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  • United States
  • Florida
  • Central Florida
  • Kissimmee

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  • Coral Cay (5)
  • Crescent Lakes (3)
  • Crestwynd Bay (1)
  • Crystal Cove Resort (3)
  • Cumbrian Lakes (1)
  • Doral Woods (1)
  • Emerald Isle Kissimmee (3)
  • Fiesta Key (1)
  • Formosa Gardens (5)
  • Indian Creek (3)
  • Indian Point (1)
  • Kissimmee City (3)
  • Lake Berkley (1)
  • Legacy Dunes Resort (1)
  • Lindfields (2)
  • Paradise Palms (4)
  • Regal Oaks (1)
  • Seasons Resort (4)
  • Sunset Lakes (1)
  • Terra Verde Resort (2)
  • The Hamlets (1)
  • Trafalgar Village (1)
  • Windsor Hills Resort (4)
  • Windsor Palms (3)

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Also consider

Emerald Isle Kissimmee
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Villas Windsor Hills Resort
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Kissimmee City
40 properties
Lake Berkley
32 properties
Crestwynd Bay
31 properties
Villas Windsor Palms
30 properties
Apartments Westside
28 properties
Cumbrian Lakes
27 properties
Bellavida Resort
27 properties
Seasons Resort
24 properties
Terra Verde Resort
22 properties
Lindfields
22 properties
Crescent Lakes
18 properties
Villas Indian Creek
16 properties
Compass Bay
16 properties
Villas Formosa Gardens
15 properties
Regal Oaks
12 properties
Sunset Lakes
12 properties
Venetian Bay Villages
12 properties
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191 Holiday homes

Filters applied: Pets allowed (191)

