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477 Holiday homes in Kissimmee

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  • Bellavida Resort (8)
  • Cane Island (5)
  • Compass Bay (2)
  • Coral Cay (3)
  • Creekside (1)
  • Crescent Lakes (6)
  • Crestwynd Bay (37)
  • Cumbrian Lakes (21)
  • Doral Woods (6)
  • Eagle Pointe (7)
  • Emerald Isle Kissimmee (32)
  • Encantada Resort (5)
  • Fiesta Key (1)
  • Formosa Gardens (9)
  • Indian Creek (13)
  • Indian Ridge (4)
  • Indian Ridge Oaks (5)
  • Kissimmee City (11)
  • Lake Berkley (18)
  • Lake Marion (1)
  • Legacy Dunes Resort (1)
  • Liberty Village (3)
  • Lindfields (13)
  • Lucaya Village (1)
  • Oak Island Cove (4)
  • Oak Island Harbor (1)
  • Orange Lake Resort (2)
  • Paradise Palms (13)
  • Regal Oaks (3)
  • Remington (6)
  • Seasons Resort (11)
  • Sunset Lakes (6)
  • Terra Verde Resort (7)
  • The Hamlets (2)
  • Trafalgar Village (3)
  • Tuscany, Florida (1)
  • Venetian Bay Villages (11)
  • Veranda Palms (5)
  • Villasol (2)
  • Vista del lago (1)
  • Westside (2)
  • Windsor Hills Resort (40)
  • Windsor Palms (38)
  • Winward Cay (1)

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477 Results  |  
13 Photos

House | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £85 /night

£594 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This is an awesome 4 bed 3 bath private pool home in the popular gated golf community  …see more

11 Photos

House | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £85 /night

£594 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This is a beautiful 4 bed 3 bath pool home with its own games room and located in the gated golf community Read more at http://www.homeaway.com/vacation-rental/p248379#ua6BggdJmiuYwmck.99  …see more

15 Photos

Villa | 5 Bedrooms | sleeps 12

Very Good 4.5/5 

5 Nights min stay

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from £75 /night

£525 - £843 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Your dream holiday starts here !! Villa Pip is nestled within a 200 acre conservation area and has a South West facing pool and spa that backs onto a beautiful conservation area.. We also offer - Free international calls - Free use of PC / high speed internet  …see more

Featured properties

16 Photos

House | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

5 Nights min stay

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from £65 /night

£450 - £550 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Come watch the sun set at sunset! ideal for families - large solar west facing pool overlooking lake - games room - 52" tv in lounge, tvs in all bedrooms, wireless high speed internet, ps2, unlimited local, long distance and international phone calls free of charge.  …see more

10 Photos

Villa | 4 Bedrooms | sleeps 10

Short stays welcome

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from £64 /night

£446 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
An exceptional 4 bed 2 bathroom villa furnished to a very high standard with a fantastic management company. Sleeps 10 people (8 in bedrooms 2 on sofa bed). It has a beautiful south facing private pool deck with open views. Games room with full size pool table.  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 13

Short stays welcome

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from £92 /night

£644 - £686 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Spacious luxury 5 bed villa, with large private pool and spa with beautiful lake view.Games room with a 8ft slate bed pool table,table tennis, air hockey and football tables.Ps.2. and internet access.Only 15 mins from disney.
fully air conditioned barbecue  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

Very Good 4/5 

1 night min stay

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from £99 /night

£689 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Luxury 5 bedroom 4.5 bathroom villa with private pool and spa overlooking lake. Situated in the prestigious gated community of Cumbrian Lakes in quiet conservation area yet close to Disney, Highway 192 and all the attractions Orlando has to offer.  …see more

14 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £61 /night

£425 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Our comfortable 4-bed 2-bath air-conditioned villa with private screened pool is situated in the quiet residential area of Indian Point Kissimmee. Just 15 minutes east of Disney, 20 minutes from Sea World and 30 minutes from Universal. Close to all amenities.  …see more

16 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

1 night min stay

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from £68 /night

£475 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Within the small gated community of Sunset Lakes, we have a newly decorated 4 bed and 3 bath air conditioned villa with a private pool situated on the lake front. The villa also provides cable television, free WiFi and Nintendo Wii The property has a king size master suite,queen sized room, two further twin rooms.  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 14

Excellent 5/5 

Short stays welcome

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from £152 /night

£1063 - £1395 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
5 star Luxury villa, you will not be disappointed at this truly charming villa, it is simply out of this world. Stunning decor and its perfectly located for access the theme parks. Sleeps up to 14. - 6 Bedrooms and 5 + 2½ bathrooms luxury villa with a total of 4184 sq ft  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £93 /night

£650 - £850 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
This beautiful 6 bedroom villa has the privilege of being in the closest residential community to the Disney Theme Parks (2 miles away)5 minutes. It is situated just off of Highway 192 in the stunning location of Rolling Hills. The Villa is just 2 minutes from a large variety of supermarkets, services, restaurants and a walk-in medical centre. There are 6 golf courses within 10 minutes of the Villa and the Villa is ideally placed for outlet malls and factory stores.  …see more

24 Photos

Townhouse | 4 Bedrooms | sleeps 8

Excellent 5/5 

4 Nights min stay

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from £50 /night

£350 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
This 1,512 sq ft , 4 bed/3 bath luxury townhouse is located in a quiet gated community with lake views. It has wall mounted LCD TV's in all rooms, Free internet and phone calls. It is just minutes away from 'Disney', supermarkets, shopping malls, cinemas & restaurants. Our Townhome has been refurbished to a high standard with comfy beds to give you a quality nights sleep.  …see more

