Kissimmee Villas, Holiday rentals and apartments

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Kissimmee

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4,242 Holiday homes

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

(3) Very Good 

81

Holiday home in USA East Coast

Kissimmee / Oak Island Harbor

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
This home is spotlessly presented and is decorated beautifully with exquisitive furniture.  …see more

from £208 / night

£1456 - £1714 / week

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from £208 / night

(8) Very Good 

17

Central Florida / Kissimmee

2 4 Min stay varies

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

 …see more

from £53 / night

£355 - £416 / week

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from £53 / night

40

Holiday townhouse in USA East Coast

Central Florida / Kissimmee

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
Lakeview, 4 bedroom 3 bathroom luxury townhouse, with private heated pool and resort facilities. Proximity to great Clubhouse with lobby/reception, snack bar, all-year heated pools, training facilites and gameroom. 10 min drive to Orlando attractions and 15 minute dri  …see more

from £65 / night

£444 - £928 / week

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from £65 / night

42

Holiday home with golf nearby in Kissimmee

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Magical Home in the Perfect Location You'll LOVE! Serendipity at Indian Creek offers you all those extra finishing touches that turn an ordinary home into your very own piece of vacation paradise. ** Totally Private Pool & Hot Tub ** Outdoor Poolside Living Space with  …see more

from £311 / night

£2033 - £2880 / week

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from £311 / night

26

Holiday home in USA East Coast

Central Florida / Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This single story 4 bedroom 3 bathroom home is ideal for a family vacation.With an equipped kitchen/ diner perfect for breakfast or morning coffee. You will find everything you need to have a great self catering vacation. It has a spacious dining area so you can relax  …see more

from £70 / night

£490 / week

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from £70 / night

19

Kissimmee holiday home rental

Central Florida / Kissimmee

6 12 5 nights min

  • 6 bedrooms
  • Sleeps 12
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Stunning 6 Bedroom 4 Bath Home with, South Facing Pool in Highly Sought after Windsor Hills Resort. This house is only ONE of a handful with an EXTRA LARGE pool area allowing seating allowing seating all around the pool. Pool lanai has a cable TV. Pool is south facing  …see more

from £162 / night

£1130 / week

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from £162 / night

58

Kissimmee holiday home rental

Central Florida / Kissimmee

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Calla Lily is a fabulous Lake front 5 bedroom 3 bathroom pool home in Crescent Lakes in Kissimmee, a fantastic, superbly well cared for community that is situated in a natural conservation area yet it is still close to all that the Orlando/Disney area has to offer to e  …see more

from £186 / night

£1299 / week

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from £186 / night

35

Holiday home with swimming pool in Kissimmee

Central Florida / Kissimmee

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Wonderful 4 Bed townhome with 3 Baths, located at Paradise Palms Resort, close to 192 and to many restaurants and markets. a few minutes from Disney Parks, only 3 miles away. 15 minutes away from Universal Studios and 20 min away from Outlet Premium. Excellent clubhouse  …see more

from £107 / night

£746 / week

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from £107 / night

35

USA East Coast holiday villa rental

Central Florida / Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This NEWLY UPGRADED 6 bedrooms 4 bathrooms 3500 sqft luxury home is located in famous Windsor Hill Resort, one of best upscale vacation home resort. This tropical vacation home has everything that you and your family could possibly need for the most magical vacation to  …see more

from £153 / night

£1067 / week

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from £153 / night

23

Holiday villa in Kissimmee

Kissimmee / Terra Verde Resort

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
This superb luxury vacation pool home with 6 bedrooms, 5.5 bathrooms and straight forward fully inclusive pricing has everything that you could possibly need for the perfect holiday.  …see more

from £125 / night

£875 - £1225 / week

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from £125 / night

(54) Excellent 

23

Holiday villa in USA East Coast

Kissimmee / Crescent Lakes

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Beyond our expectations” This was our first villa rental in USA. It exceeded our expectations, a spacious modern villa well appointed, washer , tumble dryer, TV in all rooms, dishwasher, games room with full size pool table, air hockey etc, and a love  …see more

from £90 / night

£575 - £690 / week

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from £90 / night

(1) Excellent 

31

Central Florida / Kissimmee

4 13 Min stay varies

  • 4 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £118 / night

£825 / week

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from £118 / night

(10) Excellent 

20

USA East Coast holiday villa rental

Kissimmee / Bellavida Resort

6 14 1 night min

  • 6 bedrooms
  • Sleeps 14
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
“5 star villa - everything you need for the holiday of a lifetime” This was our third visit to Orlando and was way beyond our expectations. The villa was amazing. Spacious, luxurious and well equipped with everything you need for a relaxing holiday.  …see more

from £160 / night

£1087 / week

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from £160 / 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 £95 / night

£665 - £805 / week

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from £95 / night

(6) Very Good 

29

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 72 km
  • Swimming pool

 …see more

from £56 / night

£390 / week

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from £56 / night

17

Holiday villa in Kissimmee

Central Florida / Kissimmee

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Closest Resort to Disney, one of the closest villa to the Clubhouse. No rear neighbours. Great Park-view from the pool terrace.  …see more

from £150 / night

£1045 / week

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from £150 / night

(3) Very Good 

92

USA East Coast 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 £130 / night

£910 - £1500 / week

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from £130 / night

(5) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Lindfields

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Home from Home. Great Location. Perfect.” The Villa was everything we dreamed of for our first family holiday in Florida. First impressions were just as we expected, Directions to villa were spot on. Swimming pool was fab with inflatables included. Ho  …see more

from £90 / night

£630 - £665 / week

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from £90 / night

26

Holiday townhouse with shared pool in USA East Coast

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Fabulous fully equipped town home near Disney with free WiFi. Safe, family-friendly gated community with excellent facilities.  …see more

from £58 / night

£406 - £555 / week

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from £58 / night

17

Kissimmee holiday home rental

Central Florida / Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
GREAT LOCATION!! GAMEROOM, 2 MASTER SUITES, PROFESSIONALLY DECORATED!! Property Type: 5 Bedrooms, 4.5 Baths Private Pool Home Floor Area: 2800 sq ft Location: Veranda Palms, Kissimmee, Disney Area Professionally managed and fully furnished vacation home property with Pr  …see more

from £120 / night

£840 / week

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from £120 / night

(8) Excellent 

14

Holiday townhouse in Kissimmee

Kissimmee / Bellavida Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Fantastic holiday home. Would definatley use again.” What a great holiday. Just home and couldn't wait to review this property. The resort itself is very modern and clean, with a good main pool. It has free internet access within the club house or fre  …see more

Pricing unknown

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Pricing unknown

81

Holiday home rental

Central Florida / Kissimmee

5 10 4 nights min

  • 5 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Two lounge and dining areas means this lovely house is suitable for families with children, family reunions, or larger groups travelling together. Large pool and patio area with seating, and great for get together or just relaxing after a hard day at the parks.  …see more

from £160 / night

£1120 / week

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from £160 / night

(32) Excellent 

20

Holiday townhouse in Kissimmee

Kissimmee / Regal Oaks

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“excellent house & location” This was our 2nd time staying at Vic`s house and will always be our 1st choice. the location is perfect as it is only just behind old town, which is just a short walk and there is always something going on. It is perfect f  …see more

from £75 / night

£475 - £650 / week

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from £75 / night

(1) Excellent 

41

Kissimmee / Kissimmee City

4 8 Min stay varies

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

 …see more

from £105 / night

£630 - £1109 / week

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from £105 / night

21

Central Florida / Kissimmee

6 12 2 nights min

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

 …see more

from £178 / night

£1242 / week

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from £178 / night

37

Central Florida / Kissimmee

6 14 3 nights min

  • 6 bedrooms
  • Sleeps 14
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £159 / night

£1109 / week

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from £159 / night

(7) Excellent 

24

Holiday villa with golf nearby in Kissimmee

Kissimmee / Indian Ridge Oaks

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Fantastic” The villa was ever thing we wanted, very clean and as stated very close to Walt Disney World. Our grandson is disabled and the villa was ideal for his needs.  …see more

from £128 / night

£880 / week

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from £128 / night

38

Kissimmee / Compass Bay

4 10 3 nights min

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

 …see more

from £84 / night

£588 / week

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from £84 / night

32

Holiday home in USA East Coast

Central Florida / Kissimmee

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This 6 bedroom, 5.5 bathroom house is situated in Terra Verde, Kissimmee. There are 4 master king en suite bedrooms. It has a wonderful west facing pool overlooking a huge lake. The resort offers a beautiful club house with resort manager and concierge, lounges, swimmin  …see more

from £146 / night

£851 - £1481 / week

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from £146 / night

(1) Excellent 

20

USA East Coast holiday townhouse rental

Kissimmee / Regal Oaks

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Townhouse near Disney provides comfortable home from home accommodation, together with personal service from the owners to make yours a memorable holiday or vacation in Kissimmee and the surrounding Central Florida area.  …see more

from £81 / night

£565 - £678 / week

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from £81 / night

37

Kissimmee holiday villa rental

Kissimmee / Lindfields

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This Lindfields Villa is fully air-conditioned giving a cool refreshing welcome when you open the door and is very spacious. This villa is on a quiet road just off highway 192 and only 5.7 miles (10 minute drive) to Walt Disney World. Lovely sunny 30ft private, south f  …see more

from £105 / night

£731 / week

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from £105 / night

(2) Excellent 

24

Holiday villa in USA East Coast

Kissimmee / Sunset Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fabulous villa in fabulous location” Stayed at this villa in September and had a wonderful time. The whole family thoroughly enjoyed themselves and the kids were in the pool virtually every day. The villa overlooks a lake and there are great sunsets.  …see more

from £75 / night

£495 - £650 / week

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from £75 / night

(4) Very Good 

56

Central Florida / Kissimmee

4 8 3 nights min

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

 …see more

from £80 / night

£555 / week

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from £80 / night

(11) Very Good 

59

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £49 / night

£339 / week

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from £49 / night

56

Central Florida / Kissimmee

3 6 2 nights min

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

 …see more

from £73 / night

£468 / week

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from £73 / night

(1) Excellent 

20

Holiday villa in USA East Coast

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 com  …see more

from £86 / night

£600 - £750 / week

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from £86 / night

(1) Excellent 

24

Kissimmee holiday villa rental

Kissimmee / Lake Berkley

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
7 Bed. 5 Bath Lakeside Villa. Private Pool/24Hr Spa, Gameroom, Lightening WIFI/ Sat. Nav, 5 King beds- 7 mins to Disney. Stunning Views, Tranquil surroundings on safe gated and guarded Top Resort. Close to all attractions, restaurants and, designer shopping outlets. HD  …see more

from £177 / night

£1170 - £1492 / week

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from £177 / night

(15) Excellent 

21

Holiday villa with golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic villa, great location!” Dunestone is a very smart, spacious and well-positioned villa in a great gated community. So close to Disney and only mins from the I-4 allowing easy access to all of Orlando's attractions. The owners were a pleasure  …see more

from £150 / night

£1050 - £1680 / week

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from £150 / night

(1) Excellent 

100

Kissimmee / Regal Oaks

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £53 / night

£396 / week

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from £53 / night

(1) Excellent 

50

Central Florida / Kissimmee

4 10 1 night min

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

 …see more

from £96 / night

£642 / week

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from £96 / night

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