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

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Kissimmee

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16,825 Holiday homes

40

Holiday home in Kissimmee

Central Florida / Kissimmee

4 12 3 nights min

  • 4 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £123 / night

£855 / week

Book View

Responds fast!
avg. 3 hours 32 minutes

from £123 / night

18

Holiday villa rental

Central Florida / Kissimmee

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £120 / night

£850 - £920 / week

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from £120 / night

15

Holiday townhouse rental

Kissimmee / Windsor Hills Resort

3 8 3 nights min

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

from £75 / night

£525 / week

Book View

from £75 / 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 £317 / night

£1,620 - £2,958 / week

Book View

Responds fast!
avg. 1 hour 26 minutes

from £317 / night

(2) Excellent 

19

Holiday villa 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

£600 - £750 / week

Book View

Responds fast!
avg. 3 hours 8 minutes

from £110 / night

(4) Very Good 

14

Townhouse rental in Venetian Bay Villages

Kissimmee / Venetian Bay Villages

3 6 5 nights min

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

from £57 / night

£396 / week

Book View

from £57 / night

(36) Excellent 

30

Villa rental in Cumbrian Lakes

Kissimmee / Cumbrian Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Great vacation home with a pool in a quiet neighborhood” We stayed at Robson's Retreat during Christmas week, 2017. The house is spacious, clean, and has many things to offer. We used the pool, the bicycles, the washer and dryer, and the large TV. The
…see more

from £110 / night

£750 - £900 / week

Enquire View

from £110 / night

(2) Very Good 

19

Holiday apartment with shared pool in Kissimmee

Kissimmee / Windsor Palms

3 6 5 nights min

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

from £70 / night

£488 / week

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from £70 / night

8

Holiday home in Kissimmee

Kissimmee / Emerald Isle Kissimmee

5 12 Min stay varies

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

from £121 / night

£845 / week

Book View

Responds fast!
avg. 1 hour 55 minutes

from £121 / night

(17) Excellent 

Certificate of Excellence

17

Holiday villa in Kissimmee

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £130 / night

£910 / week

Book View

Responds fast!
avg. 52 minutes

from £130 / night

45

Kissimmee holiday apartment rental

Central Florida / Kissimmee

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly

from £112 / night

£784 / week

Book View

from £112 / night

(2) Excellent 

35

Holiday home rental

Central Florida / Kissimmee

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £160 / night

£1,120 / week

Book View

Responds fast!
avg. 2 hours 8 minutes

from £160 / night

(1) Excellent 

57

Home rental in Kissimmee

Kissimmee / Oak Island Harbor

4 8 4 nights min

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

from £183 / night

£1,282 / week

Book View

from £183 / 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 £85 / night

£560 - £740 / week

Book View

Responds fast!
avg. 7 minutes

from £85 / night

(12) Excellent 

48

Kissimmee holiday villa rental

Kissimmee / The Hamlets

5 12 5 nights min

  • 5 bedrooms
  • Sleeps 12
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £100 / night

£700 - £850 / week

Book View

Responds fast!
avg. 3 hours 59 minutes

from £100 / night

29

Holiday home letting

Central Florida / Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 90 km
  • Child friendly
  • Air conditioning

from £98 / night

£686 - £995 / week

Book View

from £98 / night

(8) Very Good 

24

Kissimmee holiday villa rental

Kissimmee / Crescent Lakes

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Amazing all the way around” My wife and I booked this Villa in order to have a nice place to relax after taking our three daughters to the Disney parks. We stayed for a week and mid way through each day we spent at the parks our kids would express how
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from £110 / night

£725 / week

Book View

Responds fast!
avg. 1 hour 52 minutes

from £110 / night

(1) Very Good 

29

Holiday home in Kissimmee

Central Florida / Kissimmee

6 12 Min stay varies

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

from £113 / night

£772 - £863 / week

Book View

Responds fast!
avg. 7 minutes

from £113 / night

24

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £94 / night

£656 / week

Book View

from £94 / night

(6) Very Good 

19

Villa rental in Kissimmee with swimming pool

Kissimmee / Emerald Isle Kissimmee

5 12 Min stay varies

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

from £97 / night

£679 - £1,001 / week

Book View

Responds fast!
avg. 51 minutes

from £97 / 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 £85 / night

£592 / week

Book View

Responds fast!
avg. 2 hours 47 minutes

from £85 / 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 £212 / night

£845 - £1,894 / week

Book View

from £212 / night

(13) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“Had a wonderful holiday with all the family” Stayed at a very nice villa in a good location a couple of miles from the Disney Parks The surrounding area was always very clean & tidy & well looked after. Could not have asked for anything more, also t
…see more

from £137 / night

£890 - £1,450 / week

Book View

Responds fast!
avg. 2 hours 46 minutes

from £137 / night

(11) Excellent 

43

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee / Winward Cay

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Simply perfect! We will be coming back :)” Our first visit to Florida and from the moment we booked we knew we made the right choice. Marie went out of her way to give us lots of useful information to help us make the most off our visit. When we arri
…see more

from £68 / night

£460 - £650 / week

Book View

Responds fast!
avg. 3 hours 2 minutes

from £68 / night

21

Holiday villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 10 3 nights min

