Vacation Rentals by Owner

Key West Vacation Rentals Show this location only Back to top

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

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

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

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

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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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•   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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•   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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•   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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•   Key Haven Retreat 4BR/3BA – Sleeps 10 – Other Key West Properties #3499643ha
  4
  $250 - $284 per night

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•   Quiet Key West Old Town Home with Tropical Pool and Privacy 3BR/2.5BA – Sleeps 6 – Private Homes, Mid Town #326148
  3
  $9,000/mo in season

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

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•   Truman Annex Getaway...August & September Special! Only $1300/Week 2BR/2BA – Sleeps 4-6 – Truman Annex #472075
  0
  $1300 - $2450 per week 7 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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•   Tropical Cottage on a Quiet Lane Available Summer 2BR/1.5BA – Sleeps 2-4 – Private Homes, Old Town #434593
  1
  $3000 per month 30 night min stay

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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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•   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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•   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 #3488382ha
  42
  $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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•   Attitude Key West - Get that Chillin' Feeling 2BR+/1BA – Sleeps 4 – Truman Annex #287741
  15
  $1200- $1850

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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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•   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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•   Gracious Key West Home in 'the Meadows' of Old Town 3BR/3BA – Sleeps 6-7 – Meadows #405271
  0
  $5500/mo

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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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•   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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•   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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•   Seaport Villa 3BR/2BA – Sleeps 6 – Private Homes, Historic Seaport #3483367ha
  0
  $150 - $317 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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•   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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•   '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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•   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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•   Funky Floating Condo with Direct Ocean Access 1BR/1BA – Sleeps 4 – Other Key West Properties #400169
  8
  $900- $1500/wk

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

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

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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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•   Renovated Mid Town Historic Home 1BR/1.5BA – Sleeps 2 – Casa Marina #366748
  2
  $133 - $183 per night

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•   Beach Club #104 - Unique Oceanfront Living 2BR/2BA – Sleeps 4-6 – Other Key West Properties #366749
  1
  $260 - $485 per night

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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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•   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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•   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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•   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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•   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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•   Caribbean Duval 2BR/2.5BA – Sleeps 6 – Other Key West Properties #3245845ha
  0
  $186 - $435 per night

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•   Duval Street Hideaway 2BR/2.5BA – Sleeps 6 – Other Key West Properties #3245846ha
  0
  $200 - $456 per night

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•   Brisa Del Mar 2BR/2BA – Sleeps 6 – Other Key West Properties #3245855ha
  0
  $186 - $387 per night

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•   Tranquility 1BR/1.5BA – Sleeps 3-4 – Other Key West Properties #3245886ha
  0
  $161 - $413 per night

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•   Linger Longer 2BR/1.5BA – Sleeps 5 – Truman Annex #3245864ha
  0
  $186 - $409 per night

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•   Coral Villa 3BR/3BA – Sleeps 8 – Other Key West Properties #3491240ha
  0
  $186 - $413 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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