Kissimmee apartment or villa with a heated pool | Holiday Lettings

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Kissimmee

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1,250 Holiday homes

Filters applied: Heated pool

(3) Very Good 

Certificate of Excellence

34

Holiday villa in Crescent Lakes

Kissimmee / Crescent Lakes

4 8 4 nights min

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

Certificate of Excellence

from £88 / night

£614 / week

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from £88 / night

(5) Excellent 

44

Holiday villa with golf nearby in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Very nice villa in a quiet and peaceful area.” The villa was very tidy and well maintained. The location was excellent, being very close to a supermarket and to Kissimmee. It was also an ideal location for all the excellent theme parks. We certainly w
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from £95 / night

£585 - £595 / week

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from £95 / night

64

Holiday villa in Lindfields

Kissimmee / Lindfields

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Air conditioning
  • Private garden

from £73 / night

£511 / week

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from £73 / night

(17) Excellent 

Certificate of Excellence

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
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Certificate of Excellence

from £102 / night

£689 - £885 / week

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from £102 / 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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from £99 / 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 £123 / night

£869 - £1277 / week

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from £123 / night

(18) Very Good 

24

Townhouse rental in Kissimmee

Kissimmee / Regal Oaks

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • 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
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from £70 / night

£485 / week

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from £70 / night

(2) Excellent 

84

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £108 / night

£754 - £1094 / week

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from £108 / night

(9) 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

(3) Excellent 

28

Holiday home with golf nearby in Kissimmee

Central Florida / Kissimmee

8 16 Min stay varies

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

from £231 / night

£1385 - £1939 / week

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from £231 / night

(32) Excellent 

17

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic! Didn't want to leave!” The best vacation, my family ever had. Two small children ages 6yrs. and 4yrs. loved the kiddie pool.
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from £97 / night

£654 - £708 / week

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from £97 / night

(7) Excellent 

30

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly
“Excellent property and very helpful owners” This house is excellent and very well maintained. It had all the amenities / facilities we needed and in good working order. Very comfortable and easy to relax after long days at the theme parks. Julie and M
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from £105 / night

£550 - £670 / week

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from £105 / night

(1) Excellent 

20

Holiday villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £231 / night

£847 - £2146 / week

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from £231 / night

(6) Very Good 

34

Townhouse rental in Paradise Palms with indoor pool, golf nearby

Kissimmee / Paradise Palms

4 8 Min stay varies

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

from £70 / night

£462 - £770 / week

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from £70 / night

(2) Excellent 

29

Holiday villa in Kissimmee

Kissimmee / Seasons Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £118 / night

£826 - £1481 / week

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from £118 / night

24

Holiday villa 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 £85 / night

£595 - £735 / week

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from £85 / night

(22) Excellent 

24

Holiday townhouse rental

Kissimmee / Encantada Resort

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
“Really nice” Nice house good location, we really liked the option of being able to use the pool at the house or the two large pools by the clubhouse. Would certainly stay again.
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from £100 / night

£680 - £950 / week

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from £100 / night

(3) Excellent 

100

Emerald Isle Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

7 16 5 nights min

  • 7 bedrooms
  • Sleeps 16
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool

from £290 / night

£2030 / week

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from £290 / night

13

Villa rental in Kissimmee with shared pool

Central Florida / Kissimmee

4 10 1 night min

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

from £93 / night

£647 / week

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from £93 / 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

(20) Very Good 

68

Holiday villa in Kissimmee

Kissimmee / Lindfields

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Thanks” This was a great Vila with everything you needed and in a good area to base yourself, if any c ok militants a bit dated
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from £100 / night

£450 - £540 / week

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from £100 / night

(2) Excellent 

22

Villa rental in Kissimmee with swimming pool

Kissimmee / Cumbrian Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

from £100 / night

£700 - £910 / week

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from £100 / 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
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from £104 / night

£727 / week

Enquire View

from £104 / night

(20) Very Good 

24

Villa accommodation in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Home from home.” The villa is in a fantastic location for all the attractions and the gated community is set in an attractive environment. The photos do not do it justice- we were blown away with the space and quality of this lovely villa. It has ho
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from £75 / night

£480 - £600 / week

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from £75 / night

(75) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Bass Lakes Estate

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“Excellent location” We have been to Orlando several times as a family and location wise this is without doubt the best villa we have stayed at. In fact it is the only one we would stop at again. There's a Walmart at the end of the steeet and plenty of
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from £70 / night

£475 - £590 / week

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from £70 / 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

(4) 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

(3) Very Good 

51

Kissimmee holiday apartment rental

Central Florida / Kissimmee

3 6 3 nights min

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

from £66 / night

£458 / week

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from £66 / night

(18) 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!
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from £80 / night

£550 - £680 / week

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from £80 / night

(10) Very Good 

70

Holiday villa in Kissimmee

Kissimmee / Lake Berkley

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“beautiful” the house is beautiful and quiet, we had a great time and will definitely return, Kevin and Anne and their management are friendly and always available. thanks for everything
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from £115 / night

£795 - £1540 / week

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from £115 / night

28

Legacy Dunes Resort holiday condo rental

Kissimmee / Legacy Dunes Resort

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 150 km
  • Swimming pool

from £60 / night

£400 - £450 / week

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from £60 / 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 £181 / night

£1770 / week

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from £181 / night

(9) Excellent 

14

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
“A HOLIDAY TO REMEMBER” Cumbrian lakes drive is a well appointed 8 bed villa in very pleasant surroundings. We stayed there 4 adults and 2 young children aged 6 & 8 for 2 weeks. It is within easy access of all the parks, the malls etc and only a shor
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from £90 / night

£630 - £795 / week

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from £90 / 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 £82 / night

£570 - £730 / week

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from £82 / night

(2) Excellent 

30

Kissimmee holiday home rental

Central Florida / Kissimmee

3 8 Min stay varies

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

from £84 / night

£547 - £808 / week

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from £84 / night

(2) Very Good 

18

Kissimmee holiday condo rental

Central Florida / Kissimmee

3 8 5 nights min

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

from £77 / night

£534 / week

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from £77 / night

(10) Very Good 

20

Holiday villa letting

Kissimmee / Emerald Isle Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £75 / night

£525 - £735 / week

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from £75 / night

25

Holiday villa in Kissimmee

Kissimmee / Veranda Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 104 km
  • Swimming pool
  • Child friendly

from £99 / night

£690 / week

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from £99 / night

(4) Excellent 

Certificate of Excellence

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
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Certificate of Excellence

from £115 / night

£700 - £895 / week

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from £115 / night

18

Crescent Lakes holiday villa rental

Kissimmee / Crescent Lakes

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

from £99 / night

£693 - £847 / week

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from £99 / night

1