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455 Holiday homes in Kissimmee

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  • Acadia (16)
  • Bass Lakes Estate (3)
  • Bellavida Resort (10)
  • Calabria, Orlando (1)
  • Cane Island (5)
  • Chatham Park (3)
  • Compass Bay (2)
  • Coral Cay (3)
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  • Crescent Lakes (10)
  • Crestwynd Bay (18)
  • Crystal Cove Resort (2)
  • Cumbrian Lakes (22)
  • Doral Woods (6)
  • Eagle Pointe (6)
  • Emerald Isle Kissimmee (33)
  • Encantada Resort (4)
  • Fiesta Key (3)
  • Formosa Gardens (12)
  • Hamiltons Reserve (5)
  • Indian Creek (11)
  • Indian Point (20)
  • Indian Ridge (2)
  • Indian Ridge Oaks (6)
  • Indian Wells (1)
  • Kissimmee City (7)
  • Lake Berkley (15)
  • Lake Marion (1)
  • Legacy Dunes Resort (1)
  • Liberty Village (2)
  • Lindfields (13)
  • Lucaya Village (1)
  • Oak Island Cove (4)
  • Oak Island Harbor (3)
  • Orange Lake Resort (2)
  • Paradise Palms (11)
  • Regal Oaks (5)
  • Remington (7)
  • Reunion Resort (36)
  • Rolling Hills at Formosa (5)
  • Seasons Resort (8)
  • Sunset Lakes (6)
  • Terra Verde Resort (8)
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  • Trafalgar Village (3)
  • Tuscany, Florida (4)
  • Venetian Bay Villages (7)
  • Veranda Palms (5)
  • Villasol (3)
  • Vista del lago (2)
  • Westside (2)
  • Windsor Hills Resort (21)
  • Windsor Palms (21)
  • Winward Cay (1)

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455 Results  |  
21 Photos

Condo | 3 Bedrooms | sleeps 6

Excellent 5/5 

4 Nights min stay

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from £69 /night

£483 - £776 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
Third Floor Condo With Stunning Golf Views - Spacious 3 Bed 3 Bath Luxury Condo Located in the upscale Reunion Resort community The Villas North and overlooking the The Independence golf course by Tom Watson  …see more

13 Photos

Condo | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £69 /night

£483 - £776 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
3 Bed Terraces Condo in Reunion Resort Close to Disney Located in the upscale Reunion Resort community at the Reunion Terraces, this luxuriously appointed ground floor condo boasts a luxury contemporary furniture package.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

1 night min stay

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from £73 /night

£509 - £4402 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
This unique, one of a kind, beautiful, private custom Estate Home features over 8,200 sq/ft of luxury accommodation and balconies. This 'WOW!' factor home is private, quiet and not overlooked.  …see more

Featured properties

23 Photos

House | 5 Bedrooms | sleeps 10

1 night min stay

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from £144 /night

£1006 - £1572 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
This professionally decorated 3,284 sq ft. home is located within the Liberty Bluff neighborhood of Reunion. Furnished to appeal to all, whether it's a family vacation, a golfing adventure, or a couple of families out to see Disney and all Orlando has to offer!  …see more

10 Photos

House | 1 Bedroom | sleeps 4

1 night min stay

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from £51 /night

£357 - £608 / week

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Key info:

  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
1 Bedroom Condo, 100ft from Pool, Hot tubs, Pavilion, Fitness room, Games room  …see more

22 Photos

Villa | 5 Bedrooms | sleeps 13

5 Nights min stay

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from £195 /night

£1363 - £2201 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
Prime Location within the Resort - walk to the Grande!  …see more

21 Photos

Condo | 3 Bedrooms | sleeps 8

Very Good 4/5 

4 Nights min stay

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from £69 /night

£483 - £776 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
Second Floor Condo With Stunning Golf Views Spacious 3 Bed 3 Bath Luxury Condo with Golf Membership Located in the upscale Reunion Resort community of The Villas North at Sandy Ridge Drive and overlooking the The Independence golf course by Tom Watson  …see more

24 Photos

Condo | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £75 /night

£524 - £776 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
Beautiful Decor - New Furniture May 2013 Located in the upscale Reunion Resort community of Center Court Ridge.  …see more

22 Photos

Townhouse | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £81 /night

£566 - £776 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
Luxury Reunion Town Home next to the pool  …see more

24 Photos

Condo | 3 Bedrooms | sleeps 8

4 Nights min stay

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from £75 /night

£524 - £776 / week

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Key info:

