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Kissimmee

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2,431 Holiday homes

Filters applied: Non-Smoking property

Travellers going to Kissimmee are booking March dates now. Secure your holiday home today and have the perfect trip.

(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
6 beds, 4Bath with 3 master suites, new digital TV set in all bed rooms, a 60" TV in living room, Minutes to Disney World and shopping malls, A great place for family vacation with gated community & forest view. A Child high chair, 3 strollers are available on  …see more

from £128 / night

£904 - £1328 / week

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from £128 / night

(6) Excellent 

68

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 12 km
  • Swimming pool
  • Child friendly
“Fantastic accommodation, Ladysvilla deserves 10 stars instead of 5!!!!!!!!” This is the second time we have stayed in this villa and I cannot express enough how good it is. It is ideally located for all the attractions and theme parks in Orlando. The  …see more

from £88 / night

£560 - £888 / week

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from £88 / night

(33) Very Good 

20

Holiday home in Crescent Lakes

Kissimmee / Crescent Lakes

4 11 3 nights min

  • 4 bedrooms
  • Sleeps 11
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Amazing property!” This property really is as amazing as the photos show! Andy offers great communication before, during and after the stay, and it really is a fantastic place to stay. We visited Universal Studios and Wet'n'Wild and it's about a 20  …see more

from £99 / night

£675 / week

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from £99 / night

(1)  

5

Kissimmee holiday apartment rental

Central Florida / Kissimmee

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This lavishly decorated suite features a master bedroom with a king-size bed, flat screen TV and a Whirlpool tub for two. The living room has a queen sleeper sofa and a second flat screen TV with a stereo system and safety deposit box. Enjoy dinner in the dining room th  …see more

from £50 / night

£350 - £650 / week

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from £50 / night

(10) 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
The villa is situated in the beautiful Emerald Island Resort, regarded as one of the best resorts in the area. It is located south of Hwy 192 near Mile Marker 5 just minutes from I4. It is approximately 4 miles to the gates of Walt Disney World and within easy reach of  …see more

from £96 / night

£920 - £1040 / week

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from £96 / night

(5) Excellent 

43

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee / Winward Cay

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic villa and excellent location..” When visiting this fabulous villa I was very impressed with the layout and the pool area, much larger than expected. there was lots of additional equipment in the kitchen area. On arrival we were greeted with  …see more

from £66 / night

£460 - £640 / week

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from £66 / night

(18) Excellent 

28

Villa rental in Kissimmee

Kissimmee / Doral Woods

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“A truly amazing place to stay!” If you are looking at this page, thinking about renting this villa, just do it, you'll have no regrets. We stayed for 3 weeks in July/August and had a fantastic time. It was the perfect villa for us (a family of 2 adul  …see more

from £64 / night

£445 - £525 / week

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from £64 / night

23

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Emerald Island resort is centrally located within 3 miles to Walt Disney World, 14 miles to SeaWould, 17 Universal Studios, and just a short drive to many of the other theme parks that Central Florida has to offer.<br />3 miles to Disney 14 miles to SeaWorld 17 mi  …see more

from £240 / night

£880 - £2152 / week

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from £240 / night

(8) Excellent 

22

Holiday home with shared pool in Kissimmee

Kissimmee / Trafalgar Village

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
The Trafalgar Village community is centred around the luxurious Trafalgar Village Center (or Clubhouse), a 2 minute stroll from the property with amenities that include a man made beach and lagoon, lakes (stocked for fishing), a pool and games arcade room, a 48 seat mov  …see more

from £66 / night

£448 - £696 / week

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from £66 / night

(1) Excellent 

39

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
Villa Betty Boo is on the prestigious Hampton Lakes Community which has a swimming pool, basketball, volleyball and tennis courts for your free use. Hampton Lakes is beautifully landscaped and is a very secure community. Villa Betty Boo has 4 spacious bedrooms and can s  …see more

from £80 / night

£560 - £688 / week

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from £80 / night

(2) Very Good 

13

Holiday villa in Kissimmee

Kissimmee / Kissimmee City

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
“Amazing stay, great villa” Had a lovely stay for 2 weeks. Very easy to book and a lot of useful information emailed before and in the villa as well. Brilliant directions- made it a less daunting experience! Villa very clean with plenty of room and s  …see more

