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Key West Vacation Rentals

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Currently ignores Key West neighborhoods.  Click here to sort by Key West neighborhoods.
Truman Annex Truman Annex - Shipyard Condominium [#9633]16
  2BR/1BA (Sleeps 4) $1200-$1800/wk US Dollars
Golf Course Craig & Cindy's Key West Coral Hammock Rentals [#47580]16
  3BR+/3BA (Sleeps 6-8) $1200-$1900/wk US Dollars
Truman Annex "Old Town Oasis" @ Truman Annex: Spacious 2BR Oceanfront Condo [#71538]16
  2BR+/2BA (Sleeps 4-6) $2200-$5500/wk - $4400-$11,000/mo Dollars
Golf Course "The Spa" @ the Sanctuary: Walled Yard, Spa & 2 Master Suites! [#71542]16
  2BR+/3BA (Sleeps 4-6) $2500-$5500/mo US Dollars
Private Homes, Old Town Casa De Cuba a Beach House - Cuban Flair Steps from Duval [#98473]16
  3BR/2BA (Sleeps 6) $458-$578/nt - $3000-$4000/wk US Dollars
Truman Annex "Conch Casa Grande" @ the Annex: 11' Ceilings, 5 Master Suites [#104540]16
  5BR/6BA (Sleeps 10) $6600-$14,000/wk - $9,000-$22,000/mo US Dollars
Golf Course "Poolside Retreat": Town Home @ the Pool with 2 Master Suites [#104772]16
  2BR/2.5BA (Sleeps 4) $2000-$4900/mo US Dollars
Golf Course Key West "Coral Hammock" - Poolside [#105427]16
  3BR/3BA (Sleeps 6) $1200-$1750/wk US Dollars
Truman Annex Craig & Cindy's Truman Annex Key West Property [#108809]16
  2BR+/2.75BA (Sleeps 2-6) $1750-$2300/wk US Dollars
Golf Course "Colorful Conch" @ the Sanctuary: 3 BR, 3 Bath & Private Pool [#115109]16
  3BR+/3BA (Sleeps 6) $4,400-$11,000/mo US Dollars
Private Homes, Old Town "Southard Comfort" @ Old Town: a Dazzling Key West Conch House [#122535]16
  3BR/2BA (Sleeps 6) From $500/nt - $2500/wk - $4500/mo US Dollars
Private Homes, Old Town Villa Tropicale - Secluded Tropical Villa [#125695]16
  4BR+/5BA (Sleeps 8-9) $4600-$7900/wk US Dollars
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Kings Pointe "Oceanside Oasis" @ Kings Pointe: Direct Ocean Views & 3 BR'S [#129405]16
  3BR/2BA (Sleeps 4-6) $1700-$3300/wk US Dollars
Other Key West Properties Steps to Duval - $499 Week Summer, $79-$125 Ngt-Bikes Included [#140317]16
  Studio/1BA (Sleeps 2) $79-$125/nt US Dollars
Seaside Resort "Delightfully Tropical" @ Seaside: 3 Levels, 2BR'S, Pool & Spa [#161201]16
  2BR+/3BA (Sleeps 6-8) $3000-$8000/mo US Dollars
Private Homes, Old Town "Falling Water” @ Old Town: Breathtaking Residential Compound [#168095]16
  5BR+/4.5BA (Sleeps 10-12) $8000-$24,000/mo US Dollars
Private Homes, Old Town "Bimini" Luxurious Townhome Villa in the Heart of Old Key West [#168724]16
  2BR+/3.5BA (Sleeps 6) From $428/nt - $2700/wk US Dollars
Private Homes, UpTown "Koi House” @ Uptown Key West: Quiet Pond & Garden, 5 BR [#173985]16
  5BR+/5BA (Sleeps 10-12) $10,000-$28,000/mo US Dollars
Golf Course "Quiet Conch" @ Kingfisher: 3BR & Private Pool on Cul-De-Sac. [#183386]16
  3BR/2BA (Sleeps 6) $3300-$6600/mo US Dollars
Other Key West Properties Fisherman's Paradise Found in Summerland Key Sleeps 12 [#185832]16
  3BR+/3BA (Sleeps 10-12) $6000-$7000/mo US Dollars
1800 Atlantic Direct Ocean Front Free Wireless Internet - [#35327]14
  3BR/2.5BA (Sleeps 6) From $350/nt - $2350/wk US Dollars
Private Homes, Old Town Luxury House,Old Town Lane, Pool - Free Wireless- Monthly Only [#123424]14
  2BR/2BA (Sleeps 4) $4000-$7500/mo US Dollars
Private Homes, Historic Seaport Tropical Tranquility - 5 Star Caribbean Resort-Style Villa [#173086]14
  4BR/3.5BA (Sleeps 8) $950-$1250/nt - $4500-$6000/wk US Dollars
1800 Atlantic Henry's Piece of Paradise on the Ocean in Key West [#20873]13
  2BR/2BA (Sleeps 2-5) $245-$405/nt - $1544-$2552/wk US Dollars
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Private Homes, UpTown South Point Selection - "Viva La Grande" Villa & Cottage [#160499]13
  5BR+/5BA (Sleeps 10-12) $1100-$1350/nt - $6050-$8150/wk US Dollars
Private Homes, Old Town 200 Yards from Beach! [#170598]13
  1BR+/1BA (Sleeps 2) $2500-$3000/mo US Dollars
Private Homes, Old Town Sophisticated Southard Street Charmer [#176314]13
  2BR/2BA (Sleeps 4) $4500-$8000/mo US Dollars
Private Homes, Old Town The White House Key West's Finest Monthly Rental/4 BR [#177512]13
  4BR/3BA (Sleeps 8) $5500-$8500/mo US Dollars
Private Homes, Old Town Contemporary Gem [#177596]13
  3BR/2.5BA (Sleeps 6) $4500-$7500/mo US Dollars
Truman Annex Truman Annex, House 2BR/2.5BA Add Cottage 3BR/3.5BA, Pool [#1614]12
  3BR/3.5BA (Sleeps 6) $2100-$4500/wk US Dollars
Private Homes, Old Town Key West Lazy Lane Vacation Rental Accommodations & Cottages [#6429]12
  1BR+/1BA (Sleeps 1-6) $75-$260/nt - $700-$1600/wk US Dollars
Private Homes, Old Town Private Place- 2 BR ~ 1400 Sf ~ Key West Vacation Rental [#23531]12
  2BR+/2BA (Sleeps 4-6) $295/nt - $2000/wk US Dollars
Private Homes, Old Town Luxurious Old Town Compound - Rent as a 3 or 4 BR W/Pool [#42870]12
  4BR/4.75BA (Sleeps 8-10) $13,000-$28,000/mo US Dollars
1800 Atlantic Oceanfront Condominium - Key West's Crown Jewel [#45706]12
  2BR+/2BA (Sleeps 4-6) From $320/nt - $1900/wk US Dollars
Private Homes, Historic Seaport Experience Key West Like a Local [#55262]12
  1BR/1BA (Sleeps 2) $2000-$3500/mo US Dollars
Truman Annex Tropical Island Get-Away, Garden Level Condo in Truman Annex [#55381]12
  2BR+/1BA (Sleeps 4) $1200-$1800/wk - $2800/mo US Dollars
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La Brisa Deluxe 3 BR Oceanfront Condo [#57418]12
  3BR+/2BA (Sleeps 6-8) From $1200/wk US Dollars
Truman Annex Truman Annex Best Location it Town [#67476]12
  2BR+/2BA (Sleeps 4-6) $1000-$2600/wk US Dollars
Private Homes, Old Town "Coconut Cabana" Old Town Tropical Bungalow [#72848]12
  3BR/2BA (Sleeps 4-6) $398-$478/nt - $2300-$3200/wk US Dollars
Private Homes, Old Town Dos Casas-4 BR Compound in Beautiful Old Town Key West [#76082]12
  4BR/2BA (Sleeps 8) $5500-$8500/mo US Dollars
Private Homes, Old Town Old Town Bali Hideaway for 2, Just Steps from Duval [#82634]12
