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Best Vacation Rentals in Windsor Hills Resort - Holiday Lettings - Cabins

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6,110 Vacation rentals

Vacation condo with shared pool, golf nearby in Windsor Hills Resort

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $103 / night

$722 / week

1 / 17

Vacation condo with shared pool in Windsor Hills Resort

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $148 / night

$1,034 / week

1 / 34

Windsor Hills Resort Vacation home rental

Kissimmee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from $224 / night

$1,546 - $2,004 / week

1 / 12

Villa rental in Kissimmee with golf nearby

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

from $458 / night

$3,206 / week

1 / 20

Vacation villa with golf nearby in Windsor Hills Resort

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from $516 / night

$3,607 / week

1 / 38

Villa rental in Windsor Hills Resort with golf nearby

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

from $188 / night

$1,255 - $155,864 / week

1 / 52

Vacation villa rental

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from $247 / night

$2,175 - $2,335 / week

1 / 33

Windsor Hills Resort Vacation home rental

Kissimmee house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 13

from $241 / night

$1,602 / week

1 / 41

Vacation bungalow with swimming pool, golf nearby in Windsor Hills Resort

Kissimmee bungalow

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $225 / night

$1,575 / week

1 / 23

Great rentals within 20 miles that match your search

Vacation villa in Kissimmee

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $141 / night

$796 - $1,096 / week

1 / 36

Holiday villa with private swimming pool in Kissimmee

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $232 / night

$1,395 - $1,535 / week

1 / 57

Vacation villa with golf nearby in Davenport

Davenport villa

  • 3 bedrooms
  • 8 bathrooms
  • sleeps 8

from $241 / night

$1,145 / week

1 / 19

Vacation villa rental

Davenport villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

from $184 / night

$1,283 / week

1 / 30

Vacation villa in Kissimmee

Kissimmee villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $229 / night

$1,603 - $1,775 / week

1 / 26

Vacation villa with swimming pool, golf nearby in Haines City

Haines City villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $281 / night

$1,963 / week

1 / 46

Vacation villa in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from $371 / night

$2,594 / week

1 / 28

Kissimmee Vacation villa rental

Kissimmee villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from $258 / night

$1,804 / week

1 / 33

Vacation townhouse with shared pool in Davenport

Davenport townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from $82 / night

$573 - $630 / week

1 / 16

Kissimmee Vacation villa rental

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $232 / night

$1,143 - $1,283 / week

1 / 18

Kissimmee Vacation villa rental

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $127 / night

$834 - $883 / week

1 / 18

Vacation villa with golf nearby in Davenport

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $92 / night

$638 - $933 / week

1 / 28

Kissimmee Vacation home rental

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $183 / night

$1,276 / week

1 / 100

Davenport Vacation home rental

Davenport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $149 / night

$1,042 / week

1 / 24

Vacation villa accommodation

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $197 / night

$1,374 / week

1 / 14

Vacation townhouse in Kissimmee

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $86 / night

$600 / week

1 / 14

Vacation townhouse in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $132 / night

$876 - $1,521 / week

1 / 20

Kissimmee Vacation villa rental

Kissimmee villa

  • 6 bedrooms
  • 10 bathrooms
  • sleeps 14

from $253 / night

$1,816 / week

1 / 29

Davenport Vacation villa rental

Davenport villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

from $197 / night

$975 - $1,325 / week

1 / 22

Vacation villa with golf nearby in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 12

from $200 / night

$1,400 / week

1 / 28

Vacation villa with golf nearby in Davenport

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $113 / night

$785 - $1,227 / week

1 / 12

Vacation home with swimming pool in Kissimmee

Kissimmee house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $155 / night

$1,052 / week

1 / 24

Vacation villa in Orange Tree

Orange Tree villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $197 / night

$1,374 / week

1 / 51

Vacation villa in Sunrise Lakes

Sunrise Lakes villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $135 / night

$943 - $1,200 / week

1 / 32

Vacation villa with swimming pool in Kissimmee

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $176 / night

$771 / week

1 / 22

Davenport Vacation villa rental

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $131 / night

$912 - $982 / week

1 / 32

Kissimmee Vacation home rental

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $204 / night

$1,402 - $1,570 / week

1 / 15

Vacation villa with golf nearby in Davenport

Davenport villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from $184 / night

$1,260 - $1,832 / week

1 / 25

Vacation villa with swimming pool, golf nearby in Davenport

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from $201 / night

$1,403 / week

1 / 20

Vacation condo rental

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $106 / night

$701 - $1,332 / week

1 / 60

Vacation villa in Davenport

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $174 / night

$1,218 - $1,775 / week

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