Welcome to Hawaii! Paradise on earth! RedAwning has the perfect vacation rental for your island adventures. Beach bungalows, resort condos, and sun-kissed ocean-front villas await. Browse your island destination using the blue location links below or filter your preferences using the panel to the side. RedAwning offers easy, instant, hotel-style reservations and a simplified booking process so you can have your vacation plans covered in no time.

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  1. $1,688 to $2,250/night

    Hale Lahaina

    4 Bedrooms5.5 BathroomsSleeps 10
    5 nights minstay
    Pool
    FREE CANCELLATION
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  3. $225 to $281/night

    Koa Resort #4F

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
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  5. $214 to $332/night

    Bay Villa 33B2

    1 Bedroom1.5  BathroomSleeps 4
    4 nights minstay
    Pool
  6. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  7. $276 to $366/night

    Kahana Sunset B3

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  8. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  9. $186 to $214/night

    Kahana Sunset B3B

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
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  11. $276 to $332/night

    Kahana Sunset C7

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
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  13. $253 to $309/night

    Kahana Sunset D10

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
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  15. $428 to $484/night

    Kahana Sunset F4

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  16. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  17. $276 to $332/night

    Kahana Sunset D2

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
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  19. $501 to $619/night

    Sands Of Kahana 474

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $428 to $484/night

    Kahana Sunset F2

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
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  23. $371 to $484/night

    Kahana Sunset F6

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $236 to $332/night

    Mahana At Kaanapali 306

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
  26. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  27. $193 to $359/night

    Kaanapali Shores Studio 642

    Studio BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $330 to $513/night

    Aina Nalu D202

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $146 to $163/night

    Koa Resort #2C

    2 Bedrooms BathroomSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $175 to $449/night

    Maui Eldorado Condo G101

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  34. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  35. $336 to $806/night

    Maui Eldorado Condo D100

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
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  37. $309 to $394/night

    Kahana Sunset B7

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $197 to $309/night

    Ridge Villa 1422

    1 BedroomBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $177 to $225/night

    Lovely Condo with Pool & Hot Tub! Waikoloa Hills Uni...

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $270 to $366/night

    Golf Villa 25V1

    1 Bedroom1.5  BathroomSleeps 4
    1 night minstay
    Pool
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $201 to $277/night

    Kihei Beach, #107

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $201 to $277/night

    KIHEI BEACH, #307

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $201 to $277/night

    KIHEI BEACH, #404

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $201 to $277/night

    KIHEI BEACH, #406^

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $201 to $277/night

    KIHEI BEACH, #407

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $263 to $378/night

    KIHEI BEACH, #409

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $201 to $348/night

    SUGAR BEACH RESORT, #329

    1 Bedroom BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $312 to $453/night

    WAILEA ELUA, #2101*

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $201 to $277/night

    KIHEI BEACH, #405

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $201 to $277/night

    KIHEI BEACH, #207

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $201 to $277/night

    Kihei Beach, #603^

    1 Bedroom BathroomSleeps 3
    5 nights minstay
    Pool
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $293 to $403/night

    Kihei Beach, #501

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $217 to $293/night

    KIHEI BEACH, #606

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $263 to $474/night

    MAALAEA SURF, #G-7

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $328 to $484/night

    KAMAOLE NALU, #105

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $253 to $364/night

    KAMAOLE NALU, #303

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $253 to $364/night

    KAMAOLE NALU, #503

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $328 to $484/night

    KAMAOLE NALU, #605

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $706 to $984/night

    MAKENA SURF RESORT, #G-104

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $312 to $455/night

    ROYAL MAUIAN, #516

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $470 to $770/night

    WAILEA ELUA, #2003

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $429 to $807/night

    WAILEA ELUA, #2106

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $207 to $403/night

    Kihei Surfside, #211

    1 Bedroom1.5  BathroomSleeps 4
    5 nights minstay
    Pool
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $837 to $1,313/night

    WAILEA ELUA, #1204^

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $837 to $1,313/night

    WAILEA ELUA, #1702

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $550 to $651/night

    ROYAL MAUIAN, #518^

    3 BedroomsBathroomsSleeps 7
    5 nights minstay
    Pool
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $494 to $908/night

    WAILEA ELUA, #0702

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $651 to $959/night

    WAILEA ELUA, #2304

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $207 to $403/night

    KIHEI SURFSIDE, #612

    1 Bedroom1.5  BathroomSleeps 4
    5 nights minstay
    Pool
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $253 to $364/night

    KAMAOLE NALU, #602

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $192 to $309/night

    KAMAOLE NALU, #201

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $482 to $780/night

    WAILEA ELUA, #0302

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $272 to $394/night

    ROYAL MAUIAN, #219

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $651 to $959/night

    WAILEA ELUA, #2204*

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $292 to $426/night

    Great Summer Price! Close to the Beaches & Shopping!...

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $590 to $893/night

    Sands of Kahana 282

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $355 to $617/night

    Royal Kahana 101 2 bdr/2ba OV

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $276 to $332/night

    Kahana Sunset D8

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $516 to $620/night

    2 Bedrooms Oceanfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $278 to $341/night

    Junior Suite Oceanfront #403

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $341 to $413/night

    1 Bedroom Oceanfront #804

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $278 to $341/night

    Junior Suite Oceanfront #906

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $114 to $136/night

    Discovery Bay 2712

    1 Bedroom BathroomSleeps 4
    30 nights minstay
    Pool
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $2,900 to $5,568/night

    Wailea Inn Maui

    14 Bedrooms13 BathroomsSleeps 32
    2 nights minstay
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $109 to $131/night

    Kepuhi Beach 1234

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $131 to $152/night

    Kepuhi Beach Resort 2222

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $109 to $131/night

    Kepuhi Beach 1192

    Studio BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $147 to $190/night

    Ke Nani Kai 237

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $109 to $131/night

    Kepuhi Beach 1182

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $218 to $326/night

    Hale Hiamoe

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $163 to $218/night

    Ke Nani Kai 218

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $136 to $163/night

    Hotel Molokai 201

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $147 to $163/night

    Ke Nani Kai 113

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $147 to $179/night

    Ke Nani Kai 239

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $109 to $131/night

    Kepuhi Beach 1226

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $109 to $147/night

    Wavecrest B209

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $201 to $245/night

    Molokai Shores 234

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $125 to $163/night

    Wavecrest A203

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $312 to $352/night

    ROYAL MAUIAN, #208^

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $253 to $365/night

    KAMAOLE NALU, #104

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $201 to $348/night

    SUGAR BEACH RESORT, #518^

    1 Bedroom BathroomSleeps 2
    7 nights minstay
    Pool Hot Tub
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $437 to $627/night

    ROYAL MAUIAN, #315

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $464 to $806/night

    WAILEA ELUA, #1601

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $114 to $140/night

    Discovery Bay 3220

    1 Bedroom BathroomSleeps 2
    30 nights minstay
    Pool
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $106 to $167/night

    Discovery Bay 1815

    1 Bedroom BathroomSleeps 2
    30 nights minstay
    Pool
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $146 to $174/night

    Discovery Bay 1202

    1 Bedroom BathroomSleeps 4
    30 nights minstay
    Pool
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $133 to $154/night

    Discovery Bay 1309

    1 Bedroom BathroomSleeps 4
    30 nights minstay
    Pool
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $146 to $174/night

    Discovery Bay 2514

    1 Bedroom BathroomSleeps 2
    30 nights minstay
    Pool
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $101 to $131/night

    Discovery Bay 3615

    1 Bedroom BathroomSleeps 2
    30 nights minstay
    Pool
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $203 to $270/night

    Discovery Bay 1611

    2 BedroomsBathroomsSleeps 4
    30 nights minstay
    Pool
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $114 to $136/night

    Discovery Bay 4012

    1 Bedroom BathroomSleeps 4
    30 nights minstay
    Pool
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $79 to $114/night

    Discovery Bay 2016

    1 Bedroom BathroomSleeps 2
    30 nights minstay
    Pool
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $203 to $270/night

    Discovery Bay 2311

    2 BedroomsBathroomsSleeps 6
    30 nights minstay
    Pool
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $94 to $151/night

    Discovery Bay 3308

    1 Bedroom BathroomSleeps 4
    30 nights minstay
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $249 to $302/night

    Unit 214

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $302 to $354/night

    Unit 311

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $196 to $284/night

    Unit 213

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $196 to $284/night

    Unit 109

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