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Vacation Rentals in Florida Keys

  1. Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool
    $150
    1024 THOMAS ST
  2. Caribbean Cottage
    $150
    506 VIRGINIA ST KEY WEST
  3. Open water Sugarloaf Key House near Key West for rent
    $199
    1310 Sugarloaf Blvd, Sugarloaf Key, FL
  4. Key Haven 5th Add (5.0)
    $200
    Key West
  5. Sunrise Shores (4.0)
    $197
    Key West
  6. Ready To Move-in Nature Breathtaking Atlantic Ocean Views
    $160
    Key West
  7. The Lost Keys
    $90
    Key West
  8. New Dates OPEN
    $228
    SUMMERLAND KEY
  9. Ventura at Boca Raton 3bed 3bath Vacation Timeshare Townhouse 7 day
    $1,000
    Raton
  10. Key West 3Bdrm At It's Best Off Duval w/ Pool Parking
    $250
    Old Town Key West
  11. Tropical Elegance Off Duval ST 3BD w/ Pool Parking
    $250
    Old Town Key West
  12. Gorgeous 3 Bdrm Off Duval with Pool-Parking
    $250
    Old Town Key West
  13. Sands Sub (31.0)
    $230
    Big Pine Key
  14. Key West 3Bdrm At It's Best Off Duval w/ Pool-Parking
    $250
    Old Town Key West
  15. Off Duval ST 3Br/3Ba with Private Pool-Parking
    $260
    Old Town Key West
  16. Stunning Truman Ave 3Br/3Bat w Pool and Parking
    $255
    Old Town Key West
  17. Welcome to this vacation home along the first fairway
    $120
    Key West
  18. Rare Luxury Oceanfront Townhome in an Elegant Gated
    $170
    Key West
  19. Attention all beach bums & boaters!
    $124
    Key Colony Beach
  20. ENJOY YOUR PIECE OF KEYS' PARADISE!
    $165
    Big Pine Key
  21. CANAL-FRONT TROPICAL PARADISE
    $250
    Big Pine Key
  22. Walk or kayak to the new Pine Channel Nature Park
    $145
    Big Pine Key
  23. Endless spectacular sunsets and water views from your large deck!
    $162
    Key West
  24. If you want open ocean views with a clear view of Alligator Lighthouse
    $200
    Islamorada
  25. Atlantic Ocean from two expansive open-air verandas.
    $200
    Marathon
  26. Located on a wonderful block if Old Town.
    $197
    Key West
  27. Gorgeous CBS corner canal front home.
    $155
    Big Pine Key
  28. Tropical Elegance Off Duval ST 3Br w/ Pool Parking
    $250
    Old Town Key West
  29. Gorgeous 3BD Truman Ave with Pool-Parking
    $250
    Old Town Key West
  30. Hilton Haven Sec 1 A (2.0)
    $185
    Key West
  31. Enjoy a quiet morning sitting out on your expansive 12' X 24' TREX deck
    $170
    Marathon, FL
  32. This is the lovely BEACH RETREAT you deserve!
    $150
    Marathon, FL
  33. Pocketing sliding glass doors from the living room open to the allurin
    $250
    Pine St
  34. Key West Golf Club Dev (4.0)
    $175
    Key West
  35. Tropical Elegance Off Duval ST 3BD w/ Pool Parking
    $250
    Old Town Key West
  36. Hyatt Sunset Harbor Resort
    $2,450
    2 Blocks from Malory Square
  37. Key West 3B/3B At It's Best Off Duval w/ Pool
    $265
    Old Town Key West
  38. Tropical Elegance Off Duval ST 3B w/ Pool Parking
    $250
    Old Town Key West
  39. 2Bd/2Ba with Covered Porch!
