Viewing 40 of 539 rentals in Winter Park
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Vacation homes - vacation rentals
292 Vacation rentals
from $142 / night
$1,001 - $5,041 / week
from $2,863 / night
$20,038 / week
from $190 / night
$1,338 - $8,323 / week
from $179 / night
$1,254 - $5,041 / week
from $275 / night
$1,927 - $9,838 / week
from $179 / night
$1,254 - $5,967 / week
from $419 / night
$2,937 - $13,709 / week
from $311 / night
$2,179 - $12,278 / week
from $479 / night
$3,358 - $13,878 / week
from $166 / night
$1,169 - $5,714 / week
from $179 / night
$1,254 - $5,714 / week
from $215 / night
$1,506 - $6,051 / week
from $94 / night
$665 - $3,189 / week
from $166 / night
$1,169 - $5,041 / week
from $227 / night
$1,591 - $5,714 / week
from $311 / night
$2,179 - $11,521 / week
from $263 / night
$1,843 - $9,249 / week
from $359 / night
$2,516 - $7,314 / week
from $573 / night
$4,008 / week
from $299 / night
$2,096 - $10,090 / week
from $155 / night
$1,086 - $6,051 / week
from $142 / night
$1,001 - $5,546 / week
from $299 / night
$2,096 - $9,670 / 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 $239 / night
$1,674 - $10,258 / week
from $275 / night
$1,927 - $7,565 / 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 $359 / night
$2,516 - $12,615 / week
from $142 / night
$1,001 - $4,452 / week
from $229 / night
$1,603 / week
from $135 / night
$945 / week
from $206 / night
$1,442 / week
from $145 / night
$1,015 / week
from $2,000 / night
$14,000 / week
from $485 / night
$3,395 / week