50 Best Kissimmee Villas and Holiday rentals – Holiday Lettings - Holiday Rentals Kissimmee

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  • United States
  • Florida
  • Central Florida
  • Kissimmee

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  • Bass Lakes Estate (1)
  • Bellavida Resort (22)
  • Calabria, Orlando (3)
  • Cane Island (4)
  • Chatham Park (2)
  • Compass Bay (16)
  • Coral Cay (10)
  • Country Creek (2)
  • Creekside (2)
  • Crescent Lakes (17)
  • Crestwynd Bay (7)
  • Crystal Cove Resort (5)
  • Cumbrian Lakes (22)
  • Doral Woods (9)
  • Eagle Pointe (11)
  • Emerald Isle Kissimmee (66)
  • Encantada Resort (9)
  • Fiesta Key (7)
  • Formosa Gardens (15)
  • Hamilton's Reserve (2)
  • Indian Creek (17)
  • Indian Point (3)
  • Indian Ridge (5)
  • Indian Ridge Oaks (7)
  • Kissimmee City (37)
  • Lake Berkley (29)
  • Lake Marion (3)
  • Legacy Dunes Resort (6)
  • Liberty Village (5)
  • Lindfields (22)
  • Lucaya Village (2)
  • Oak Island Cove (6)
  • Oak Island Harbor (3)
  • Orange Lake Resort (9)
  • Paradise Palms (31)
  • Regal Oaks (12)
  • Remington (2)
  • Rolling Hills at Formosa (4)
  • Seasons Resort (23)
  • Sunset Lakes (12)
  • Terra Verde Resort (21)
  • The Hamlets (3)
  • Trafalgar Village (8)
  • Tuscany, Florida (2)
  • Venetian Bay Villages (12)
  • Veranda Palms (9)
  • Villasol (5)
  • Vista del lago (2)
  • Westside (28)
  • Windsor Hills Resort (35)
  • Windsor Palms (27)
  • Winward Cay (5)

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Lake Berkley
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Villas Windsor Palms
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Seasons Resort
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Bellavida Resort
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Cumbrian Lakes
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Lindfields
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Terra Verde Resort
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Crescent Lakes
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Villas Indian Creek
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Compass Bay
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Villas Formosa Gardens
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Sunset Lakes
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Regal Oaks
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Venetian Bay Villages
12 properties
Eagle Pointe
11 properties
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4,772 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

(8) Excellent 

1 / 48

Holiday home in Kissimmee

Central Florida / Kissimmee

5 bedroomsSleeps 11Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies

from $145 / night

$910 - $1391 / week

Book Book View

from $145 / 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

(8) Excellent 

1 / 23

Holiday home in Kissimmee

Central Florida / Kissimmee

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from $95 / night

$696 - $870 / week

Book Book View

from $95 / 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

(7) Excellent 

1 / 51

Holiday home in Kissimmee

Central Florida / Kissimmee

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies

from $209 / night

$1436 - $2012 / week

Book Book View

from $209 / night

(21) Excellent 

1 / 77

Home rental in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $141 / night

$950 - $1095 / week

Book Book View

from $141 / 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

(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

(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

(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

(2) Excellent 

1 / 21

Kissimmee holiday townhouse rental

Central Florida / Kissimmee

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $130 / night

$851 / week

Book Book View

from $130 / night

(8) Excellent 

1 / 31

Holiday home with shared pool in Paradise Palms

Kissimmee / Paradise Palms

5 bedroomsSleeps 11Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies

from $99 / night

$1148 / week

Book Book View

from $99 / 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

(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

(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

(7) Excellent 

1 / 19

Holiday home rental

Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $139 / night

$1043 - $1664 / week

Book Book View

from $139 / night

(3) Excellent 

1 / 20

Holiday home in Kissimmee

Kissimmee / Emerald Isle Kissimmee

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies

from $222 / night

$1554 - $2800 / week

Book Book View

from $222 / night

(3) Excellent 

1 / 100

Holiday home with indoor pool in Kissimmee

Kissimmee / Paradise Palms

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies

from $170 / night

$1673 / week

Book Book View

from $170 / night

(4) Excellent 

1 / 22

Home rental in Kissimmee with swimming pool

Central Florida / Kissimmee

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies

from $199 / night

$1394 - $1730 / week

Book Book View

from $199 / 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

(4) Excellent 

1 / 54

Holiday townhouse with golf nearby in Kissimmee

Kissimmee / Compass Bay

3 bedroomsSleeps 65 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min stay

from $105 / night

$695 / week

Book Book View

from $105 / 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

(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

(4) Excellent 

1 / 39

Holiday home with golf nearby, tennis court in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 bedroomsSleeps 13Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies

from $251 / night

$1751 - $2773 / week

Book Book View

from $251 / 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

(3) Excellent 

1 / 18

Condo rental in Kissimmee

Central Florida / Kissimmee

3 bedroomsSleeps 81 night min stay

  • 3 bedrooms
  • Sleeps 8
  • 1 night min stay

from $150 / night

$991 / week

Book Book View

from $150 / 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

(6) Excellent 

1 / 39

Home accommodation in Kissimmee

Central Florida / Kissimmee

7 bedroomsSleeps 15Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies

from $286 / night

$2000 - $3151 / week

Book Book View

from $286 / 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 / 26

Holiday home with swimming pool in Kissimmee

Central Florida / Kissimmee

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies

from $199 / night

$1394 - $1730 / week

Book Book View

from $199 / 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

(2) Excellent 

1 / 26

Holiday townhouse rental

Central Florida / Kissimmee

4 bedroomsSleeps 83 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay

from $121 / night

$840 - $1301 / week

Book Book View

from $121 / night

(25) Excellent 

1 / 48

Holiday townhouse with golf nearby in Compass Bay

Kissimmee / Compass Bay

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies

from $80 / night

$700 / week

Book Book View

from $80 / night

(2) Excellent 

1 / 55

Kissimmee holiday home rental

Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $110 / night

$2000 / week

Book Book View

from $110 / 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

1 / 100

Holiday villa in Kissimmee

Central Florida / Kissimmee

8 bedroomsSleeps 20Min stay varies

  • 8 bedrooms
  • Sleeps 20
  • Min stay varies

from $249 / night

$1600 - $2299 / week

Book Book View

from $249 / night

(8) Very Good 

1 / 14

Kissimmee holiday home rental

Central Florida / Kissimmee

4 bedroomsSleeps 103 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min stay

from $101 / night

$701 / week

Book Book View

from $101 / night

(6) Excellent 

1 / 17

Holiday home in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $135 / night

$944 - $1242 / week

Book Book View

from $135 / night

(4) Very Good 

1 / 49

Holiday home in Kissimmee

Central Florida / Kissimmee

6 bedroomsSleeps 124 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 4 nights min stay

from $170 / night

$1101 / week

Book Book View

from $170 / night

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