    $150
    Spanish Main Dr #410, Cudjoe Key, FL 33042
  40. Gorgeous 3BD Truman Ave with Pool-Parking OPEN
    $250
    Old Town Key West
  41. Tropical Elegance Off Duval ST 3B w/ Pool Parking
    $250
    Old Town Key West
  42. Stunning Truman Ave 3BR/3Ba w Pool and Parking
    $255
    Old Town Key West
  43. RV Lot for Rent- Florida Keys
    $1,300
    Big Pine Key
  44. 2Bdrm Adorable Cottage
    $1,700
    Key West
  45. Key West 3 Bdrm At It's Best Off Duval w/ Pool
    $250
    Old Town Key West
  46. Relax and Revitalize in this Stylish Island Home!
    $120
    Key Largo
  47. Turn what's next into right now at ''Pescayo Paradise''
    $130
    Marathon Shores
  48. Explore the nearby Florida Keys Offshore Islands
    $100
    Summerland Key
  49. Key West 3 Bdrm At It's Best Off Duval w/ Pool-Parking
    $250
    Old Town Key West
  50. Caribbean Cottage
    $130
    506 VIRGINIA ST KEY WEST
  51. ISLAND PERFECTION
    $150
    1118 CURRY LN
  52. 2 bedroom, July 13 to 20, Coconut Mallory
    $1,499
    key west
  53. VACATION HOME RENTAL BOOKINGS $1290 to $2980
    $1,890
    Marathon
  54. Fantastic Getaway ,Pool & Fishing access
    $1,299
    Marathon,Florida Keys
  55. Special Tropical Pool Seaside Home
    $7,990
    Cudjoe Key,Florida Keys
  56. 5/5 House WATERFRONT w/POOL, JACUZZI, TIKI BAR, OUTDOOR KIT, 70' DOCK.
    $0
    Key Largo
  57. Gorgeous 3 Bdrm Off Duval with Pool and Parking
    $250
    Old Town Key West
  58. SPACIOUS TWO BEDROOM TWO BATH HOME
    $0
    Big Pine Key
  59. You get the best of both worlds, boating with easy access to the Gulf or Ocean
    $125
    Key West
  60. Open water Sugarloaf Key House near Key West for rent
    $199
    1310 Sugarloaf Blvd, Sugarloaf Key, FL
  61. Old Port Cove Condo Two
    $180
    Key West
  62. Old Port Cove Condo Two
    $180
    Key West
  63. Gorgeous 3BD Off Duval with Pool and Parking
    $250
    Old Town Key West
  64. Key West 3 Bdrm At It's Best Off Duval w/ Pool
    $250
    Old Town Key West
  65. RV LOT Florida Keys
    $100
    Cudjoe Key
  66. Key West 3 Bdrm At It's Best Off Duval w/ Pool Parking
    $250
    Old Town Key West
  67. Open water Sugarloaf Key House near Key West for rent
    $199
    1310 Sugarloaf Blvd, Sugarloaf Key, FL
  68. Open water Sugarloaf Key House near Key West for rent
    $199
    1310 Sugarloaf Blvd, Sugarloaf Key, FL
  69. Park and Play
    $1,493
    Marathon
  70. Tropical Elegance Off Duval ST 3B/3B w/ Pool
    $255
    Old Town Key West
  71. Gorgeous Gulf-front home with dock, private pool & gas grill
    $1
    Marathon, FL
  72. Adorable cottage
    $1,700
    Key West
  73. Stunning Truman Ave 3B/3Ba w Pool and Parking
    $255
    Old Town Key West
  74. Hands Down THE Best Deal IN KEY West!
    $150
    Key West, FL
  75. Spectacular Paradise With Heated Waterfall Pool!
    $100
    Key West, FL
  76. "TIDES ON SIMONTON" Perfectly located just off Duval and all the fun
    $150
    Key West, FL
  77. Beautiful Conch house in Old Town Key West
    $250
    Elizabeth St
  78. SCAM WARNING BY LEGIT OWNER
    $150
    KEY WEST
  79. Phenomenal water access to Bogie Channel
    $150
    Big Pine Key
  80. Private & Breathtaking 99% oceanfront home- Executives, Families, Retirees
    $315
    Marathon, FL
  81. GALLEON, RESORT, OLD TOWN REDUCED !! 4-6-24
    $2,800
    KEY WEST
  82. Stunning Truman Ave 3B/3B w Pool and Parking
    $255
    Old Town Key West
  83. 2Bed 2Bath
    $95
    Key West
  84. 1Bed 1Bath
    $70
    Key West
  85. SPECIAL RATE: KEY LARGO @Kawama Tower
    $210
    Key Largo
  86. COTTAGES SAILBOATS, KAYAKS, Bikes + More
    $225
    KEY LARGO, FLORIDA
  87. Endless spectacular sunsets and water views from your large deck!
    $162
    Key West
  88. Located on a wonderful block if Old Town.
    $197
    Key West
  89. Rare Luxury Oceanfront Townhome in an Elegant Gated
    $170
    Key West
  90. BOATERS DELIGHT & SUNSET VIEWS!
    $180
    Big Pine Key
  91. 2 bedroom, 2 bath upstairs spacious unit in Truman Annex !
