Vacation Rentals by Owner

Key West Vacation Rentals Show this location only Back to top

•   Tiki Beach Too, Charming Townhome, Old Town, Pool Access, Great Porch! 2BR/1BA – Sleeps 4-6 – Other Key West Properties #3539485ha
  0
  $1195 - $1895 per week 7 night min stay

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•   'Casa, Suite Casa @ Casa Marina': Lavish New Home W/ 4 Suites + Pool... 4BR/5BA – Sleeps 8-10 – Other Key West Properties #3485544ha
  3
  $300 - $667 per night

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•   3bdrm/2bath with Pool 3BR/2BA – Sleeps 6 – Private Homes, Old Town #439570
  0
  Per Month $6500- $10000

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•   Estate Home on the Water with Private Pool and Dockage 4BR/4.5BA – Sleeps 8 – Key Haven #380616
  1
  5,250

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•   A Truman Annex Condo 2BR+/1BA – Sleeps 4-6 – Truman Annex #296278
  0
  $1100- $1800/wk

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•   'Paradise Perfected @ Smathers Beach': Handsome Beach House + Pool... 3BR/2BA – Sleeps 6-8 – Other Key West Properties #3545074ha
  0
  $5500 - $14000 per month 28 night min stay

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•   This House is Sooo Perfect in Key West 2BR/2BA – Sleeps 4-5 – Private Homes, DownTown #443056
  0
  4500- 6500 pcm

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•   Stunning Interiors and Glorious Views at La Brisa 2BR/0BA – Sleeps 4 – La Brisa #443962
  0
  $4500- $6000/mo

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•   Sea Glass - Exquisite Key West Home and Cottage 4BR/4BA – Sleeps 8 – Private Homes, Old Town #476425
  0
  $6000 - $14000 per month 28 night min stay

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•   Enchanted Garden Compound in Best Old Town Location 4BR/3.5BA – Sleeps 8 – Private Homes, DownTown #261246
  0
  $15,000 to $25,000/month

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•   Charming Gated Community Just Off Duval 1BR/2BA – Sleeps 2 – Private Homes, DownTown #391946
  0
  $4000- $6000 p/m

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•   Petronia Palms, Just Off Duval St. Sleeps 6 Has a Large Pool! Hot-Tub Studio/0BA – Sleeps 6 – Private Homes, Old Town #442437
  2
  $1750 - $2250 per week 7-28 night min stay

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•   South Street Serenity - Summer Special 10% Off May-September! 3BR+/2.5BA – Sleeps 8 – Private Homes, Old Town #411277
  0
  $5500- $9500

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•   Home 1/2 Block from Duval Street 1BR+/1BA – Sleeps 4 – Private Homes, Old Town #439833
  0
  $389 - $429 per night 3-4 night min stay

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•   Beautiful House in the Best Location in Key West! Studio/0BA – Sleeps 6-8 – Private Homes, Old Town #448222
  0
  $4900 - $9520 per month 28 night min stay

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•   Sea Biscuit - Beautiful Home - Private Pool, Steps to Duval 3BR/3BA – Sleeps 6 – Private Homes, Old Town #381900
  2
  weekly $2750 to $3300

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•   Buena Vista Cottage - 1/2 Block from Duval Street!!! 1BR/1BA – Sleeps 2 – Private Homes, DownTown #440647
  0
  $349 - $389 per night 3-4 night min stay

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•   Secret Villa - a Key West Hidden Gem 3BR+/3BA – Sleeps 6-8 – Private Homes, Old Town #425095
  0
  $4200- $5530 US

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•   Luxury Townhouse Key West Gated Community. Easy Walk to Downtown 2BR/2.5BA – Sleeps 6 – Truman Annex #453182
  0
  $1750/wk - $8250/mo

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•   Summertime Special 10% Off June-September! 4BR/4.5BA – Sleeps 8 – Private Homes, Old Town #426633
  0
  $8000- $17000

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•   'Casa Amorita' - Affordable Luxury in the Heart of Old Town 1BR/1BA – Sleeps 3 – Private Homes, Old Town #443385
  1
  $2,400 - $4,400 monthly