  Studio/1BA (Sleeps 2) $168-$220/nt - $1100-$1470/wk US Dollars
Private Homes, Old Town Harbor Inn Condominium [#82650]12
  2BR+/2BA (Sleeps 6) $1000-$1500/wk US Dollars
Private Homes, Old Town Historic Conch Cottage 1/2 Block Off Duval -- "Casa Louisa" [#88122]12
  3BR/2BA (Sleeps 6) $2695-$3325/wk US Dollars
Private Homes, Old Town Key West * Laid-Back Sophistication and Understated Glamour * [#89318]12
  3BR/2BA (Sleeps 4-6) $6000-$9000/mo US Dollars
Private Homes, Old Town "Tranquility " at Ann Street Gardens Steps from Duval [#98557]12
  1BR/1BA (Sleeps 2) $188-$250/nt - $1400-$1660/wk* US Dollars
Private Homes, Old Town Beautiful Private House with Three Bedrooms [#99427]12
  3BR/3BA (Sleeps 6) $8000-$14,000/mo US Dollars
Private Homes, Unspecified House with Guest Cottage [#103479]12
  3BR/3.5BA (Sleeps 6-8) $5500-$9500/mo US Dollars
1800 Atlantic Oceanfront Condominium - Paradise Found [#107925]12
  2BR+/2BA (Sleeps 4-6) $995-$2750/wk US Dollars
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Private Homes, Old Town Old Town Historic Eyebrow House (3 BR/2 BA) [#108861]12
  3BR/2BA (Sleeps 5-6) $7,500-8,500/mo US Dollars
Golf Course Key West - Poolside Conch Paradise at Key West Golf Club [#113115]12
  2BR/1.5BA (Sleeps 4) $2250-$4000/mo US Dollars
Private Homes, Unspecified Historic 4 BR/3 BA Luxury Home in Key West [#116745]12
  4BR/3BA (Sleeps 4-8) $6500-$8000/mo US Dollars
Private Homes, Old Town "The Real Deal" in Key West, Only a Block Off Duval on Southar [#117148]12
  1BR/1BA (Sleeps 2-4) $188-$248/nt - $1197-$1597/wk US Dollars
Galleria Quaint, Artistic Key West Guest House [#118363]12
  1BR/1BA (Sleeps 1-2) $89-$98/nt US Dollars
Private Homes, Old Town "Old Town" Key West Charmer [#118424]12
  1BR+/1BA (Sleeps 2-14) From $99/nt - $895/wk US Dollars
Private Homes, Historic Seaport Historic Seaport Home [#120234]12
  4BR+/4.75BA (Sleeps 10) $9,000-$15,000/mo US Dollars
Private Homes, Old Town A Royal Home with 4 Master Suites, Style, and a Sunset Sail [#123121]12
  4BR/4.75BA (Sleeps 6-8) $10,000-$13,500/mo US Dollars
Truman Annex Pirate's Cove - #316 in Truman Annex's Harbour Place Luxury [#127790]12
  3BR/3BA (Sleeps 6-7) $3000-$4500/wk US Dollars
Truman Annex Elegant Sol Y Sombra - #5 Foundry Section in Truman Annex [#127806]12
  2BR/2.75BA (Sleeps 4) $1800-$2700/wk US Dollars
Private Homes, Old Town Sophisticated Elegance on Fleming Street (Pool, Parking) [#128058]12
  3BR/2.75BA (Sleeps 6) $8000-$14,000/mo US Dollars
Private Homes, Old Town Precious Pink Cottage with Private Pool & 4 Blocks from Duval [#129563]12
  2BR+/1BA (Sleeps 4-5) $1500-$1700/wk US Dollars
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La Brisa Luxury Beachfront Condo [#133090]12
  2BR+/2BA (Sleeps 8) $1200-$2500/wk US Dollars
Private Homes, Old Town Secret Villa - Hidden Gem in a Heart of Old Town Key West [#137683]12
  3BR/3BA (Sleeps 6) $438-$578/nt - $2800-$4000/wk US Dollars