    $250
    620 Thomas St Unit 297 Key West, FL
  92. 2Bd Vacation Cottage- Off duval
    $150
    Key West
  93. Waterfront Home in Islamorada, Private Beach
    $165
    Islamorada
  94. Paradise Bay - 4 Bedrooms (with 2 Master Suites) & 4 Bathrooms
    $1
    Marathon, FL
  95. CASA AZUL IS AN OPEN WATER 5 BEDROOM 3 BATH HOME WITH POOL AND HOT TUB
    $1
    Marathon, FL
  96. Welcome to this vacation home along the first fairway
    $120
    Key West
  97. Over a double size lot with spectacular ocean views!
    $145
    Cudjoe Key, FL
  98. Take in the beautiful Florida Keys sunrise
    $170
    Little Torch Key, FL
  99. overlooking Summerland key Cove Park!
    $155
    Summerland Key
  100. CHARMING WATERFRONT CONCRETE home
    $150
    Summerland Key
  101. Boat-lovers will adore this home's canal-front
    $0
    Marathon Shores
  102. Waterfront Home in Islamorada, Private Beach
    $165
    Islamorada
  103. WELCOME TO OUR HOME
    $230
    Keywest
  104. Oceanfront vacation rental 4th floor Islamorada
    $295
    Tavernier Florida
  105. Beautiful POOL HOME on canal Tav creek.
    $260
    Islamorada.
  106. Discover a blend of historic charm and modern elegance in this wonderful Old Tow
    $198
    Key West
  107. Boat-lovers will adore this home's canal-front
    $0
    Marathon Shores
  108. Waterfront Home in Islamorada, Private Beach
    $165
    Islamorada
  109. Old Town
    $120
    Key West
  110. Villas of Key West
    $115
    Key West
  111. BEACHFRONT SUNSET Home with private heated pool., Private & Breathtaking- Pool
    $300
    Key West, FL 33040
  112. Key West Truman Ave 3BD with Private Pool-Parking
    $250
    Old Town Key West
  113. Florida Keys RV Lot for Rent with Ocean View
    $1,800
    Cudjoe Key
  114. 4BD / 4BA beautiful home located in the desirable Pine Channel Estates!!
    $255
    Big Pine Key
  115. OFF Duval St 3B/3Ba with A Pool-Parking
    $250
    Old Town Key West
  116. Key West Truman Ave with Private Pool-Parking
    $255
    Old Town Key West
  117. Presidents Lane (1.0)
    $260
    Key West
  118. 2 br- Angela Cottage, short to Duval Old Town with Parking + Pool
    $180
    Key West
  119. Key West Truman Ave with Private Pool-Parking
    $250
    Old Town Key West
  120. Caroline Street Condominium (0.5)
    $195
    Key West
  121. Gorgeous 3BD Truman Ave with Pool-Parking
    $250
    Old Town Key West
  122. Modern Grand Home & Pool
    $3,950
    Key West, FL
  123. Stunning Truman Ave 3B/3Bat w Pool and Parking
    $255
    Old Town Key West
  124. 3B/3Ba block from Duval with Pool, Parking
    $250
    Old Town Key West
  125. Key West Truman Ave with A Private Pool-Parking
    $255
    Old Town Key West
  126. One Bedroom/Bathroom Separate Entry
    $1,500
    Tavernier
  127. Recently updated Charming Condo designed 2/2 with bonus room
    $100
    Islamorada
  128. MAJESTIC PARADISE @ Truman Annex
    $3,450
    Key West, FL
  129. 3 Bed/3.5 Bath Home on Quaint
    $3,650
    Key West, FL
  130. Charming 2 BR, 1 Ba Cottage
    $3,450
    Key West, FL
  131. Wonderful waterfront Harbour Place condo
    $100
    Key West
  132. Have you been hunting for a turn key waterfront condo in paradise?
    $90
    Key Colony Beach
  133. Atlantic Ocean from two expansive open-air verandas.
    $200
    Marathon
  134. Walk or kayak to the new Pine Channel Nature Park
    $145
    Big Pine Key
  135. ENJOY YOUR PIECE OF KEYS' PARADISE!
    $165
    Big Pine Key
  136. La Casa de Luna- Steps from the Beach and Duval - Sleeps up to 4
    $100
    Key West, FL
  137. 3 BDR/2BA home with 1BDR/1BA Cottage and Jacuzzi!
