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  1. $118 to $152/night

    Bay Bliss

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    Prime Now
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  3. $167 to $279/night

    Midnight Cove II 214F- Best of the Bayside!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
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  5. $333/night

    Coastal Chic Oasis w/ Private Screened Pool & Patio

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    Prime Now
    FREE CANCELLATION
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  7. $201 to $301/night

    Our House at the Beach C-202 Townhouse Pool Side

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    Prime Now
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  9. $192 to $363/night

    Gulf and Bay Club- C105 Beautiful and walk right out to ...

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  11. $232 to $397/night

    Gulf and Bay Club- C702 Beautifully updated!

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  13. $190 to $325/night

    Gulf and Bay Club- M100

    3 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  15. $192 to $363/night

    Gulf and Bay Club- D101 Ground floor walk out!

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  17. $207 to $392/night

    Gulf and Bay Club- A207 Updated!

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  19. $188 to $358/night

    Gulf and Bay Club- E204 Awesome location!

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  21. $210 to $383/night

    Gulf and Bay Club- C505 Nicely updated!

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  23. $192 to $363/night

    Gulf and Bay Club- D208- Beautifully Updated w/ Lake Vie...

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  25. $202 to $360/night

    Gulf and Bay Club- C609 Excellent views!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  27. $225 to $410/night

    Gulf and Bay Club- C503 Beautifully updated with great v...

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  29. $210 to $346/night

    Gulf and Bay Club- C409 Excellent views!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  31. $188 to $346/night

    Gulf and Bay Club- D404 Excellent views!

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  33. $207 to $392/night

    Gulf and Bay Club- A104 Beautiful walk out to the beach!...

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  35. $210 to $346/night

    Gulf and Bay Club- B301 Updated end unit!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  37. $225 to $410/night

    Gulf and Bay Club- A310 Great updates and view!

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  39. $232 to $397/night

    Gulf and Bay Club- C707 Nicely updated and great views!

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  41. $210 to $383/night

    Gulf and Bay Club- D405 Beautifully updated and handicap...

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  43. $207 to $392/night

    Gulf and Bay Club- A106 Updated ground floor walk out!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  45. $188 to $346/night

    Gulf and Bay Club- C402- Amazing Views

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    Prime Now
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  47. $188 to $346/night

    Gulf and Bay Club- B504 Spectacular Views and Peaceful S...

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    Prime Now
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  49. $210 to $286/night

    Jamaica Royale 012 Updated & beachy!

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pool
    Prime Now
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  51. $151 to $241/night

    Jamaica Royale 028 Close to the pool!

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    Prime Now
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  53. $167 to $237/night

    Jamaica Royale 062 Updated unit!

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    Prime Now
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  55. $167 to $237/night

    Jamaica Royale 064 Great kitchen!

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    Prime Now
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $167 to $237/night

    Jamaica Royale 065 Great location!

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    Prime Now
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  59. $282 to $383/night

    Jamaica Royale 705 Updated & Great views!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
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  61. $257 to $383/night

    Jamaica Royale T53 Great updates and views!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
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  63. $138 to $238/night

    Jamaica Royale 017 Close to the Pool!

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    Prime Now
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  65. $126 to $198/night

    Jamaica Royale 035 Across from the pool!

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    Prime Now
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  67. $295 to $405/night

    Jamaica Royale 404 Beautiful unit & amazing view!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $235 to $329/night

    Jamaica Royale 078 Updated and close to the beach!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
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  71. $235 to $329/night

    Jamaica Royale 072 Beautiful unit!

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    Prime Now
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  73. $167 to $237/night

    Jamaica Royale 061 Beautiful unit and close to the pool!...

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    Prime Now
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  75. $188 to $310/night

    Jamaica Royale 099 Nice Gulf side unit!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $207 to $329/night

    Jamaica Royale 085 Updated & close to the beach!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $151 to $310/night

    Jamaica Royale 107 Updated Gulfside villa!

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    Prime Now
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $188 to $310/night

    Jamaica Royale 102 Updated and great Gulf side location!...

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $295 to $405/night

    Jamaica Royale 506 Great views!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
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  85. $245 to $383/night

    Jamaica Royale 304 Tower views!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $226 to $329/night

    Jamaica Royale 077 Beautiful & Close to the pool!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $270 to $405/night

    Jamaica Royale 604 Beautfully updated and great views!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $192 to $363/night

    Gulf and Bay Club- B207 Great updated unit!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    Prime Now
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $179 to $290/night

    Midnight Cove II 133A- Bayside Views!

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    Prime Now
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $157 to $270/night

    Midnight Cove II 134F- Bayside Views!

    2 Bedrooms1.5  BathroomSleeps 4
    2 nights minstay
    Pool
    Prime Now
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $167 to $279/night

    Midnight Cove II 111F- Spectacular Vacation Rental!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $153 to $221/night

    Midnight Cove II 932C-Spectacular View-Updated

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    Prime Now
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $157 to $270/night

    Midnight Cove II 724F- Great Rental with Pool View!

    2 Bedrooms1.5  BathroomSleeps 4
    2 nights minstay
    Pool
    Prime Now
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $157 to $270/night

    Midnight Cove II 110F Bay View!

    2 Bedrooms1.5  BathroomSleeps 6
    2 nights minstay
    Pool
    Prime Now
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $183 to $300/night

    Midnight Cove II 955B- What a view!

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    Prime Now
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $179 to $290/night

    Midnight Cove II 944C- Exceptional Views!