Private Homes, Old Town Colony Cabanas - Tropical Bungalow in the Heart of Old Town [#137869]12
  1BR+/1.5BA (Sleeps 2-4) $168-$238/nt - $1150-$1550/wk US Dollars
Private Homes, Old Town Historic Restored "Eyebrow" Home [#139799]12
  3BR/3BA (Sleeps 6) $6000-$8500/mo US Dollars
Private Homes, Old Town "Old Town" Guesthouse,1 Block Off Duval on Southard Street [#144522]12
  3BR/3BA (Sleeps 6-12) From $168/nt - $1,056/wk - $3,400/mo US Dollars
Private Homes, Old Town "The Secret Garden" Very Private & Classic Key West [#153214]12
  2BR/1.75BA (Sleeps 2-6) $2,900-$6400/mo US Dollars
Private Homes, Old Town "Harvey's Haven" Vintage Charm in the Perfect Location [#154275]12
  Studio+/1BA (Sleeps 2-4) From $168/nt - $1056/wk US Dollars
Truman Annex Truman Annex - Foundry Townhouse - One of a Kind! [#159305]12
  2BR/2.5BA (Sleeps 4) From $1800/Week US Dollars
Golf Course "Tropic Oasis" @ the Sanctuary: Private Home & Pool, Sleeps 8 [#161495]12
  4BR+/3BA (Sleeps 6-8) $3300-$8800/mo US Dollars
Private Homes, DownTown Duval Street Condo, Brand New & Best Location in Key West [#166862]12
  2BR/1BA (Sleeps 4) From $1200/wk US Dollars
Private Homes, DownTown Key West Oasis [#168182]12
  3BR/3BA (Sleeps 6) $7000/mo US Dollars
Casa Marina Peaceful East Casa Marina Retreat [#181343]12
  3BR+/3BA (Sleeps 6-8) $415-$596/nt - $2700-$3990/wk US Dollars
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Truman Annex Best Key West Vacation Rentals, Truman Annex,Oceanside, & More [#113763]11
  2BR/1BA (Sleeps 4) $900-$1800/wk US Dollars
Galleria Caribbean "Styled" Condo in Paradise, Key West Florida [#138036]11
  1BR+/1BA (Sleeps 2-4) $95/nt US Dollars
Private Homes, Old Town Duncan Beach House, Private Pool, Steps from Duval Street [#164094]11
  3BR+/2BA (Sleeps 6) $3000-$7000/mo US Dollars
Private Homes, Old Town Stop Looking Now! Historic Old Town [#166113]11
  1BR/1BA (Sleeps 2) $3000-$5000/mo US Dollars
Private Homes, Unspecified 2/2 with Pool , Tennis, Marina, Free Double Kayak & Bikes [#183679]11
  2BR/2BA (Sleeps 4-6) $800/wk - $2800/mo US Dollars
Private Homes, Old Town Old Town Cottage Home with Tropical Decor & Pool [#30517]10
  2BR/2BA (Sleeps 4) $3500-$6600/mo US Dollars
Truman Annex Gated Private Luxurious Getaway-Truman Annex (Private Pool) [#99721]10
  4BR/4BA (Sleeps 8) $5500-$7500/wk US Dollars
Truman Annex Waterfront Luxury Condo in Old Town Key West [#110202]10
  2BR/2BA (Sleeps 4) From $2500/wk - $8500/mo US Dollars
Golf Course Showcase Great House on the Key West Golf Course [#118166]10
  3BR/2.5BA (Sleeps 6) $3500-$9000/mo US Dollars
Kings Pointe Kings Pointe Ocean-Side Luxury 3 BR Condo [#138365]10
  3BR/2BA (Sleeps 6) $1600-$2900/wk US Dollars
Private Homes, Old Town Southern Most City Historic Vacation Home [#148393]10
  3BR/3BA (Sleeps 6-8) $4000-$10,000/mo US Dollars
La Brisa Serenity at La Brisa [#148855]10
  2BR+/2BA (Sleeps 4-6) $3000-$5000/mo US Dollars
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1800 Atlantic All New Rental! Key West Ocean Side Luxury at 1800 Atlantic [#156314]10
