Vacation Rentals by Owner

Key West Vacation Rentals Show this location only Back to top

•   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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• Special offer Summer Special - $1,000.00/Week Jul 1, 2013 to Oct 18, 2013
    Coral Hammock - Beautiful Home at the Entrance to Key West (35) 2BR+/2.5BA – Sleeps 4 – Other Key West Properties #3177011ha
  4
  $117 - $275 per night

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•   Beautiful Key West Condo, Great Location in Truman, Near All 2BR/1BA – Sleeps 4 – Truman Annex #138096
  0
  $1200- $2100/wk

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•   Truman Annex Key West D & D's Paradise 2BR/1BA – Sleeps 4 – Truman Annex #291222
  4
  $1225- $1925/wk

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•   Private Cottage 2 Blocks from Duval Street! 1BR+/1BA – Sleeps 2-4 – Private Homes, Old Town #411925
  0
  $208 - $419 per night 3-6 night min stay

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•   Real World Mtv House---Your Own Private Resort! 10BR+/5.5BA – Sleeps 20-24 – Private Homes, Unspecified #313960
  14
  $10,000 +/week

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•   The Pavilion Villa - A Private Paradise in Downtown Key West 4BR+/3BA – Sleeps 8-10 – Private Homes, DownTown #253814
  2
  $750-$850/nt - $4000-$5100/wk

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•   Historic 'Tobago House' in-Ground Private Spa, Lush Gardens 2BR/2BA – Sleeps 2-4 – Private Homes, Old Town #301138
  1
  From $3,500- $5,750/month

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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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•   Historic Tropical Beauty 1BR+/1BA – Sleeps 2-4 – Private Homes, Unspecified #369554
  2
  $2500 to $3500

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•   Supermodel Home - Old Town Hideaway, Pool, Perfect Location 2BR/2BA – Sleeps 4-5 – Private Homes, Old Town #185246
  3
  $226- $486/nt/mo

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•   Key West's Only Real Beach House,Private Beach,Tropical Gated 2BR+/2BA – Sleeps 2-4 – Other Key West Properties #176024
  0
  $2400- $3300/wk

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•   Elegant European Sail Catamaran Yacht Charter in Private Luxury Marina 4BR+/4BA – Sleeps 8 – Key West Harbour Yacht Club #362848
  2
  From $300/nt

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•   Coral Hammock - Tropical Paradise Home (15) 3BR/3BA – Sleeps 6 – Other Key West Properties #3543556ha
  0
  $250 - $350 per night 3 night min stay

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•   Large and Private Waterfront Luxury Living 4BR/4BA – Sleeps 8-10 – Other Key West Properties #958239ha
  3
  $400 per night

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•   Single Family Home, 3 Bedroom, 2 Bath, Pool and Electric Car 3BR/2BA – Sleeps 6 – Private Homes, New Town #365108
  3
  $2,500- $4,000/mo plus tax

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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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•   The Hollinsed House "Victorian Delights" - Large 1 Bedroom 1BR+/1BA – Sleeps 2-4 – Private Homes, Old Town #400912
  3
  From $189/nt/ $1095 wk (Summer)

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•   Gated Community Near Key West 2BR/2.5BA – Sleeps 4 – Coral Hammock #370684
  0
  $258 - $425 per night 3-6 night min stay

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•   Beautiful 4 Bedroom Home with Pool 4BR/3BA – Sleeps 8 – Private Homes, Old Town #466412
  0
  $5000 - $9500 per month 28 night min stay

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•   The Hollinsed House "Poolside Suite" - Deluxe King Studio 1BR/1BA – Sleeps 2 – Private Homes, Old Town #400907
  2
  From $169/nt/ $995 wk (Summer)

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•   Absolute Dream Cottage, with Private Hot Tub, Walk Everywhere! Studio/1BA – Sleeps 2 – Private Homes, Old Town #267650
  5
  From $198/nt

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•   Key West's Only Real Beach House,Private Beach,Tropical,Gated 2BR/2BA – Sleeps 2-4 – Private Homes, Unspecified #218396
  0
  $2400- $3300/wk

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•   The Hollinsed House "Michael's Retreat" - Large 1 Bedroom 1BR+/1BA – Sleeps 2-4 – Private Homes, Old Town #400911
  1
  From $189/nt/ $1095 wk (Summer)

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•   Always Your Paradise - Old Town Truman Annex Condo 2BR+/1BA – Sleeps 4 – Truman Annex #283300
  3
  $900- $1800/wk

