Viewing 40 of 479 rentals in Winter Park
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Vacation homes - vacation rentals
479 Vacation rentals
Great rentals within 20 miles that match your search
from $172 / night
$1,203 / week
Great rentals within 20 miles that match your search
from $199 / night
$1,065 - $1,207 / week
Great rentals within 20 miles that match your search
from $137 / night
$954 / week
Great rentals within 20 miles that match your search
from $344 / night
$1,827 - $2,119 / week
Great rentals within 20 miles that match your search
from $172 / night
$1,203 / week
Great rentals within 20 miles that match your search
from $235 / night
$1,643 / week
Great rentals within 20 miles that match your search
from $160 / night
$1,054 - $1,455 / week
Great rentals within 20 miles that match your search
from $368 / night
$2,573 / week
Great rentals within 20 miles that match your search
from $178 / night
$1,242 - $1,292 / week
Great rentals within 20 miles that match your search
from $146 / night
$1,018 - $1,114 / week
Great rentals within 20 miles that match your search
from $178 / night
$1,140 / week
Great rentals within 20 miles that match your search
from $184 / night
$1,283 / week
Great rentals within 20 miles that match your search
from $107 / night
$745 / week
Great rentals within 20 miles that match your search
from $350 / night
$2,061 / week
Great rentals within 20 miles that match your search
from $270 / night
$1,890 / week
Great rentals within 20 miles that match your search
Vacation townhouse with shared pool in Davenport
Davenport townhouse
- 2 bedrooms
- 3 bathrooms
- sleeps 6
from $86 / night
$571 / week
Great rentals within 20 miles that match your search
Vacation villa with swimming pool, golf nearby in Orlando
Orlando villa
- 7 bedrooms
- 5 bathrooms
- sleeps 16
from $189 / night
$1,317 - $2,245 / week
Great rentals within 20 miles that match your search
from $401 / night
$2,806 / week
Great rentals within 20 miles that match your search
from $172 / night
$1,203 - $1,401 / week
Great rentals within 20 miles that match your search
from $256 / night
$1,271 - $1,562 / week
Great rentals within 20 miles that match your search
from $184 / night
$1,283 / week
Great rentals within 20 miles that match your search
from $106 / night
$687 - $808 / week
Great rentals within 20 miles that match your search
from $343 / night
$2,393 / week
Great rentals within 20 miles that match your search
from $212 / night
$1,483 / week
Great rentals within 20 miles that match your search
from $138 / night
$1,042 / week
Great rentals within 20 miles that match your search
Villa rental in Kissimmee with swimming pool, golf nearby
Kissimmee villa
- 9 bedrooms
- 5 bathrooms
- sleeps 18
from $552 / night
$3,864 / week
Great rentals within 20 miles that match your search
from $552 / night
$3,864 / week
Great rentals within 20 miles that match your search
from $552 / night
$3,864 / week
Great rentals within 20 miles that match your search
from $552 / night
$3,864 / week
Great rentals within 20 miles that match your search
from $552 / night
$3,864 / week
Great rentals within 20 miles that match your search
from $287 / night
$2,004 / week
Great rentals within 20 miles that match your search
from $368 / night
$2,573 / week
Great rentals within 20 miles that match your search
from $178 / night
$1,042 / week
Great rentals within 20 miles that match your search
from $335 / night
$2,341 / week
Great rentals within 20 miles that match your search
Vacation villa with swimming pool, golf nearby in Kissimmee
Kissimmee villa
- 5 bedrooms
- 5 bathrooms
- sleeps 10
from $335 / night
$2,341 / week
Great rentals within 20 miles that match your search
Villa rental in Davenport with swimming pool, golf nearby
Davenport villa
- 9 bedrooms
- 5 bathrooms
- sleeps 18
from $552 / night
$3,864 / week
Great rentals within 20 miles that match your search
from $138 / night
$962 - $1,203 / week
Great rentals within 20 miles that match your search
from $369 / night
$2,414 / week
Great rentals within 20 miles that match your search
from $189 / night
$1,323 / week
Great rentals within 20 miles that match your search
from $213 / night
$1,491 / week