50 Best Kissimmee villas on Holiday Lettings - Holiday rentals

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  • United States
  • Florida
  • Central Florida
  • Kissimmee

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  • Bass Lakes Estate (1)
  • Bellavida Resort (9)
  • Calabria, Orlando (2)
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  • Country Creek (2)
  • Creekside (1)
  • Crescent Lakes (8)
  • Crystal Cove Resort (2)
  • Cumbrian Lakes (18)
  • Doral Woods (9)
  • Eagle Pointe (6)
  • Emerald Isle Kissimmee (38)
  • Formosa Gardens (9)
  • Hamilton's Reserve (2)
  • Indian Creek (12)
  • Indian Point (3)
  • Indian Ridge (4)
  • Indian Ridge Oaks (4)
  • Kissimmee City (13)
  • Lake Berkley (19)
  • Lake Marion (1)
  • Liberty Village (1)
  • Lindfields (12)
  • Oak Island Cove (4)
  • Oak Island Harbor (1)
  • Orange Lake Resort (5)
  • Paradise Palms (3)
  • Remington (1)
  • Rolling Hills at Formosa (1)
  • Seasons Resort (12)
  • Sunset Lakes (10)
  • Terra Verde Resort (9)
  • The Hamlets (3)
  • Trafalgar Village (3)
  • Tuscany, Florida (1)
  • Veranda Palms (3)
  • Villasol (2)
  • Vista del lago (1)
  • Westside (2)
  • Windsor Hills Resort (14)
  • Windsor Palms (14)
  • Winward Cay (4)

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Lindfields
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1,186 Holiday homes

Travellers going to Kissimmee are booking July dates now. Secure your holiday home today and have the perfect trip.

(10) Excellent 

1 / 44

Holiday villa in Kissimmee

Central Florida / Kissimmee

7 bedroomsSleeps 16Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies

from $196 / night

$1301 - $2800 / week

Book Book View

from $196 / night

(11) Excellent 

1 / 18

Holiday villa with golf nearby in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies

from $218 / night

$1523 - $2436 / week

Book Book View

from $218 / night

(18) Excellent 

1 / 63

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 105 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min stay

from $145 / night

$1015 - $1218 / week

Book Book View

from $145 / night

(4) Excellent 

1 / 55

Holiday villa with golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

6 bedroomsSleeps 14Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies

from $225 / night

$0 / week

Book Book View

from $225 / night

(3) Excellent 

1 / 28

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $181 / night

$996 - $2395 / week

Book Book View

from $181 / night

(20) Very Good 

1 / 75

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $101 / night

$800 - $1000 / week

Book Book View

from $101 / night

(14) Excellent 

1 / 109

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $71 / night

$0 / week

Book Book View

from $71 / night

(8) Excellent 

1 / 88

Kissimmee holiday villa rental

Kissimmee / Bellavida Resort

6 bedroomsSleeps 145 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 5 nights min stay

from $216 / night

$1505 - $1995 / week

Book Book View

from $216 / night

(7) Excellent 

1 / 39

Holiday villa rental

Kissimmee / Kissimmee City

7 bedroomsSleeps 16Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies

from $179 / night

$1394 - $2450 / week

Book Book View

from $179 / night

(6) Excellent 

1 / 16

Villa rental in Kissimmee

Kissimmee / Indian Creek

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $145 / night

$1117 - $1160 / week

Book Book View

from $145 / night

(13) Excellent 

1 / 21

Holiday villa with golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies

from $218 / night

$1523 - $2436 / week

Book Book View

from $218 / night

(4) Excellent 

1 / 77

Holiday villa in Kissimmee

Central Florida / Kissimmee

7 bedroomsSleeps 145 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 5 nights min stay

from $231 / night

$1580 - $3076 / week

Book Book View

from $231 / night

(17) Excellent 

1 / 51

Villa rental in Kissimmee

Kissimmee / Villasol

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay

from $144 / night

$0 / week

Book Book View

from $144 / night

(18) Excellent 

1 / 24

Villa rental in Sunset Lakes

Kissimmee / Sunset Lakes

4 bedroomsSleeps 105 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min stay

from $145 / night

$1015 - $1218 / week

Book Book View

from $145 / night

(13) Excellent 

1 / 75

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $101 / night

$701 - $840 / week

Book Book View

from $101 / night

(2) Excellent 

1 / 29

Holiday villa with indoor pool in Lake Berkley

Kissimmee / Lake Berkley

6 bedroomsSleeps 14Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies

from $197 / night

$1379 - $1589 / week

Book Book View

from $197 / night

(13) Excellent 

1 / 46

Kissimmee holiday villa rental

Central Florida / Kissimmee

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies

from $216 / night

$1505 - $2380 / week

Book Book View

from $216 / night

(7) Very Good 

1 / 25

Holiday villa in Kissimmee

Central Florida / Kissimmee

7 bedroomsSleeps 16Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies

from $199 / night

$1000 - $2600 / week

Book Book View

from $199 / night

(38) Excellent 

1 / 32

Holiday villa rental

Central Florida / Kissimmee

6 bedroomsSleeps 14Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies

from $225 / night

$1576 / week

Book Book View

from $225 / night

(66) Excellent 

1 / 24

Villa rental in Kissimmee

Kissimmee / Windsor Palms

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay

from $228 / night

$1595 - $2296 / week

Book Book View

from $228 / night

(13) Very Good 

1 / 33

Holiday villa rental

Central Florida / Kissimmee

7 bedroomsSleeps 16Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies

from $150 / night

$1000 - $2200 / week

Book Book View

from $150 / night

(1) Excellent 

1 / 59

Holiday villa in Kissimmee

Central Florida / Kissimmee

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies

from $189 / night

$1305 - $1414 / week

Book Book View

from $189 / night

(5) Excellent 

1 / 58

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $110 / night

$745 - $895 / week

Book Book View

from $110 / night

(11) Excellent 

1 / 31

Holiday villa in Kissimmee

Central Florida / Kissimmee

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies

from $216 / night

$1505 - $2380 / week

Book Book View

from $216 / night

(2) Very Good 

1 / 70

Kissimmee holiday villa rental

Central Florida / Kissimmee

5 bedroomsSleeps 123 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min stay

from $142 / night

$996 - $1196 / week

Book Book View

from $142 / night

(11) Excellent 

1 / 34

Villa rental in Kissimmee with swimming pool

Kissimmee / Kissimmee City

4 bedroomsSleeps 9Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies

from $119 / night

$783 - $957 / week

Book Book View

from $119 / night

(15) Excellent 

1 / 20

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay

from $109 / night

$762 - $870 / week

Book Book View

from $109 / night

(3) Very Good 

1 / 12

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 84 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min stay

from $110 / night

$770 / week

Book Book View

from $110 / night

(6) Excellent 

1 / 42

Holiday villa in Kissimmee

Central Florida / Kissimmee

6 bedroomsSleeps 14Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies

from $185 / night

$1295 - $2975 / week

Book Book View

from $185 / night

(1) Excellent 

1 / 33

Holiday villa in Kissimmee

Central Florida / Kissimmee

5 bedroomsSleeps 11Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies

from $205 / night

$1435 - $2020 / week

Book Book View

from $205 / night

(7) Very Good 

1 / 45

Kissimmee holiday villa rental

Central Florida / Kissimmee

5 bedroomsSleeps 12Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies

from $150 / night

$1150 - $1501 / week

Book Book View

from $150 / night

(4) Excellent 

1 / 31

Villa rental in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $141 / night

$950 - $1156 / week

Book Book View

from $141 / night

(1) Excellent 

1 / 29

Holiday villa with shared pool in Terra Verde Resort

Kissimmee / Terra Verde Resort

7 bedroomsSleeps 16Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies

from $171 / night

$1199 - $2278 / week

Book Book View

from $171 / night

1 / 15

Villa rental in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

7 bedroomsSleeps 15Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies

from $210 / night

$1400 - $2701 / week

Book Book View

from $210 / night

(4) Excellent 

1 / 44

Holiday villa with golf nearby in Kissimmee

Central Florida / Kissimmee

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $116 / night

$812 - $820 / week

Book Book View

from $116 / night

(18) Excellent 

1 / 62

Holiday villa in Kissimmee

Kissimmee / Lindfields

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $99 / night

$689 - $907 / week

Book Book View

from $99 / night

(2) Very Good 

1 / 100

Holiday villa in Kissimmee

Central Florida / Kissimmee

8 bedroomsSleeps 19Min stay varies

  • 8 bedrooms
  • Sleeps 19
  • Min stay varies

from $275 / night

$1200 - $3415 / week

Book Book View

from $275 / night

(11) Excellent 

1 / 30

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 bedroomsSleeps 84 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min stay

from $167 / night

$1131 / week

Book Book View

from $167 / night

(11) Very Good 

1 / 77

Kissimmee holiday villa rental

Central Florida / Kissimmee

5 bedroomsSleeps 133 nights min stay

  • 5 bedrooms
  • Sleeps 13
  • 3 nights min stay

from $80 / night

$600 - $875 / week

Book Book View

from $80 / night

(3) Very Good 

1 / 48

Holiday villa with golf nearby in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $45 / night

$793 - $1400 / week

Book Book View

from $45 / night

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