Kissimmee Villas, Holiday rentals and apartments

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Kissimmee

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4,245 Holiday homes

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

(7) Very Good 

16

Holiday villa with swimming pool in Kissimmee

Kissimmee / Eagle Pointe

4 8 Min stay varies

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

from £80 / night

£560 - £1036 / week

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from £80 / night

(12) Excellent 

32

Kissimmee / Paradise Palms

5 12 Min stay varies

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

 …see more

from £96 / night

£924 / week

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from £96 / night

(6) Very Good 

45

Holiday villa with golf nearby in Indian Creek

Kissimmee / Indian Creek

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Fantastic well equipped/maintained villa in a perfect location close to everything, will definitely be back” We chose this villa as it was well equipped and in a location we knew well, we found a lot of villas can be a bit of a drive away from anythin  …see more

from £110 / night

£750 - £1200 / week

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from £110 / night

Featured properties

22

Kissimmee holiday villa rental

Kissimmee / Winward Cay

3 8 7 nights min

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

from £50 / night

£350 - £500 / week

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from £50 / night

(3) Very Good 

43

Holiday villa rental

Kissimmee / Emerald Isle Kissimmee

4 10 4 nights min

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

from £78 / night

£546 / week

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from £78 / night

(1) Excellent 

55

Holiday condo with shared pool in Kissimmee

Kissimmee / Cane Island

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £40 / night

£260 - £476 / week

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from £40 / night

21

Holiday villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £100 / night

£660 - £960 / week

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from £100 / night

(7) Very Good 

37

Kissimmee / Terra Verde Resort

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

from £72 / night

£504 / week

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from £72 / night

(3) Very Good 

14

Kissimmee holiday villa let

Kissimmee / Windsor Hills Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly

from £165 / night

£1154 / week

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from £165 / night

16

Townhouse rental in Venetian Bay Villages with shared pool

Kissimmee / Venetian Bay Villages

3 8 Min stay varies

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

from £76 / night

£532 - £728 / week

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from £76 / night

(1) Very Good 

23

Holiday home rental

Central Florida / Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Child friendly

from £65 / night

£450 / week

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from £65 / night

(9) Very Good 

24

Holiday home in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 130 km
  • Swimming pool
“Fabulous House, Fabulous Holiday” We loved this house!!! It was spotlessly clean, and the furnishings were of a high standard. The beds were really comfy and the children loved the playroom and pool. Great for two families. It is a great location  …see more

from £165 / night

£825 - £1255 / week

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from £165 / night

(3) Very Good 

23

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £128 / night

£904 - £1328 / week

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from £128 / night

(11) Very Good 

20

Holiday villa with indoor pool in Paradise Palms

Kissimmee / Paradise Palms

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic villa and resort in good location for attractions” Stayed in the villa for 2 weeks. There were 10 of us yet the villa was so roomy. Very comfortable and modern with all you could need. The paradise palms resort is also excellent. Great  …see more

from £200 / night

£1400 - £1680 / week

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from £200 / night

(3) Excellent 

20

Villa rental in Windsor Hills Resort with golf nearby

Kissimmee / Windsor Hills Resort

6 12 4 nights min

  • 6 bedrooms
  • Sleeps 12
  • 4 nights min
  • Nearest beach 116 km
  • Swimming pool
  • Child friendly

from £160 / night

£1120 / week

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from £160 / night

20

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £240 / night

£880 - £2232 / week

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from £240 / night

(1) Excellent 

40

Central Florida / Kissimmee

6 14 Min stay varies

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

from £216 / night

£1360 - £1640 / week

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from £216 / night

(2) Very Good 

75

Kissimmee holiday villa let

Kissimmee / Cumbrian Lakes

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £85 / night

£595 - £945 / week

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from £85 / night

(2) Excellent 

54

Kissimmee holiday home rental

Central Florida / Kissimmee

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £340 / night

£1920 - £3360 / week

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from £340 / night

(18) Excellent 

23

Kissimmee holiday villa rental

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Lovely property. Really enjoyed our stay.” I would highly recommend this villa. It was nicely decorated and very clean. The air conditioning and fans kept it nice and cool as well as a dip in the pool which was a really nice size. I found the property  …see more

from £99 / night

£695 - £795 / week

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from £99 / night

(15) Excellent 

37

Villa rental in Kissimmee with swimming pool

Kissimmee / Kissimmee City

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
“One word to sum up this villa...... PERFECT !!!” Choosing a villa was quite a hard task to ensure that the whole family enjoyed their vacation in Florida. It needed to be centrally located to all the main parks, be furnished to a good standard & have  …see more

from £113 / night

£752 - £920 / week

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from £113 / night

(1) Very Good 

22

Holiday townhouse in Kissimmee

Kissimmee / Encantada Resort

4 10 4 nights min

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

from £96 / night

£672 / week

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from £96 / night

99

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool

from £150 / night

£1050 / week

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from £150 / night

(1) Excellent 

13

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning

from £65 / night

£450 - £600 / week

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from £65 / night

23

Holiday home in Kissimmee

Central Florida / Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £200 / night

£1400 - £2280 / week

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from £200 / night

(5) Very Good 

74

Villa rental in Kissimmee with swimming pool, golf nearby

Kissimmee / Windsor Hills Resort

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Lovely villa” Very good if you are visiting Disney parks they are very close by. The villa was in a very nice neighbourhood also it was well maintained. Also the security gates made us feel very secure. Slightly further away from International D  …see more

from £108 / night

£756 / week

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from £108 / night

(7) Excellent 

31

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee / Winward Cay

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Spacious villa with everything we needed” I stayed at this villa with my husband and 3 boys aged 13, 10 and 7yrs old. The property was very spacious with a double bedroom and bathroom downstairs which we used, leaving the boys to have loads of roo  …see more

from £66 / night

£460 - £640 / week

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from £66 / night

(3) Very Good 

12

Holiday home rental

Kissimmee / Emerald Isle Kissimmee

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £85 / night

£595 / week

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from £85 / night

(1) Very Good 

19

Holiday apartment with shared pool in Kissimmee

Kissimmee / Windsor Palms

3 6 Min stay varies

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

from £64 / night

£443 / week

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from £64 / night

(16) Excellent 

28

Holiday villa with golf nearby in Kissimmee

Kissimmee / Sunset Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £118 / night

£825 - £1090 / week

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from £118 / night

(6) Excellent 

18

Holiday villa in Kissimmee

Kissimmee / Lake Berkley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Excellent living in secure environment for family” Well equipped house for a family, from kitchen, over bedrooms and living area to pool, close to attractions, dining and shopping  …see more

from £100 / night

£695 - £750 / week

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from £100 / night

(18) Very Good 

19

Townhouse rental in Kissimmee

Kissimmee / Regal Oaks

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Excellent value, good facilities, close to the Disney Parks” The accommodation was excellent value for money. It was more than spacious enough for 2 adults and 2 children, and had good facilities (although it lacked wi-fi, which was sorely missed by s  …see more

from £72 / night

£668 / week

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from £72 / 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

from £115 / night

£800 / week

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from £115 / night

30

Home rental in Kissimmee

Central Florida / Kissimmee

4 4 Min stay varies

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

from £90 / night

£796 / week

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from £90 / night

25

Holiday villa rental

Central Florida / Kissimmee

5 10 3 nights min

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

from £125 / night

£875 / week

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from £125 / night

(2) Very Good 

18

Holiday villa with shared pool, golf nearby in Orange Lake Resort

Kissimmee / Orange Lake Resort

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
“Perfect family spot.” At the time of our check in our wonderful vacation began. The villa was classically appointed. Everything was spotless and functional. The lush landscape was a fitting tropical backdrop for the winding river. All common a  …see more

from £171 / night

£1200 / week

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from £171 / night

13

Holiday apartment rental

Central Florida / Kissimmee

2 8 7 nights min

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

from £150 / night

£1050 / week

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from £150 / night

(4) Excellent 

21

Villa rental in Kissimmee

Kissimmee / Indian Ridge

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“great villa with a great pool area” Not far from all the theme parks and a great pool area to chill out after a long day. The villa was in good condition and equipped with all the home comforts you could need for a great holiday  …see more

from £115 / night

£700 - £900 / week

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from £115 / 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 £100 / night

£700 - £896 / week

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from £100 / night

23

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £220 / night

£800 - £2152 / week

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from £220 / night

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