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•   10% Summer Discount - Available Now 2BR+/0BA – Sleeps 6 – Private Homes, Old Town #473461
  0
  $6000 - $9510 per month 30 night min stay

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•   1 Bedroom Apartment with Pullout Couch, 7 Blocks from Duval Street 1BR/1BA – Sleeps 2-4 – White St. Gallery #450009
  0
  $259 - $289 per night 3-4 night min stay

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•   1 Bedroom Apartment with Pullout Couch, 7 Blocks from Duval Street 1BR/1BA – Sleeps 2-4 – White St. Gallery #450014
  0
  $259 - $289 per night 3-4 night min stay

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•   Old Town Cottages 3BR/0BA – Sleeps 6-8 – Private Homes, Old Town #453776
  0
  seasonal $695- $1050.

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•   Affordable Studio Apartment (Sleeps 4) in Downtown Area Studio/1BA – Sleeps 4 – White St. Gallery #450016
  0
  $219 - $249 per night 3-4 night min stay

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•   Affordable Studio Apartment (Sleeps 4) in Downtown Area Studio/1BA – Sleeps 4 – White St. Gallery #450104
  0
  $219 - $249 per night 3-4 night min stay

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•   200 Feet from Duval. Perfect Location. 1BR/1BA – Sleeps 2 – Villas Key West #453781
  0
  Seasonal $195- $295

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•   Secluded, Private, Tropical Retreat in Old Town, Key West. 2BR/1BA – Sleeps 4-6 – Private Homes, Old Town #453779
  0
  $325- $475 per night

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•   516 Louisa Street 2BR/1.5BA – Sleeps 2-4 – Private Homes, Old Town #3483364ha
  0
  $321 - $650 per night

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•   Key West Lazy Lane Vacation Rental Accommodations & Cottages 1BR+/1BA – Sleeps 2-6 – Private Homes, Old Town #6429
  22
  $85-$400/nt - $800- $1800/wk

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•   Ocean Out Your Windows!? Intown Key West? Yes! Studio Studio/1BA – Sleeps 2 – Casa Marina #41312
  20
  $249 - $279 per night 5 night min stay

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•   Direct Oceanfront 50% Off May Free High Speed Wifi & Hbo 3BR/2.5BA – Sleeps 6 – 1800 Atlantic #35327
  22
  $375/nt (low)- $550/nt (high)

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•   Key West Jasmine House - Tropical Inn with Private Spa 4BR/4BA – Sleeps 8 – Private Homes, Old Town #27325
  26
  $85-$840/nt - $800- $3900/wk

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•   Luxury and Spacious Condo on Duval Steet 2BR+/2BA – Sleeps 4-6 – Key West Cuban Club #178773
  28
  Starting at $295.00/nt 2 - 6 guests

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•   Casa De Cuba a Beach House - Cuban Flair Steps from Duval 3BR/2BA – Sleeps 6 – Private Homes, Old Town #98473
  6
  $510-$680/nt - $3360-$4520/wk

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•   'Avalynn House @ the Annex': Elegant 5BR/3.5BA Home & Lagoon Pool... 5BR+/3.5BA – Sleeps 10-12 – Private Homes, Unspecified #168095
  8
  $8000-11,500/wk, $30,000-$40,000/mo

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•   The Mermaids House - Old Town, Historic Bahama Conch House 2BR/1.5BA – Sleeps 4 – Private Homes, Old Town #129511
  26
  $225 - $300 per night 3 night min stay

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•   "The Real Deal" Key West, Only 1 Block Off Duval on Southard 1BR/1BA – Sleeps 1-4 – Private Homes, Old Town #117148
  80
  From $215/nt or $1,393-$1,799/wk

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•   Southern Palm 2BR/2.5BA Townhome in Historic Truman Annex 2BR+/2.5BA – Sleeps 4-6 – Truman Annex #215928
  36
  $1750- $2750 Special events may be more

