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. $163 to $319/night

    Tiffanie by the Sea 319D

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
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  3. $154 to $344/night

    Thunder Island 75B

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
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  5. $130 to $694/night

    Ocean Hideaway 205

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
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  7. $175 to $562/night

    Ocean Hideaway 211

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
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  9. $153 to $272/night

    Seabay Vista II 304

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
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  11. $152 to $306/night

    Club Ocean Villas II 182

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
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  13. $175 to $383/night

    Gullway Townhouse 2834

    3 Bedrooms BathroomSleeps 8
    3 nights minstay
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  15. $175 to $499/night

    Constellation House 510

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
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  17. $152 to $351/night

    Mariner's Wharf 105

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
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  19. $175 to $1,510/night

    Harbour Island 22C

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
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  21. $130 to $256/night

    Jamaica II 208

    1 Bedroom BathroomSleeps 4
    2 nights minstay
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  23. $152 to $296/night

    Club Ocean Villas II 25

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
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  25. $175 to $356/night

    Barge Road 13609

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pets OK
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  27. $163 to $357/night

    Thunder Island 16A

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
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  29. $109 to $217/night

    Bayshore West 24

    1 Bedroom BathroomSleeps 6
    2 nights minstay
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  31. $121 to $285/night

    Barracuda 2

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pets OK
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  33. $109 to $314/night

    Polynesian 502

    1 Bedroom BathroomSleeps 4
    2 nights minstay
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  35. $281 to $612/night

    Braemar 1801S

    3 BedroomsBathroomsSleeps 9
    3 nights minstay
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  37. $167 to $788/night

    Barge Road 13605

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pets OK
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  39. $109 to $256/night

    Seatime 303S

    1 Bedroom BathroomSleeps 6
    2 nights minstay
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  41. $130 to $211/night

    Surf Haven 202

    1 Bedroom BathroomSleeps 4
    3 nights minstay
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  43. $120 to $356/night

    Kelly Road 710

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pets OK
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  45. $141 to $433/night

    Capri 1908

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
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  47. $109 to $351/night

    Harbour Bay 23

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
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  49. $130 to $281/night

    Royal Palm Court 1208-10

    2 Bedrooms BathroomSleeps 8
    2 nights minstay
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  51. $506/night

    Sparkling Bayfront Condo w/ Pool- Walk to Beach

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
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  53. $155 to $471/night

    Casa Rosa Getaway in Parrot Bay with Pool

    2 Bedrooms BathroomSleeps 7
    2 nights minstay
    Pool Pets OK
    FREE CANCELLATION
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  55. $141 to $450/night

    Coastal Getaway at the Vintage with Ocean Views

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
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  57. $128 to $424/night

    Bayside Getaway with Pool | Walk to Beach & Dining

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  59. $827/night

    9th Street Beach Retreat | 4 Private Units

    10 BedroomsBathroomsSleeps 32
    2 nights minstay
    FREE CANCELLATION
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  61. $235 to $561/night

    Sandy Cheeks | Balcony, Pool & Private Beach

    3 Bedrooms2.5 BathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
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  63. $471 to $996/night

    Ocean-View El Capitan Escape | 2 Balconies & Pool

    2 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pool
    FREE CANCELLATION
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  65. $223/night

    Beach House | Unit 8 | Top-Floor Ocean Peek

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
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  67. $623/night

    Beach House | Unit 7 | 2.5 Blocks to Pier & Beach

    3 BedroomsBathroomsSleeps 10
    2 nights minstay
    FREE CANCELLATION
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  69. $136 to $294/night

    Seascape-Heron Harbour 200-9

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
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  71. $175 to $484/night

    Bimini 106

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
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  73. $145 to $339/night

    High Point South 3F

    1 Bedroom BathroomSleeps 6
    3 nights minstay
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  75. $231 to $289/night

    2BR Furnished Apartment in Baltimore Downtown

    2 BedroomsBathroomsSleeps 5
    1 night minstay
    Pets OK
    FREE CANCELLATION
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  77. $193 to $694/night

    Ocean Hideaway 607

    Multiple Units Available
    2 nights minstay
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  79. $87 to $256/night

    Ocean Princess 207

    1 Bedroom BathroomSleeps 4
    2 nights minstay
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  81. $121 to $285/night

    Barracuda 1

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pets OK
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  83. $175 to $383/night

    Gullway Townhouse 2821

    3 Bedrooms BathroomSleeps 8
    3 nights minstay
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  85. $175 to $420/night

    Oceana II 406

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
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  87. $195 to $407/night

    Holiday Cottage

    3 Bedrooms BathroomSleeps 10
    3 nights minstay
    Pets OK
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  89. $127 to $292/night

    Summer Winds 202E

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
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  91. $76 to $179/night

    Westward Ho 408

    Studio BathroomSleeps 5
    2 nights minstay
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  93. $113 to $253/night

    Jamaica Bay 307A

    1 Bedroom BathroomSleeps 6
    2 nights minstay
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  95. $132 to $280/night

    New Listing! Cozy Canal-Side Condo, Walk to Beach

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $124 to $392/night

    Canal-Front Condo w/ Pools & Walkable Locale

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  99. $142 to $443/night

    Ocean & Bay-View Condo with Pool, Easy Beach Access!...

    2 Bedrooms1.5  BathroomSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  101. $136 to $608/night

    Lovely Waterfront Condo with Balcony, Near Beach!

    3 Bedrooms3.5 BathroomsSleeps 9
    3 nights minstay
    FREE CANCELLATION
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  103. $56 to $358/night

    Ocean Pines Hideaway near Beach, Pools & Golf

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  105. $291 to $495/night

    Coastal Getaway with 2 Living Areas, Walk to Beach

    4 Bedrooms2.5 BathroomsSleeps 10
    2 nights minstay
    FREE CANCELLATION
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  107. $176 to $482/night

    Bayfront Bliss | Rooftop Pool | Short Walk to Beach

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
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  109. $135 to $398/night

    Bayside Retreat with Pool, Walk to Beach & Dining

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $169 to $488/night

    Bayfront Condo with Updated Decor, Balcony & Shared ...

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  113. $151 to $483/night

    Stylish Beachfront Condo with Pool- Steps to Sand

    3 Bedrooms2.5 BathroomsSleeps 9
    2 nights minstay
    Pool
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $293 to $534/night

    Waterfront Ocean Pines Home with Private Dock

    5 Bedrooms3.5 BathroomsSleeps 10
    3 nights minstay
    FREE CANCELLATION
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  117. $143 to $306/night

    Summer Winds Condo | Pool & Grill, Walk to Beach

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $349 to $1,089/night

    Oceanfront Oasis with 3 Big Decks | Steps to Beach

    4 BedroomsBathroomsSleeps 13
    3 nights minstay
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $177 to $439/night

    Updated Oceanfront Patio Condo at the Colonial

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $181 to $371/night

    Bayside Gem with Deck, Canal Views & Pool

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  125. $168 to $541/night

    Montego Bay Retreat | Pools, Mini-Golf & Tennis

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pool
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $276 to $503/night

    Top-Floor Corner Condo | Balcony & Ocean Views

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $194 to $548/night

    Ocean-Side at The Waves | Balcony, Walk to Beach

    3 BedroomsBathroomsSleeps 9
    2 nights minstay
    Pool
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $183 to $674/night

    Canvasback | Beachside Getaway | Stroll to Dining

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $226 to $890/night

    The Gateway Grand | Oceanfront Condo | 2 Pools

    3 BedroomsBathroomsSleeps 8
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $186 to $421/night

    Montego Bay Gem | 2 Pools, Putt-Putt, Walk to Beach

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $293 to $568/night

    Private Bay-View Getaway with Pool | Walk to Beach

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $578 to $1,087/night

    Spacious Home | Office & Game Room | Near Beach

    5 Bedrooms3.5 BathroomsSleeps 20
    3 nights minstay
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $182 to $385/night

    Bay-View Beach Condo | Balconies, Fireplace, Pool

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $224 to $429/night

    Top-Floor Condo | Balcony, Walk 1 Minute to Beach!

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $304 to $699/night

    Bay-View Beach Duo | 3 Balconies, Fireplace & Pool

    4 BedroomsBathroomsSleeps 14
    2 nights minstay
    Pool
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $182 to $385/night

    Bay-View Beach Retreat | Balconies | Walk to Beach

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $143 to $331/night

    Updated Colonial Condo | Patio | 200’ to Beach

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $180 to $406/night

    Thunder Island 161D

    2 BedroomsBathroomsSleeps 7
    3 nights minstay
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $152 to $382/night

    Ocean Hideaway 206

    Multiple Units Available
    2 nights minstay
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $164 to $320/night

    Harbour Club B16

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $170 to $212/night

    Waterside Six 302

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $195 to $473/night

    Sungate 402

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $184 to $357/night

    High Point South 1F

    1 Bedroom BathroomSleeps 6
    2 nights minstay
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $131 to $423/night

    Bimini 107

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $164 to $397/night

    Beach Place 7

    2 Bedrooms BathroomSleeps 8
    3 nights minstay
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $206 to $667/night

    Ocean Hideaway 503

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $76 to $194/night

    Jockey Beach 330

    1 Bedroom BathroomSleeps 6
    365 nights minstay
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $152 to $553/night

    Sandpiper Dunes 506

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $175 to $383/night

    Thunder Island 10A

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $157 to $396/night

    Fountain Road 13701

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pets OK
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $184 to $610/night

    Ocean Hideaway 404

    Multiple Units Available
    2 nights minstay
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $109 to $321/night

    Frogs F4

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pets OK
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $186 to $586/night

    Ocean Hideaway 508

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $148 to $323/night

    Atlantic View 101

    2 BedroomsBathroomsSleeps 7
    3 nights minstay
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $321 to $578/night

    Century I 1621

    2 BedroomsBathroomsSleeps 7
    3 nights minstay
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $141 to $379/night

    Thunder Island 61B

    2 BedroomsBathroomsSleeps 9
    3 nights minstay
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $302 to $1,081/night

    Harbour Island 308M

    3 BedroomsBathroomsSleeps 10
    3 nights minstay
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $134 to $337/night

    Sunset Bay 417

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $130 to $319/night

    Our Place At The Beach 205I

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $194 to $355/night

    Jamaican Sun 203

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $562 to $1,383/night

    Harbour Island 69J

    3 BedroomsBathroomsSleeps 10
    2 nights minstay
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $175 to $509/night

    Crab Cove On The Bay 406

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations