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634 Holiday homes in Kissimmee

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  • Acadia (18)
  • Bass Lakes Estate (5)
  • Bellavida Resort (15)
  • Calabria, Orlando (1)
  • Cane Island (5)
  • Chatham Park (3)
  • Compass Bay (2)
  • Coral Cay (3)
  • Creekside (1)
  • Crescent Lakes (11)
  • Crestwynd Bay (44)
  • Crystal Cove Resort (2)
  • Cumbrian Lakes (26)
  • Doral Woods (6)
  • Eagle Pointe (7)
  • Emerald Isle Kissimmee (42)
  • Encantada Resort (6)
  • Fiesta Key (4)
  • Formosa Gardens (13)
  • Hamiltons Reserve (3)
  • Heritage Key (1)
  • Indian Creek (17)
  • Indian Point (21)
  • Indian Ridge (4)
  • Indian Ridge Oaks (7)
  • Indian Wells (1)
  • Kissimmee City (18)
  • Lake Berkley (19)
  • Lake Marion (1)
  • Legacy Dunes Resort (1)
  • Liberty Village (4)
  • Lindfields (16)
  • Lucaya Village (1)
  • Oak Island Cove (5)
  • Oak Island Harbor (4)
  • Orange Lake Resort (4)
  • Paradise Palms (17)
  • Regal Oaks (5)
  • Remington (9)
  • Reunion Resort (45)
  • Rolling Hills at Formosa (6)
  • Seasons Resort (11)
  • St Cloud (1)
  • Sunset Lakes (8)
  • Tema (1)
  • Terra Verde Resort (9)
  • The Hamlets (2)
  • Trafalgar Village (4)
  • Tuscany, Florida (4)
  • Venetian Bay Villages (12)
  • Veranda Palms (5)
  • Villasol (3)
  • Vista del lago (2)
  • Westside (2)
  • Windsor Hills Resort (42)
  • Windsor Palms (44)
  • Winward Cay (1)

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634 Results  |  
11 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

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from £89 /night

£623 - £826 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Private Pool Heated Pool Stereo or CD player Television Satellite or cable TV  …see more

24 Photos

Condo | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £55 /night

£379 - £435 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
Located in Grand Palms Resort, this Kissimmee Florida vacation rental is just FIVE miles from the Walt Disney World  …see more

18 Photos

Townhouse | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £52 /night

£363 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
Located in a private community of Paradise Cove, amid lush and beautifully landscaped surroundings, this Kissimmee Florida vacation rental by owner is a perfect family getaway  …see more

Featured properties

24 Photos

House | 3 Bedrooms | sleeps 6

1 night min stay

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from £45 /night

£311 - £363 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
Vacationing Central Florida Feel At Home  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £59 /night

£410 - £468 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Pool Villa in Sunny Kissimmee! Free Wi-fi & PhoneVacation Villa in the heart of the Disney area! Open, bright and airy floor plan with a separate dining area and eat-in kitchen. Covered deck area and screened-in pool as well as billiards table are great for staying at h  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 14

Very Good 4.5/5 

Short stays welcome

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from £152 /night

£1063 - £1395 / week

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Late Deal: save up to £437

Key info:

  • Swimming pool
  • Suitable 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

17 Photos

House | 3 Bedrooms | sleeps 9

3 Nights min stay

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from £62 /night

£430 - £560 / week

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Key info:

  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
vacation home, Kissimmee,  …see more

23 Photos

House | 4 Bedrooms | sleeps 10

3 Nights min stay

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from £84 /night

£586 - £747 / week

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Key info:

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

14 Photos

Apartment | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £68 /night

£473 - £647 / week

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Key info:

  • Suitable for children of all ages
  • No pets allowed
vacation home, Disney, casa de temporada, kissimmee  …see more

12 Photos

House | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £62 /night

£430 - £560 / week

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Key info:

  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
magnificent house, house in kissimmee, disney  …see more

10 Photos

Apartment | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £74 /night

£517 - £777 / week

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Key info:

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

18 Photos

House | 5 Bedrooms | sleeps 16

3 Nights min stay

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from £97 /night

£673 - £864 / week

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Key info:

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

16 Photos

House | 3 Bedrooms | sleeps 8

1 night min stay

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from £68 /night

£473 - £647 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
CHARMING HOUSE, VACATION HOME, DISNEY  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £77 /night

£539 - £729 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • 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
  • Suitable for children of all ages
  • 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 £109 /night

£760 - £847 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • 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

21 Photos

House | 6 Bedrooms | sleeps 12

4 Nights min stay

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from £121 /night

£847 - £977 / week

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Key info:

  • Swimming pool
  • Suitable 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

20 Photos

Villa | 5 Bedrooms | sleeps 12

4 Nights min stay

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from £102 /night

£713 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
  • 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

15 Photos

Villa | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £75 /night

£521 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
ACCUEIL FRANCOPHONE SUR PLACE  …see more

16 Photos

Villa | 6 Bedrooms | sleeps 13

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Suitable for children of all ages
  • 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

20 Photos

Apartment | 3 Bedrooms | sleeps 6

Min stay varies

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Our first floor unit is ideally located within walking distance to the resort clubhouse and its amenities. Close to everything, this community is one of the most sought after communities in Central Florida. Less than 5 miles to Disney!  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 13

Excellent 5/5 

Min stay varies

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from £179 /night

£1250 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
6 bedrooms, gated community, Windsor palms, swimming pool, Jacuzzi, Disney, air conditioned, clubhouse  …see more

14 Photos

Villa | 4 Bedrooms | sleeps 10

Excellent 5/5 

Min stay varies

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from £67 /night

£467 - £615 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Oak Island Cove is located in the middle of all the fun parks and attractions Orlando has to offer, only a few minutes from what makes Orlando so famous. Disney World is only 3 miles away and Universal Studies & Sea World a mere 20 minute  …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
  • Suitable 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

23 Photos

Villa | 8 Bedrooms | sleeps 17

Min stay varies

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from £45 /night

£310 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
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. 3 miles to Disney 14 miles to SeaWorld 17 miles to Universal. Minutes to Super Market and Restaurants  …see more

7 Photos

Villa | 3 Bedrooms | sleeps 10

Min stay varies

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from £122 /night

£848 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Next to Disney World in Orlando Florida (Kissimee). Sleeps 10. Flat screen TV. Private jacuzzi. Outdoor pools plus other amenities within the resort.  …see more

15 Photos

Villa | 4 Bedrooms | sleeps 8

Min stay varies

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Key info:

  • Swimming pool
  • Suitable 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

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
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
South Beach 5 room Art Deco Pool Villa  …see more

23 Photos

Villa | 3 Bedrooms | sleeps 8

Min stay varies

Add to shortlist

Key info:

  • Swimming pool
  • Suitable 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

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
  • Suitable 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

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
  • Suitable 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 | 5 Bedrooms | sleeps 10

Min stay varies

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from £85 /night

£594 / week

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Key info:

  • Suitable 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

11 Photos

Townhouse | 3 Bedrooms | sleeps 8

Min stay varies

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from £106 /night

£742 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Luxury 3 bed home with private pool in The Luxury Windsor Hill's Resort only 1.5 miles from Disney World  …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
  • Suitable 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

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.