Villas in Kissimmee and Holiday rentals - Holiday Lettings - Holiday Rentals Kissimmee

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Kissimmee

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5,101 Holiday homes

(13) Excellent 

18

Holiday villa with golf nearby in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“A fantastic place to stay, would highly recommend!” This is a perfect villa for a family holiday to Orlando! The complex is pristine and very safe. The villa itself had everything you could wish for and more. The owners had thought of everything to ma
…see more

from £180 / night

£1260 - £1925 / week

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from £180 / night

18

Holiday villa rental

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £110 / night

£700 - £1070 / week

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from £110 / night

(1) Excellent 

20

Regal Oaks holiday townhouse rental

Kissimmee / Regal Oaks

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £87 / night

£607 / week

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from £87 / night

(70) Excellent 

27

Villa rental in Kissimmee

Kissimmee / Windsor Palms

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £183 / night

£1280 - £1729 / week

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from £183 / night

21

Holiday home accommodation

Central Florida / Kissimmee

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £182 / night

£1274 / week

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from £182 / night

22

Holiday villa with golf nearby in Lindfields

Kissimmee / Lindfields

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £111 / night

£709 - £729 / week

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from £111 / night

8

Kissimmee holiday villa rental

Central Florida / Kissimmee

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £64 / night

£445 - £540 / week

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from £64 / night

11

Kissimmee holiday villa rental

Kissimmee / Trafalgar Village

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £83 / night

£579 / week

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from £83 / night

17

Kissimmee holiday villa rental

Central Florida / Kissimmee

6 13 5 nights min

  • 6 bedrooms
  • Sleeps 13
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Child friendly

from £175 / night

£1225 / week

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from £175 / night

46

Villa rental in Kissimmee with swimming pool

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool

from £96 / night

£635 - £818 / week

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from £96 / night

17

Holiday villa with golf nearby in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 14 5 nights min

  • 6 bedrooms
  • Sleeps 14
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool

from £120 / night

£830 / week

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Responds fast!
avg. 3 hours 53 minutes

from £120 / night

(1) Excellent 

41

Holiday home in Kissimmee

Kissimmee / Kissimmee City

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £95 / night

£662 / week

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Responds fast!
avg. 53 minutes

from £95 / night

11

Holiday home with indoor pool in Kissimmee

Central Florida / Kissimmee

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £83 / night

£579 / week

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from £83 / night

(1) Excellent 

15

Kissimmee holiday villa rental

Kissimmee / Lake Berkley

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
“FABULOUS all round” Villa location excellent , pool area fantastic , Lake Views Stunning , wildlife & Bird Watching Endless enjoyment The Best of Furniture & Soft Furnishing through out And the Owners a joy to deal with If you think the PHOTOS
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from £410 / night

£570 / week

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from £410 / night

(22) Excellent 

27

Holiday villa with golf nearby in Kissimmee

Kissimmee / Windsor Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 68 km
  • Swimming pool
  • Child friendly
“What a fantastic experience from start to finish!” The house was beautiful and well taken care of. The pool was very nice and even had things to use in the pool. The outside furniture was nice to relax in by the pool. The rooms were all very nice and
…see more

from £118 / night

£780 - £1338 / week

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from £118 / night

31

Holiday home in Kissimmee

Central Florida / Kissimmee

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £182 / night

£1274 / week

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from £182 / night

28

Holiday villa with golf nearby in Kissimmee

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 10 km
  • Swimming pool
  • Child friendly

from £134 / night

£938 - £1103 / week

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from £134 / night

(1) Excellent 

55

Kissimmee holiday villa rental

Kissimmee / Lake Berkley

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Loved it so much” Just spent 2 weeks in this villa, loved it so much! Many happy memories of a great holiday, we are definitely looking into coming again. Slept 6 more then comfortably and the pool is in a great position, gets a few hours sunlight bu
…see more

from £99 / night

£650 - £847 / week

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from £99 / night

44

Holiday home with golf nearby in Kissimmee

Central Florida / Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly

from £99 / night

£689 / week

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Responds fast!
avg. 3 hours 11 minutes

from £99 / night

81

Holiday home rental

Central Florida / Kissimmee

5 10 4 nights min

  • 5 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £158 / night

£1103 / week

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from £158 / night

26

Home rental in Kissimmee

Central Florida / Kissimmee

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £106 / night

£742 - £896 / week

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Responds fast!
avg. 2 hours 43 minutes

from £106 / night

37

Kissimmee holiday villa rental

Kissimmee / Lindfields

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £105 / night

£731 / week

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from £105 / night

(1) Excellent 

21

Kissimmee holiday villa rental

Kissimmee / The Hamlets

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

Pricing unknown

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Pricing unknown

(8) Excellent 

20

Holiday bungalow with swimming pool, golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £131 / night

