Viewing 40 of 54 rentals in Winter Park
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Vacation homes - vacation rentals
27 Vacation rentals
from $2,863 / night
$20,038 / week
from $190 / night
$1,338 - $8,323 / week
from $407 / night
$2,853 - $12,363 / week
from $184 / night
$1,145 / week
from $215 / night
$1,506 - $6,051 / week
from $94 / night
$665 - $3,189 / week
from $172 / night
$1,145 / week
from $227 / night
$1,591 - $5,714 / week
from $275 / night
$1,927 - $10,007 / week
from $263 / night
$1,843 - $9,249 / week
from $573 / night
$4,008 / week
from $287 / night
$2,011 - $10,007 / week
from $155 / night
$1,086 - $6,051 / week
from $142 / night
$1,001 - $5,546 / week
from $227 / night
$1,591 - $5,546 / week
from $155 / night
$1,086 - $6,219 / week
from $118 / night
$833 - $2,937 / week
from $172 / night
$1,374 / week
from $215 / night
$1,506 - $7,060 / week
from $149 / night
$1,042 / week
from $190 / night
$1,338 - $6,304 / week
from $155 / night
$1,086 - $6,304 / week
from $142 / night
$1,001 - $5,041 / week
from $250 / night
$1,748 / week
from $359 / night
$2,516 - $12,615 / week
from $147 / night
$1,026 / week
from $476 / night
$3,327 / week
Great rentals within 20 miles that match your search
from $231 / night
$1,450 - $1,851 / week
from $144 / night
$853 - $2,027 / week
from $288 / night
$1,714 - $5,236 / week
from $195 / night
$1,363 / week
from $132 / night
$922 / week
from $1,373 / night
$9,610 / week
from $413 / night
$2,886 / week
from $218 / night
$1,306 - $1,466 / week
from $212 / night
$1,317 / week
from $132 / night
$831 - $1,804 / week
from $205 / night
$1,431 / week
from $194 / night
$1,355 / week
from $195 / night
$1,260 / week