Kissimmee villas, Holiday rentals and apartments

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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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Also consider

Emerald Isle Kissimmee
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Villas Paradise Palms
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Lake Berkley
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Apartments Westside
28 properties
Villas Windsor Palms
27 properties
Seasons Resort
23 properties
Bellavida Resort
22 properties
Cumbrian Lakes
22 properties
Lindfields
22 properties
Terra Verde Resort
21 properties
Crescent Lakes
17 properties
Villas Indian Creek
17 properties
Compass Bay
16 properties
Villas Formosa Gardens
15 properties
Sunset Lakes
12 properties
Regal Oaks
12 properties
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.

(3) Excellent 

1 / 25

Townhouse rental in Kissimmee

Kissimmee / Bellavida Resort

4 bedroomsSleeps 83 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay

from $115 / night

$0 / week

Book Book View

from $115 / night

(2) Very Good 

1 / 100

Kissimmee holiday home rental

Central Florida / Kissimmee

4 bedroomsSleeps 106 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 6 nights min stay

from $131 / night

$849 / week

Book Book View

from $131 / night

(2) Very Good 

1 / 16

Holiday home with swimming pool in Veranda Palms

Kissimmee / Veranda Palms

4 bedroomsSleeps 9Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies

from $179 / night

$991 - $1090 / week

Book Book View

from $179 / night

(1) Excellent 

1 / 14

Villa rental in Kissimmee

Kissimmee / Bellavida Resort

4 bedroomsSleeps 104 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min stay

from $135 / night

$929 / week

Book Book View

from $135 / night

1 / 26

Home rental in Kissimmee

Central Florida / Kissimmee

7 bedroomsSleeps 16Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies

from $150 / night

$1394 - $2794 / week

Book Book View

from $150 / night

(4) Very Good 

1 / 21

Holiday villa in Kissimmee

Kissimmee / Terra Verde Resort

5 bedroomsSleeps 125 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 5 nights min stay

from $127 / night

$883 - $1051 / week

Book Book View

from $127 / night

(6) Excellent 

1 / 67

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $133 / night

$932 - $1400 / week

Book Book View

from $133 / night

(22) Excellent 

1 / 56

Holiday villa with private swimming pool in Kissimmee

Kissimmee / Doral Woods

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $182 / night

$1088 - $1378 / week

Book Book View

from $182 / night

(7) Excellent 

1 / 48

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 bedroomsSleeps 14Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies

from $240 / night

$1696 - $2800 / week

Book Book View

from $240 / night

(1) Excellent 

1 / 24

Kissimmee holiday home rental

Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $144 / night

$1005 - $1208 / week

Book Book View

from $144 / night

(38) Excellent 

1 / 100

Kissimmee holiday villa rental

Central Florida / Kissimmee

2 bedroomsSleeps 53 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay

from $95 / night

$576 / week

Book Book View

from $95 / night

1 / 40

Holiday home in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $130 / night

$901 - $1200 / week

Book Book View

from $130 / night

(19) Very Good 

1 / 23

Kissimmee holiday hotel apartment rental

Central Florida / Kissimmee

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $141 / night

$988 - $1505 / week

Book Book View

from $141 / night

(4) Very Good 

1 / 78

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $120 / night

$795 - $1083 / week

Book Book View

from $120 / night

(14) Excellent 

1 / 48

Townhouse rental in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $69 / night

$0 / week

Book Book View

from $69 / night

(4) Excellent 

1 / 30

Holiday home in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $109 / night

$834 / week

Book Book View

from $109 / night

1 / 50

Holiday home with indoor pool in Kissimmee

Central Florida / Kissimmee

3 bedroomsSleeps 83 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay

from $95 / night

$0 / week

Book Book View

from $95 / night

(6) Excellent 

1 / 46

Villa rental in Indian Point with shared pool

Kissimmee / Indian Point

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $103 / night

$725 - $870 / week

Book Book View

from $103 / night

(2) Excellent 

1 / 49

Holiday home with shared pool 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

(3) Excellent 

1 / 44

Villa accommodation in Kissimmee with swimming pool

Central Florida / Kissimmee

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies

from $139 / night

$1150 - $2301 / week

Book Book View

from $139 / night

(1) Good 

1 / 68

Holiday home with swimming pool in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 102 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min stay

from $150 / night

$1101 / week

Book Book View

from $150 / night

(7) Very Good 

1 / 10

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

4 bedroomsSleeps 94 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 4 nights min stay

from $95 / night

$653 / week

Book Book View

from $95 / night

(1) Excellent 

1 / 44

Home rental in Kissimmee with swimming pool

Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $161 / night

$1051 - $1701 / week

Book Book View

from $161 / night

(24) Excellent 

1 / 77

Holiday condo with golf nearby in Kissimmee

Kissimmee / Windsor Palms

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies

from $92 / night

$566 - $979 / week

Book Book View

from $92 / night

(15) Excellent 

1 / 30

Holiday villa with shared pool in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $100 / night

$693 - $980 / week

Book Book View

from $100 / night

(3) Excellent 

1 / 49

Holiday home with indoor pool in Kissimmee

Kissimmee / Kissimmee City

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies

from $196 / night

$0 / week

Book Book View

from $196 / night

(14) Excellent 

1 / 42

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 bedroomsSleeps 85 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min stay

from $106 / night

$742 / week

Book Book View

from $106 / night

(4) Very Good 

1 / 37

Terra Verde Resort holiday home rental

Kissimmee / Terra Verde Resort

3 bedroomsSleeps 81 night min stay

  • 3 bedrooms
  • Sleeps 8
  • 1 night min stay

from $91 / night

$631 / week

Book Book View

from $91 / night

(5) Excellent 

1 / 51

Kissimmee holiday home rental

Central Florida / Kissimmee

4 bedroomsSleeps 83 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay

from $161 / night

$1121 / week

Book Book View

from $161 / night

(5) Excellent 

1 / 25

Holiday villa with golf nearby in Kissimmee

Kissimmee / Indian Creek

5 bedroomsSleeps 12Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies

from $174 / night

$885 - $1146 / week

Book Book View

from $174 / night

1 / 33

Kissimmee holiday home rental

Kissimmee / Veranda Palms

6 bedroomsSleeps 13Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies

from $196 / night

$1295 / week

Book Book View

from $196 / night

(2) Excellent 

1 / 21

Holiday townhouse in Kissimmee

Kissimmee / Windsor Hills Resort

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $110 / night

$770 / week

Book Book View

from $110 / night

(9) Excellent 

1 / 25

Holiday villa in Kissimmee

Kissimmee / Calabria, Orlando

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay

from $192 / night

$1339 / week

Book Book View

from $192 / night

1 / 18

Holiday home in Veranda Palms

Kissimmee / Veranda Palms

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay

from $199 / night

$1394 / week

Book Book View

from $199 / night

(10) Excellent 

1 / 51

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $102 / night

$653 - $863 / week

Book Book View

from $102 / night

(3) Good 

1 / 23

Holiday home with swimming pool in Terra Verde Resort

Kissimmee / Terra Verde Resort

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies

from $126 / night

$851 - $1051 / week

Book Book View

from $126 / night

(3) Very Good 

1 / 23

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

6 bedroomsSleeps 13Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies

from $159 / night

$1130 - $1899 / week

Book Book View

from $159 / night

(1) Excellent 

1 / 15

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 bedroomsSleeps 84 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min stay

from $101 / night

$701 / week

Book Book View

from $101 / night

(2) Excellent 

1 / 82

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $141 / night

$980 - $1350 / week

Book Book View

from $141 / night

(3) Excellent 

1 / 119

Holiday villa rental

Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $133 / night

$932 - $1400 / week

Book Book View

from $133 / night

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