Viewing 40 of 2,201 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
1 Vacation rentals
from $120 / night
$840 / week
Great rentals within 20 miles that match your search
from $91 / night
$634 / week
from $304 / night
$2,124 / week
from $144 / night
$1,002 / week
from $171 / night
$1,195 / week
from $197 / night
$1,374 / week
from $101 / night
$2,576 / week
from $114 / night
$745 - $1,088 / week
from $257 / night
$1,590 / week
from $107 / night
$745 / week
from $217 / night
$1,546 / week
Vacation villa with shared pool, golf nearby in Orlando
Orlando villa
- 2 bedrooms
- 2 bathrooms
- sleeps 6
from $171 / night
$1,195 / week
from $295 / night
$2,061 / week
from $430 / night
$1,832 / week
from $114 / night
$1,031 / week
from $888 / night
$6,212 / week
from $344 / night
$2,405 / week
from $352 / night
$2,462 / week
from $597 / night
$4,176 / week
from $409 / night
$2,857 / week
Vacation hotel apartment with indoor pool in Orlando
Orlando hotel apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
from $217 / night
$1,515 / week
from $287 / night
$1,832 / week
from $262 / night
$1,831 / week
from $101 / night
$2,003 / week
Vacation apartment with shared pool in Kissimmee
Kissimmee apartment
- 4 bedrooms
- 3 bathrooms
- sleeps 8
from $200 / night
$1,395 / week
from $172 / night
$1,203 / week
Vacation apartment with shared pool, golf nearby in Orlando
Orlando apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 8
from $121 / night
$842 / week
from $229 / night
$1,603 / week
from $168 / night
$1,171 / week
from $246 / night
$1,718 / week
from $148 / night
$1,040 - $2,563 / week
from $232 / night
$1,621 - $4,714 / week
from $228 / night
$1,373 / week
from $148 / night
$904 / week
Condo rental in Central Florida with shared pool
Central Florida condo
- 2 bedrooms
- 2 bathrooms
- sleeps 8
from $409 / night
$2,863 / week
Apartment rental in Orlando with shared pool, golf nearby
Orlando apartment
- 1 bedroom
- 1 bathroom
- sleeps 4
from $184 / night
$1,283 / week
from $161 / night
$1,088 / week
Vacation villa with shared pool in Buena Ventura Lakes
Buena Ventura Lakes villa
- 1 bedroom
- 1 bathroom
- sleeps 4
from $287 / night
$2,004 / week
from $315 / night
$2,205 / week