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

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Kissimmee

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3,282 Holiday homes

Filters applied: Swimming pool

(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

(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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Responds fast!
avg. 3 hours 39 minutes

from £50 / night

11

Holiday villa in Kissimmee

Kissimmee / Formosa Gardens

2 10 Min stay varies

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

from £174 / night

£1048 / week

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from £174 / night

(7) Excellent 

23

Kissimmee holiday villa rental

Kissimmee / Country Creek

3 6 Min stay varies

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

from £85 / night

£560 - £665 / week

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from £85 / night

(1) Excellent 

24

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 £123 / night

£860 / week

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from £123 / night

15

Kissimmee holiday home accommodation

Kissimmee / Emerald Isle Kissimmee

3 8 4 nights min

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

from £71 / night

£481 / week

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from £71 / night

(1) Very Good 

19

Holiday apartment with shared pool in Kissimmee

Kissimmee / Windsor Palms

3 6 Min stay varies

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

from £78 / night

£546 / week

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from £78 / night

(29) Excellent 

24

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
“Brilliant stay loved this villa 5☆☆” When we arrived after a long flight we were welcomed with a beautiful villa,in a gated community so easy to find and looks amazing, everything was clean and the kitchen had had new appliances which look brilliant
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from £110 / night

£750 - £900 / week

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from £110 / night

(6) Very Good 

34

Townhouse rental in Paradise Palms with indoor pool, golf nearby

Kissimmee / Paradise Palms

4 8 3 nights min

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

from £71 / night

£473 - £788 / week

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Responds fast!
avg. 2 hours 35 minutes

from £71 / night

6

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 10 7 nights min

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

from £79 / night

£550 / week

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from £79 / night

(10) Excellent 

Certificate of Excellence

27

Kissimmee holiday villa rental

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Swimming pool

Certificate of Excellence

from £125 / night

£875 - £1073 / week

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from £125 / 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 £79 / night

£552 / week

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from £79 / 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 £86 / night

£622 / week

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from £86 / 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

(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

11

Holiday apartment in Kissimmee

Central Florida / Kissimmee

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £136 / night

£952 / week

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from £136 / night

(7) Excellent 

Certificate of Excellence

60

Cumbrian Lakes holiday villa rental

Kissimmee / Cumbrian Lakes

6 12 7 nights min

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

Certificate of Excellence

from £90 / night

£630 / week

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Responds fast!
avg. 2 hours 6 minutes

from £90 / 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 £178 / night

£1812 / week

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Responds fast!
avg. 52 minutes

from £178 / night

(2) Very Good 

14

Villa rental in Kissimmee

Kissimmee / Bellavida Resort

4 10 4 nights min

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

from £107 / night

£737 / week

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from £107 / 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 £111 / night

£772 - £1120 / week

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from £111 / night

11

Kissimmee holiday villa rental

Kissimmee / Trafalgar Village

4 8 3 nights min

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

from £83 / night

£579 / week

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from £83 / night

(1) Excellent 

21

Kissimmee holiday villa rental

Kissimmee / The Hamlets

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

Pricing unknown

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Pricing unknown

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

(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

(4) 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 £110 / night

£770 - £1050 / week

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Responds fast!
avg. 2 hours 27 minutes

from £110 / 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 £55 / night

£381 / week

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Responds fast!
avg. 2 hours 41 minutes

from £55 / night

24

Emerald Isle Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £237 / night

£867 - £2108 / week

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from £237 / night

(2) Very Good 

20

Kissimmee holiday villa rental

Kissimmee / Windsor Hills Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
“Lovely villa in a super location” We all thoroughly enjoyed our stay at Harmony Haven with its good standard, spacious accommodation and super swimming pool. We travelled with our children and grandchildren and we all enjoyed the water shoot at th
…see more

from £95 / night

£662 / week

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from £95 / night

15

Kissimmee holiday townhouse rental

Kissimmee / Fiesta Key

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 123 km
  • Swimming pool

from £99 / night

£630 / week

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from £99 / night

11

Holiday home with shared pool in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

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

from £104 / night

£723 / week

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from £104 / night

14

Holiday home with indoor pool in Kissimmee

Central Florida / Kissimmee

5 10 Min stay varies

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

from £133 / night

£926 / week

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from £133 / 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

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from £237 / night

(18) 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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Responds fast!
avg. 2 hours 6 minutes

from £65 / 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

Enquire View

from £107 / 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

16

Townhouse rental in Venetian Bay Villages with shared pool

Kissimmee / Venetian Bay Villages

3 8 Min stay varies

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

from £75 / night

£524 - £717 / week

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from £75 / 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.
…see more

from £130 / night

£840 - £1450 / week

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from £130 / night

(1) Excellent 

5

Holiday villa with shared pool, golf nearby in Kissimmee

Kissimmee / Orange Lake Resort

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Excellent experience” It's a resort within a golf course. Very close to Disney World and other attractions. Staff was very friendly and helpful. Pools are wonderful for the kids. The resort was close to supermarket. It was a wonderful destination for
…see more

from £118 / night

£821 / week

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from £118 / 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

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from £65 / night

(2) Very Good 

18

Holiday villa with shared pool, golf nearby in Orange Lake Resort

Kissimmee / Orange Lake Resort

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
“Perfect family spot.” At the time of our check in our wonderful vacation began. The villa was classically appointed. Everything was spotless and functional. The lush landscape was a fitting tropical backdrop for the winding river. All common a
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from £171 / night

£1200 / week

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from £171 / night