Viewing 40 of 71 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
34 Vacation rentals
from $2,863 / night
$20,038 / week
from $239 / night
$1,674 - $11,016 / week
from $190 / night
$1,338 - $8,323 / week
from $347 / night
$2,432 - $10,427 / week
from $155 / night
$1,086 - $5,041 / week
from $540 / night
$3,779 - $21,452 / 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 $203 / night
$1,422 - $12,026 / 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 $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 $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 $239 / night
$1,674 - $10,258 / week
from $190 / night
$1,338 - $6,304 / week
from $155 / night
$1,086 - $6,304 / week
from $359 / night
$2,516 - $12,615 / week
from $142 / night
$1,001 - $4,452 / week
from $960 / night
$6,724 - $20,189 / week
Great rentals within 20 miles that match your search
from $132 / night
$922 / week
from $286 / night
$1,603 / week
from $224 / night
$1,374 - $1,661 / week
from $201 / night
$1,546 / week
from $109 / night
$705 - $859 / week
from $94 / night
$544 - $745 / week