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

1 / 17

Kissimmee holiday condo rental

Kissimmee / Kissimmee City

3 8 3 nights min stay

Condo / 3 bedrooms / sleeps 8 / 3 nights min stay

Add to shortlist

from £242 / night

£863 / week

Book

from £242 / night

(1) Excellent 

1 / 19

Townhouse rental in Kissimmee with indoor pool

Kissimmee / Paradise Palms

4 10 1 night min stay

Townhouse / 4 bedrooms / sleeps 10 / 1 night min stay

Add to shortlist

from £118 / night

£759 / week

Book

from £118 / night

(1) Excellent 

1 / 13

Home rental in Kissimmee with swimming pool

Central Florida / Kissimmee

4 10 Min stay varies

House / 4 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £104 / night

£966 / week

Book

from £104 / night

1 / 13

Seasons Resort holiday villa rental

Kissimmee / Seasons Resort

5 11 Min stay varies

Villa / 5 bedrooms / sleeps 11 / Min stay varies

Add to shortlist

from £132 / night

£897 - £1063 / week

Book

from £132 / night

1 / 100

Holiday villa in Kissimmee

Central Florida / Kissimmee

8 20 Min stay varies

Villa / 8 bedrooms / sleeps 20 / Min stay varies

Add to shortlist

from £152 / night

£1034 - £1586 / week

Book

from £152 / night

(1) Excellent 

1 / 99

Holiday villa in Kissimmee

Kissimmee / Paradise Palms

6 14 1 night min stay

Villa / 6 bedrooms / sleeps 14 / 1 night min stay

Add to shortlist

from £165 / night

£1153 - £2289 / week

Book

from £165 / night

1 / 42

Holiday villa in Kissimmee

Kissimmee / Crystal Cove Resort

7 16 1 night min stay

Villa / 7 bedrooms / sleeps 16 / 1 night min stay

Add to shortlist

from £165 / night

£1153 - £2289 / week

Book

from £165 / night

1 / 44

Villa letting in Kissimmee

Kissimmee / Windsor Palms

6 14 3 nights min stay

Villa / 6 bedrooms / sleeps 14 / 3 nights min stay

Add to shortlist

from £194 / night

£1207 / week

Book

from £194 / night

(1) Excellent 

1 / 39

Kissimmee holiday home rental

Central Florida / Kissimmee

6 14 Min stay varies

House / 6 bedrooms / sleeps 14 / Min stay varies

Add to shortlist

from £145 / night

£966 - £1311 / week

Book

from £145 / night

(2) Very Good 

1 / 76

Holiday home in Kissimmee

Central Florida / Kissimmee

5 12 Min stay varies

House / 5 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £76 / night

£532 - £773 / week

Book

from £76 / night

1 / 24

Holiday villa in Kissimmee

Central Florida / Kissimmee

2 8 7 nights min stay

Villa / 2 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £109 / night

£763 / week

Book

from £109 / night

1 / 29

Kissimmee holiday townhouse rental

Kissimmee / Paradise Palms

4 8 5 nights min stay

Townhouse / 4 bedrooms / sleeps 8 / 5 nights min stay

Add to shortlist

from £115 / night

£802 - £947 / week

Book

from £115 / night

(2) Excellent 

1 / 55

Holiday villa with golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

Villa / 6 bedrooms / sleeps 14 / Min stay varies

Add to shortlist

from £150 / night

£1000 - £1500 / week

Book

from £150 / night

(1) Excellent 

1 / 19

Holiday villa in Kissimmee

Kissimmee / Indian Creek

4 10 Min stay varies

Villa / 4 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £83 / night

£575 - £958 / week

Book

from £83 / night

1 / 35

Kissimmee holiday villa rental

Kissimmee / Windsor Hills Resort

6 12 7 nights min stay

Villa / 6 bedrooms / sleeps 12 / 7 nights min stay

Add to shortlist

from £178 / night

£1242 - £1345 / week

Book

from £178 / night

(8) Excellent 

1 / 30

Villa rental in Kissimmee with swimming pool

Central Florida / Kissimmee

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £63 / night

£483 - £535 / week

Book

from £63 / night

(8) Excellent 

1 / 54

Holiday home in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

House / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £80 / night

£503 - £522 / week

Book

from £80 / night

(1) Very Good 

1 / 40

Holiday apartment in Kissimmee

Central Florida / Kissimmee

3 8 3 nights min stay

Apartment / 3 bedrooms / sleeps 8 / 3 nights min stay

Add to shortlist

from £69 / night

£478 / week

Book

from £69 / night

1 / 17

Holiday townhouse accommodation

Central Florida / Kissimmee

4 10 Min stay varies

Townhouse / 4 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £90 / night

£628 / week

Book

from £90 / night

1 / 11

Villa rental in Kissimmee

Central Florida / Kissimmee

2 10 7 nights min stay

Villa / 2 bedrooms / sleeps 10 / 7 nights min stay

Add to shortlist

from £125 / night

£869 / week

Book

from £125 / night

(1) Excellent 

1 / 9

Home rental in Kissimmee

Kissimmee / Sunset Lakes

4 8 Min stay varies

House / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £96 / night

£642 - £1058 / week

Book

from £96 / night

1 / 20

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 11 1 night min stay

Villa / 4 bedrooms / sleeps 11 / 1 night min stay

Add to shortlist

from £90 / night

£628 - £894 / week

Book

from £90 / night

1 / 16

Holiday villa in Kissimmee

Kissimmee / Trafalgar Village

4 8 Min stay varies

Villa / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £124 / night

£700 / week

Book

from £124 / night

(1) Very Good 

1 / 35

Home rental in Kissimmee

Central Florida / Kissimmee

3 8 1 night min stay

House / 3 bedrooms / sleeps 8 / 1 night min stay

Add to shortlist

from £66 / night

£442 / week

Book

from £66 / night

1 / 19

Kissimmee holiday apartment rental

Central Florida / Kissimmee

2 8 4 nights min stay

Apartment / 2 bedrooms / sleeps 8 / 4 nights min stay

