30 Best Vacation Rentals in Kissimmee City - Holiday Lettings - Cabins

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30 Vacation rentals

(18) Very Good 

17

Vacation villa in Kissimmee

Kissimmee / Kissimmee City

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
A 3 bedroomed villa which sleeps 6. Approximately 3 miles Disney. Own screened swimming pool with large decking area with gas barbecue with patio furniture and loungers. The villa inside is decorated with blinds and window pelmets. 3 TV's all with cable, VCR and a Mu  …see more

from $82 / night

$374 - $594 / week

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from $82 / night

(3) Excellent 

24

Vacation villa in Kissimmee

Kissimmee / Kissimmee City

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Living AreaOur recently upgraded and spacious lounge is the ideal place to just relax after a hard day at the theme parks! The comfortable lounge benefits from a 42" LCD HD cable television with DVD, video-player, Playstation 2 and a selection of children&#  …see more

from $138 / night

$687 - $875 / week

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from $138 / night

(1) Very Good 

20

Condo rental in Kissimmee with golf nearby

Kissimmee / Kissimmee City

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This spacious 3 bedrooms and 2 bedrooms vacation home includes the Following Amenities: 4 miles to Disney , 1 King Bed, 1 Queen Bed, 2 Twin Beds, COMMUNITY has heated pool, spa, fitness center, theater room, basketball and tennis court and children playground, Complemen  …see more

from $89 / night

$599 - $850 / week

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from $89 / night

(12) Excellent 

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 mi
  • Swimming pool
  • Child friendly
~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~ YOUR DREAM VACATION RENTAL IN THE SUNSHINE CAPITAL IS HERE ... COME AND ENJOY: A Beautiful Sun Drenched 4 bedroom 2 storey fully a  …see more

from $130 / night

$865 - $1150 / week

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from $130 / night

(2) Excellent 

91

Villa accommodation in Kissimmee

Kissimmee / Kissimmee City

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful 5 bed villa in Kissimmee, Florida, the holiday destination of the world. Just 10 minutes from Disney in one of the most sought after communities in Orlando. Our villa is luxuriously furnished, with its own secluded pool & spa, a fabulous games room and min  …see more

from $107 / night

$750 - $1438 / week

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from $107 / night

(1) Very Good 

56

Vacation townhouse in Kissimmee

Kissimmee / Kissimmee City

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This Terra Verde townhome has a patio and Hot Tub which overlooks the resort's lake. It has just been totally revamped. The interior has been painted in a subtle modern color .This is complemented by new tile downstairs and in the homes bathrooms. All three bedroom  …see more

from $94 / night

$657 - $788 / week

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from $94 / night

(6) Excellent 

75

Vacation villa rental

Kissimmee / Kissimmee City

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This large executive luxury detached roomy largely open plan airy villa is very well equipped, lavishly and comfortably furnished and decorated to a high standard. Recently built to our own design, this 4 bedroom, 3 bathroom luxury villa with private heated and scree  …see more

from $135 / night

$950 - $1185 / week

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from $135 / night

(1) Excellent 

13

Vacation villa in Kissimmee

Kissimmee / Kissimmee City

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 45 mi
  • Swimming pool
  • Child friendly
Disney Vacation Home Rentals -3Beds 2 baths Villa with Heated Pool $89-$109US/Night. .Located near Disney, this modern 3 Bed Room, 1400 square foot bungalow holds all the amenities that you would expect to have a wonderful relaxing vacation. This home features Master b  …see more

from $99 / night

$623 - $763 / week

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from $99 / night

(2) Excellent 

71

Vacation villa with shared pool in Kissimmee

Kissimmee / Kissimmee City

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sunset Lakes is a semi-residential gated community situated off the 192 Irlo Bronson Highway approximately 2 miles west of Interstate 4. World Drive, which is the entrance to all the Disney theme parks is less than 10 minutes drive away. Universal Studios, Sea Worl  …see more

from $88 / night

$563 - $619 / week

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from $88 / night

27

Vacation townhouse in Kissimmee

Kissimmee / Kissimmee City

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
This townhome with 3 bedrooms and 2/5 bathrooms, is located in the attractive gated community, Compass Bay, only few min. from Disney. Nearby are also restaurants, shopping outlets, golf courses and a Walmart-store. The house is elegantly furnished, with all the kitchen  …see more

from $80 / night

$560 / week

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from $80 / night

(1) Excellent 

41

Kissimmee / Kissimmee City

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly

 …see more

from $130 / night

$780 - $1375 / week

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from $130 / night

(3) Very Good 

20

Kissimmee Vacation villa rental

Kissimmee / Kissimmee City

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Cumbrian Lakes is located just off the Highway 192. The gated community is set around conservation and lakes. What more do you want when you have enjoyed your days in the busy theme parks than to come back to the peaceful surroundings this wonderful area has to offer. O  …see more

from $108 / night

$750 / week

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from $108 / night

(3) Good 

30

Kissimmee / Kissimmee City

2 6 Min stay varies

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

 …see more

from $50 / night

$400 / week

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from $50 / night

24

Kissimmee / Kissimmee City

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 119 mi
  • Swimming pool

 …see more

from $165 / night

$1155 / week

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from $165 / night

35

Kissimmee / Kissimmee City

4 10 Min stay varies

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

 …see more

from $170 / night

$1190 / week

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from $170 / night

26

Kissimmee / Kissimmee City

4 10 3 nights min

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

 …see more

from $71 / night

$497 / week

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from $71 / night

21

Kissimmee / Kissimmee City

8 20 Min stay varies

  • 8 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $209 / night

$1199 - $2699 / week

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from $209 / night

(4) Excellent 

49

Kissimmee / Kissimmee City

5 10 Min stay varies

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

 …see more

from $160 / night

$1120 / week

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from $160 / night

22

Kissimmee / Kissimmee City

3 8 Min stay varies

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

 …see more

from $79 / night

$553 - $770 / week

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from $79 / night

42

Kissimmee / Kissimmee City

4 8 Min stay varies

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

 …see more

from $120 / night

$840 / week

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from $120 / night

20

Kissimmee / Kissimmee City

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from $90 / night

$630 - $1015 / week

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from $90 / night

17

Kissimmee / Kissimmee City

3 8 3 nights min

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

 …see more

from $350 / night

$1250 / week

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from $350 / night

(8) Excellent 

39

Kissimmee / Kissimmee City

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from $179 / night

$2450 / week

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from $179 / night

(1)  

14

Kissimmee / Kissimmee City

1 4 7 nights min

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

 …see more

from $75 / night

$525 - $1075 / week

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from $75 / night

25

Kissimmee / Kissimmee City

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 93 mi
  • Swimming pool

 …see more

from $90 / night

$625 / week

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from $90 / night

4

Kissimmee / Kissimmee City

2 6 3 nights min

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

 …see more

from $190 / night

$1300 / week

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from $190 / night

24

Kissimmee / Kissimmee City

3 6 5 nights min

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

 …see more

from $99 / night

$630 / week

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from $99 / night

13

Kissimmee / Kissimmee City

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 81 mi
  • Swimming pool
  • Child friendly

 …see more

from $208 / night

$1450 / week

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from $208 / night

19

Kissimmee / Kissimmee City

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 81 mi
  • Swimming pool
  • Child friendly

 …see more

from $80 / night

$560 / week

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from $80 / night

8

Kissimmee / Kissimmee City

1 4 7 nights min

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

 …see more

from $100 / night

$700 / week

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from $100 / night

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