    $3,750
    Key West, FL
  138. JULY 4TH WEEK IN NEW SMYRNA BEACH, FL.
    $1,150
    NEW SMYRNA BEACH, FL
  139. Renovated 3 Bedroom Home with Private Pool!
    $3,650
    Key West, FL
  140. Hilton Haven
    $140
    Key West
  141. Fully furnished light and airy 3 bedroom 2 bath home
    $90
    Ramrod Key
  142. Stunning Truman Ave 3B/3Ba w Pool and Parking
    $255
    Old Town Key West
  143. Attention all beach bums & boaters!
    $124
    Key Colony Beach
  144. Seaside Home 4BR Tiki, Dock, Jacuzzi
    $1,990
    Marathon
  145. Stunning Truman Ave 3B/3Ba w/ Pool and Parking
    $255
    Old Town Key West
  146. Location Steps to Duval W/ A Private Pool Patio Parking
    $250
    Old Town Key West
  147. Off Duval ST 3B/3Ba with Private Pool-Parking
    $250
    Old Town Key West
  148. Chic 4BR Home & Pool
    $3,850
    Key West, FL
  149. We welcome you to Calypso Corner for your next vacation!
    $90
    Summerland Key
  150. Location, Steps from Duval with a Private Pool and Parking
    $250
    Old Town Key West
  151. Off Duval ST 3B/3B with A Private Pool-Parking
    $250
    Old Town Key West
  152. Elegant Cottage Near Duval
    $3,750
    Key West, FL
  153. Charming Oceanfront Home with private heated pool., Private & Breathtaking- Pool
    $255
    Summerland Key, FL
  154. $250 / 3br - Location Steps to Duval W/ a Private Pool Patio Parking
    $250
    Old Town Key West
  155. Charming Oceanfront Home with private heated pool., Private & Breathtaking- Pool
    $255
    Summerland Key, FL
  156. Off Duval ST 3B/3Ba with Private Pool and Parking
    $250
    Old Town Key West
  157. Special - 4 Bedroom Tiki, Dock, Jacuzzi
    $1,990
    Marathon
  158. Fantastic Getaway ,Pool & Fishing access
    $1,699
    Marathon,Florida Keys
  159. Boaters Dream - Special /40 ft dock-Kayaks
    $1,690
    Florida Keys, Marathon
  160. GG Watson Sub (1.0)
    $155
    Key West
  161. Harbour Place (1.0)
    $480
    Key West
  162. Stunning Truman Ave 3 bedroom with Private Pool
    $255
    Old Town Key West
  163. $250 / 3br - Location Steps to Duval W/ a Private Pool Patio Parking
    $250
    Old Town Key West
  164. Off Duval ST 3B/3Ba with Private Pool-Parking
    $250
    Old Town Key West
  165. Location, Location, Steps from Duval with Private Pool
    $250
    Old Town Key West
  166. Off Duval 3B/3Ba with Private Pool-Parking
    $250
    Old Town Key West
  167. HAVANA HOUSE
    $3,000
    915 Grinnell St, Key West, FL
  168. Location, Location, Steps from Duval with A Private Pool
    $250
    Old Town Key West
  169. A beautiful 4 bedroom / 3 bath totally renovated waterfront house
    $215
    Key West
  170. This spacious and light filled three bedroom, three bath home.
    $188
    Key West
  171. SCAM ALERT
    $0
    1112 W. Shore Dr., Big Pine Key, FL
  172. Charming Oceanfront Home with private heated pool., Private & Breathtaking- Pool
    $255
    Summerland Key, FL
  173. Empty Lot
    $1,600
    55 Boca Chica Rd
  174. Ocean Front Open water Sugarloaf Key House near Key West for rent
    $199
    1310 Sugarloaf Blvd, Sugarloaf Key, FL
  175. Special Vacation last of summer-Keys (Marathon, FL)r-t
    $300
    Marathon, FL
  176. A Wonderful 2bedroom - 2bathroom Vacation rental Ocean and Harbor view
    $177
    Key West
  177. Key West 3 Br Gulf view, private pool home
    $425
    KeyWest
  178. Lot for rent
    $2,200
    Key largo
  179. nestled in the Leeward Isle Retreat'
