Vacation Rentals by Owner

Key West Vacation Rentals Show this location only Back to top

•   Key West Oceanfront Condominium 2BR+/2BA – Sleeps 6 – La Brisa #64489
  0
  $1275- $1800/wk

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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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•   Pelican Landing Flamingo Room 1BR/1BA – Sleeps 4 – Other Key West Properties #3174225ha
  5
  $100 - $200 per night

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•   The Cristol Condo - Classic Key West Oceanfront Charm 4BR/4BA – Sleeps 8 – Harbour Place #432905
  3
  $750- $21989 Great Vacation Value

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•   Seaside Place 5 Bedroom 4 Bath Vacation House Old Town 5BR+/4BA – Sleeps 12 – Private Homes, Old Town #364907
  5
  From $700/Night

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•   Attitude Key West - Get that Chillin' Feeling 2BR+/1BA – Sleeps 4 – Truman Annex #287741
  15
  $1200- $1850

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•   Pelican Landing Dominica Room 1BR/1BA – Sleeps 4 – Other Key West Properties #3174220ha
  6
  $100 - $200 per night

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•   Pelican Landing Antigua Room 1BR/1BA – Sleeps 4 – Other Key West Properties #3174211ha
  3
  $100 - $200 per night

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•   Elegant Key West Getaway 4BR/4.5BA – Sleeps 7 – Private Homes, Old Town #276136
  3
  $4250- $9,000/mo

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•   Key West Historic Seaport Tree Houseefficiency with Deck 1BR+/1BA – Sleeps 3 – Private Homes, Historic Seaport #397437
  6
  $3000/mo

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•   Pelican Landing Aruba Room 1BR/1BA – Sleeps 4 – Other Key West Properties #3174213ha
  3
  $100 - $200 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 #3488379ha
  24
  $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 #3488387ha
  33
  $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 #3488367ha
  23
  $117 - $299 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488360ha
  23
  $117 - $299 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488385ha
  26
  $117 - $299 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 #3488372ha
  26
  $117 - $299 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488390ha
  28
  $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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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488394ha
  23
  $117 - $299 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488382ha
  42
  $117 - $299 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488397ha
  22
  $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 #3488362ha
  16
  $117 - $299 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488389ha
  16
  $117 - $299 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488393ha
  13
  $117 - $299 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 4 – Other Key West Properties #3488391ha
  12
  $117 - $299 per night

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•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488380ha
  44
  $117 - $299 per night

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•   Turquoise Mermaid ~ Old Town Key West 2BR/2BA – Sleeps 4 – Other Key West Properties #368424ha
  2
  $133 - $200 per night

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•   Gracious Key West Home in 'the Meadows' of Old Town 3BR/3BA – Sleeps 6-7 – Meadows #405271
  0
  $5500/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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•   Pelican Cove at La Brisa, Condo with a Stunning Ocean View 2BR+/2BA – Sleeps 4-6 – La Brisa #384569
  0
  From $4000/mo - $6000/mo

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•   3rd Floor Balcony Sunsets. 1 Week Free for Month-Long Stays! 2BR/2.5BA – Sleeps 6 – Harbour Place #450440
  0
  $1820 - $2730 per week 7 night min stay

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•   Beautiful Sunset Views, 2 Bedroom 2 Bath, Waterfront Condo 2BR/2BA – Sleeps 4 – Sunset Marina #398020
  1
  $3875 per month 31 night min stay

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•   Funky Floating Condo with Direct Ocean Access 1BR/1BA – Sleeps 4 – Other Key West Properties #400169
  8
  $900- $1500/wk

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•   Beautiful Centrally Located Cottage-Condo - Monthly Rental 1BR+/1BA – Sleeps 2 – Private Homes, Old Town #339927
  3
  From $2750/mo.

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•   2 BR House in Old Town Key West - Quiet 2BR+/1BA – Sleeps 4 – Private Homes, Old Town #110480
  1
  $4000/mo Dollars

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•   Garden Villa 1BR/1BA – Sleeps 4 – Other Key West Properties #3174181ha
  1
  $100 - $124 per night

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•   Captains Hideout Central Location by the Big Beach and Bay 2BR/1BA – Sleeps 2-4 – Private Homes, Unspecified #264421
  4
  $3500- $4500/mo

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•   Private Oriental Tropical Hideaway 1BR+/1BA – Sleeps 2-4 – Private Homes, Old Town #382095
  5
  $110 - $185 per night 2-7 night min stay

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•   'Tropical Splendor' 3BR/2BA Luxury Condo, Ocean View & Marina 3BR/2BA – Sleeps 6-7 – Oceanside Marina (formerly Kings Pointe) #252117
  0
  $400 per night 3 night min stay