  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
Located in the upscale Reunion Resort community of Centre Court Ridge.  …see more

22 Photos

House | 3 Bedrooms | sleeps 6

1 night min stay

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from £19 /night

£132 - £1027 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
2,000 sq,ft. Modern Decor in the centre of Reunion Resort  …see more

24 Photos

Condo | 3 Bedrooms | sleeps 8

4 Nights min stay

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from £78 /night

£545 - £835 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
Spacious 3 Bed 3 Bath Luxury Condo with Golf Views and Resort membership ALL BRAND NEW LUXURY FURNITURE AND APPLIANCES MAY 2013  …see more

23 Photos

Condo | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £75 /night

£524 - £776 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
Top Floor (4th), Corner Unit Condo With Stunning Golf Views and Resort Membership This fourth floor, corner unit with stunning Golf views has three beds and three bathrooms.  …see more

21 Photos

Condo | 2 Bedrooms | sleeps 6

4 Nights min stay

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from £90 /night

£629 - £839 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
Third floor unit overlooking the golf driving range with night time Disney fireworks views  …see more

18 Photos

House | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £78 /night

£545 - £835 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
This third floor, corner unit condo with stunning Golf views has three beds and three bathrooms. This condo is in one of the most popular neighborhoods in Reunion Resort. Centre Court Ridge is a centrally-located community, made up of a large 55,000 gallon heated swimmi  …see more

18 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

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from £77 /night

£539 - £784 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Internet Access Hot Tub/Jacuzzi Television Satellite or cable TV DVD Player  …see more

12 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

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from £89 /night

£623 - £707 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Sunset Lakes is a small gated community located right in the heart of Disneys most desirable area  …see more

20 Photos

House | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £95 /night

£665 - £749 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Internet Access eated Pool Private Pool DVD Player Satellite or cable TV VCR Garage  …see more

13 Photos

House | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £89 /night

£623 - £875 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Internet Access Private Pool Heated Pool Shared outdoor pool (unheated) VCR DVD Player Television Satellite or cable TV  …see more

10 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £77 /night

£539 - £791 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Internet Access DVD Player Satellite or cable TV Shared outdoor pool (unheated)  …see more

11 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £83 /night

£581 - £665 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Internet Access Private Pool Shared outdoor pool (unheated) Heated Pool VCR Satellite or cable TV Television DVD Player  …see more

18 Photos

House | 6 Bedrooms | sleeps 14

2 Nights min stay

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from £137 /night

£959 - £1127 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Internet Access Heated Pool Private Pool VCR DVD Player Television  …see more

22 Photos

House | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £101 /night

£707 - £791 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Intern Private Pool Shared outdoor pool (unheated) VCR Satellite or cableTV DVD Player Television  …see more

12 Photos

House | 3 Bedrooms | sleeps 8

2 Nights min stay

Add to shortlist

from £83 /night

£581 - £665 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Internet Access Heated Pool Private Pool Satellite or cable TV Television DVD Player  …see more

7 Photos

House | 3 Bedrooms | sleeps 8

2 Nights min stay

Add to shortlist

from £95 /night

£665 - £749 / week

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Key info:

  • Great for children of all ages 5
  • No pets allowed
Internet Access Private Pool Satellite or cable TV DVD Player Television VCR  …see more

17 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £77 /night

£539 - £791 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Internet Access Shared outdoor pool (unheated) Hot Tub/Jacuzzi VCR Satellite or cable TV Television DVD Player  …see more

13 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £57 /night

£399 - £449 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
Internet Access Private Pool Heated Pool VCR Television DVD Player  …see more

14 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £83 /night

£581 - £665 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Internet Access Private Pool Satellite or cable TV DVD Player Television VCR  …see more

15 Photos

House | 4 Bedrooms | sleeps 10

1 night min stay

Add to shortlist

from £101 /night

£707 - £791 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Internet Access Heated Pool DVD Player Satellite or cable TV Television  …see more

8 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £95 /night

£665 - £749 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Internet Access Heated Pool Private Pool Shared outdoor pool (unheated)  …see more

14 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £101 /night

£707 - £791 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Internet Access Heated Pool Private Pool Television VCR Satellite or cable TV DVD Player  …see more

13 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £77 /night

£539 - £791 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Internet Access Shared outdoor pool (unheated) Satellite or cable TV DVD Player Television  …see more

11 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £89 /night

£623 - £707 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Internet Access Private Pool Heated Pool Stereo or CD player Television Satellite or cable TV  …see more