13 Photos

Apartment | 3 Bedrooms | sleeps 8

4 Nights min stay

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from £74 /night

£513 - £642 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
CHILDREN FRIENDLY BUT BUILT IN SUCH A WAY THAT NOISE IS NOT AN ISSUE. A PRINT OUT OF CLIENT'S CREDIT CARD WILL BE NEEDED UPON CHECK-IN IN LIEU OF A SECURITY DEPOSIT. UNITS ARE DEEP-CLEANSED BEFORE EVERY BOOKING AND CLEANING FEE IS NOT INCLUDED IN PRICE AND IS USD 85. PRICE CAN BE DIFFERENT FROM MONTH TO MONTH SO PLEASE INQUIRE. D O N O T PAY UNLESS YOU RECEIVE CONFIRMATION  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 12

4 Nights min stay

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from £109 /night

£758 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
VILLA 5 CHAMBRES 3 SALLES DE BAIN GAME ROOM PISCINE SPA BONUS ROOM ORDINATEUR FOURNI PS2 ET JEUX FOURNIS WIFI TELE DANS TOUTES LES CHAMBRES IDEALE POUR LES FAMILLES NOMBREUSES OU GROUPE SITUEE A 10 MIN DES PARCS DISNEY  …see more

21 Photos

House | 6 Bedrooms | sleeps 12

4 Nights min stay

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from £129 /night

£899 - £1037 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
casa orlando casa para alugar em orlando casa perto da disney casa na disney ferias em orlando alugar casa em orlando alugar casa na disney alugar casa perto da disney casa nos estados unidos casa na florida casa em kissimme alugar casa na florida alugar casa feiras eua  …see more

23 Photos

Townhouse | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

3 Nights min stay

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from £69 /night

£477 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Palm Heaven Villa is a luxurious four bedroomed family townhouse in a quiet location close to all the resort facilities, with its' own private screen enclosed heated pool. Featuring brand new flat screen TVs in all the bedrooms: come and sample the luxury! Relax and watch the brand new 50inch flat screen TV in the lounge area on our super comfy new sofas!  …see more

16 Photos

Apartment | 3 Bedrooms | sleeps 8

Excellent 5/5 

1 night min stay

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from £53 /night

£371 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
A great place to relax on days away from Disney with 4 swimming pools, children's play area, tennis coursts, baseball court, and indoor fitness centre or stay in air cond. home and watch 250 channels on 48" TV, or log onto desktop computer supplied with free broadband.  …see more

14 Photos

Townhouse | 3 Bedrooms | sleeps 6

Excellent 5/5 

Min stay varies

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Enjoy the fabulous climate and amenities of the Central Florida area without breaking the bank. This is a 3 bedroom townhouse, fully air conditioned, with private pool, conveniently located in the recently completed BellaVida resort in Kissimmee.  …see more

16 Photos

Villa | 4 Bedrooms | sleeps 10

Min stay varies

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from £75 /night

£524 - £721 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
4 bed 3 bath heated pool close to Disney flat screen tv's  …see more

23 Photos

Villa | 3 Bedrooms | sleeps 8

Min stay varies

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
FACILITIES AVAILABLE IN OUR SUPERIOR ACCOMMODATION Indoor open courtyard private swimming pool. Jacuzzi both heated. Large sundeck with sun loungers. 3 large bedrooms all on suit with TV and video. 3 Bathrooms one being disabled equipped. Air conditioning throughout. H When you stay at our luxury villa you will be within three miles of the Disney complex.  …see more

8 Photos

Townhouse | 3 Bedrooms | sleeps 8

Min stay varies

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from £46 /night

£318 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Emerald Island has a great location, only minutes from Disney and theres loads of shops and restaurants close by. Our house has a brilliant position right infront of the heated pool and spa and you can just sit on the balcony and chill out after a busy day at the parks  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 10

Min stay varies

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from £85 /night

£594 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Super five bed Lakeside villa on the private gated and 24-hour guarded community of Lake Berkely Extended deck and pool magnificent uninterrupted views over the beautiful large lake All major theme parks restaurants and shopping within easy reach  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 8

Min stay varies

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from £142 /night

£990 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
South Beach 5 room Art Deco Pool Villa  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 16

Excellent 5/5 

Min stay varies

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from £572 /night

£4000 - £4750 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
The Oasis features 7 bedroom suites all with Private Bathrooms, a huge family room with seating for 14, a dedicated games room with seating area, a separate study with third seating area, a resort style swimming pool, separate kids pool and much more. Your own movie theatre, a summer kitchen & outdoor lounge are just some of the additional luxuries on offer.  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 16

Excellent 5/5 

Min stay varies

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from £458 /night

£3200 - £3700 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
The Getaway is a unique luxury villa located within 10 minutes of Disneyworld and features 3 lounges, 7 bedrooms, 12 person home theatre, gym, huge private pool & outdoor kitchen with living space. At over 6500sq ft our home caters for even the largest of groups. Completely refurbished in 2010 The Getaway offers 'brand new everything' with luxury furnishings throughout  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 9

Excellent 5/5 

Min stay varies

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Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury villa on Indian Creek Estate with large south facing Pool & Spa enclosed and not overlooked from the back, only 5 minutes from Disney, Master en-suite room, Queen en-suite room a double room and one Nemo themed kids room, also games room with pool and air hockey.  …see more

15 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

Min stay varies

Add to shortlist

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Soon You'll Be Staying at a Individually Designed Luxury 4 Bed villa with all of the home comforts you expect.Our Disney area villa comes with its very own private swimming pool where you can escape all the thrills and spills down the road and have some family time.  …see more