Add to shortlist

from £173 / night

£966 / week

Book

from £173 / night

1 / 10

Holiday apartment rental

Central Florida / Kissimmee

2 8 7 nights min stay

Apartment / 2 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £98 / night

£686 / week

Book

from £98 / night

1 / 24

Holiday home in Kissimmee

Central Florida / Kissimmee

6 12 Min stay varies

House / 6 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £145 / night

£1014 - £1521 / week

Book

from £145 / night

(37) Excellent 

1 / 100

Kissimmee holiday villa rental

Central Florida / Kissimmee

2 5 3 nights min stay

Villa / 2 bedrooms / sleeps 5 / 3 nights min stay

Add to shortlist

from £59 / night

£397 / week

Book

from £59 / night

1 / 15

Kissimmee holiday home let

Central Florida / Kissimmee

3 6 Min stay varies

House / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £110 / night

£768 / week

Book

from £110 / night

1 / 47

Holiday villa with swimming pool in Kissimmee

Kissimmee / Terra Verde Resort

6 12 Min stay varies

Villa / 6 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £100 / night

£1200 / week

Book

from £100 / night

1 / 18

Holiday home in Kissimmee

Central Florida / Kissimmee

4 11 3 nights min stay

House / 4 bedrooms / sleeps 11 / 3 nights min stay

Add to shortlist

from £62 / night

£428 - £594 / week

Book

from £62 / night

(1) Excellent 

1 / 21

Kissimmee holiday villa rental

Kissimmee / The Hamlets

5 10 7 nights min stay

Villa / 5 bedrooms / sleeps 10 / 7 nights min stay

Add to shortlist

from £115 / night

£800 / week

Book

from £115 / night

(22) Excellent 

1 / 14

Holiday home in Kissimmee

Central Florida / Kissimmee

3 6 4 nights min stay

House / 3 bedrooms / sleeps 6 / 4 nights min stay

Add to shortlist

from £59 / night

£411 / week

Book

from £59 / night

1 / 11

Holiday villa in Indian Point

Kissimmee / Indian Point

4 8 3 nights min stay

Villa / 4 bedrooms / sleeps 8 / 3 nights min stay

Add to shortlist

from £102 / night

£710 / week

Book

from £102 / night

1 / 24

Holiday home letting

Central Florida / Kissimmee

6 14 Min stay varies

House / 6 bedrooms / sleeps 14 / Min stay varies

Add to shortlist

from £111 / night

£773 - £1352 / week

Book

from £111 / night

(1) Excellent 

1 / 15

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 8 3 nights min stay

Villa / 3 bedrooms / sleeps 8 / 3 nights min stay

Add to shortlist

from £69 / night

£483 / week

Book

from £69 / night

(1) Excellent 

1 / 48

Kissimmee holiday villa rental

Kissimmee / Indian Creek

5 10 3 nights min stay

Villa / 5 bedrooms / sleeps 10 / 3 nights min stay

Add to shortlist

from £90 / night

£630 / week

Book

from £90 / night

(10) Excellent 

1 / 33

Villa rental in Kissimmee with swimming pool

Kissimmee / Kissimmee City

4 9 Min stay varies

Villa / 4 bedrooms / sleeps 9 / Min stay varies

Add to shortlist

from £82 / night

£540 - £660 / week

Book

from £82 / night

(2) Excellent 

1 / 10

Holiday condo with golf nearby in Kissimmee

Central Florida / Kissimmee

3 8 Min stay varies

Condo / 3 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £52 / night

£407 - £687 / week

Book

from £52 / night

1 / 20

Holiday home in Kissimmee

Central Florida / Kissimmee

6 13 Min stay varies

House / 6 bedrooms / sleeps 13 / Min stay varies

Add to shortlist

from £125 / night

£869 / week

Book

from £125 / night

1 / 43

Holiday home in Kissimmee

Kissimmee / Crescent Lakes

4 8 Min stay varies

House / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £73 / night

£638 / week

Book

from £73 / night

1 / 17

Home rental in Kissimmee with golf nearby

Central Florida / Kissimmee

3 8 3 nights min stay

House / 3 bedrooms / sleeps 8 / 3 nights min stay

Add to shortlist

from £69 / night

£476 / week

Book

from £69 / night

1 / 12

Home rental in Kissimmee with swimming pool

Central Florida / Kissimmee

3 6 Min stay varies

House / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £83 / night

£575 - £816 / week

Book

from £83 / night

1 / 6

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 16 Min stay varies

Villa / 4 bedrooms / sleeps 16 / Min stay varies

Add to shortlist

from £228 / night

£2759 / week

Book

from £228 / night

(1) Excellent 

1 / 24

Holiday home in Crescent Lakes

Kissimmee / Crescent Lakes

4 8 Min stay varies

House / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £80 / night

£720 / week

Book

from £80 / night

1 / 13

Holiday condo in Kissimmee

Kissimmee / Legacy Dunes Resort

2 6 Min stay varies

Condo / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £66 / night

£459 - £532 / week

Book

from £66 / night

1 / 37

Holiday condo in Windsor Palms

Kissimmee / Windsor Palms

3 7 Min stay varies

Condo / 3 bedrooms / sleeps 7 / Min stay varies

Add to shortlist

from £62 / night

£432 - £618 / week

Book

from £62 / night

1 / 11

Holiday apartment in Kissimmee

Central Florida / Kissimmee

4 8 3 nights min stay

Apartment / 4 bedrooms / sleeps 8 / 3 nights min stay

Add to shortlist

from £90 / night

£621 / week

Book

from £90 / night

(1) Poor 

1 / 15

Villa rental in Kissimmee

Central Florida / Kissimmee

4 10 Min stay varies

Villa / 4 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £62 / night

£556 / week

Book

from £62 / night

1 / 20

Holiday condo rental

Kissimmee / Windsor Palms

2 6 Min stay varies

Condo / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £59 / night

£387 - £604 / week

Book

from £59 / night

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