Viewing 40 of 3,556 rentals in Winter Park
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Vacation homes - vacation rentals
24 Vacation rentals
from $115 / night
$802 / week
from $366 / night
$2,562 / week
from $115 / night
$805 / week
from $116 / night
$812 / week
from $194 / night
$1,358 / week
from $276 / night
$1,932 / week
from $103 / night
$721 / week
from $115 / night
$805 / week
from $113 / night
$791 / week
from $156 / night
$1,092 / week
from $127 / night
$889 / week
from $118 / night
$826 / week
from $408 / night
$2,856 / week
from $365 / night
$2,555 / week
from $352 / night
$2,464 / week
from $376 / night
$2,632 / week
from $368 / night
$2,576 / week
from $321 / night
$2,247 / week
from $324 / night
$2,268 / week
from $125 / night
$875 / week
from $117 / night
$819 / week
from $116 / night
$812 / week
from $124 / night
$868 / week
Great rentals within 20 miles that match your search
from $91 / night
$634 / week
from $203 / night
$1,419 / week
from $258 / night
$2,061 - $2,519 / week
from $98 / night
$1,718 - $2,176 / week
from $171 / night
$1,195 / week
from $630 / night
$4,409 / week
from $491 / night
$3,435 / week
from $344 / night
$2,405 / week
from $200 / night
$1,397 / week
from $197 / night
$1,374 / week
from $101 / night
$2,576 / week
Vacation apartment with shared pool in Williamsburg
Williamsburg apartment
- 1 bedroom
- 1 bathroom
- sleeps 4
from $99 / night
$687 / week
from $458 / night
$3,206 / week
from $360 / night
$2,519 / week
from $193 / night
$1,351 / week