from £80 / night

£499 - £611 / week

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from £80 / night

40

Central Florida / Kissimmee

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £136 / night

£947 / week

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from £136 / night

42

Condo rental in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Windsor Hills is perhaps the finest resort community in the Disney area. With world famous theme parks and attractions just minutes away, a stay here will create family memories to last a lifetime.  …see more

from £88 / night

£621 - £960 / week

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from £88 / night

(7) Excellent 

25

Kissimmee / Lucaya Village

4 10 Min stay varies

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

 …see more

from £92 / night

£776 / week

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from £92 / 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
Gorgeous fully furnished 4 bed 2 bath corporate rental apartment Orlando, FLLocation: Legacy DunesAbsolutely gorgeous, 4-bed, 2-bath condo located in the fabulous Resort Style privately gated community of Legacy Dunes. It comes fully furnished to accommodate 8 persons v  …see more

from £75 / night

£475 - £850 / week

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from £75 / night

(6) Excellent 

17

Holiday villa in Kissimmee

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
This beautiful and spacious villa with a private pool is in Calabria- a small exclusive villa estate in Kissimmee. With 5 bedrooms and 4.5 bathrooms including 2 master en-suite bedrooms, the villa is well designed for 2 families to share. The villa is furnished to an  …see more

from £100 / night

£700 / week

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from £100 / night

(18) Excellent 

24

Home rental in Bellavida Resort

Kissimmee / Bellavida Resort

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“East 192, Where Tink@Bella waits for Youuuuuuu” The Bella Vida resort is a Great, Gated Community. Where inside awaits the the Fantastic Tink@Bella Villa. Approx 30 mins from Orlando Int. Perfect location for all that awaits you, Disney, Universal,  …see more

from £143 / night

£995 - £1395 / week

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from £143 / 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
Disney World, Universal Studio, SeaWorld, Resort, Private Heated Pool, Spa, WIFI, Game room, Internet, Cable TVs<br />3 miles to Disney 14 miles to SeaWorld 17 miles to Universal. Minutes to Super Market and Restaurants  …see more

from £240 / night

£880 - £2341 / week

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from £240 / night

51

Holiday villa in Kissimmee

Kissimmee / Hamilton's Reserve

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 85 km
  • Swimming pool
Heated swimming Pool completely resurfaced in 2016, Jacuzzi for up to 6 people, House wide high speed Wi-Fi, 2 Large screen TVs and DVD players in the pool lounge and master bedroom, Quiet seated area in the front lounge, recently refurbished Kitchen, large airy house,  …see more

from £112 / night

£740 - £840 / week

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from £112 / night

(2) Very Good 

15

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our beautiful spacious home is only 3 miles from Disney World and close to numerous golf courses, restaurants and malls. Ideal for two families sharing. Enjoy your own hot tub and heated large pool, with a BBQ and watching the incredible sunsets after a busy day at the  …see more

from £72 / night

£500 - £560 / week

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from £72 / night

(14) Excellent 

23

Kissimmee holiday home rental

Kissimmee / Windsor Palms

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic Villa, Perfect Location for Disney etc., Food & Shopping” It was a very straightforward process booking 'Mickey's Clubhouse', questions were answered very promptly by the owners - the whole process was quick, efficient and informative.The vi  …see more

from £115 / night

£750 / week

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from £115 / 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
Secret Key Cove Villa Luxury Award Winning Vacation villa rental, in Orlando, FloridaSet in a Gated CommunityThis 2 story upgraded Villa has, 4 bedrooms, 3 bathrooms, air conditioning and is set in a private location with its own private pool and spa. <br />Emer  …see more

from £112 / night

£784 - £1138 / week

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from £112 / night

(26) 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
“Amazing” We stayed in Robsons Retreat in August 2013 there were 6 of us in total. This consisted of two couples, a teenager and a 10yr old. We arrived mid evening as flight delayed, to find a fantastic villa with everything we needed for a comfortabl  …see more

from £110 / night

£750 - £900 / week

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from £110 / 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
This is a luxurious stunning spacious modern 3 bedroom, 2.5 Bathroom Townhouse two-storey. As you enter the home you are greeted by light, bright and airy open feel of the home is the perfect base for a relaxing, stress free vacation, situated by a 3-acre lake view from  …see more