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•   Casa Amor - 3BR Residence 2 Blocks from Duval Street 3BR+/2.5BA – Sleeps 6-8 – Private Homes, Old Town #177596
  13
  $8,500- 11,000.00

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•   Location, Location, Location! Ocean View, Lagoon Beach Front 3BR/2BA – Sleeps 10 – Key West Harbour Yacht Club #342886
  14
  $360 per night 3 night min stay

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•   Truman Annex - Shipyard Condominium 2BR/1BA – Sleeps 4 – Truman Annex #9633
  0
  $1200-$1800/wk - $3000/mo

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•   Luxury Yacht - Lagoon 440 Sailing Catamaran 3BR+/3BA – Sleeps 6-8 – Key West Harbour Yacht Club #290130
  9
  $295 - $395 per night 2 night min stay

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•   1,300/wk - Best Deal in Key West - Plus 8 Bikes Included! 2BR+/2.5BA – Sleeps 4-6 – Coral Hammock #200307
  31
  $250-$450/nt - $1300-$2200/wk

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•   Tropical Island Get-Away, Garden Level Condo in Truman Annex 2BR+/1BA – Sleeps 4 – Truman Annex #55381
  8
  $1050-$1900/wk - $2800/mo

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•   'Oceanside Oasis' @ Kings Pointe: Direct Ocean Views & 3 BR'S 3BR/2BA – Sleeps 4-6 – Oceanside Marina (formerly Kings Pointe) #129405
  2
  $1500- $2000/wk

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•   Luxurious Truman Annex 4 BR/3 Full BA (Private Pool) 4BR/3BA – Sleeps 8 – Truman Annex #219779
  24
  $2900- $4900/wk

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•   Henry's Piece of Paradise on the Ocean in Key West - Weekly 2BR/2BA – Sleeps 2-5 – 1800 Atlantic #20873
  13
  $245-$405/nt - $1544-$2552/wk

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•   Beautiful Truman Annex End Unit Townhouse with Side Courtyard 2BR+/2.5BA – Sleeps 4-6 – Truman Annex #140996
  12
  $1800- $2100/wk

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•   Luxury Beachfront Condo 2BR+/2BA – Sleeps 8 – BeachSide #133090
  8
  From $1200/wk

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•   Harbor Inn Condominium 2BR+/2BA – Sleeps 4 – Private Homes, Old Town #82650
  7
  $1450- $2050/wk

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•   Truman Annex Flamingo Beach Garden Level 2BR/1BA – Sleeps 4 – Truman Annex #215927
  26
  $1300- $1950/wk some special Event rates

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•   Villa Tropicale - Secluded Tropical Villa 4BR+/5BA – Sleeps 8-9 – Private Homes, Old Town #125695
  0
  $710- 1228/nt

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•   Sunshine Luxury Condo with 2 Free Bikes & Garage 2BR+/2BA – Sleeps 4-6 – Sunrise Suites #324602
  24
  $1200- $2400/wk

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•   Classic Key West Estate ~ Spectacular Historic Seaport Home 7BR+/5BA – Sleeps 12-14 – Private Homes, Historic Seaport #138048
  1
  $1150-$1450nt - $5200-$7700/wk

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•   The Hollinsed House "Caribbean Suite" - Large 2 Bedroom 2BR+/1BA – Sleeps 4 – Private Homes, Old Town #118424
  22
  From $249/nt/ $1495 wk (Summer)

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•   'Suzy'S Parrot Perch @ Southernmost': Cozy 2BR/1BA Suite Near Duval... 2BR/1BA – Sleeps 4 – Other Key West Properties #3469827ha
  13
  $250 - $425 per night 4 night min stay

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•   Tropical Retreat in a Key West Conch Cottage 2BR/1BA – Sleeps 4 – Private Homes, Old Town #360092
  13
  $3000- $4500/mo

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•   Bahama Gardens - Historic Key West Old Town, Near Duval /Beach 4BR+/1.5BA – Sleeps 6-8 – Private Homes, Old Town #142507
  2
  $3,000. - $9,000.

