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. $170 to $401/night

    Barge Road 136O9

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pets OK
    FREE CANCELLATION
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  5. $136 to $343/night

    Salty Sands I 402

    1 Bedroom BathroomSleeps 6
    3 nights minstay
    FREE CANCELLATION
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  7. $155 to $638/night

    Crab Cove On The Bay 407

    3 BedroomsBathroomsSleeps 9
    2 nights minstay
    FREE CANCELLATION
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  9. $175 to $462/night

    Thunder Island 10A

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  11. $363 to $1,502/night

    The Charleston 201

    4 BedroomsBathroomsSleeps 14
    2 nights minstay
    FREE CANCELLATION
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  13. $183 to $383/night

    High Point South 3E

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
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  15. $139 to $402/night

    Baltimore's Best Home Away From Home

    2 BedroomsBathroomsSleeps 4
    1 night minstay
  16. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  17. $152 to $454/night

    Sandpiper Dunes 605

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  19. $155 to $286/night

    Harbour Bay 19

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $164 to $478/night

    Crab Cove On The Bay 406

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  23. $104 to $351/night

    Ocean Trail 102

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
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  25. $204 to $467/night

    Sungate 402

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
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  27. $115 to $240/night

    Fountainhead 702

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
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  29. $155 to $391/night

    Sea Jay Townhouse 616C

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $184 to $1,179/night

    Harbour Island 46G

    2 BedroomsBathroomsSleeps 9
    2 nights minstay
    FREE CANCELLATION
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  33. $194 to $411/night

    Thunder Island 43B

    2 BedroomsBathroomsSleeps 7
    3 nights minstay
    FREE CANCELLATION
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  35. $104 to $304/night

    Worcester House 302

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  37. $87 to $240/night

    Mirabella 1D

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
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  39. $170 to $944/night

    Harbour Island 306L

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
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  41. $175 to $578/night

    Ocean Hideaway 508

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
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  43. $115 to $421/night

    Thunder Island 141D

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  45. $155 to $400/night

    Thunder Island 61B

    2 BedroomsBathroomsSleeps 9
    3 nights minstay
    FREE CANCELLATION
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  47. $115 to $266/night

    Montego Bay-Peachtree Road 122

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $146 to $411/night

    Fountain Road Home

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $130 to $329/night

    Braemar 503N

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  53. $130 to $279/night

    Blaire Isle 101N

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
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  55. $130 to $314/night

    Our Place At The Beach 205I

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  57. $199 to $695/night

    Ocean Hideaway 404

    Multiple Units Available
    3 nights minstay
    FREE CANCELLATION
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  59. $140 to $354/night

    Thunder Island 112C

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $140 to $304/night

    Ann Elizabeth 305

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  63. $128 to $704/night

    Harbour Island 402L

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
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  65. $145 to $427/night

    Bimini 107

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $97 to $252/night

    Jockey Beach 378

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $155 to $377/night

    Harbour Bay 34

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
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  71. $194 to $779/night

    Ocean's Edge 403

    3 BedroomsBathroomsSleeps 10
    2 nights minstay
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $184 to $677/night

    Harbour Island 403L

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
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  75. $161 to $830/night

    Harbour Island 304K

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
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  77. $375 to $983/night

    Family Tides- 311- 139th Street

    4 Bedrooms3.5 BathroomsSleeps 12
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $87 to $251/night

    Orleans Court 224

    1 Bedroom BathroomSleeps 6
    3 nights minstay
    FREE CANCELLATION
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  81. $98 to $348/night

    Parrot Bay-Key West Cabanas 43

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $90 to $293/night

    Bianchi 1- Ocean City, MD

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $146 to $331/night

    Nanticoke Square 207B

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $107 to $343/night

    Towers 401

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $127 to $274/night

    Bay Colony 16

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  91. $252 to $638/night

    Twin Tree Road 511

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $179 to $320/night

    Atlantic View 101

    2 BedroomsBathroomsSleeps 7
    3 nights minstay
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $329 to $797/night

    Amber Waves 300

    3 BedroomsBathroomsSleeps 10
    3 nights minstay
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $150 to $241/night

    The Lodge at Wisp-Deluxe Apartment Sleeps 4

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $399 to $948/night

    Leo Farm Villa- Beautiful Country Retreat

    5 BedroomsBathroomsSleeps 10
    1 night minstay
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $164 to $398/night

    Dune Mist I 102

    3 BedroomsBathroomsSleeps 12
    2 nights minstay
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $182 to $414/night

    Beach Place 7

    2 Bedrooms BathroomSleeps 8
    3 nights minstay
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $213 to $670/night

    Ocean Hideaway 503

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $153 to $321/night

    Club Ocean Villas II 88

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $127 to $294/night

    Montego Bay-South Ocean Drive 203

    3 Bedrooms BathroomSleeps 8
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $204 to $1,610/night

    Harbour Island 21C

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $184 to $558/night

    Towers 402

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $116 to $297/night

    Bridgepoint II 5D

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $581 to $1,297/night

    Pilot House 5

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $285 to $1,332/night

    Ocean Club 4011

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $76 to $220/night

    Shore Lea 102

    1 Bedroom BathroomSleeps 5
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $108 to $358/night

    Severn I 208

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $194 to $869/night

    Ocean's Edge 401

    3 BedroomsBathroomsSleeps 10
    3 nights minstay
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $204 to $524/night

    Alameda 5- Ocean City, MD

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $291 to $592/night

    Century I 1621

    2 BedroomsBathroomsSleeps 7
    3 nights minstay
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $232 to $1,570/night

    Harbour Island 305L

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $503 to $592/night

    Ocean Place 315

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $165 to $457/night

    Waterfront Baltimore 2BR Furnished Apartment

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub Pets OK
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $164 to $426/night

    Parrot Bay-Key Lime 7

    3 Bedrooms1.5  BathroomSleeps 10
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $230 to $454/night

    Ocean Hideaway 406

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $171 to $262/night

    The Lodge at Wisp-Standard Apt 1 BDRM Q Sleeps 4

    Multiple Units Available
    1 night minstay
    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-1 BDRM King Apartment Sleeps 4

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $150 to $241/night

    The Lodge at Wisp-Studio Apt Efficiency Sleeps 4

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $110 to $336/night

    High Point South 3F

    1 Bedroom BathroomSleeps 6
    3 nights minstay
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $76 to $381/night

    Barge Road 136O5

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $193 to $336/night

    Beachcrest 17

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $170 to $291/night

    Tranquil Getaway In Gated Community- Free Wifi and lapto...

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pets OK
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $118 to $258/night

    Inner Harbor's Best Luxury Furnished Apartments

    Studio BathroomSleeps 2
    1 night minstay
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $139 to $484/night

    Hobbit House on a Gentleman's Farm

    3 Bedrooms BathroomSleeps 6
    1 night minstay
    Pets OK
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $164 to $631/night

    Diamond Beach 414

    3 BedroomsBathroomsSleeps 10
    2 nights minstay
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $153 to $493/night

    Constellation House 510

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $130 to $210/night

    Surf Haven 202

    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. $163 to $317/night

    Harbour Club B16

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $237 to $659/night

    Ocean Hideaway 205

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $251 to $473/night

    Tunnel Avenue Home

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $136 to $290/night

    Seascape-Heron Harbour 200-9

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $175 to $554/night

    Ocean Hideaway 211

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $109 to $308/night

    Polynesian 502

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $175 to $414/night

    Oceana II 406

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $197 to $460/night

    Thunder Island 161D

    2 BedroomsBathroomsSleeps 7
    3 nights minstay
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $109 to $253/night

    Seatime 303S

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $175 to $470/night

    Surfside 60 Unit 303

    3 BedroomsBathroomsSleeps 10
    2 nights minstay
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $175 to $377/night

    Gullway Townhouse 2821

    3 Bedrooms BathroomSleeps 8
    3 nights minstay
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $184 to $386/night

    Holiday Cottage

    3 Bedrooms BathroomSleeps 10
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $110 to $344/night

    Harbour Bay 23

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $130 to $253/night

    Jamaica II 208

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $388 to $728/night

    Braemar 1801S

    3 BedroomsBathroomsSleeps 9
    3 nights minstay
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $129 to $296/night

    Inner Harbor's Best Furnished Luxury Apartments

    1 Bedroom BathroomSleeps 2
    1 night minstay
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $152 to $478/night

    Bimini 106

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $113 to $301/night

    Jamaica Bay 307A

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