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

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Kissimmee

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5,413 Holiday homes

10

Holiday home rental

Central Florida / Kissimmee

3 8 3 nights min

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

from £71 / night

£473 / week

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from £71 / night

(1) Excellent 

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 £54 / night

£375 - £550 / week

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from £54 / night

(11) Very Good 

90

Holiday townhouse in Kissimmee

Kissimmee / Terra Verde Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Fab villa” We just returned from a week at the Palm Heaven Villa. The villa is fab and located in the beautiful Terra Verde resort. It is close to the clubhouse and resort pool. The villa itself is very comfortable and has everything you need. The poo
…see more

from £65 / night

£495 / week

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from £65 / night

(2) Very Good 

24

Kissimmee holiday home rental

Central Florida / Kissimmee

4 10 Min stay varies

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

from £99 / night

£693 - £770 / week

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Responds fast!
avg. 3 hours 24 minutes

from £99 / night

(4) Excellent 

39

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children age 5+
“Very enjoyable stay at Simba's Magic home.” Very enjoyable stay at Simba's Magic home. Dealing with the owner, Sri, was super easy and our group really liked the house. Having stayed in Emerald Island several times, this was the best property we've r
…see more

from £186 / night

£1812 / week

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Responds fast!
avg. 52 minutes

from £186 / 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

16

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 2 nights min

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

from £91 / night

£634 / week

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Responds fast!
avg. 41 minutes

from £91 / 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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Responds fast!
avg. 3 hours 8 minutes

from £85 / 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 £95 / night

£626 - £827 / week

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from £95 / night

9

Holiday townhouse in Venetian Bay Villages

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

from £75 / night

£524 - £717 / week

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from £75 / night

22

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 £95 / night

£662 - £77166 / week

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from £95 / night

(2) Excellent 

11

Kissimmee holiday townhouse rental

Kissimmee / Compass Bay

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 101 km
  • Swimming pool

from £90 / night

£635 - £730 / week

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from £90 / night

(3) Very Good 

81

Holiday home in Oak Island Harbor

Kissimmee / Oak Island Harbor

6 13 4 nights min

  • 6 bedrooms
  • Sleeps 13
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £197 / night

£1378 / week

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Responds fast!
avg. 3 hours 38 minutes

from £197 / night

(19) Very Good 

13

Holiday villa with swimming pool in Kissimmee

Kissimmee / Indian Point

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“A beautiful, clean, home away from home!” We are staying for the month of February in this absolutely awesome, Prairie Point Blvd.home. It's comfortable, spacious and clean, and the pool is to die for! We would highly recommend this home to anyone!
…see more

from £80 / night

£550 - £680 / week

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from £80 / night

16

Legacy Dunes Resort holiday condo rental

Kissimmee / Legacy Dunes Resort

4 8 Min stay varies

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

from £99 / night

£475 - £950 / week

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Responds fast!
avg. 2 hours 9 minutes

from £99 / night

(3) Very Good 

14

Kissimmee holiday villa let

Kissimmee / Windsor Hills Resort

6 13 1 night min

  • 6 bedrooms
  • Sleeps 13
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly

from £182 / night

£1260 / week

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from £182 / night

(1) Very Good 

24

Kissimmee holiday home rental

Central Florida / Kissimmee

5 12 3 nights min

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

from £154 / night

£1075 / week

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from £154 / night

(33) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Our Family 4th of July Vacation” I was looking for a place where my family and myself could go to spend time in Florida from where I live in NYC. We chose the perfect location. Check in was simple, directions to the home were easy to understand, and i
…see more

from £107 / night

£745 - £895 / week

Enquire View

from £107 / night

37

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 8 3 nights min

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

from £65 / night

£425 - £525 / week

Book View

from £65 / night

(23) Very Good 

Certificate of Excellence

10

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

4 9 4 nights min

  • 4 bedrooms
  • Sleeps 9
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £65 / night

£450 / week

Book View

Responds fast!
avg. 1 hour 34 minutes

from £65 / night

(3) Very Good 

15

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 8 7 nights min

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

from £72 / night

£500 - £630 / week

Book View

from £72 / night

(27) Very Good 

Certificate of Excellence

56

Holiday home rental

Kissimmee / Lindfields

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 90 km
  • Swimming pool
“Great accommodation” Stayed here for two weeks for our honeymoon. Location of the villa is excellent if visiting the Disney Parks. Clean and tidy, very large living area and bedrooms. Couldn't have asked for anything better.
…see more

Certificate of Excellence

from £50 / night

£350 / week

Book View

Responds fast!
avg. 3 hours 39 minutes

from £50 / 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 £205 / night

£1434 / week

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Responds fast!
avg. 3 hours 38 minutes

from £205 / 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 £237 / night

£867 - £2197 / week

Book View

from £237 / night

(1) Excellent 

17

Kissimmee holiday home rental

Central Florida / Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly

from £111 / night

£772 / week

Book View

from £111 / night

(2) Excellent 

50

Holiday home with indoor pool in Kissimmee

Central Florida / Kissimmee

3 8 3 nights min

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

from £75 / night

£524 / week

Book View

Responds fast!
avg. 2 hours 45 minutes

from £75 / night

(2) Excellent 

71

Holiday villa with shared pool in Kissimmee City

Kissimmee / Kissimmee City

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect in every way” we have stayed here several times (approx. 10) and every time the house delivers what we expect in a Florida villa. Villa is cleaned to a high standard on arrival, the kitchen has everything you have in your own kitchen at home s
…see more

from £80 / night

£550 / week

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from £80 / night

85

Holiday villa with swimming pool 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 £95 / night

£665 - £1000 / week

Book View

Responds fast!
avg. 1 hour 22 minutes

from £95 / night

(23) Excellent 

Certificate of Excellence

56

Kissimmee holiday villa rental

Kissimmee / Crescent Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 150 km
  • Swimming pool
“Gorgeous villa !” Our first visit to Florida and we had an amazing time i really can't see us going any where else.. the villa is beautiful I felt like a queen for two weeks :) everything u need and more the location is so peaceful, perfect for relaxi
…see more

Certificate of Excellence

from £107 / night

£750 - £900 / week

Book View

Responds fast!
avg. 1 hour 42 minutes

from £107 / night

(4) Excellent 

20

Holiday townhouse in Kissimmee

Kissimmee / Encantada Resort

4 10 5 nights min

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

from £99 / night

£630 / week

Book View

Responds fast!
avg. 3 hours 43 minutes

from £99 / night

(13) Very Good 

Certificate of Excellence

47

Villa rental in Indian Point with shared pool

Kissimmee / Indian Point

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Outstanding Villa - Real Home from Home” Superb villa - really clean, airy and well-decorated with a lovely pool and patio area. Plenty of room for everyone in the 4 bedrooms & especially liked having 3 bathrooms to make leaving for the parks much qui
…see more

Certificate of Excellence

from £66 / night

£460 - £690 / week

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from £66 / 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

(1) Excellent 

29

Kissimmee holiday home rental

Kissimmee / Formosa Gardens

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“An Excellent Choice” We had a wonderful time at Whispering Palms and think it is an excellent choice of villa both for the quality of accommodation and its location. It is large, comfortable and well maintained. We were an extended family group com
…see more

from £219 / night

£1530 - £2300 / week

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from £219 / night

(6) Excellent 

Certificate of Excellence

48

Apartment rental in Kissimmee with shared pool

Central Florida / Kissimmee

3 6 3 nights min

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

Certificate of Excellence

from £67 / night

£469 - £552 / week

Book View

from £67 / 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

38

Holiday home in Kissimmee

Kissimmee / Compass Bay

4 10 3 nights min

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

from £79 / night

£788 / week

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from £79 / night

(2) Excellent 

12

Holiday villa in Windsor Palms

Kissimmee / Windsor Palms

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 5 km
  • Swimming pool
  • Child friendly

from £134 / night

£938 / week

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from £134 / night

30

Holiday home with golf nearby in Kissimmee

Central Florida / Kissimmee

4 10 3 nights min

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

from £69 / night

£449 - £589 / week

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from £69 / night

(2) Excellent 

18

Kissimmee holiday apartment rental

Central Florida / Kissimmee

4 8 3 nights min

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

from £79 / night

£552 / week

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Responds fast!
avg. 3 hours 31 minutes

from £79 / night

(11) Very Good 

48

Holiday villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

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

from £56 / night

£386 / week

Book View

Responds fast!
avg. 2 hours 41 minutes

from £56 / night

1