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10 Best Vacation Rentals in Kissimmee City - Holiday Lettings - Cabins

22,175 Vacation rentals

Vacation villa in Kissimmee

Kissimmee villa

35

  • Nearest beach 60 mi
  • •  Swimming pool
  • •  Child friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $79 / night

$467 - $690 / week

Villa accommodation in Kissimmee City

Kissimmee villa

3

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from $194 / night

$1,359 / week

Vacation villa in Kissimmee City

Kissimmee villa

24

  • Nearest beach 120 mi
  • •  Swimming pool
  • •  Child friendly
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

from $196 / night

$1,046 - $1,889 / week

Condo rental in Kissimmee City with golf nearby

Kissimmee condo

1

  • Beach/lakeside relaxation
  • •  Nearest beach 100 mi
  • •  Swimming pool
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $103 / night

$722 / week

Vacation villa rental

Kissimmee villa

6

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $161 / night

$1,071 / week

Vacation home in Kissimmee City

Kissimmee house

2

  • Nearest beach 100 mi
  • •  Swimming pool
  • •  Child friendly
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $149 / night

$1,042 / week

Vacation townhouse with swimming pool in Kissimmee

Kissimmee townhouse

1

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $160 / night

$1,114 - $1,275 / week

Vacation villa in Kissimmee

Kissimmee villa

5

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

from $286 / night

$1,717 - $3,205 / week

Vacation home with indoor pool in Kissimmee City

Kissimmee house

4

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from $401 / night

$2,806 / week

Kissimmee Vacation apartment rental

Kissimmee apartment

  • Child friendly
  • •  Air conditioning
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $91 / night

$634 / week

Kissimmee Vacation condo rental

Kissimmee condo

1

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $172 / night

$716 - $1,117 / week

Great rentals within 20 miles that match your search

Orlando Vacation home rental

Orlando house

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $217 / night

$1,515 / week

Vacation home in Orlando

Orlando house

  • Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from $360 / night

$2,519 / week

Vacation home in Four Corners

Four Corners house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

from $218 / night

$1,523 - $4,617 / week

Vacation townhouse with swimming pool in Kissimmee

Kissimmee townhouse

  • Swimming pool
  • •  Car not necessary
  • •  Air conditioning
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $208 / night

$1,451 - $3,711 / week

Davenport Vacation home rental

Davenport house

19

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $109 / night

$762 / week

Vacation home with swimming pool in Four Corners

Four Corners house

  • Swimming pool
  • •  Car not necessary
  • •  Air conditioning
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $245 / night

$1,716 / week

Vacation villa rental

ChampionsGate villa

  • Swimming pool
  • •  Car not necessary
  • •  Air conditioning
  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

from $252 / night

$1,764 - $2,557 / week

Home rental in Orlando with shared pool

Orlando house

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $328 / night

$2,290 / week

Vacation home with swimming pool in Kissimmee

Kissimmee house

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from $342 / night

$2,389 / week

Vacation villa with golf nearby in Davenport

Davenport villa

6

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

from $453 / night

$3,166 / week

Vacation townhouse rental

Four Corners townhouse

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $121 / night

$834 - $2,453 / week

Vacation villa with swimming pool in Four Corners

Four Corners villa

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from $162 / night

$1,131 - $1,523 / week

Vacation villa with swimming pool, golf nearby in ChampionsGate

ChampionsGate villa

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 8 bedrooms
  • 5 bathrooms
  • sleeps 16

from $392 / night

$2,734 - $4,689 / week

Villa rental in ChampionsGate with swimming pool, golf nearby

ChampionsGate villa

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $212 / night

$1,483 / week

Villa rental in Kissimmee with shared pool

Kissimmee villa

1

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $126 / night

$773 - $939 / week

Vacation home in Intercession City

Intercession City house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $358 / night

$2,501 / week

Vacation home with swimming pool in Kissimmee

Kissimmee house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $201 / night

$1,403 - $3,808 / week

Vacation villa with swimming pool in Kissimmee

Kissimmee villa

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from $302 / night

$2,108 / week

Vacation home with shared pool in Davenport

Davenport house

  • Swimming pool
  • •  Car not necessary
  • •  Air conditioning
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $172 / night

$2,838 / week

Vacation villa with swimming pool, golf nearby in ChampionsGate

ChampionsGate villa

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $187 / night

$1,307 / week

Vacation villa in Four Corners

Four Corners villa

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from $224 / night

$1,563 - $2,685 / week

Vacation home rental

Kissimmee house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $106 / night

$738 - $1,860 / week

Vacation villa in ChampionsGate

ChampionsGate villa

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from $289 / night

$2,012 - $3,455 / week

Vacation home rental

Kissimmee house

  • Nearest beach 90 mi
  • •  Child friendly
  • •  Air conditioning
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $161 / night

$1,123 - $1,672 / week

Vacation villa in ChampionsGate

ChampionsGate villa

1

  • Nearest beach 110 mi
  • •  Swimming pool
  • •  Child friendly
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $109 / night

$762 / week

Vacation home in ChampionsGate

ChampionsGate house

4

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $88 / night

$612 / week

Home rental in Four Corners with swimming pool

Four Corners house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

from $203 / night

$1,411 - $1,611 / week

Home rental in Winter Garden

Winter Garden house

  • Child friendly
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $144 / night

$859 / week

Ventura Vacation apartment rental

Ventura apartment

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $124 / night

$866 - $1,371 / week