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•   Monthly Rental - Tropical Paradise Elegant Large Home in Old Town 3BR/4BA – Sleeps 6 – Private Homes, DownTown #458940
  0
  $1 - $6500 per night 2-30 night min stay

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•   Sunset Key, Private Island Key West, Florida 2BR+/2.5BA – Sleeps 6-8 – Other Key West Properties #125430
  0
  $13,000/mo

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•   'Coral Garden' Elegant 2 BR/2.5 BA Town Home in Coral Hammock 2BR+/2.5BA – Sleeps 4-6 – Coral Hammock #388611
  0
  $150 - $245 per night 3-5 night min stay

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•   Catherine House 2BR/2BA – Sleeps 4 – Private Homes, Old Town #366746
  0
  From $290- $460/nt

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•   "Concha Cabana" - Cutest Home North of Havana! 1BR/1BA – Sleeps 2 – Private Homes, Old Town #395871
  1
  From $2,200 to $3,950/mo.

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•   Relaxing, Quiet, Get-Away Close to Duval Street and the Beach 3BR+/2.5BA – Sleeps 6-8 – Private Homes, Old Town #294667
  4
  From $2700/wk - $4000/mo

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•   Seaside 33 2BR/3BA – Sleeps 4 – Other Key West Properties #3174186ha
  2
  $150 - $196 per night

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•   Turtle Cay Spa 2BR/2.5BA – Sleeps 6 – Other Key West Properties #3175770ha
  1
  $133 - $178 per night

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•   Summertime Special 10% Off June-September! 2BR/1BA – Sleeps 2-4 – Private Homes, Historic Seaport #440909
  0
  $4480 per month 28 night min stay

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•   Summertime Special 10% Off June-September! 3BR/2.5BA – Sleeps 6 – Private Homes, Old Town #440374
  0
  $9800 per month 28 night min stay

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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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•   'Coral Isle' Beautiful 3 BR/3 BA Town Home at Coral Hammock 3BR/3BA – Sleeps 6 – Coral Hammock #252100
  1
  $300 per night 3 night min stay

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•   Private Hidden Gem 4BR/2BA – Sleeps 8 – Bahama Village #441791
  0
  $4500 - $5550 per month 30 night min stay

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•   La Brisa-Beach Location 2BR/2BA – Sleeps 4-6 – La Brisa #466458
  0
  $175 - $250 per night 3-5 night min stay

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•   Ocean Breezes Beach Retreat on the Atlantic Ocean in Key West 2BR+/2BA – Sleeps 6 – Other Key West Properties #443957
  0
  $315 - $440 per night 5 night min stay

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•   'Two Fins' Luxury Poolside Villa in Old Town Sleeps up to 12 2BR/2.5BA – Sleeps 6-12 – Other Key West Properties #444361
  0
  $1750 - $2750 per week 7 night min stay

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•   The 'Shark Tank' 5 BR, 5 BA Luxury Weekly Only Beach Home in Old Town 5BR/5BA – Sleeps 10-12 – Private Homes, Old Town #444503
  0
  $9000 per week 7 night min stay

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•   Southernmost City Historic Vacation Home II 2BR/2.5BA – Sleeps 4-6 – Private Homes, Old Town #449895
  0
  from $3000/month

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•   Old Town Conch Cottage Close to All the Action! 2BR/1BA – Sleeps 4 – Private Homes, Old Town #435844
  0
  $4980 per month 30 night min stay

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•   Pet-Friendly 3BR/2BA – Sleeps 6-8 – Key Haven #448440
  0
  $5600 per month 28 night min stay

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•   One Bedroom Oceanfront Condo on Smathers Beach in Key West 1BR/1BA – Sleeps 2 – Other Key West Properties #415201
  0
  $2,190 to $4,290 per mo.

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•   Classic Conch House 2BR/2BA – Sleeps 6 – Bahama Village #441811
  0
  $4500 - $6000 per month 30 night min stay

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•   Private Classic Eyebrow Conch House Studio/0BA – Sleeps 6-8 – Private Homes, DownTown #449543
  0
  $7000 - $10000 per month 30 night min stay

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•   3 Bedroom Yacht on the Atlantic Ocean 3BR/3BA – Sleeps 6 – Oceanside Marina (formerly Kings Pointe) #450495
  0
  $300 - $375 per night 1-4 night min stay

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•   1214 Packer St 2BR/1BA – Sleeps 6 – Other Key West Properties #3174231ha
  0
  $133 - $178 per night

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•   The Orchid Cottage Nestled in the Peaceful Meadows 1BR/0BA – Sleeps 1-2 – Meadows #451542
  0
  $2400 - $3750 per month 30 night min stay

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•   Beautiful Newly-Renovated Historic House 3BR+/3.5BA – Sleeps 6-8 – Casa Marina #430840
  0
  $4,500 - $7,500

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•   Charming Old Town Cottage for Single or Couple 1BR/1BA – Sleeps 2 – Private Homes, Historic Seaport #384413
  3
  $3500 high season Feb., March, April

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•   Ellen's Retreat - Tropical Living, 28 Days Minimum Stay. 3BR/2BA – Sleeps 2-6 – Private Homes, Old Town #422831
  0
  $5488 - $9520 per month 28 night min stay

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•   Private Waterfront Key West Home with Pool 3BR/3BA – Sleeps 6 – Other Key West Properties #3002764ha
  0
  $133 per night

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•   Gracious Family Home in the Sanctuary 3BR/3BA – Sleeps 6-7 – Key West Golf Club #470626
  0
  $1000- $2000/week, 2 week minimum

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•   Seaport Villa 3BR/2BA – Sleeps 6 – Private Homes, Historic Seaport #3483367ha
  0
  $150 - $317 per night

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•   Shipyard Tropical Retreat 2BR/1BA – Sleeps 4-5 – Truman Annex #465554
  0
  $3480 - $5673 per month 30-31 night min stay

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•   Tropical Paradise Surrounds 2BR 2BA Old Town Cottage 2BR/2BA – Sleeps 4 – Private Homes, Old Town #308865
  0
  $2200- $5000/mo

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•   Great Taste - Great Location - Newly Restored 2 Bedroom - Pool 2BR/2BA – Sleeps 4 – Private Homes, Old Town #252753
  1
  $4000- $6000/mo

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•   Garden Studio in Historic Old Town Studio/1BA – Sleeps 2 – Private Homes, Old Town #330201
  3
  $2500- $4000/mo

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•   Villa Al Mar 6BR/6BA – Sleeps 13 – Key Haven #295078
  0
  $7000-$8000/wk, $2800-$32000/mo

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•   Downtown Historic District 2BR/2BA – Sleeps 4-6 – Private Homes, Old Town #466457
  0
  $200 - $300 per night 2 night min stay

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•   Galleon Ocean Splendor 2BR+/2BA – Sleeps 6 – Galleon #466459
  0
  $485 - $565 per night 5 night min stay

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•   Scullys Key West Condo : Truman Annex: Best Spot in Key West 2BR+/2BA – Sleeps 2-4 – Truman Annex #309732
  0
  $1400-$2000/wk - $4200-$6000/mo

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•   Beach Club #104 2BR+/2BA – Sleeps 4-6 – Other Key West Properties #366749
  0
  From $270/nt to $480/nt

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•   Tropical Serenity 1BR/1.5BA – Sleeps 2 – Casa Marina #366748
  0
  From $4000/mo to $7000/mo

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•   Studio Apartment in Downtown Key West Studio/1BA – Sleeps 2 – White St. Gallery #450018
  0
  $219 - $249 per night 3-4 night min stay

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•   Ocean View Key West Condo 2BR/2BA – Sleeps 4-6 – 1800 Atlantic #377163
  1
  2500- 4500/mo

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•   Steps to Famous Dvual Street 2BR/1BA – Sleeps 4-6 – Truman Annex #466455
  0
  $1099 - $1575 per week 7 night min stay

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•   Studio & Private Bath, Old Town Studio/1BA – Sleeps 2 – Bahama Village #459387
  0
  $85 - $100 per night 3 night min stay

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•   Oceanfront 2bd/2bath Condo on One of Keywest's Natural Beaches! 2BR+/2BA – Sleeps 6 – Casa Marina #431375
  1
  $2500 per week

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•   Your Own Private Island Getaway 2BR/2.5BA – Sleeps 4 – Other Key West Properties #3483359ha
  0
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•   Writer's Personal Residence in Old Town 2BR/1.5BA – Sleeps 4 – Private Homes, Historic Seaport #381042
  0
  $7000.00/mo

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•   Turtle House: Paradise Retreat in Charming Old Town Key West 2BR+/2BA – Sleeps 4 – Private Homes, Old Town #384490
  2
  From $4500.00 to $6000.00/mo

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•   Conch Wind Windward Park 2BR/2BA – Sleeps 4 – Truman Annex #3246322ha
  0
  $186 - $471 per night

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•   Southern Wind 2BR/2BA – Sleeps 4 – Other Key West Properties #3245883ha
  0
  $225 - $471 per night

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•   Crowner's Jewel 2BR/2.5BA – Sleeps 6 – Other Key West Properties #3245874ha
  0
  $214 - $450 per night

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•   Key West Crown Jewel 2BR/2BA – Sleeps 6 – Other Key West Properties #3245869ha
  0
  $306 - $531 per night

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•   Osprey 1BR/1BA – Sleeps 2 – Other Key West Properties #3245887ha
  0
  $93 - $321 per night

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