Villas in Kissimmee City and Townhouses – Holiday Lettings - Holiday Rentals Kissimmee City

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23,548 Holiday homes

(3) Excellent 

91

Villa accommodation in Kissimmee City

Kissimmee / Kissimmee City

5 10 6 nights min

  • 5 bedrooms
  • sleeps 10
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £129 / night

£903 / week

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from £129 / night

(1) Very Good 

20

Condo rental in Kissimmee City with golf nearby

Kissimmee / Kissimmee City

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool

from £69 / night

£480 - £647 / week

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from £69 / night

(31) Very Good 

22

Holiday villa in Kissimmee

Kissimmee / Kissimmee City

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £59 / night

£350 - £465 / week

Enquire View

from £59 / night

(21) Very Good 

38

Villa rental in Kissimmee City 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

from £95 / night

£585 - £715 / week

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Responds fast!
avg. 1 hour 6 minutes

from £95 / night

(17) Excellent 

Certificate of Excellence

25

Holiday villa in Kissimmee City

Kissimmee / Kissimmee City

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £95 / night

£625 - £1,210 / week

Book View

Responds fast!
avg. 1 hour 34 minutes

from £95 / night

(2) Excellent 

41

Holiday home in Kissimmee City

Kissimmee / Kissimmee City

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £84 / night

£586 / week

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Responds fast!
avg. 2 hours 30 minutes

from £84 / night

(6) Excellent 

75

Holiday villa rental

Kissimmee / Kissimmee City

4 8 5 nights min

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

from £107 / night

£712 / week

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Responds fast!
avg. 2 hours 21 minutes

from £107 / night

(8) Excellent 

39

Holiday villa rental

Kissimmee / Kissimmee City

7 16 min stay varies

  • 7 bedrooms
  • sleeps 16
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

from £152 / night

£1,060 / week

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from £152 / night

(4) Excellent 

49

Holiday home with indoor pool in Kissimmee City

Kissimmee / Kissimmee City

5 10 4 nights min

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

from £267 / night

£1,864 / week

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from £267 / night

24

Holiday townhouse with golf nearby in Kissimmee City

Kissimmee / Kissimmee City

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Child friendly
  • Air conditioning

from £76 / night

£479 / week

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from £76 / night

(1) Excellent 

26

Holiday townhouse with swimming pool in Kissimmee

Kissimmee / Kissimmee City

4 10 1 night min

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

from £106 / night

£741 - £847 / week

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Responds fast!
avg. 2 hours 5 minutes

from £106 / night

20

Holiday townhouse in Kissimmee City

Kissimmee / Kissimmee City

3 7 1 night min

  • 3 bedrooms
  • sleeps 7
  • 1 night min
  • Child friendly
  • Air conditioning

from £69 / night

£480 / week

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from £69 / night

(4) Very Good 

21

Holiday villa in Kissimmee

Kissimmee / Kissimmee City

8 20 min stay varies

  • 8 bedrooms
  • sleeps 20
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £190 / night

£1,141 - £2,206 / week

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Responds fast!
avg. 1 hour 28 minutes

from £190 / night

22

Kissimmee holiday apartment rental

Kissimmee / Kissimmee City

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Child friendly
  • Air conditioning

from £60 / night

£421 / week

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from £60 / night

8

Holiday villa in Kissimmee

Kissimmee / Kissimmee City

1 4 7 nights min

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

from £76 / night

£533 / week

Book View

Responds fast!
avg. 2 hours 25 minutes

from £76 / night

Great rentals within 20 miles that match your search

Distance approx 17.5 miles from Kissimmee City Show on Map

(26) Very Good 

15

Orlando holiday villa rental

Central Florida / Orlando

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool

from £90 / night

£490 - £565 / week

Book View

Responds fast!
avg. 2 hours 7 minutes

from £90 / night

Distance approx 18.68 miles from Kissimmee City Show on Map

(14) Very Good 

Certificate of Excellence

51

Holiday villa in Orlando

Orlando / Orange Tree

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £120 / night

£840 / week

Book View

Responds fast!
avg. 3 hours 59 minutes

from £120 / night

Distance approx 18.18 miles from Kissimmee City Show on Map

(2) Average 

12

Holiday villa with golf nearby in Haines City

Central Florida / Haines City

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £101 / night

£704 - £857 / week

Book View

from £101 / night

Distance approx 10.99 miles from Kissimmee City Show on Map

10

Holiday villa in ChampionsGate

Central Florida / ChampionsGate

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £99 / night

£689 - £738 / week

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from £99 / night

Distance approx 5.82 miles from Kissimmee City Show on Map

(2) Excellent 

11

Kissimmee holiday townhouse rental

Kissimmee / Compass Bay

4 9 2 nights min

  • 4 bedrooms
  • sleeps 9
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 101 km
  • Swimming pool

from £90 / night

£635 / week

Book View

Responds fast!
avg. 2 hours 41 minutes

from £90 / night

Distance approx 14.88 miles from Kissimmee City Show on Map

20

Townhouse rental in Four Corners

Central Florida / Four Corners

5 11 4 nights min

  • 5 bedrooms
  • sleeps 11
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £110 / night

£771 / week

Book View

Responds fast!
avg. 3 hours 6 minutes

from £110 / night

Distance approx 16.03 miles from Kissimmee City Show on Map

19

Holiday villa letting

Central Florida / Four Corners

4 8 5 nights min

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

from £100 / night

£686 / week

Book View

from £100 / night

Distance approx 14.36 miles from Kissimmee City Show on Map

20

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 10 4 nights min

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

from £110 / night

£768 / week

Book View

Responds fast!
avg. 2 hours 39 minutes

from £110 / night

Distance approx 16.06 miles from Kissimmee City Show on Map

(8) Excellent 

31

Davenport holiday villa rental

Central Florida / Davenport

4 8 5 nights min

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

from £90 / night

£630 / week

Book View

Responds fast!
avg. 3 hours 50 minutes

from £90 / night

Distance approx 5.81 miles from Kissimmee City Show on Map

(36) Excellent 

Certificate of Excellence

39

Kissimmee holiday townhouse rental

Kissimmee / Compass Bay

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 81 km
  • Swimming pool

Certificate of Excellence

from £68 / night

£455 - £607 / week

Book View

Responds fast!
avg. 1 hour 45 minutes

from £68 / night

Distance approx 9.23 miles from Kissimmee City Show on Map

(3) Very Good 

8

Holiday apartment in Orlando

Central Florida / Orlando

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Air conditioning

from £198 / night

£1,384 / week

Book View

Responds fast!
avg. 57 minutes

from £198 / night

Distance approx 16.47 miles from Kissimmee City Show on Map

(2) Very Good 

18

Holiday villa rental

Lake County / Clermont

5 13 min stay varies

  • 5 bedrooms
  • sleeps 13
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £91 / night

