Villas with a pool Kissimmee | Apartments to rent with swimming facilities | Holiday Lettings

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Kissimmee

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3,026 Holiday homes

Filters applied: Swimming pool

(3) Very Good 

12

Holiday villa rental

Central Florida / Kissimmee

3 6 5 nights min

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

from £72 / night

£450 / week

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from £72 / 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
…see more

from £100 / night

£450 - £540 / week

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from £100 / night

(2) Average 

20

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

6 14 1 night min

  • 6 bedrooms
  • Sleeps 14
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £172 / night

£1204 / week

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from £172 / night

(2) Very Good 

49

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

6 12 Min stay varies

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

from £125 / night

£895 - £1565 / week

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from £125 / night

(14) Excellent 

Certificate of Excellence

12

Kissimmee holiday villa rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £84 / night

£550 - £700 / week

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from £84 / 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

(17) Excellent 

48

Townhouse rental in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 104 km
  • Swimming pool
  • Child friendly
“Absolutely fabulous -we will rent this villa again next time we go to Forida” There really wasn't anything about this property that disappointed us. It was clean, beautifully decorated and furnished, kitchen had more equipment that we ever used - an
…see more

from £65 / night

£400 - £525 / week

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from £65 / night

(1) Excellent 

20

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 6 7 nights min

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

from £86 / night

£600 - £750 / week

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from £86 / 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

15

Holiday villa rental

Central Florida / Kissimmee

8 20 4 nights min

  • 8 bedrooms
  • Sleeps 20
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £265 / night

£1855 / week

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from £265 / 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

(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.
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Certificate of Excellence

from £50 / night

£350 / week

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from £50 / 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

(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

(2) Very Good 

100

Holiday villa in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 8 5 nights min

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

from £108 / night

£754 - £1094 / week

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from £108 / 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

(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
…see more

from £90 / night

£630 - £795 / week

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from £90 / 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

(4) Excellent 

23

Holiday villa in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

6 14 2 nights min

  • 6 bedrooms
  • Sleeps 14
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Spacious House” The house was great very spacious and all 12 of us enjoyed it very much. The downside of getting to a property after being delayed for over 2 hours was it was late at night and other properties we had rented before left us a welcome
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from £154 / night

£1077 / week

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from £154 / night

(12) Excellent 

Certificate of Excellence

16

Villa rental in Kissimmee

Kissimmee / Indian Creek

4 8 Min stay varies

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

Certificate of Excellence

from £114 / night

£850 - £1200 / week

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from £114 / night

17

Holiday villa with shared pool, golf nearby in Kissimmee

Kissimmee / Orange Lake Resort

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

from £171 / night

£950 / week

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from £171 / 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 £104 / night

£727 / week

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from £104 / 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
…see more

from £115 / night

£795 - £1540 / week

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from £115 / night

(24) Excellent 

23

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
…see more

from £135 / night

£945 - £1250 / week

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from £135 / 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

(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!
…see more

from £80 / night

£550 - £680 / week

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from £80 / night

(13) Excellent 

Certificate of Excellence

32

Holiday home with swimming pool in Paradise Palms

Kissimmee / Paradise Palms

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Wonderful vacation” The house was beautiful, clean and very well-kept. Plenty of bedroom space, beautiful bathrooms, ample linens and towels supplied. We especially enjoyed the patio area at the pool. We spent many hours there, reading, relaxing and v
…see more

Certificate of Excellence

from £104 / night

£889 / week

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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
…see more

from £75 / night

£480 - £600 / week

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from £75 / 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

29

Kissimmee holiday home rental

Central Florida / Kissimmee

5 10 Min stay varies

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

from £108 / night

£712 - £997 / week

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from £108 / night

(2) Very Good 

38

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £174 / night

£1770 / week

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from £174 / 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 £181 / night

£1770 / week

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from £181 / 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

(11) Very Good 

20

Holiday villa with indoor pool in Paradise Palms

Kissimmee / Paradise Palms

6 12 5 nights min

  • 6 bedrooms
  • Sleeps 12
  • 5 nights min
  • 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 £193 / night

£1347 / week

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from £193 / 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
…see more

from £70 / night

£539 / week

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from £70 / 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

(8) Excellent 

43

Holiday townhouse in Kissimmee

Central Florida / Kissimmee

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Nearest beach 114 km
  • Swimming pool
  • Child friendly

from £75 / night

£525 / 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

(17) Excellent 

21

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“3 weeks of luxury” I have just arrived back in the UK from a fantastic 3 weeks in this Villa and am already looking at booking it again for next year. Excellent location in terms of parks, shops, places to eat and night time peace. Lovely clean, spa
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from £70 / night

£465 - £595 / week

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from £70 / night

32

Villa rental in Oak Island Cove

Kissimmee / Oak Island Cove

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 125 km
  • Swimming pool
  • Child friendly

from £112 / night

£866 - £981 / week

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from £112 / night

1