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485 Holiday homes in Kissimmee

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  • Acadia (4)
  • Bass Lakes Estate (4)
  • Bellavida Resort (10)
  • Calabria, Orlando (1)
  • Cane Island (5)
  • Chatham Park (3)
  • Compass Bay (2)
  • Coral Cay (3)
  • Creekside (1)
  • Crescent Lakes (11)
  • Crestwynd Bay (23)
  • Crystal Cove Resort (2)
  • Cumbrian Lakes (23)
  • Doral Woods (6)
  • Eagle Pointe (7)
  • Emerald Isle Kissimmee (37)
  • Encantada Resort (6)
  • Fiesta Key (4)
  • Formosa Gardens (13)
  • Hamiltons Reserve (5)
  • Indian Creek (14)
  • Indian Point (19)
  • Indian Ridge (4)
  • Indian Ridge Oaks (6)
  • Indian Wells (1)
  • Kissimmee City (12)
  • Lake Berkley (18)
  • Lake Marion (1)
  • Legacy Dunes Resort (1)
  • Liberty Village (4)
  • Lindfields (15)
  • Lucaya Village (1)
  • Oak Island Cove (5)
  • Oak Island Harbor (4)
  • Orange Lake Resort (4)
  • Paradise Palms (11)
  • Regal Oaks (5)
  • Remington (8)
  • Reunion Resort (38)
  • Rolling Hills at Formosa (6)
  • Seasons Resort (11)
  • Seven Dwarfs Lane (1)
  • Sunset Lakes (7)
  • Terra Verde Resort (8)
  • The Hamlets (2)
  • Trafalgar Village (4)
  • Tuscany, Florida (4)
  • Venetian Bay Villages (8)
  • Veranda Palms (5)
  • Villasol (3)
  • Vista del lago (2)
  • Westside (2)
  • Windsor Hills Resort (25)
  • Windsor Palms (27)
  • Winward Cay (1)

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485 Results  |  
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

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

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

Featured properties

12 Photos

Apartment | 3 Bedrooms | sleeps 8

4 Nights min stay

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from £73 /night

£509 - £636 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

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

16 Photos

House | 3 Bedrooms | sleeps 8

1 night min stay

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from £76 /night

£529 - £707 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
CHARMING HOUSE, VACATION HOME, DISNEY  …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

17 Photos

House | 3 Bedrooms | sleeps 9

3 Nights min stay

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from £70 /night

£485 - £618 / week

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Key info:

  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
vacation home, Kissimmee,  …see more

12 Photos

House | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £70 /night

£485 - £618 / week

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Key info:

  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
magnificent house, house in kissimmee, disney  …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

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

15 Photos

Villa | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £77 /night

£534 / 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

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

18 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

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from £72 /night

£504 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
You wont be disapointed with this vacation home  …see more

17 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

7 Nights min stay

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from £166 /night

£1161 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Close to Disney Parks Secure Gated Entrance Clubhouse 58 seat 3D Movie Theater Nintendo Wii Suite Fitness Room & Gym Billiard Room Video Arcade Lighted Tennis Courts Lighted Basketball Courts Volleyball Courts Children's Play Area Olympic Size Swimming Pool Belle's has won awards 3 Years running 2011,2012 & 2013 for top holiday rental in the Disney area.  …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

21 Photos

Villa | 4 Bedrooms | sleeps 10

2 Nights min stay

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from £69 /night

£477 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Just a few steps from the pool, the spa, the fitness, playground, tennis court, basketball court. From our home you can see your family members swimming in the pool. Our home is furnished up to a 5* residence, brand-new and air-conditioned and offers a cozy, homely f  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 10

Min stay varies

Add to shortlist

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

16 Photos

House | 3 Bedrooms | sleeps 8

Min stay varies

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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

15 Photos

Villa | 2 Bedrooms | sleeps 6

Min stay varies

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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
-- 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

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

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

7 Nights min stay

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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

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
  • Great for children of all ages 5
  • 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

18 Photos

House | 5 Bedrooms | sleeps 10

4 Nights min stay

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from £127 /night

£889 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
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

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 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 

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 5
  • 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

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 5
  • 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
  • Great for children of all ages 5
  • 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

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 5
  • 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

15 Photos

Villa | 4 Bedrooms | sleeps 8

Min stay varies

Add to shortlist

Key info:

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

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 5
  • 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.