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

from £99 / night

£691 / week

Book View

Responds fast!
avg. 2 hours 17 minutes

from £99 / night

(5) Excellent 

24

Holiday villa with golf nearby in Kissimmee

Kissimmee / Remington

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
“A fantastic villa that felt just like home!” I would highly recommend this villa, it was perfect in every way and I would recommend it to anyone, who needed accommodation in Orlando.
…see more

from £114 / night

£795 - £1,195 / week

Book View

from £114 / night

(9) Excellent 

22

Lake Berkley holiday villa rental

Kissimmee / Lake Berkley

5 10 4 nights min

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

from £136 / night

£951 / week

Book View

Responds fast!
avg. 2 hours 30 minutes

from £136 / night

(1) Very Good 

28

Home rental in Kissimmee

Central Florida / Kissimmee

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £145 / night

£1,015 / week

Book View

Responds fast!
avg. 2 hours 8 minutes

from £145 / night

(3) Very Good 

23

Holiday villa with swimming pool, golf nearby in Kissimmee

Central Florida / Kissimmee

6 13 Min stay varies

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

from £112 / night

£795 - £1,338 / week

Book View

Responds fast!
avg. 2 hours 49 minutes

from £112 / night

(2) Excellent 

20

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £124 / night

£867 / week

Book View

Responds fast!
avg. 2 hours 36 minutes

from £124 / night

(4) Very Good 

35

Holiday townhouse rental

Kissimmee / Windsor Hills Resort

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“FANTASTIC!” I would highly recommend this 3 bedroom townhouse with heated pool. It was everything and more when we arrived. The outdoor pool was perfect for the kids and the park in the back yard was great to have them play frisbee and soccer. The loc
…see more

from £81 / night

£564 / week

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from £81 / night

14

Holiday condo with shared pool in Kissimmee

Central Florida / Kissimmee

3 6 3 nights min

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

from £60 / night

£353 / week

Book View

from £60 / night

(13) Excellent 

24

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 £120 / night

£838 / week

Enquire View

from £120 / night

(7) Excellent 

24

Holiday villa with golf nearby in Kissimmee

Kissimmee / Indian Ridge Oaks

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Great villa in a great location” This is a large, clean, comfortable villa on a quiet estate close to Disney. It isn't overlooked, and the pool is separated from one neighbour by a fence and the other is set back so you get good privacy. There was a f
…see more

from £160 / night

£1,000 - £1,100 / week

Book View

from £160 / night

(3) Excellent 

11

Holiday hotel apartment in Kissimmee

Kissimmee / Compass Bay

3 8 4 nights min

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

from £91 / night

£648 / week

Book View

Responds fast!
avg. 3 hours 50 minutes

from £91 / night

(21) Excellent 

28

Villa rental in Kissimmee

Kissimmee / Doral Woods

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“A truly amazing place to stay!” If you are looking at this page, thinking about renting this villa, just do it, you'll have no regrets. We stayed for 3 weeks in July/August and had a fantastic time. It was the perfect villa for us (a family of 2 adul
…see more

from £69 / night

£485 - £575 / week

Book View

Responds fast!
avg. 38 minutes

from £69 / night

(3) Excellent 

100

Holiday home in Kissimmee

Kissimmee / Paradise Palms

4 12 3 nights min

  • 4 bedrooms
  • Sleeps 12
  • 3 nights min
  • Nearest beach 103 km
  • Swimming pool
  • Child friendly

from £85 / night

£592 / week

Book View

Responds fast!
avg. 3 hours 44 minutes

from £85 / night

(21) Excellent 

28

Holiday villa in Kissimmee

Kissimmee / Windsor Palms

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Immaculate - delivers above and beyond ..” An immaculate villa, perfectly presented and equipped with everything you could need. Choosing a villa always comes with a little bit of interpretation but Sundown Palm delivered above and beyond the descrip
…see more

from £190 / night

£1,330 / week

Book View

from £190 / night

(1)  

24

Guest house rental in Kissimmee with golf nearby

Central Florida / Kissimmee

7 16 Min stay varies

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

from £162 / night

£986 - £1,867 / week

Book View

from £162 / night

(5) Excellent 

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 £60 / night

£420 / week

Book View

Responds fast!
avg. 2 hours 12 minutes

from £60 / night