Viewing 40 of 1,198 rentals in Winter Park
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Vacation homes - vacation rentals
21 Vacation rentals
from $115 / night
$802 / week
from $200 / night
$1,400 / week
from $220 / night
$1,540 / week
from $140 / night
$980 / week
from $137 / night
$959 / week
from $356 / night
$2,492 / week
from $214 / night
$1,498 / week
from $158 / night
$1,106 / week
from $120 / night
$840 / week
from $189 / night
$1,323 / week
from $98 / night
$686 / week
from $325 / night
$2,275 / week
from $115 / night
$805 / week
from $275 / night
$1,925 / week
from $114 / night
$798 / week
from $115 / night
$805 / week
from $156 / night
$1,092 / week
from $174 / night
$1,218 / week
from $127 / night
$889 / week
from $105 / night
$735 / week
Great rentals within 20 miles that match your search
from $630 / night
$4,409 / week
from $197 / night
$1,374 / week
from $114 / night
$745 - $1,088 / week
from $193 / night
$1,352 / week
from $561 / night
$3,928 / week
from $409 / night
$2,857 / week
from $109 / night
$796 / week
Vacation apartment with shared pool, golf nearby in Orlando
Orlando apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
from $87 / night
$606 / week
from $257 / night
$1,590 / week
from $107 / night
$745 / week
from $217 / night
$1,546 / week
from $129 / night
$859 / week
from $344 / night
$2,405 / week
from $203 / night
$1,419 / week
from $258 / night
$2,061 - $2,519 / week
from $158 / night
$1,004 / week