£917 / week

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from £131 / night

(56) Excellent 

23

Holiday villa in Crescent Lakes

Kissimmee / Crescent Lakes

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Dream Villa” This is our second year at this villa and we could find nothing to fault, set on the side of a lake with swimming pool covered by Florida room ( mosquito netting) with heated hot tube, extensive games room, cable tv in all rooms extreme
…see more

from £90 / night

£575 - £690 / week

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from £90 / night

26

Holiday townhouse with shared pool in Venetian Bay Villages

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £65 / night

£455 - £628 / week

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from £65 / night

19

Holiday villa in Kissimmee

Central Florida / Kissimmee

7 16 7 nights min

  • 7 bedrooms
  • Sleeps 16
  • 7 nights min
  • Child friendly

from £231 / night

£1615 / week

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from £231 / night

(2) Average 

11

Holiday villa in Kissimmee

Kissimmee / Formosa Gardens

2 10 7 nights min

  • 2 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £154 / night

£1075 / week

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from £154 / night

(1) Average 

52

Villa rental in Kissimmee with golf nearby

Kissimmee / Indian Ridge

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £80 / night

£495 - £695 / week

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from £80 / night

(1) Excellent 

20

Holiday home rental

Kissimmee / Lake Berkley

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £125 / night

£800 / week

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Responds fast!
avg. 3 hours 28 minutes

from £125 / night

(59) Excellent 

20

Holiday villa with golf nearby in Kissimmee

Kissimmee / Formosa Gardens

7 22 4 nights min

  • 7 bedrooms
  • Sleeps 22
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“This place is heaven!!” Close to all the attractions yet private enough to give you relaxation!!! Can't wait to book here again!! The owners were very easy to work with and very patient with us!!! Thanks again for renting to us!!!
…see more

from £312 / night

£2186 / week

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from £312 / night

43

Kissimmee holiday villa rental

Central Florida / Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Child friendly

from £220 / night

£1540 / week

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Responds fast!
avg. 2 hours 26 minutes

from £220 / night

32

Holiday condo in Kissimmee

Central Florida / Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £86 / night

£596 / week

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from £86 / night

(3) Very Good 

92

Cumbrian Lakes holiday home rental

Kissimmee / Cumbrian Lakes

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“This place is amazing” We stayed here for a week after a tiring but fun road trip and as a base station for the theme parks! It was exactly what we needed for a group of 7 friends! Good location for the parks, lovely area and amazing view of the sunse
…see more

from £195 / night

£1365 / week

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from £195 / night

(4) Very Good 

13

Villa rental in Kissimmee with shared pool, golf nearby

Kissimmee / Orange Lake Resort

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Nice accommodation and location.” 20 minutes to theme parks. 10 minutes to super market. 30 minutes to outlet shops. Easy to find on Sat Nav and no hassles with traffic. Lacking a few kitchen utensils, but nothing worth fussing over.
…see more

from £135 / night

£945 / week

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from £135 / night

29

Holiday home with swimming pool in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £95 / night

£662 / week

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Responds fast!
avg. 3 hours 6 minutes

from £95 / night

28

Villa rental in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £215 / night

£1505 / week

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from £215 / night

19

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 11 1 night min

  • 4 bedrooms
  • Sleeps 11
  • 1 night min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £112 / night

£784 / week

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from £112 / night

(1) Excellent 

4

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £66 / night

£460 - £599 / week

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Responds fast!
avg. 1 hour 30 minutes

from £66 / night

17

Kissimmee holiday home rental

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £110 / night

£767 / week

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from £110 / night

1