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Vacation Rentals in Florida Keys

  1. One Bedroom/Bathroom Separate Entry
    $1,300
    Tavernier
  2. Boaters Dream - Special /40 ft dock-Kayaks
    $1,690
    Florida Keys, Marathon
  3. CASA AZUL IS AN OPEN WATER 5 BEDROOM 3 BATH HOME WITH POOL AND HOT TUB
    $1
    Marathon, FL
  4. KW Golf Course Townhouse 2 br 1.5 ba available June 1-Oct 1
    $3,400
    Key West Golf Course
  5. Ground Floor 2 Bedroom 2 Bath. New AC
    $150
    Tavernier
  6. Luxurious & Spacious garden filled with orchids
    $100
    Summerland Key
  7. Captivating 2-bedroom, 2-bathroom charmer
    $100
    Tavernier
  8. Paradise Place @Open the door to Paradise Place and find yourself transported to
    $210
    Key West
  9. Perfect Florida Keys Getaway
    $5,500
    Big Pine Key
  10. Fully renovated 5-bedroom 3-bathroom vacation style home for rent in Islamorada
    $350
    Islamorada
  11. In Heart Of Key West your Ocean View Flat! Public beach too!
    $299
    Key West --- Casa Marina neighborhood
  12. Tucked Away is set on a small lane just one block charming.
    $220
    Key West
  13. Walk or kayak to the new Pine Channel Nature Park
    $145
    Big Pine Key
  14. ENJOY YOUR PIECE OF KEYS' PARADISE!
    $165
    Big Pine Key
  15. Luxury Pool Home,Ocean View, Beach access
    $2,490
    Key Colony Beach
  16. Luxury Condo ,Ocean View, Pool & Fishing
    $990
    Marathon
  17. Special - 4 Bedroom Tiki, Dock, Jacuzzi
    $1,990
    Marathon
  18. Discounts Save $300-$800 / Priced $990-$2490
    $990
    Marathon
  19. Atlantic Ocean from two expansive open-air verandas.
    $200
    Marathon
  20. Serene Casa Marina Hideaway with Authentic Tropical Charm
    $125
    Key West
  21. Phenomenal water access to Bogie Channel
    $150
    Big Pine Key
  22. 4 Bedroom, Kayaks, Dockage, Cabana Club, Bikes, Spacious
    $1
    Key Colony Beach, FL
  23. 2 Bed/1 Bath & Pool in Islamorada
    $1
    Islamorada, FL
  24. Tropical Waterfront Home - Dock
    $5,990
    Florida Keys, Summerland
  25. Summerland Key
    $150
    Gulf Dr, Summerland Key, FL 33042
  26. SCAM WARNING BY LEGIT OWNER
    $120
    KEY WEST
  27. CANAL-FRONT TROPICAL PARADISE
    $250
    Big Pine Key
  28. If you want open ocean views with a clear view of Alligator Lighthouse
    $200
    Islamorada
  29. Rare Luxury Oceanfront Townhome in an Elegant Gated
    $170
    Key West
  30. Welcome to this vacation home along the first fairway
    $120
    Key West
  31. Endless spectacular sunsets and water views from your large deck!
    $162
    Key West
  32. Gorgeous CBS corner canal front home.
    $155
    Big Pine Key
  33. Located on a wonderful block if Old Town.
    $197
    Key West
  34. SPACIOUS TWO BEDROOM TWO BATH HOME
    $0
    Big Pine Key
  35. OCEANFRONT Home Available Now! Great Views. Perfect for Boaters!
    $399
    92.3 Tavernier
  36. BEACHFRONT SUNSET Home with private heated pool., Private & Breathtaking- Pool
    $300
    Key West, FL 33040
  37. Marathon House with Heated Pool and Spa, Boat Dock and Ice Make, Private & Breat
    $300
    Marathon, FL 33050
  38. Private & Breathtaking 99% oceanfront home- Executives, Families, Retirees
    $315
    Marathon, FL
  39. ► Hyatt Sunset Harbor (Old Town) Timeshare Rental - Feb 9-16 2025
    $2,300
    Key West
  40. Turn what's next into right now at ''Pescayo Paradise''
    $130
    Marathon Shores
  41. Explore the nearby Florida Keys Offshore Islands
    $100
    Summerland Key
  42. A gorgeous waterfront family home.
    $130
    Marathon Shores
  43. Beautiful POOL HOME on canal Tav creek.
    $260
    Islamorada
  44. Key West 3Bdrm At It's Best Off Duval w Pool Parking
    $250
    Old Town Key West
  45. Elegance Key West 3 Bdrm Off Duval w Pool
    $255
    Old Town Key West
  46. 2 BEDROOM COTTAGE AVAILABLE JUNE & JULY
    $5,950
    Key West
  47. RV Lot for Rent- Florida Keys
    $1,300
    Big Pine Key
  48. Tastefully renovated piece of lower Keys serenity waiting to welcome you home!
    $100
    Summerland Key
  49. Super nice and totally updated 3 bedroom, 3 bath home in sought after Jolly Roge
    $130
    Summerland Key
  50. Recently renovated/elevated 4 bedroom, 2 bath home
    $120
    Summerland Key
  51. Picturesque open water views from all angles at this tropical oasis in the prest
    $130
    Summerland Key
  52. Gorgeous 3BD Truman Ave with Pool Parking
    $250
    Old Town Key West
  53. Open water Sugarloaf Key House near Key West for rent
    $199
    1310 Sugarloaf Blvd, Sugarloaf Key, FL
  54. KEY WEST Florida HYATT SUNSET HARBOR 7 nts - Studio slp 2 AUG 7 to 14
    $970
    KEY WEST Florida
  55. Oceanfront RV Lot for Rent in June, August to January 2025
    $1,950
    Cudjoe Key
  56. Stunning Keys Resort Fully Furnished Home 2 Bed 2 Bath
    $150
    Big Pine Key
  57. 44ft Seawall at Sportsman's Paradise! TRANSIENT RENTAL LICENSED! A True Island
    $250
    Cudjoe Key, FL
  58. Big Pine Key Fl
    $3,600
    Ave D
  59. Gorgeous 3BD Truman Ave with Pool-Parking
    $250
    Old Town Key West
  60. All the wonders the Florida Keys offers are here in Lower Matecumbe Key
    $170
    Islamorada
  61. Canal Pool home with with open Water & Sunset Views
    $140
    Big Pine Key
  62. Last Minute Home Specials $990-$2490
    $990
    Marathon
  63. Elegance Key West 3 Bdrm Off Duval w Pool
    $255
    Old Town Key West
  64. SPACIOUS TWO BEDROOM TWO BATH HOME
    $0
    Big Pine Key
  65. AUGUST -- The better Lobster Season
    $228
    SUMMERLAND KEY
  66. 1Bed 3Bath
    $75
    Key West
  67. Mid-Century Masterpiece in the heart of town
    $300
    Key West
  68. Townhome for Rent
    $2,500
    Fort Walton Beach
  69. 1800 Atlantic (2.0)
    $300
    Key West
  70. 2Bd/2Ba with Covered Porch!
    $150
    Spanish Main Dr #410, Cudjoe Key, FL 33042
  71. Fla Keys private pool home on canal off Tavernier Creek Avail Aug 1st
    $260
    Islamorada
  72. TIDES ON SIMONTON!!
    $150
    Key West, FL
  73. Spectacular porch and other amenities. Classy property and upgrades!
    $150
    Colony Beach, FL
  74. Key Haven Canalfront home with Dock and Pool
    $100
    Key West
  75. Special April May-June-July-Aug Seaside Home
    $3,990
    Ramrod Key,Florida Keys
  76. October Luxury KeyWest Rental
    $240
    Key West, Florida
  77. Open water Sugarloaf Key House near Key West for rent
    $199
    1310 Sugarloaf Blvd, Sugarloaf Key, FL
  78. Welcome to the epitome of comfort and convenience in this fully furnished two-be
    $300
    Summerland Key
  79. Vacation rental
    $700
    Key west
  80. Memorial Day week in Key West! 10 Nights!
    $2,000
    Key West
  81. Quintessential Key West Cottage
    $3,500
    Old Town
  82. Located in the desirable New Town
    $145
    Key West, FL
  83. Enjoy the quintessential Key West lifestyle
    $218
    Key West, FL
  84. SPACIOUS TWO BEDROOM TWO BATH HOME
    $0
    Big Pine Key
  85. "KEY WEST GALLEON RESORT May 25th - June 1st
    $300
    Key West
  86. Fully furnished light and airy 3 bedroom 2 bath home
    $90
    Ramrod Key
  87. Open water Sugarloaf Key House near Key West for rent
    $199
    1310 Sugarloaf Blvd, Sugarloaf Key, FL
  88. 2 BR/2BA Rental House, Pool + Off-Street Parking for 1 car not SUV or long Vehi
    $197
    Key West
  89. 2 BR/2Ba Rental House, Pool + Off-Str Prkng for 1 Car not Suv or Long Vehicle
    $197
    Key West
  90. Step outside 4 BR/4BA to lounge out by the pool on your tanning deck
    $269
    Key West
  91. Xcellent Chills Old Town 3 B/3B w/ Pool + Parking
    $255
    Key West
  92. BEACHFRONT SUNSET Home with private heated pool., Private & Breathtaking- Pool
    $300
    Key West, FL 33040
  93. Private & Breathtaking 99% oceanfront home- Executives, Families, Retirees
    $315
    Marathon, FL
  94. Charming Oceanfront Home with private heated pool., Private & Breathtaking- Pool
    $255
    Summerland Key, FL
  95. Charming Oceanfront Home with private heated pool., Private & Breathtaking- Pool
    $255
    Summerland Key, FL
  96. Tropical wonderful 3BD stay w/ Private Pool Off Duval
    $250
    Old Town Key West
  97. LARGE 5/5 House w/POOL, JACUZZI, TIKI BAR, OUTDOOR KIT, 70' DOCK.
    $0
    Key Largo
  98. SCAM ALERT
    $0
    1112 W. Shore Dr., Big Pine Key, FL
  99. Enjoy the breath taking waterfront views from every vantage point
    $100
    Key Largo
  100. This home sits in Key Lime Grove Subdivision
    $145
    2928 HARRIS AVE
  101. Tropical Wonderful 3BD Stay w/ Private Pool Off Duval
    $250
    Old Town Key West
  102. Stunning Key West 3Br/3Ba w Pool and Parking
    $240
    Old Town Key West
  103. 3/2 Island Home with Pool on canal Tav creek.
    $260
    Islamorada.
  104. Key West 3 Bdrm At It's Best Off Duval w Pool Parking
    $250
    Old Town Key West
  105. Key Haven 5th Add (5.0)
    $200
    Key West
  106. Sunrise Shores (4.0)
    $197
    Key West
  107. Quiet and peaceful casa marina district
    $135
    Key West
  108. AVAILABLE FOR RENTAL NOW
    $90
    Little Torch Key
  109. Step ou of 4 BR/4BA to lounge out by the pool on your tanning deck
    $270
    Old Town Key West
  110. 2 br~ Adorable Cottage
    $1,700
    Key West
  111. Key West 3 Bdrm At It's Best Off Duval w Pool Parking
    $250
    Old Town Key West
  112. Special Vacation last of summer-Keys (Marathon, FL)r-t
    $275
    Marathon, FL
  113. Marathon Ocean Getaway
    $295
    Marathon
  114. Key West 3 Bdrm At It's Best Off Duval w Pool/ Parking
    $250
    Old Town Key West
  115. two bedroom 2 bath home Oceanside Little Torch
    $0
  116. 2Bd Vacation Cottage- Off duval
    $150
    Key West
  117. Gorgeous 3BD Off Duval with Pool and Parking
    $250
    Old Town Key West
  118. PERFECTLY POOLSIDE TWO BED/3BATH
    $2,500
    Key West
  119. TJ1 Beach, Pool, Kitchen, Sleep 6, HotTub, W&D, Dock, BBQ, WiFi, Parking, Tennis
    $190
    Key Colony Beach
  120. Blue Vacation Home with private heated pool., Private & Breathtaking
    $300
    Cudjoe Key, FL
  121. Charming Oceanfront Home with private heated pool., Private & Breathtaking- Pool
    $255
    Summerland Key, FL
  122. Key West Historic Home
    $4,900
    Old Town Virginia@Duval
  123. The Keys Cabin
    $1,900
    Key Largo
  124. Beautiful 3-Bedroom Mission Style Home
    $230
    Key West
  125. Hyatt Sunset Harbor Resort
    $350
    2 Blocks from Malory Square
  126. This is the perfect island getaway home in paradise
    $134
    Sugarloaf Key
  127. Oceanmist Vacation Rental
    $10,500
    Beautiful Summerland Cove
  128. Gorgeous 3 Bdrm Off Duval with Pool-Parking
    $250
    Old Town Key West
  129. Vacation rental Oceanfront in Islamorada
    $325
    Seagulls Condominiums mile marker 90
  130. Special Million $$$ Tropical Pool Seaside Home
    $5,990
    Cudjoe Key,Florida Keys
  131. Furnished one bedroom single home
    $1,300
    Key West
  132. True Condo by the Ocean with Ocean View, Pool & Breathtaking
    $100
    Key West, FL 33040
  133. Charming Oceanfront Home with private heated pool., Private & Breathtaking- Pool
    $255
    Summerland Key, FL
  134. Stunning Truman Ave 3B/3B w Pool and Parking
    $255
    Old Town Key West
  135. Stunning Truman Ave 3Br/3Bat w Pool and Parking
    $255
    Old Town Key West
  136. Tropical Elegance Off Duval ST 3B w/ Pool Parking
    $250
    Old Town Key West
  137. Beautiful Conch house in Old Town Key West
    $250
    Elizabeth St
  138. the galleon resort
    $2,600
    key west florida
  139. Tropical Elegance Off Duval ST 3BD w/ Pool Parking
    $250
    Old Town Key West
  140. This is not just a residence; it's a lifestyle..
    $120
    Key Largo
  141. Old Port Cove Condo Two
    $180
    Key West
  142. This is the ultimate Florida Keys retreat for all your recreational adventures
    $100
    Key Largo
  143. Tropical Elegance Off Duval ST 3BD w/ Pool Parking
    $250
    Old Town Key West
  144. "TIDES ON SIMONTON" Perfectly located just off Duval and all the fun
    $150
    Key West, FL
  145. La Casa de Luna- Steps from the Beach and Duval - Sleeps up to 4
    $100
    Key West, FL
  146. Gorgeous 3BD Truman Ave with Pool-Parking OPEN
    $250
    Old Town Key West
  147. Tropical Elegance Off Duval ST 3B w/ Pool Parking
    $250
    Old Town Key West
  148. Spacious 5/5.5, Pool, Waterfront Home in Islamorada
    $0
    Islamorada
  149. Oceanfront 2 Bedroom Vacation Rental
    $1,500
    Islamorada
  150. Tropical Elegance Off Duval ST 3Br w/ Pool Parking
    $250
    Old Town Key West
  151. Wonderful waterfront Harbour Place condo now available for rental.
    $120
    Key West
  152. Ready To Move-in Nature Breathtaking Atlantic Ocean Views
    $160
    Key West
  153. Monthly rentals are allowed, with this home rented on occasion,
    $120
    Key West
  154. The Lost Keys
    $90
    Key West
  155. Old Port Cove Condo Two
    $180
    Key West
  156. GALLEON RESORT KEY WEST_By Owner
    $3,200
    Key West
  157. GALLEON RESORT KEY WEST_By Owner
    $3,200
    Key West
  158. Fla Keys private pool home on canal off Tavernier Creek Avail
    $260
    Islamorada
  159. Fantastic Getaway ,Pool & Fishing access
    $1,299
    Marathon,Florida Keys
  160. VACATION HOME RENTAL BOOKINGS $1290 to $2980
    $1,890
    Marathon
  161. 1800 Atlantic (2.0)
    $290
    Key West