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    Prime Now
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $167 to $279/night

    Midnight Cove II 411F- Beautifully Appointed Vacation Re...

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    Prime Now
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $201 to $301/night

    Our House at the Beach C-105 Spacious Villa perfect for ...

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $1,249/night

    Hyatt Residences Unit 511

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $265 to $353/night

    Spacious Home with Heated Pool- Near Beach

    4 Bedrooms2.5 BathroomsSleeps 8
    3 nights minstay
    Pool
    Prime Now
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $323 to $513/night

    Family Retreat with Pool, Games, Dock, Fishing, Golf

    4 BedroomsBathroomsSleeps 10
    1 night minstay
    Pool
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $140 to $194/night

    Quiet Retreat Near Siesta Key Beaches

    2 BedroomsBathroomsSleeps 10
    3 nights minstay
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $427 to $622/night

    Beachfront End-Unit Condo with Lovely Gulf Views

    3 BedroomsBathroomsSleeps 6
    7 nights minstay
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $138 to $278/night

    New Listing! Island Escape Steps to Stunning Beach

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pets OK
    Prime Now
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $179 to $290/night

    Midnight Cove II 934C- Breathtaking Views!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $282 to $538/night

    534 Avanti Villa on Grand Canal-close to the village!

    4 BedroomsBathroomsSleeps 9
    2 nights minstay
    Hot Tub
    Prime Now
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $179 to $247/night

    Aloha Kai- Unit 10- Your own private villa!

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    Prime Now
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $206 to $309/night

    Our House at the Beach W-504 Beautifully renovated, Gulf...

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $213 to $251/night

    15 SS Cottage- Close to Beach and Village

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pets OK
    Prime Now
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $235 to $329/night

    Jamaica Royale 074 Close to the pool!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $157 to $270/night

    Midnight Cove II 614F- Beautiful Bayside Location!

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    Prime Now
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $157 to $270/night

    Midnight Cove II 830F- Marina View!

    2 Bedrooms1.5  BathroomSleeps 4
    2 nights minstay
    Pool
    Prime Now
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $305 to $472/night

    24 Aloha Kai-Full Gulf Front!

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $133 to $238/night

    Sunset Royale- 308- Stunning Sunset Views

    1 Bedroom BathroomSleeps 2
    2 nights minstay
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $179 to $290/night

    Midnight Cove II 941C- Wow! That View!

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    Prime Now
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $197 to $279/night

    Aloha Kai- Unit 50-close to the pool!

    2 Bedrooms1.5  BathroomSleeps 6
    2 nights minstay
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $345 to $628/night

    313-315 Canal Rd- Awesome village location!

    4 BedroomsBathroomsSleeps 14
    2 nights minstay
    Pets OK
    Prime Now
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $157 to $225/night

    Gulf Holiday Unit 12- Close to Beach and Siesta Key Vill...

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    Prime Now
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $954 to $1,707/night

    309-315 Canal Rd- Awesome village location!

    8 BedroomsBathroomsSleeps 24
    2 nights minstay
    Pets OK
    Prime Now
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $157 to $238/night

    Jamaica Royale 006 close to the beach!

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    Prime Now
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $126 to $198/night

    Jamaica Royale 009 Updated and across from pool!

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    Prime Now
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $235 to $329/night

    Jamaica Royale 010 Updated, close to the beach & by ...

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $138 to $238/night

    Jamaica Royale 019 Close to the Pool!

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    Prime Now
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $144 to $237/night

    Jamaica Royale 039 Updated and close to the pool!

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    Prime Now
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $138 to $198/night

    Jamaica Royale 008 close to the pool & beach!

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    Prime Now
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $157 to $281/night

    Jamaica Royale 033 Close to pool!

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
    Pool
    Prime Now
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $144 to $237/night

    Jamaica Royale 048 Updated and close to the pool!

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    Prime Now
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $144 to $241/night

    Jamaica Royale 044 Nicely updated!

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool
    Prime Now
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $242 to $428/night

    Gulf and Bay Club- A604 Beautifully Updated w/ Gulf View...

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    Prime Now
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $138 to $198/night

    Jamaica Royale 014 Close to pool & Beach!

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    Prime Now
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $226 to $329/night

    Jamaica Royale 076 Beautiful & Close to the pool!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $126 to $190/night

    Jamaica Royale 031 Nicely Updated!

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    Prime Now
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $151 to $238/night

    Jamaica Royale 030 Nicely Updated!

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    Prime Now
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $179 to $247/night

    Aloha Kai- Unit 48-close to the pool!

    1 Bedroom BathroomSleeps 6
    2 nights minstay
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $225 to $410/night

    Gulf and Bay Club- A302 Coastal updates and amazing view...

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    Prime Now
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $225 to $410/night

    Gulf and Bay Club- E306 Updated with amazing views!

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    Prime Now
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $329 to $492/night

    Gulf and Bay Club- B601- Totally renovated with endless ...

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    Prime Now
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $144 to $237/night

    Jamaica Royale 052 Great updates and close to the pool!

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    Prime Now
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $353 to $437/night

    Jamaica Royale T42 Beachfront with Views, Views, Views!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $336 to $507/night

    Jamaica Royale 401 Great views!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $251 to $383/night

    Jamaica Royale T64 Great location!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    Prime Now
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $144 to $237/night

    Jamaica Royale 054 Nice Kitchen and close to the pool!

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    Prime Now
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations