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Kissimmee

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266 Holiday homes

Filters applied: Cot available

(5) Excellent 

28

Holiday home rental

Kissimmee / Emerald Isle Kissimmee

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
“Super Spring Break” My family spent the week of April 7 - 14, 2012 at "Jewel In The Crown", which is located in Emerald Island Resort. This is our sixth trip to Orlando and one of the best times we've had!!! Our "home away from home" was comfortable,
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from £157 / night

£1097 / week

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Responds fast!
avg. 3 hours 37 minutes

from £157 / 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 £237 / night

£1103 - £2118 / week

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from £237 / night

(1) Very Good 

22

Holiday townhouse in Kissimmee

Kissimmee / Encantada Resort

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £95 / night

£662 / week

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from £95 / night

(5) Very Good 

Certificate of Excellence

88

Holiday villa in Kissimmee

Kissimmee / Seasons Resort

5 10 4 nights min

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

Certificate of Excellence

from £110 / night

£695 / week

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from £110 / night

99

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

7 14 5 nights min

  • 7 bedrooms
  • Sleeps 14
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool

from £245 / night

£1715 / week

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from £245 / 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

(38) Excellent 

62

Holiday villa in Kissimmee

Kissimmee / Lindfields

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Mrs” EXCELLENT...doesn't do it justice. Great location Great accommodation Great facilities Would have liked to have stayed longer. A lot of thought and care has gone into making this your home for your stay. Disney is easy to access.... food shops
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from £80 / night

£550 - £675 / week

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from £80 / night

(24) Excellent 

27

Holiday villa with golf nearby in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
“You must stay in this Home” We have stayed at Emerald Island Resort on several occasions because we like the closeness of the location to the main attractions and the safety of the gated community with 24 hour security. So, when looking for a property
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from £135 / night

£945 - £1250 / week

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from £135 / night

(10) Very Good 

20

Holiday townhouse in Kissimmee

Kissimmee / Paradise Palms

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £95 / night

£575 - £900 / week

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from £95 / night

(10) Very Good 

Certificate of Excellence

22

Holiday villa in Kissimmee

Kissimmee / Terra Verde Resort

5 12 5 nights min

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

Certificate of Excellence

from £100 / night

£695 - £827 / week

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from £100 / night

(4) Very Good 

12

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Idyllic base for Orlando holiday” Just got back from this lovely villa where we spent a wonderful two weeks. The owners have made this feel just like home, with everything necessary for a comfortable stay. From the extended pool deck with comfy sunbed
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from £87 / night

£626 / week

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from £87 / night

(1) Excellent 

13

Apartment rental in Kissimmee

Kissimmee / Windsor Palms

3 6 5 nights min

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

from £71 / night

£472 / week

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Responds fast!
avg. 3 hours 10 minutes

from £71 / night

(4) Excellent 

45

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Lovely villa and ideal location” The villa was lovely, very clean and spacious with a great view of the lake behind. It was situated in an ideal location - especially for Disney! Would definitely stay again.
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from £95 / night

£670 - £768 / week

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from £95 / night

(8) Excellent 

55

Holiday villa with golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £189 / night

£1323 / week

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from £189 / 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
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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

(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

(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
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from £107 / night

£745 - £895 / week

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from £107 / 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

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Responds fast!
avg. 1 hour 34 minutes

from £65 / 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
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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

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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

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Responds fast!
avg. 1 hour 42 minutes

from £107 / 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
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Certificate of Excellence

from £66 / night

£460 - £690 / week

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from £66 / 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

(10) Very Good 

17

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 106 km
  • Swimming pool
  • Child friendly
“Lovely Villa, well placed” Villa was clean & spacious. Pool was lovely & clean with nice garden view. Mostly quiet neighbourhood. Very close to 192 with all the restaurants & shopping. Ian was easy to contact & kept in touch throughout the stay. Pool
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from £65 / night

£450 / week

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from £65 / night

23

Holiday villa in Kissimmee

Kissimmee / Windsor Palms

6 12 Min stay varies

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

from £150 / night

£1050 - £1150 / week

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from £150 / night

(8) Excellent 

24

Villa rental in Kissimmee

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Honeymoon” Brilliant can't fault it at all, everything you need to hand, recommend this villa plenty of space great
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from £75 / night

£485 / week

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Responds fast!
avg. 1 hour 39 minutes

from £75 / night

(19) Very Good 

30

Villa rental in Kissimmee with swimming pool

Central Florida / Kissimmee

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic” 1   person found this review helpful Our stay in the villa was incredibly pleased! Zakir, was quick to respond, and very easy to work with.We have stayed in the Orlando/Kissimee area before, but this was our best stay so far. Vill
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from £71 / night

£552 / week

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from £71 / night

23

Holiday villa in Kissimmee

Kissimmee / Terra Verde Resort

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool

from £125 / night

£875 - £1295 / week

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from £125 / 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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Responds fast!
avg. 3 hours 32 minutes

from £118 / night

(1) Excellent 

35

Holiday home rental

Central Florida / Kissimmee

5 11 1 night min

  • 5 bedrooms
  • Sleeps 11
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £150 / night

£1050 / week

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Responds fast!
avg. 31 minutes

from £150 / night

56

Holiday apartment with shared pool in Kissimmee

Central Florida / Kissimmee

3 6 2 nights min

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

from £71 / night

£457 / week

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from £71 / 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

(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
“Excellent Villa highly recommend it, great location.” Property was excellent, close to Disney and places to eat. The weather was nice and the complex where the villa was situated was well looked after, nice and clean and staff was pleasant.
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from £130 / night

£840 - £1450 / week

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from £130 / night

(2) Excellent 

27

Holiday villa in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
“Great rental experience” As the title of the listing states, this villa was only 5 minutes to Disney. We found the description and the pictures to be quite accurate too. The community is well maintained and it is gated which made us feel secure. Also
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from £178 / night

£1812 / week

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Responds fast!
avg. 52 minutes

from £178 / 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

(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 £158 / night

£1103 / week

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from £158 / night

(2) 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
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from £90 / night

£630 / week

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from £90 / night

(5) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Lindfields

3 8 90 nights min

  • 3 bedrooms
  • Sleeps 8
  • 90 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Home from Home. Great Location. Perfect.” The Villa was everything we dreamed of for our first family holiday in Florida. First impressions were just as we expected, Directions to villa were spot on. Swimming pool was fab with inflatables included. Ho
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from £50 / night

£350 / week

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from £50 / night

(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
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from £180 / night

£1260 - £1925 / week

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from £180 / night