18 Photos

House | 5 Bedrooms | sleeps 16

3 Nights min stay

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from £105 /night

£734 - £929 / week

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Key info:

  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
  • Private garden
VACATION HOME, REUNION, DISNEY,KISSIMMEE  …see more

10 Photos

Apartment | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £89 /night

£618 - £840 / week

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Key info:

  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
Orlando, International Dr, Universal studios, Orange Convention Center  …see more

23 Photos

House | 4 Bedrooms | sleeps 10

3 Nights min stay

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from £93 /night

£645 - £809 / week

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Key info:

  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
vacation homes, Disney, house with pool  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £79 /night

£551 - £747 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Spacieuse villa 8 personnes , piscine chauffée , avec vue imprenable sur le lac Spacious villa 8 people, heated pool, with stunning views of the lake  …see more

10 Photos

Townhouse | 3 Bedrooms | sleeps 6

Very Good 4/5 

1 night min stay

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from £47 /night

£327 - £416 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
Beautiful three bedrooms two baths townhouse with amenities. Venetian Bay Villages has a beautiful village concept setting with a resort-style clubhouse that includes gym, 4 pools, business center. There are tennis courts, volleyball, basketball, picnic area, children's  …see more

10 Photos

House | 5 Bedrooms | sleeps 10

1 night min stay

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from £112 /night

£778 - £867 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Casa no condomínio Cubrian Lakes para até 10 pessoas, bela vista para o lago. Agradável experiência em família de passar alguns dias próximo ao mágico mundo da Disney. 5 quartos, um suíte , 3 banheiros, cozinha completa, piscina aquecida e internet wi-fi. Seja bem vindo  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 12

4 Nights min stay

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from £105 /night

£730 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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 £124 /night

£867 - £1000 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

17 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

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from £76 /night

£530 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
  • Private garden
This villa is ideal for families with small children. Very kiddy orientated  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 10

1 night min stay

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from £91 /night

£631 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
4 bed villa near Disney, FREE wifi, private pool and jacuzzi,air con, 2 bathrooms, 220 channel hdtv's, PS3, Xbox360, Windsor Palms Resort, secure gated community with communal pool, tiki bar, playground, sports courts, gym, games room, cinema, shop, bike/dvd/bbq rentals More info on our villa, Windsor Palms Resort and Florida attractions on lawrencevacationhomes website  …see more

15 Photos

Villa | 2 Bedrooms | sleeps 6

Min stay varies

Add to shortlist

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • Some pets are welcome - please contact the owner
-- Next to Walt Disney World. -- Walt Disney Tickets Sold on Site from Resort. -- -- Available At a Huge Discount than market rates. -- -- Available At a Huge Discount than market rates.  …see more

16 Photos

House | 3 Bedrooms | sleeps 8

Min stay varies

Add to shortlist

Key info:

  • Suitable for children over
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Townhouse / Townhome - Terra Verde - 03 BEDROOMS  …see more

16 Photos

Villa | 6 Bedrooms | sleeps 13

Min stay varies

Add to shortlist

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Windsor Hills Luxury Lake View Villa, Free Wifi, Games Rooms, Themed Disney Rooms,Close to Disney Tax included, Bedroom, Bunk Bed, Child Friendly Private Pool Spa No rear neighbors, free high speed wifi, free international calls pool table, foosball, air hockey , bbq This is a wonderful family villa minutes from Disney and includes many extra's to enhance your stay  …see more

7 Photos

Hotel apartment | 1 Bedroom | sleeps 4

Min stay varies

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from £76 /night

£530 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
Our resort in Orlando provides a premiere Florida vacation at a hotel that is 100% smoke free. Our spacious apartment has a fully equipped kitchens. Our deluxe Orlando resort provides 9 restaurants and dining options and free Wi-Fi Internet access. Your perfect Florida vacation begins at our Orange Lake Resort.  …see more

16 Photos

Villa | 4 Bedrooms | sleeps 10

3 Nights min stay

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from £86 /night

£600 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

8 Photos

Townhouse | 3 Bedrooms | sleeps 8

Min stay varies

Add to shortlist

from £46 /night

£318 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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 | 7 Bedrooms | sleeps 16

Excellent 5/5 

1 night min stay

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from £529 /night

£3700 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

Orlando Kissimmee is a great location for a family holiday, with easy access to Florida's big attractions - Disney World, Busch Gardens and Universal Studios. There are also rides through the Florida Everglades and plenty of children-friendly activities to keep everyone happy. The area has some excellent beaches, amongst them Clearwater Beach and Daytona Beach.