£532 - £987 / week

Book View

Responds fast!
avg. 1 hour 34 minutes

from £91 / night

Distance approx 15.38 miles from Kissimmee City Show on Map

(8) Very Good 

Certificate of Excellence

38

Orlando holiday home let

Central Florida / Orlando

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Certificate of Excellence

from £38 / night

£266 / week

Book View

Responds fast!
avg. 19 minutes

from £38 / night

Distance approx 14.96 miles from Kissimmee City Show on Map

13

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 10 5 nights min

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

from £122 / night

£850 / week

Book View

from £122 / night

Distance approx 2.81 miles from Kissimmee City Show on Map

(10) Excellent 

35

Holiday home in Kissimmee

Central Florida / Kissimmee

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly

from £103 / night

£608 - £683 / week

Book View

Responds fast!
avg. 2 hours 14 minutes

from £103 / night

Distance approx 7.75 miles from Kissimmee City Show on Map

20

Villa rental in Orlando with shared pool

Central Florida / Orlando

2 6 3 nights min

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

from £190 / night

£1,101 / week

Book View

from £190 / night

Distance approx 14.52 miles from Kissimmee City Show on Map

28

Holiday home in Four Corners

Central Florida / Four Corners

10 22 min stay varies

  • 10 bedrooms
  • sleeps 22
  • min stay varies
  • Child friendly

from £272 / night

£2,060 - £4,369 / week

Book View

Responds fast!
avg. 2 hours 1 minutes

from £272 / night

Distance approx 8.39 miles from Kissimmee City Show on Map

9

Holiday villa with golf nearby in Orlando

Central Florida / Orlando

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £87 / night

£608 / week

Book View

from £87 / night

Distance approx 3.54 miles from Kissimmee City Show on Map

(8) Excellent 

Certificate of Excellence

42

Holiday home in Kissimmee

Central Florida / Kissimmee

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Certificate of Excellence

from £167 / night

£1,164 - £1,472 / week

Book View

Responds fast!
avg. 3 hours 25 minutes

from £167 / night

Distance approx 15.52 miles from Kissimmee City Show on Map

38

Davenport holiday villa rental

Central Florida / Davenport

7 15 min stay varies

  • 7 bedrooms
  • sleeps 15
  • min stay varies
  • Nearest beach 40 km
  • Swimming pool
  • Child friendly

from £183 / night

£1,275 / week

Book View

from £183 / night

Distance approx 13.7 miles from Kissimmee City Show on Map

19

Four Corners holiday villa rental

Central Florida / Four Corners

5 10 3 nights min

  • 5 bedrooms
  • sleeps 10
  • 3 nights min
  • Child friendly

from £142 / night

£1,031 / week

Book View

from £142 / night

Distance approx 10.46 miles from Kissimmee City Show on Map

37

Holiday home with shared pool in Reunion

Central Florida / Reunion

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £110 / night

£771 / week

Book View

Responds fast!
avg. 1 hour 51 minutes

from £110 / night

Distance approx 0.1 miles from Kissimmee City Show on Map

13

Kissimmee holiday hotel apartment rental

Central Florida / Kissimmee

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Child friendly

from £82 / night

£574 / week

Book View

from £82 / night

Distance approx 12.49 miles from Kissimmee City Show on Map

12

Holiday home in Loughman

Central Florida / Loughman

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £253 / night

£1,768 / week

Book View

from £253 / night

Distance approx 15.01 miles from Kissimmee City Show on Map

14

Holiday home in Davenport

Central Florida / Davenport

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Suitable for children age 5+

from £141 / night

£983 / week

Book View

from £141 / night

Top Destination reviews

Funshine Magical Villa with Gameroom and WiFi
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 enough to keep the children of 10 & 13 years old occupied on our relaxing days between parks. After hours of research, we found Villa Londra which on paper ticked all the boxes. We were all delighted when we arrived at the villa. The description & photos on the website were all spot on. The villa was clean, well kitted out & the pool was lovely (many an hour spent relaxing in it!). Within minutes drive there is everything you could hope for - supermarkets, gas stations & many places to eat. The parks we went to were all within easy access (Universal, Sea World & Busch Gardens). Right from our initial enquiry on the website, Jan was very helpful & very professional - nothing was too much trouble. After having had the best vacation ever, we are now saving to return in 2014. 10 out of 10 Paul, Jo & Familysee more
Very Nr Disney 3 Bedroom Villa With Free WIFI
Magnificent Accomadation

We arrived for our stay of 2 weeks after travelling for 20 hours, we found the place easily everything was as described, the only disappointment my girls had was the pool was cold , however it soon warmed up after a couple of days in the sun. The house was beautifully furnished everything in good condition only the main living room showing signs of general wear and tear, this to be expected with a rental home as it caters for everybody and the main lounge being the focal point as this is where the tv is and also overlooks the swimming pool. I would highly recommend this holiday home to anybody. The owner was quick to furnish me with additional information when requested and kept me informed at all times and sent the keys about a month before our visit was due. I would recommend this property as it is suitable for anybody it is easily accessed even by a wheel chair.see more
Special offer dates ! 'Trebor Villa' Kissimmee executive 4 bed custom villa.
Huge villa in a quiet residential area and close to Disney

This villa is huge and finished to an excellent standard. It is well appointed, very spacious with a great pool and Jacuzzi. Plenty of room to unwind after a hard day at a Park. The villa is sited in a safe residential area where the local residents are happy to talk. There is a Walmart and all the 'chain' restaurants within a few minutes drive. Disney Parks are only a short uncomplicated 20 minute drive west along the 192. We had a two centre holiday in Florida with the other week at an equally impressive villa in Englewood on the Gulf Coast which is owned by the same owner.see more