  2BR+/2BA (Sleeps 4-6) $3900-$5800/mo US Dollars
Private Homes, DownTown Down Island Digs - Ideal Location Downtown, Private Pool. [#184018]10
  2BR+/2BA (Sleeps 4-6) $375-$450/nt - $2050-$2700/wk US Dollars
Private Homes, Unspecified Beautiful Ocean View Home [#42772]9
  3BR+/2.5BA (Sleeps 6-8) $6000-$8500/mo US Dollars
Truman Annex Ann's Tropical Paradise in Key West [#73629]9
  2BR/1BA (Sleeps 3-4) $150-$225/nt US Dollars
Private Homes, Unspecified Low Rates Guarantee! in Key West Luxury Water Front Home [#93387]9
  5BR/4.5BA (Sleeps 2-10) $6000-$8500/mo US Dollars
Private Homes, Old Town A Hop, Skip and Jump to Duval Street (1 1/2 Blocks) 3bd/2.5BA [#100392]9
  3BR+/2.5BA (Sleeps 6-8) $3000-$6500/mo US Dollars
Truman Annex Villa Soleil - Key West, Enjoy America's Caribbean in Style [#103426]9
  2BR+/2.5BA (Sleeps 4-6) $2000/wk (7 nts) - $2500/wk (7 nts) US Dollars
Private Homes, Old Town The Mermaids House - Old Town, Historic Bahama Conch House [#129511]9
  2BR+/1.25BA (Sleeps 3-6) $2000-$6000-mo US Dollars
Private Homes, Old Town Fabulous Key West Retreat [#150680]9
  2BR/2BA (Sleeps 4) From $5000/mo US Dollars
Private Homes, Old Town Ashe Splash--Award-Winning Classic Home in Old Key West [#177438]9
  3BR/3BA (Sleeps 6-7) $3950--$7500/mo US Dollars
BeachSide Exclusive Key West Beach Front - Amazing View of the Ocean. [#183996]9
  2BR+/3BA (Sleeps 4-6) From $375/nt - $2000/wk US Dollars
Windward Park Island Oasis Garden Home - Hidden in the Heart of Old Town [#184037]9
  2BR/2BA (Sleeps 4) $300-$400/nt - $1500-$2100/wk US Dollars
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Private Homes, Old Town Heart of Old Town - Nightly 1 BR - Upscale, Pool, & Breakfast! [#89723]8
  1BR+/1BA (Sleeps 2-4) $215-$335/nt US Dollars
Truman Annex Shipyard at Truman Annex "Where the Sun Sets in Old Key West" [#103761]8
  2BR/1BA (Sleeps 4) $1000-$1500/wk US Dollars
Seaside Resort Key West... America's Caribbean Island [#111817]8
  2BR/2BA (Sleeps 4-6) $4000-$6000/mo US Dollars
Other Key West Properties Quiet Key West for Two! One Month Minimum Stay Required. [#127995]8
  1BR+/1BA (Sleeps 2) $2500-$3500/mo US Dollars
Private Homes, Old Town Exclusive "Old Town" Cottage [#156551]8
  1BR/1BA (Sleeps 2) $3300/mo US Dollars
Private Homes, Old Town Bella Grande Premier - 5 Star Quality Victorian Estate [#157257]8
  5BR/5.5BA (Sleeps 10) $9000-$14,500/mo US Dollars
Sunrise Suites Beautiful Condo Across from Ocean [#163862]8
  2BR+/2BA (Sleeps 4-6) From $179/nt - $1253/wk US Dollars
Meadows Key West Rental (Casa De Suenos) House of Dreams! [#171894]8
  1BR+/1BA (Sleeps 2-4) $2200-$3500/mo US Dollars
Truman Annex "Paradise on the Ocean" Truman Annex 2BR Oceanfront Condo [#176171]8
  2BR+/2.5BA (Sleeps 4-5) $2000-$3000/wk US Dollars
Private Homes, DownTown Secret Courtyard Cottage - Downtown with Privacy! [#184021]8
  2BR+/1BA (Sleeps 4-5) $275-$350/nt - $1400-$1750/wk US Dollars
Casa Marina Mediterranean Caribbean Villa - High-End Living at its Best [#184043]8
  3BR/2.5BA (Sleeps 6) From $5000/mo US Dollars
Private Homes, Old Town Babalu Cottage - a Colorful Vacation Rental Home in Key West [#6735]7
  3BR/1.5BA (Sleeps 6) From $302/nt - $1800/wk US Dollars
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Other Key West Properties Henry's Penthouse on the Ocean in Key West [#45061]7
  2BR+/2BA (Sleeps 4-6) $265-$425/nt - $1575-$2678/wk US Dollars
Truman Annex Gated Private Luxurious Getaway-Truman Annex (Private Pool) [#99722]7
  3BR/3.5BA (Sleeps 7) $4500-$6500/wk US Dollars
Private Homes, Old Town Summer Rates from $3000/Month - Louisa Bella [#101530]7
  2BR+/1BA (Sleeps 4-6) $3000-$6500/mo US Dollars
Private Homes, Old Town Key West Charmer Offers Serenity, Simplicity & Close to Beach [#114836]7
  1BR/1BA (Sleeps 2-3) $90-$180/nt - $695-$1195/wk US Dollars
Other Key West Properties Smather's Beach - Oceanfront Condominium Two [#117235]7
  2BR/1BA (Sleeps 2-4) $2,200-$4,000/mo US Dollars
Truman Annex Secret Garden-Special Rate April 07-May 02! Ask for Details! [#123674]7
  2BR/1BA (Sleeps 4) $1100-$2500/wk US Dollars
Other Key West Properties Modern Key West Golf Course Townhome [#129642]7
  2BR/1.5BA (Sleeps 4) From $100-$500/nt US Dollars
Galleria Cozy Condo in Key West [#138062]7
  1BR/1BA (Sleeps 2) $95 & up US Dollars
Truman Annex Tropical Love Nest in Old Town Key West [#144223]7
  2BR+/1BA (Sleeps 4) $850-$1000/wk - $2500-$3000/mo US Dollars
Private Homes, Old Town Architects Home on Poorhouse [#148598]7
  2BR+/1.5BA (Sleeps 4-6) $3500-$6000/mo US Dollars
Truman Annex Hurricane's Rebellion - Key West's Best Port in the Storm [#150175]7
  2BR+/1BA (Sleeps 4-6) $1200-$1800/wk US Dollars
Private Homes, Old Town Abaco Dreams 3BR/2BA Old Town Private Paradise Key West [#151361]7
  3BR+/2BA (Sleeps 5-6) From $550/nt - $3850/wk US Dollars
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Private Homes, Old Town Hidden Palm Villa - a Private Key West Resort Residence [#157248]7
  3BR+/3BA (Sleeps 6-8) $700-$800/nt - $3800-$4800/wk US Dollars
Private Homes, Old Town Royal Street Gardens --Enjoy Off Season Rates Now--Welcome! [#159307]7
  1BR/1BA (Sleeps 1-2) $2000-$3500/mo US Dollars
White St. Gallery Large Private Yard in Historic District [#161989]7
  2BR/1.25BA (Sleeps 2-4) From $2500/mo US Dollars
Truman Annex Harbour Place Siren of the Sea - Waterfront Floridian Condo [#165220]7
  2BR+/2BA (Sleeps 4-6) $2400-$3500/wk USD
Private Homes, Historic Seaport Island Village Cottage-Historic Seaport of Key West [#183984]7
  2BR+/2BA (Sleeps 4-6) $325-$400/nt - $1850-$2550/wk US Dollars
Private Homes, Mid Town Coco's Poolside Retreat - Three Story Town Home by Giant Pool. [#183994]7
  3BR+/2.5BA (Sleeps 6-8) From $300/nt - $1600/wk US Dollars
Private Homes, Historic Seaport Darling Old Town Cottage for Single or Couple [#31609]6
  1BR/1BA (Sleeps 2) $2000-$3500/mo US Dollars