Good morning Baltimore! Home of the Baltimore Ravens and the Chesapeake Bay, Maryland is an absolutely gorgeous place to vacation no matter what time of year. Visit some of the most beautiful beaches and breathtaking mountains in the country, or enjoy some live theatre and some o' Maryland's famous blue crabs. Whatever tickles your fancy, RedAwning has the vacation rental for you. Browse your favorite Baltimore region using the blue location links below, or filter your preferences using the panel on the side. With our simplified booking process you'll have the most important part of your trip buttoned in no time.

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  1. $211 to $332/night

    The Lodge at Wisp-1 BDRM Luxury Apartment Sleeps 4

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
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  3. $363 to $1,502/night

    The Charleston 201

    4 BedroomsBathroomsSleeps 14
    2 nights minstay
    FREE CANCELLATION
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  5. $152 to $454/night

    Sandpiper Dunes 605

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  7. $155 to $286/night

    Harbour Bay 19

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  9. $164 to $478/night

    Crab Cove On The Bay 406

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  11. $204 to $467/night

    Sungate 402

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
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  13. $115 to $240/night

    Fountainhead 702

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
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  15. $194 to $411/night

    Thunder Island 43B

    2 BedroomsBathroomsSleeps 7
    3 nights minstay
    FREE CANCELLATION
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  17. $104 to $304/night

    Worcester House 302

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  19. $140 to $304/night

    Ann Elizabeth 305

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  21. $145 to $427/night

    Bimini 107

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
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  23. $179 to $320/night

    Atlantic View 101

    2 BedroomsBathroomsSleeps 7
    3 nights minstay
    FREE CANCELLATION
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  25. $329 to $797/night

    Amber Waves 300

    3 BedroomsBathroomsSleeps 10
    3 nights minstay
    FREE CANCELLATION
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  27. $150 to $241/night

    The Lodge at Wisp-Deluxe Apartment Sleeps 4

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
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  29. $164 to $398/night

    Dune Mist I 102

    3 BedroomsBathroomsSleeps 12
    2 nights minstay
    FREE CANCELLATION
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  31. $182 to $414/night

    Beach Place 7

    2 Bedrooms BathroomSleeps 8
    3 nights minstay
    FREE CANCELLATION
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  33. $213 to $670/night

    Ocean Hideaway 503

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
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  35. $153 to $321/night

    Club Ocean Villas II 88

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  37. $127 to $294/night

    Montego Bay-South Ocean Drive 203

    3 Bedrooms BathroomSleeps 8
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $204 to $1,610/night

    Harbour Island 21C

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
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  41. $184 to $558/night

    Towers 402

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
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  43. $116 to $297/night

    Bridgepoint II 5D

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $581 to $1,297/night

    Pilot House 5

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
    FREE CANCELLATION
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  47. $285 to $1,332/night

    Ocean Club 4011

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
    Pets OK
    FREE CANCELLATION
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  49. $76 to $220/night

    Shore Lea 102

    1 Bedroom BathroomSleeps 5
    3 nights minstay
    Pets OK
    FREE CANCELLATION
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  51. $108 to $358/night

    Severn I 208

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $194 to $869/night

    Ocean's Edge 401

    3 BedroomsBathroomsSleeps 10
    3 nights minstay
    FREE CANCELLATION
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  55. $204 to $524/night

    Alameda 5- Ocean City, MD

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $232 to $1,570/night

    Harbour Island 305L

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
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  59. $164 to $426/night

    Parrot Bay-Key Lime 7

    3 Bedrooms1.5  BathroomSleeps 10
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $175 to $462/night

    Thunder Island 10A

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  63. $104 to $351/night

    Ocean Trail 102

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
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  65. $155 to $400/night

    Thunder Island 61B

    2 BedroomsBathroomsSleeps 9
    3 nights minstay
    FREE CANCELLATION
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  67. $115 to $421/night

    Thunder Island 141D

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  69. $115 to $266/night

    Montego Bay-Peachtree Road 122

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $155 to $391/night

    Sea Jay Townhouse 616C

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $146 to $411/night

    Fountain Road Home

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $130 to $329/night

    Braemar 503N

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $184 to $1,179/night

    Harbour Island 46G

    2 BedroomsBathroomsSleeps 9
    2 nights minstay
    FREE CANCELLATION
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  79. $87 to $240/night