from £75 / night

£525 / week

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from £75 / night

(2) Excellent 

12

Holiday villa in Windsor Palms

Kissimmee / Windsor Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 5 km
  • Swimming pool
  • Child friendly
Disney World ( 10 minutes ) - Special Pool Heater - Salt Water Pool - Safety Fence - 2 en-suite master king-bedrooms - Themed bedrooms - High chair , Stroller , Car seats , Crib Fan cooled Lanai - Close to Clubhouse - Gameroom - BBQ - Multi Color Pool Light  …see more

from £136 / night

£952 / week

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from £136 / night

25

Holiday villa rental

Central Florida / Kissimmee

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Two master king ensuite bedrooms offer plenty of space, both rooms open to the pool area allowing guests to venture out for a swim undetected by guests in the rest of the rooms. The first master bedroom has a ensuite bathroom with large oval tub and separate shower. Th  …see more

from £125 / night

£875 / week

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from £125 / night

16

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
We are ideally located for the numerous Florida attractions including Disney, Universal Studios, and Seaworld. For golfers the townhouse is ideally located with many fantastic courses within easy reach, with the closest being Falcons Fire Golf Club and Celebration Golf  …see more

from £92 / night

£644 / week

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from £92 / 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
Our beautiful family owned villa is located only 10 mins from WDW and close to many other attractions such as Sea World, Aquatica, Universal Studios and Universal Islands of Adventure. Our home from home is comfortably furnished and equipped with all the amenities to m  …see more

from £85 / night

£560 - £665 / week

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from £85 / night

(2) Excellent 

69

Villa rental in Kissimmee

Kissimmee / Sunset Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
“Excellent” Superb villa beautiful view of the lake really enjoyed our stay didn't want to come home! definitely recommend  …see more

from £90 / night

£630 - £840 / 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
This house is close to all the main attraction's, shopping outlets, restaurants. It is in a gated community it has a private patio with a view of the lake, close to one of the children's play area.  …see more

from £82 / night

£570 - £730 / week

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from £82 / night

(7) Excellent 

18

Condo rental in Kissimmee

Central Florida / Kissimmee

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Top rated in trip advisor condo 10 mins away for Disney currently voted 2 in whole area. Spacious, quality nothing better  …see more

from £120 / night

£792 / week

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from £120 / night

52

Holiday villa in Eagle Pointe

Kissimmee / Eagle Pointe

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 115 km
  • Swimming pool
The house is all on one level and has two large separate living/dining areas, a games room and a large pool.  …see more

from £131 / night

£789 - £978 / week

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from £131 / night

14

Central Florida / Kissimmee

5 10 2 nights min

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

 …see more

from £115 / night

£801 / week

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from £115 / night

(1) Excellent 

8

Holiday home in Kissimmee

Kissimmee / Lake Marion

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Self-catering condo with communal pool and free WiFi in the property, along with a full set of cable channels<br />Totally Renovated 2 Bed Family Home With Pool & Free Wi-Fi  …see more

from £35 / night

£250 / week

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from £35 / night

(2) Very Good 

18

Central Florida / Kissimmee

3 8 5 nights min

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

 …see more

from £80 / night

£559 / week

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from £80 / night

(2) Very Good 

75

Kissimmee holiday villa let

Kissimmee / Cumbrian Lakes

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
Gated CommunityQuiet Nice Walks  …see more

from £80 / night

£560 - £840 / week

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from £80 / night

(2) Very Good 

24

Kissimmee holiday home rental

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxury tropical five star resort and house. Close to Disney parks and within range of Florida's west coast beaches.  …see more

from £99 / night

£693 - £910 / week

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from £99 / night

(3) Very Good 

12

Holiday home rental

Kissimmee / Emerald Isle Kissimmee

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Crystal Cove Gem is located in the fabulous Emerald Island Resort the nearest gated community to from Disney World.<br />Only 3 miles from Disney World  …see more

from £85 / night

£595 / week

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from £85 / night

(1) Excellent 

33

Lake Berkley holiday villa rental

Kissimmee / Lake Berkley

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“A great base for a family holiday” Having used other villas around Orlando I came across this one as our normal one was booked, I contacted the owner who could not of been more helpfull and booked up our stay. When we arrived at the villa it was a  …see more

from £140 / night

£980 / week

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from £140 / 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
Beautiful 3 bedroom 2 bathroom villa in Kissimmee. This villa has a private screened pool overlooking a lake. Situated in the tranquil community of Eagle Pointe only 15 minutes from Disney. Living Room – Light and airy open plan room overlooking the pool with two  …see more

from £86 / night

£600 - £750 / week

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from £86 / night