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•   'Azure Morning @ Oceanside Marina': Lavish 3BR/2BA Oceanfront Condo + Pool.... 3BR/2BA – Sleeps 6 – Other Key West Properties #390183ha
  8
  $1850 - $2950 per week 7 night min stay

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•   Boli Townhouse - a Key West Luxury Rental Close to Everything ! ! ! 2BR+/2BA – Sleeps 6 – Other Key West Properties #364315ha
  21
  $183 - $229 per night

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•   Ashe Splashe-Award Winning Historic Restoration 3BR+/3BA – Sleeps 6 – Private Homes, Old Town #177438
  4
  $4500- $8500/mo

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•   A Royal Home with 4 Master Suites & an Attic Suite 4BR/4.75BA – Sleeps 6-10 – Private Homes, Old Town #123121
  2
  $1250 per night 5 night min stay

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•   Captain's Mansion - April Availability 3BR/3.5BA – Sleeps 6 – Private Homes, Old Town #99427
  5
  $7000- $11,000/mo

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•   Noona'S Mansion-by-the-Sea @ the Annex': 7BR/5.5BA Home with Pool.... 7BR+/5.5BA – Sleeps 14 – Private Homes, Unspecified #173985
  1
  $10,500-14,900/wk, $39,000-$55,000/mo

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•   'Southard Comfort' @ Old Town: a Dazzling Key West Conch House 3BR/2.5BA – Sleeps 6 – Private Homes, Old Town #122535
  30
  From $321/nt - $2250/wk - $6000/mo

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•   Villa Paradiso a Peaceful Retreat 3BR+/3BA – Sleeps 6-8 – Casa Marina #181343
  0
  $380- $730/nt

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•   Summertime Special 10% Off June-September! 3BR+/3BA – Sleeps 8 – Key West Golf Club #115109
  3
  Monthly

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•   Coral Hammock - Beautiful Poolside Home (28) 3BR/3BA – Sleeps 6 – Other Key West Properties #994631ha
  9
  $140 - $350 per night

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•   The Grande Dame Key West - (the Watson House) 7BR+/7BA – Sleeps 14-16 – Private Homes, Unspecified #139805
  0
  From $1400/nt - $6950/wk

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•   'Sweet Caroline'S Sanctuary @ the Seaport': Cozy 1BR/1BA Condo + Pool, Spa... 1BR/1BA – Sleeps 2-4 – Other Key West Properties #390174ha
  0
  $3000 - $5000 per month 28 night min stay

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•   Sunset Key Escape (Monthly Rental) 2BR+/2.5BA – Sleeps 4-6 – Private Homes, DownTown #406826
  9
  $6750 - $12000 per month 30 night min stay

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•   Beach Club #303 2BR/2BA – Sleeps 4 – Other Key West Properties #256052
  3
  From $270/nt - $480/nt

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•   Annex, Harbor Place Best Location Key West 2BR+/2.5BA – Sleeps 4-6 – Truman Annex #230431
  11
  $2600.00 3500/wk

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•   'Sunset Dreams 2 @ Florida Bay': Luxurious 2BR/2BA Waterfront Condo... 2BR+/2BA – Sleeps 4 – Other Key West Properties #390198ha
  3
  $3000 - $6600 per month 28 night min stay

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•   Perfect Luxury Ultra Modern Ocean View All Amenities Free Wifi 2BR+/2BA – Sleeps 4-6 – 1800 Atlantic #380454
  15
  From $4000- $6500/mo

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•   Southard House - Lovely Home in the Heart of Old Town 4BR+/4BA – Sleeps 8 – Private Homes, Old Town #256054
  0
  $730- $1100/nt

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•   XXX Special,(Quiet)House with Guest Cottage,Close to Duval St 3BR+/3.5BA – Sleeps 6-8 – Private Homes, Old Town #103479
  4
  $5800- $10,200/mo

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•   Dos Casas-4 BR Compound in Beautiful Old Town Key West 4BR/2BA – Sleeps 8 – Private Homes, Old Town #76082
  2
  $5500 - 9500/mo

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•   Brass Palm Villa - Luxurious Tropical Private Home 3BR/2.5BA – Sleeps 6 – Private Homes, Old Town #314995
  4
  $5500- $8200/mo

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•   Petronia Palms, Just Off Duval St. Safe! and Has a Large Pool! 1BR+/1BA – Sleeps 4 – Private Homes, Old Town #208439
  32
  $3100- $7500/mo

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•   New Potter's Cottage -Private Pool, Quiet, Yet Steps Off Duval 2BR+/2BA – Sleeps 5 – Private Homes, Old Town #340360
  11
  $314 - $400 per night

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•   Petronia Palms, Just Off Duval St.Safe! and Has a Large Pool! 1BR+/1BA – Sleeps 4 – Private Homes, Old Town #219051
  33
  From $3000/mo

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•   The Grand Marshal Key West - a Rare One-of-a-Kind Estate Home 5BR+/4BA – Sleeps 10-14 – Private Homes, Historic Seaport #139521
  0
  $1050-$1375/nt - $5000-$6900/wk

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•   Abaco Dreams 3BR/2BA Old Town Private Paradise Key West 3BR/2BA – Sleeps 6 – Private Homes, Old Town #151361
  0
  From $550/nt - $3500/wk

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•   Paradise at Smathers Beach, Deluxe 2BR Condo May 25-June 1closeout 2BR+/2BA – Sleeps 4-6 – La Brisa #302783
  9
  From $1000/wk

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•   Down Island Digs - Ideal Location Downtown, Private Pool. 2BR+/2BA – Sleeps 4-6 – Private Homes, DownTown #184018
  1
  $375-$450/nt - $2050-$2700/wk

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•   Hollinsed House - Stay in "Eve's Paradise" 2BR+/1.75BA – Sleeps 6 – Private Homes, Old Town #144522
  20
  $4000- $5000/mo

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•   One of a Kind Estate 1/2 Block from Duval! 3BR/2.5BA – Sleeps 6 – Other Key West Properties #346785ha
  1
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•   Welcome to Serendipity! Pet Friendly, Pool & Hot Tub on Geiger Key! 3BR+/1BA – Sleeps 4-6 – Geiger Key #417144
  2
  $250 per night US Funds Only

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•   Beautiful Private Home in Old Town; Great Nightly/Weekly Rates 1BR+/1BA – Sleeps 2-4 – Private Homes, Old Town #243086
  3
  From $258/nt

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•   'Southard Comfort' -- Famous Old Town Conch Cottage 2BR+/2BA – Sleeps 6 – Private Homes, Old Town #243222
  0
  $4750- $8000/mo

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• Special offer Summer Deal! Book June 2013 for $2500 Jun 1, 2013 to Jun 30, 2013
    Home (2bdrm/1bath) with Private Pool, Deck and Garden 2BR+/1BA – Sleeps 4 – Private Homes, Mid Town #394779
  6
  $3000- $4800/mo

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•   Family Reunion - 3 Homes and a Cottage in Pool Garden Compound 12BR+/10BA – Sleeps 22-28 – Private Homes, Old Town #202539
  0
  From $7,950/wk - $11,450/wk

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•   Havana Hideaway, Downtown, Pool, Parking, 1 Block Off Duval 2BR+/2.5BA – Sleeps 4-6 – Private Homes, Old Town #220196
  2
  $368- $408/nt

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•   Historic Seaport Home 4BR+/4.5BA – Sleeps 10 – Private Homes, Historic Seaport #120234
  0
  $7,500- $15,000/mo

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•   Key West Golf Course 3BR/2.5BA – Sleeps 3-6 – Private Homes, Old Town #179222
  0
  $4500 per month 30 night min stay

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•   Petronia Palms for Budget Minded by Duval St Has a Large Pool! Studio/1BA – Sleeps 1-2 – Private Homes, Old Town #265376
  19
  $2500- $4000/mo

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•   Petronia Palms, Just Off Duval St.Safe! and Has a Large Pool! 1BR+/1BA – Sleeps 2-4 – Private Homes, Old Town #249689
  15
  $3200- $6500/mo All

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