    Mirabella 1D

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $170 to $944/night

    Harbour Island 306L

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $175 to $578/night

    Ocean Hideaway 508

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $194 to $779/night

    Ocean's Edge 403

    3 BedroomsBathroomsSleeps 10
    2 nights minstay
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $130 to $279/night

    Blaire Isle 101N

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $130 to $314/night

    Our Place At The Beach 205I

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $199 to $695/night

    Ocean Hideaway 404

    Multiple Units Available
    3 nights minstay
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $140 to $354/night

    Thunder Island 112C

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $128 to $704/night

    Harbour Island 402L

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $170 to $401/night

    Barge Road 136O9

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $161 to $830/night

    Harbour Island 304K

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
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  101. $375 to $983/night

    Family Tides- 311- 139th Street

    4 Bedrooms3.5 BathroomsSleeps 12
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $87 to $251/night

    Orleans Court 224

    1 Bedroom BathroomSleeps 6
    3 nights minstay
    FREE CANCELLATION
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  105. $183 to $383/night

    High Point South 3E

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $136 to $343/night

    Salty Sands I 402

    1 Bedroom BathroomSleeps 6
    3 nights minstay
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $97 to $252/night

    Jockey Beach 378

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $155 to $377/night

    Harbour Bay 34

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $155 to $638/night

    Crab Cove On The Bay 407

    3 BedroomsBathroomsSleeps 9
    2 nights minstay
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $184 to $677/night

    Harbour Island 403L

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $98 to $348/night

    Parrot Bay-Key West Cabanas 43

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $90 to $293/night

    Bianchi 1- Ocean City, MD

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $146 to $331/night

    Nanticoke Square 207B

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $107 to $343/night

    Towers 401

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $252 to $638/night

    Twin Tree Road 511

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $127 to $274/night

    Bay Colony 16

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $139 to $387/night

    Baltimore's Best Home Away From Home

    2 BedroomsBathroomsSleeps 4
    1 night minstay
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $291 to $592/night

    Century I 1621

    2 BedroomsBathroomsSleeps 7
    3 nights minstay
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $399 to $944/night

    Leo Farm Villa- Beautiful Country Retreat

    5 BedroomsBathroomsSleeps 10
    1 night minstay
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $503 to $592/night

    Ocean Place 315

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $230 to $454/night

    Ocean Hideaway 406

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $165 to $457/night

    Waterfront Baltimore 2BR Furnished Apartment

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub Pets OK
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $181 to $671/night

    Delightful Pet Friendly Family Home In Great Location

    4 BedroomsBathroomsSleeps 9
    1 night minstay
    Pets OK
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $191 to $282/night

    The Lodge at Wisp-One-BDRM Apartment Sleeps 6

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $109 to $554/night

    Eagle Bay 204

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $405 to $788/night

    Harbour Island 403M

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $173 to $434/night

    Barefoot Country 508

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $155 to $288/night

    Jada 4H- Ocean City, MD

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $136 to $336/night

    Seascape-Heron Harbour 204-4

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $133 to $408/night

    Sea Watch 1319

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $99 to $247/night

    Breakaway East 109

    1 Bedroom BathroomSleeps 6
    3 nights minstay
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $182 to $723/night

    Harbour Island 102M

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $470 to $1,004/night

    Bel Mare 100

    4 BedroomsBathroomsSleeps 14
    3 nights minstay
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $127 to $343/night

    Surf Crest 103

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $99 to $279/night

    Barefoot Country 304

    1 Bedroom BathroomSleeps 6
    3 nights minstay
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $329 to $987/night

    Bahia Vista I 508

    4 BedroomsBathroomsSleeps 12
    2 nights minstay
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $176 to $316/night

    Beachmark 3D

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $243 to $444/night

    Surfwood 203

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $130 to $304/night

    Worcester House 503

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $109 to $340/night

    Sunrise Sea 308

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $146 to $365/night

    Marigot Beach 407

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $109 to $434/night

    Century I 702

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $268 to $838/night

    Ocean Hideaway 111

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $230 to $434/night

    Bonaire 404

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $170 to $624/night

    High Point South 1C

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $204 to $570/night

    Irene 506- Ocean City, MD

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $146 to $400/night

    Thunder Island 157D

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $115 to $271/night

    Bay Vista 102

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $194 to $478/night

    Atlantis 909

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $164 to $320/night

    Baywatch III 302A

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $159 to $434/night

    Thunder Island 7A

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $291 to $797/night

    Beachwalk II 12

    4 BedroomsBathroomsSleeps 14
    2 nights minstay
    FREE CANCELLATION
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations