Viewing 40 of 436 rentals in Winter Park
Tell us your dates, and we will find the most accurate rates and availability for you
Updating
Vacation homes - vacation rentals
289 Vacation rentals
from $2,863 / night
$20,038 / week
from $117 / night
$818 / week
from $207 / night
$1,443 / week
from $172 / night
$1,145 / week
from $224 / night
$1,563 / week
from $172 / night
$1,374 / week
from $239 / night
$1,674 - $9,670 / week
from $186 / night
$1,299 / week
from $334 / night
$2,333 / week
from $132 / night
$922 / week
from $250 / night
$1,748 / week
from $147 / night
$1,026 / week
from $134 / night
$938 / week
from $134 / night
$938 / week
from $147 / night
$1,026 / week
from $132 / night
$922 / week
from $147 / night
$1,026 / week
from $135 / night
$945 / week
from $191 / night
$1,337 / week
from $103 / night
$721 / week
from $150 / night
$1,050 / week
from $95 / night
$665 / week
from $274 / night
$1,918 / week
from $263 / night
$1,841 / week
from $139 / night
$973 / week
from $150 / night
$1,050 / week
from $291 / night
$2,037 / week
from $187 / night
$1,309 / week
from $517 / night
$3,619 / week
from $231 / night
$1,617 / week
from $135 / night
$945 / week
from $187 / night
$1,309 / week
from $325 / night
$2,275 / week
from $161 / night
$1,127 / week
from $193 / night
$1,351 / week
from $511 / night
$3,577 / week
from $179 / night
$1,253 / week
from $225 / night
$1,575 / week
from $137 / night
$959 / week