    $150
    Old Town
  180. stunning wood finished walls, sparkling quartz kitchen
    $160
    Washington St
  181. secured entrance, private heated pool and immaculate tropical grounds
    $110
    Duval Street
  182. Unwind in Style: Experience the Ultimate Getaway at Our Tranquil 3-Bed
    $7,000
    Marathon
  183. Charming Oceanfront Home with private heated pool., Private & Breathtaking- Pool
    $200
    Summerland Key, FL
  184. Your Dream Waterfront Home in Big Pine Key Awaits You!
    $6,000
    Big Pine Key
  185. RV VACANT lot #90W in “Key by the Sea”
    $1,000
    Marathon, 33050
  186. Boaters Dream -LAST MINUTE DEAL /45ft dock-Kayaks
    $1,690
    Florida Keys, Marathon
  187. Indulge in Luxury: Discover the Ultimate Vacation Rental in Marathon
    $7,500
    Marathon
  188. Experience Luxury and Comfort in Marathon, FL: Book Now!
    $5,800
    Marathon
  189. Private RV lot on quiet lagoon available now
    $0
    key largo
  190. Tropical landscape Home, for living the Key's Island lifestyle
    $180
    Key West
  191. Historic Old Town Getaway 1 Bedroom with Pool, Lots of Privacy
    $150
    Key West
  192. RV Lot in Gated Resort Near Key West
    $1,950
    Key West
  193. True Condo by the Ocean with Ocean View, Pool & Breathtaking
    $99
    Key West, FL 33040
  194. Charming Oceanfront Home with private heated pool., Private & Breathtaking- Pool
    $255
    Summerland Key, FL
  195. Key West Truman Ave with Private Pool-Parking
    $255
    Old Town Key West
  196. TIDES ON SIMONTON!!
    $150
    Key West, FL
  197. The Perfect Place To Vacation!
    $100
    Summerland Key
  198. Key Haven Canalfront home with Dock and Pool
    $100
    Key West
  199. Perfect Florida Keys Getaway
    $5,500
    Big Pine Key
  200. TJ1 Beach, Pool, Kitchen, Sleep 6, HotTub, W&D, Dock, BBQ, WiFi, Parking, Tennis
    $190
    Key Colony Beach
  201. fabulous blue waters of Duck Key Great outdoor entertaining areas
    $100
    Duck Key
  202. Bottom's Up Bungalow!
    $150
    Key West, FL
  203. Home, Sweet Home @ KW GOLF CLUB gated community,
    $100
    Key West
  204. Location, Location, Steps from Duval w/A Private Pool
    $250
    Old Town Key West
  205. 3 Bed with Pool /Key West off Duval/ Patio, Parking
    $250
    Old Town Key West
  206. Location, Location, Steps from Duval with A Private Pool
    $250
    Old Town Key West
  207. Investment co sub (1.0)
    $117
    Key West
  208. 3/2 Island Home with Pool on canal Tav creek.
    $260
    Islamorada
  209. MINUTES FROM OCEAN WITH DEEP WATER CANAL
    $150
    Little Torch Key
  210. South Of Eden Pines Colony
    $220
    Big Pine Key
  211. Pine Channel Estates
    $220
    Big Pine Key
  212. Eden Pines Colony
    $160
    Big Pine Key
  213. Pine Channel Estates
    $170
    Big Pine Key
  214. Sweet Big pine
    $160
    Big Pine Key
  215. LARGE 5/5 House w/POOL, JACUZZI, TIKI BAR, OUTDOOR KIT, 70' DOCK.
    $0
    Key Largo
  216. 3BD Location, Location, Steps from Duval w/A Private Pool
    $250
    Old Town Key West
  217. 3BD Location, Location Steps from Duval w/A Private Pool
    $250
    Old Town Key West
  218. Awesome Open Water View
    $100
    Ramrod Key
  219. Special May-June Seaside Home
    $4,590
    Ramrod Key,Florida Keys
  220. SPACIOUS TWO BEDROOM TWO BATH HOME
    $0
    Big Pine Key
  221. Cutthroat Harbor Est (23.0)
    $258
    Summerland Key
  222. Cudjoe Ocean Shores (23.0)
    $320
    Summerland Key
  223. RV for sale
    $1,700
    Key Largo
  224. CASA AZUL IS AN OPEN WATER 5 BEDROOM 3 BATH HOME WITH POOL AND HOT TUB
    $1
    Marathon, FL
  225. Easy boating access to world class fishing
    $225
    Cudjoe Key, FL
  226. Quiet and peaceful casa marina district
    $135
    Key West