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•   Beautiful ~ Ocean View ~ 2 Story Conch Style Home in Key West 3BR+/2.5BA – Sleeps 6-8 – Other Key West Properties #242369
  2
  $1500- $3000/wk

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•   Heavenly Hideout at Key West Mile Zero ~ Rainbow's End 4BR/4BA – Sleeps 8 – Private Homes, Old Town #445226
  1
  $575-$775/nt - $3400-$2400/wk

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•   Classic Pet-Friendly 3/2 for the Tropical Arts Aficionado 3BR/2BA – Sleeps 6 – White St. Gallery #474320
  0
  $5000 - $7500 per month 30 night min stay

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•   4 Bed/4 Bath Retreat at the End of the Road 4BR/4BA – Sleeps 6-8 – Private Homes, Old Town #474319
  0
  $7500 - $12000 per month 30 night min stay

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•   The Cutest Private Home Stay North of Havana! 1BR/1BA – Sleeps 2 – Private Homes, DownTown #474317
  0
  $3000 - $5000 per month 30 night min stay

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•   'Aqui Su Casa En Key West' is 'Your Home Here in Key West' 3BR+/3.5BA – Sleeps 6 – Casa Marina #357027
  4
  $6,000 - $8,500 / month

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•   Luxurious, Elegant, Quiet 3BR/3BA – Sleeps 6 – Private Homes, Unspecified #267031
  3
  From $3000/wk - $12,000/mo

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•   Sawyer's Escape 3BR/0BA – Sleeps 6 – Private Homes, Historic Seaport #459582
  0
  $6500 per month 28 night min stay

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•   Sunrise Suites Resort Key West 2BR+/2BA – Sleeps 4-6 – Sunrise Suites #256494
  1
  $199- $299/nt

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•   Chosen Property on House Hunters on Vacation! 75' Motor Yacht 4BR/4.5BA – Sleeps 8 – Key West #280131
  6
  $1600- $2000/nt

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•   Duval Square Penthouse 4BR+/4.5BA – Sleeps 8-10 – Duval Square #435156
  1
  $410- $720/night

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•   Seaport Suite, Perfect Downtown Location, Walk Everywhere! 4BR+/2BA – Sleeps 8-10 – Private Homes, Historic Seaport #324984
  0
  $348- $445/nt

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•   Papa's Catch 2BR/1BA – Sleeps 4 – Other Key West Properties #3485751ha
  0
  $1300 - $1750 per week 7 night min stay

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•   The Hollinsed House "Shangrila Suite" - Deluxe Queen Studio 1BR/1BA – Sleeps 2 – Private Homes, Old Town #400909
  3
  From $159/nt/ $895 wk (Summer)

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•   Key West Retreat at Marriott Beachside 3BR+/3BA – Sleeps 6-8 – BeachSide #398872
  3
  From $400/nt or $2,650/wk

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•   Frangipani Oasis (H.G.T.V. Featured Home) 2BR/1BA – Sleeps 4 – White St. Gallery #435885
  0
  From $3500.00 to $6000.00 per month

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•   New Home in Old Town 4BR/4BA – Sleeps 8 – Other Key West Properties #952427ha
  0
  $14000 per month 28 night min stay

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•   Fabulous Luxury Yacht Rental! 2BR/2BA – Sleeps 5 – Key West Harbour Yacht Club #3511642ha
  0
  $250 - $350 per night 2 night min stay

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•   Close to it All - Fishing, Boating, Golfing, Dining, Shopping! 3BR+/3BA – Sleeps 8 – Coral Hammock #471083
  0
  $275 - $375 per night 3 night min stay

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•   Grand Four Bedroom Home, Ideal Location, with Dipping Pool 4BR/3.5BA – Sleeps 8 – Meadows #405140
  1
  $222 - $444 per night 27 night min stay

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•   Truman Annex Town Home 2BR/2.5BA – Sleeps 4-6 – Truman Annex #465198
  1
  $1645 - $2100 per week 7 night min stay

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•   Island Oasis 3BR/2BA – Sleeps 6 – Other Key West Properties #347931
  4
  From $368/nt - $2576/wk

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•   Absolutely Paradise 3BR/2.5BA – Sleeps 6 – Private Homes, Old Town #347826
  1
  From $408/nt - $2856/wk

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•   Key West Cottage: Bahama House, Key West, Fl, 33040 2BR/2BA – Sleeps 6 – Other Key West Properties #347871
  1
  From $298/nt - $2086/wk

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•   Treetop Island Treasure, Palm Isle, Just Off Duval Studio+/1BA – Sleeps 2-4 – Other Key West Properties #347930
  3
  From $168/nt - $1176/wk

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•   Tropical Village Cottage 2BR/2BA – Sleeps 5 – Other Key West Properties #347855
  0
  From $245/nt - $1719/wk

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•   Tropical Retreat 2BR/1BA – Sleeps 4 – Other Key West Properties #347853
  0
  From $198/nt - $1386/wk

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•   Tropical Hideaway 1BR/1BA – Sleeps 4 – Other Key West Properties #347842
  0
  From $198/nt - $1386/wk

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•   Pet Friendly Cottage Studio/1BA – Sleeps 4 – Other Key West Properties #347923
  0
  From $128/nt - $896/wk

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•   Artist House 2BR+/2.5BA – Sleeps 6 – Duval Square #442918
  0
  $268 - $358 per night 3-5 night min stay

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•   Key West Hidaway 3BR/3.5BA – Sleeps 10 – Other Key West Properties #347933
  0
  From $5000/mo

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•   Southern Cross 2BR/2BA – Sleeps 6 – Other Key West Properties #347858
  0
  From $258/nt - $1806/wk

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•   Toon Hall 3BR/2BA – Sleeps 10 – Other Key West Properties #347862
  0
  From $348/nt - $2436/wk

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•   Poolside Paradise 1BR/1BA – Sleeps 2 – Other Key West Properties #347835
  0
  $168/nt - $1176/wk

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•   5 Apartments Can Sleep 2-14/Small and Large Groups! 'Colors on White' 5BR+/5BA – Sleeps 10-14 – Private Homes, Mid Town #390827
  0
  $995

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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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•   Sundown Refuge 2BR/2BA – Sleeps 5 – Other Key West Properties #3468745ha
  0
  $257 - $518 per night

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•   Tropical Tranquility - 5 Star Caribbean Resort-Style Villa 4BR/3.5BA – Sleeps 8 – Private Homes, Historic Seaport #173086
  1
  $950-$1250/nt - $4500-$6000/wk

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•   Victoria House 5 Bedroom Beauty Key West Rental 5BR/5.5BA – Sleeps 12 – Private Homes, Old Town #251638
  1
  $865-$1225/nt - $5800-$8300/wk

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•   Secluded Getaway Just Off Duval 3BR+/3BA – Sleeps 6-8 – Private Homes, Old Town #346291
  0
  $450 - $720/nt.

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•   Sophisticated Elegance on Fleming Street (Pool, Parking) 3BR/2.5BA – Sleeps 6 – Private Homes, Old Town #128058
  11
  $9000- $15,000/mo

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•   Quintessential Charming Hideaway 2BR+/2BA – Sleeps 4-6 – Private Homes, Old Town #238475
  7
  $3000- $6000 monthly

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•   Exclusive Key West Beach Front - Amazing View of the Ocean. 2BR+/3BA – Sleeps 4-6 – BeachSide #183996
  1
  From $375/nt - $2000/wk

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•   Key West Dreamin' - Downtown Location with a Private Pool 2BR+/2BA – Sleeps 4-6 – Private Homes, DownTown #184033
  0
  $450-$550/nt - $2500-$3200/wk

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•   Secret Courtyard Cottage - Downtown with Privacy! 2BR+/1BA – Sleeps 4-5 – Private Homes, DownTown #184021
  0
  $275-$350/nt - $1400-$1750/wk

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•   A Touch of Bermuda at Truman Annex 2BR+/2BA – Sleeps 6 – Truman Annex #361238
  6
  $2100 per week 7 night min stay

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•   To the Nines - Penthouse Villa with Balcony Over Duval Street 3BR+/3BA – Sleeps 6-8 – Other Key West Properties #322397
  0
  $850-$950/nt - $3950-$5000/wk

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•   Quaint Houseboat with Wet Bar and Awesome Views - Key West Fishing Vacation 2BR/2BA – Sleeps 5 – Other Key West Properties #411266ha
  51
  $240 per night 2 night min stay

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•   "Tranquility " at Ann Street Gardens Steps from Duval 1BR/1BA – Sleeps 2 – Private Homes, Old Town #98557
  12
  $230-$310/nt - $1540-$2030/wk

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•   Historic 4 /3 Luxury Beach Home in Key West 4BR/3BA – Sleeps 4-8 – Private Homes, Old Town #116745
  3
  $5600 per week 7 night min stay

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•   Hollinsed House - Key West Old Town - Great Location!! Studio/1BA – Sleeps 2 – Private Homes, Old Town #255530
  26
  $148-$228/nt - $959- $1400/wk

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•   Truman Annex - Foundry Townhouse - One of a Kind! 2BR/2.5BA – Sleeps 4 – Truman Annex #159305
  33
  From $2350 per week

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•   Colony Cabanas - Tropical Bungalow in the Heart of Old Town 1BR+/1BA – Sleeps 2-3 – Private Homes, Old Town #137869
  0
  $190- $320/nt

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•   Old Town Bali Hideaway for 2, Just Steps from Duval Studio/1BA – Sleeps 2 – Private Homes, Old Town #82634
  5
  $210-$280/nt - $1400-$1820/wk

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•   Modern Luxury and Privacy Just Steps from Duval 2BR+/2BA – Sleeps 6 – Private Homes, Old Town #302200
  40
  $425/nt and Up

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•   Sophisticated Southard Street Charmer 3BR/3BA – Sleeps 6 – Private Homes, Old Town #176314
  1
  $4800 to $10,000 per month

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•   Gated Private Luxurious Getaway-Truman Annex (Private Pool) 4BR/4BA – Sleeps 8 – Truman Annex #99721
  0
  $5500- $7500/wk

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•   Amelia's Hideaway - Hidden Courtyard Villa with Private Pool 4BR/3.5BA – Sleeps 8-10 – Private Homes, Old Town #137983
  2
  $750-$850/nt - $4000-$5100/wk

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•   Fleming Street Townhouse in the Sky! 2BR+/2.5BA – Sleeps 4-6 – Private Homes, Old Town #289989
  4
  $3500- $5500/mo

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•   Charming Home in Old Town Key West 3BR+/3BA – Sleeps 6-8 – Truman Annex #310066
  5
  $3500- $5500/wk

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•   Peaceful Gated Community -- Close to Everything! 3BR/3BA – Sleeps 6 – Coral Hammock #213322
  8
  $1100- $1800/wk

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•   Paradise Found 2BR+/1.5BA – Sleeps 4-5 – Key West Golf Club #311501
  2
  $1015 - $1120 per week 7 night min stay

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•   Condo at Oceanside Marina, Stock Island, Key West 3BR/2BA – Sleeps 6-7 – Other Key West Properties #386233
  5
  1600.00- 2400wk

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•   House by the Beautiful Sea- Stunning Key West Sunsets 3BR+/3BA – Sleeps 6-8 – Truman Annex #240137
  0
  $4800/wk

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•   Tropical Hideaway for Laid Back Living 2BR+/1BA – Sleeps 4-6 – Truman Annex #263478
  6
  $1250- $1600

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•   Waterfront Views from Dolphin Watch 4BR/3BA – Sleeps 8 – Truman Annex #297639
  1
  $4500- $6500/wk

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•   Designer Dream 2BR/2BA with Heated Pool 2BR/2BA – Sleeps 2-4 – Private Homes, Old Town #190172
  0
  $4000- $7000/mo

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•   Old Town Historic Eyebrow -One Block to Duval-Private Pool/Spa 4BR+/4BA – Sleeps 8 – Private Homes, Old Town #150378
  1
  3490/wk

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•   Sea Breeze Cottage-Gulf View in Truman Annex 3BR/2BA – Sleeps 3-6 – Truman Annex #987489ha
  0
  $357 per night

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•   Key West 3 Bedroom Condo- Direct Beach Front 3BR+/2BA – Sleeps 2-8 – 1800 Atlantic #205631
  0
  $2600- $3100/wk

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•   Blue Lagoon 3BR/2BA – Sleeps 6 – Truman Annex #264827
  1
  $2500- $3500/wk

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•   Stay in the Nicest Part of Key West 2BR+/1.5BA – Sleeps 4-6 – Truman Annex #279984
  5
  $1400- $2800/wk

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•   Elegantly Furnished Key West Condo in the Truman Annex. 2BR+/1BA – Sleeps 3-6 – Truman Annex #347511
  0
  $165 per night 3 night min stay

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•   Quaint Townhouse in the Heart of Old Town Key West 2BR/1.5BA – Sleeps 4-5 – Truman Annex #446454
  1
  $1505 - $2380 per week 7 night min stay

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•   One of a Kind Luxury Home - Admirals Treasure 4BR/4BA – Sleeps 8 – Truman Annex #290548
  0
  $5900- $8900/wk

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