, Old Town #92567
  0
  $1050- $1550/wk

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•   Summer Rates from $3000/Month - Louisa Bella 2BR+/1BA – Sleeps 4-6 – Private Homes, Old Town #101530
  0
  $3000- $6500/mo

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•   Sailor House, Luxurious Two Bedroom 1/2 Block from Duval St. 2BR+/1.5BA – Sleeps 4-6 – Private Homes, Old Town #321456
  1
  $265- $399/nt plus 12.5% tax

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•   Beautiful Key West Condo on the Ocean 2BR+/2BA – Sleeps 4-6 – 1800 Atlantic #249337
  3
  $225- $425/nt

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•   Southern Wind Two Bedroom Home in Old Town Key West 2BR/2BA – Sleeps 4 – Windward Park #93459
  2
  From $1300/wk

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•   A Zen Ocean Garden - 2 BR/2 BA - Ocean View - 1800 Atlantic 2BR+/2BA – Sleeps 6 – 1800 Atlantic #92460
  0
  $300-$390/nt - $1800-$2425/wk

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•   Duval Street Hideaway - Two Bedroom Townhome W/Private Jacuzzi 2BR+/2.5BA – Sleeps 6 – Duval Square #93296
  0
  $240- $315/nt

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•   Spa on Duval Two Bedroom W/Private Jacuzzi Just Steps to Duval 2BR+/2.5BA – Sleeps 6 – Duval Square #93476
  0
  $240-$315/nt - $1400-$1900/wk

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•   Key West 2 Bedroom 2 Bath Condo Rental 2BR+/2BA – Sleeps 6 – La Brisa #362097
  0
  3,250- 4,200/mo long term

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•   Cozy Condo in Key West 1BR/1BA – Sleeps 2 – Galleria #138062
  26
  $120 OR $95

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•   Quiet and Beautiful Truman Annex 2 BR End-Unit Old Town 2BR+/1BA – Sleeps 4 – Truman Annex #420646
  13
  From $1100 - $1875 / week

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•   Papaya Place Pops with Color! 2BR+/2BA – Sleeps 4-6 – 1800 Atlantic #138915
  0
  $220-$305/nt - $1250-$1825/wk

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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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•   Last Minute April Special $2200 Beach Condo 2 Pools One Month Min. 1BR+/1BA – Sleeps 2 – Seaside Resort #358407
  2
  From $1400/mo

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•   Key West Truman Annex 2bed/3bath Sleeps 6 Min to Duval/Water 2BR/2.5BA – Sleeps 3-6 – Truman Annex #373185
  0
  From $1600/wk

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•   Conch Retreat in Key West Truman Annex with 2 Bikes 2BR/1BA – Sleeps 4 – Truman Annex #226298
  22
  $171 per night

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•   Truman Annex - 1BR/1BA - Renovated Corner Unit with Great Reviews!!! 1BR+/1BA – Sleeps 2-4 – Truman Annex #50666
  19
  $1050- $5400/mo

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•   Hemingway's Hideaway 2BR+/2.5BA – Sleeps 4 – Truman Annex #175251
  13
  $1855 per week 7 night min stay

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•   Céad Míle Fáilte - a Thousand Welcomes to Our Innisfree 2BR/1BA – Sleeps 4 – Truman Annex #78945
  10
  $1400- $1900/wk

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•   Villa Soleil-Enjoy America's Caribbean with Style and Comfort 2BR+/2.5BA – Sleeps 6 – Other Key West Properties #141421ha
  3
  $229 - $257 per night

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•   Henry's Penthouse on the Ocean in Key West - Weekly / Nightly 2BR+/2BA – Sleeps 4-6 – Other Key West Properties #45061
  15
  $265-$425/nt - $1575-$2678/wk

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•   Chilmark South Tropical Key West Waterfront Condo 2BR+/2BA – Sleeps 6 – Truman Annex #165220
  5
  $2400- $3800/wk

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•   Super Fun Key West Vacation Home on Canal, Swim Spa, More... 3BR+/2BA – Sleeps 7-8 – Key Haven #181624
  11
  $1850/wk - $4800/mo

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•   An Artistic Hideaway in Paradise 1BR+/1BA – Sleeps 2-4 – Galleria #129956
  29
  $105 - $119 per night 1-2 night min stay

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•   Carpe Diem- a Tropical Conch Cottage in Old Town Key West - 2BR/2BA – Sleeps 6 – Private Homes, Old Town #287462
  4
  $3300 - $6000 per month 30 night min stay

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•   Private & Peaceful Cottage Feel-with 7 Night Stay 1 Night Free 1BR/1BA – Sleeps 2-4 – Private Homes, Old Town #114836
  18
  From125 nt to 215 a nt for lodging

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•   Key West Gem - Large, Bright 2 BR Condo on Ocean W/ Olympic-Size Pool 2BR+/2BA – Sleeps 4-6 – 1800 Atlantic #420183
  10
  $205- $340/nt (depending on season)

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•   Key West Cottage Charmer 2BR+/2BA – Sleeps 2-5 – Private Homes, Old Town #321956
  18
  $1700 - $7200

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•   Waterfront Luxury Condo in Old Town Key West 2BR/2BA – Sleeps 4 – Truman Annex #110202
  6
  From $2500/wk + housekeeping +bed taxes

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•   Relax in the Keys Aboard My 42ft Sailing Yacht! 2BR+/2BA – Sleeps 2-5 – Key West Harbour Yacht Club #352155
  5
  $190 - $215 per night 3-4 night min stay

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•   Island Rendezvous - Like Having Your Own Little Private Resort 6BR+/5BA – Sleeps 12-16 – Other Key West Properties #141726
  0
  $1100-$1250/nt - $7500-$5850/wk

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•   Quiet Key West for Two! One Month Minimum Stay Required. 1BR+/1BA – Sleeps 2 – Other Key West Properties #127995
  1
  $1700- $3500/mo

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•   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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•   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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•   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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•   Three Bedroom Shipyard Townhome 3BR/2BA – Sleeps 6 – Truman Annex #236720
  0
  $2000- $4500/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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•   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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•   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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•   Spacious Key West Vacation Retreat 2BR+/2BA – Sleeps 6 – 1800 Atlantic #298292
  2
  From $3000/mo

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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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•   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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•   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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•   Rent a Piece of Paradise! 2BR/1BA – Sleeps 4 – Truman Annex #201892
  5
  From $1000/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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•   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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•   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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•   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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•   Duval Street Private Compound 4BR+/4BA – Sleeps 8-12 – Private Homes, DownTown #438179
  0
  $700 per night 4 night min stay

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

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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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•   Calico Cove -- Charming, Key West Apartment Nestled in Old Town. 2BR/1BA – Sleeps 4 – Other Key West Properties #3006638ha
  0
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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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•   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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•   Parrot Perch 2BR/2BA – Sleeps 5 – Other Key West Properties #3245862ha
  0
  $157 - $362 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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•   Conch Condo 2BR/2BA – Sleeps 4 – Truman Annex #3245865ha
  0
  $186 - $399 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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•   The Victoria House 5BR/5.5BA – Sleeps 12 – Other Key West Properties #3245888ha
  0
  $829 - $1776 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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•   Finn Key 2BR/1BA – Sleeps 4 – Truman Annex #3245854ha
  0
  $157 - $362 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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