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140 Holiday homes in Kissimmee

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  • Bass Lakes Estate (2)
  • Bellavida Resort (4)
  • Cane Island (3)
  • Chatham Park (2)
  • Creekside (1)
  • Crescent Lakes (8)
  • Crestwynd Bay (1)
  • Cumbrian Lakes (14)
  • Doral Woods (1)
  • Eagle Pointe (5)
  • Emerald Isle Kissimmee (10)
  • Encantada Resort (2)
  • Fiesta Key (1)
  • Formosa Gardens (4)
  • Hamiltons Reserve (1)
  • Indian Creek (1)
  • Indian Point (5)
  • Indian Wells (1)
  • Kissimmee City (5)
  • Lake Berkley (10)
  • Legacy Dunes Resort (1)
  • Liberty Village (2)
  • Lindfields (3)
  • Oak Island Cove (1)
  • Oak Island Harbor (1)
  • Orange Lake Resort (4)
  • Paradise Palms (1)
  • Regal Oaks (2)
  • Remington (3)
  • Reunion Resort (1)
  • Rolling Hills at Formosa (1)
  • Seasons Resort (1)
  • Sunset Lakes (6)
  • Terra Verde Resort (4)
  • Trafalgar Village (4)
  • Tuscany, Florida (1)
  • Venetian Bay Villages (3)
  • Veranda Palms (2)
  • Villasol (1)
  • Westside (2)
  • Windsor Hills Resort (4)
  • Windsor Palms (3)

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140 Results  |  
18 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £54 /night

£375 - £450 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Stunning American Lakeside Villa with private pool and beautiful views of wildlife and conservation area. Fully equipped villa with everything you need in your holiday home. Ideal for relaxing and proximity to attractions.Free Wi-Fi internet and free global phone calls.  …see more

17 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

Short stays welcome

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from £108 /night

£750 - £950 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Private villa with private lake views. Villa is not overlooked by other villas. Private pool, jacuzzi, just 10 minutes from Disney, situated in Kissimmee.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

Very Good 4/5 

7 Nights min stay

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from £122 /night

£850 - £1300 / 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
Villa Lazy Days is a 6 bedroom luxury Disney area vacation home located on a 5 star gated community overlooking the lake. Furnished to a high standard with private pool, spa & games area. Approx. 4 miles from Disney and only 20 minutes to most other main attractions. The club house offers a pool / spa / gym / volleyball beach court / kids area / internet, all free of charge  …see more

Featured properties

24 Photos

Villa | 5 Bedrooms | sleeps 10

Very Good 4.5/5 

4 Nights min stay

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from £71 /night

£495 - £600 / 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
5* south facing villa with wonderful lake & conservation views. Large pool/spa area, 5 bedrooms & 3.5 bathrooms in the fabulous secure gated community of Cumbrian Lakes with Wi Fi + 55" flatscreen TV. Only 12 mins from Disney & 20 from Universal & close to waterparks. 2 King size master en suite bedrooms (Downstairs leads to the pool & upstairs with balcony over the pool).  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 8

Excellent 5/5 

Short stays welcome

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from £58 /night

£403 - £525 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
One storey villa with 3 bedrooms that can easily accommodate 8 people as there is a sofa bed. Ideally located within easy reach of Disney World and is just minutes from the new West Gate entrance to the Walt Disney World Resort  …see more

15 Photos

Villa | 4 Bedrooms | sleeps 8

4 Nights min stay

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from £105 /night

£735 - £910 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Minutes from Disney, emerald island resort, 4 bed, not overlooked, private heated pool & spa, 3 bath, games area, free broadband, resort facilities.  …see more

14 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £124 /night

£868 - £1178 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 92 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Exclusive, large villa (approx. 2500 Sq Ft) with a capacity to sleep 12 people comfortably with 6 bedrooms and 4 bathrooms. Luxurious private heated pool and hot tub with games room for the kids - both big and little alike. A great place to Rest, Relax & Play!  …see more

12 Photos

House | 4 Bedrooms | sleeps 10

Very Good 4/5 

Short stays welcome

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from £74 /night

£515 - £631 / 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
Looking for a family vacation villa so close to Disney that it's almost on Mickey's doorstep? This immaculate 4 bedroom, 3 bathroom villa is ideally situated only 3 miles from Disney World in a peaceful residential neighbourhood overlooking a tranquil lake.  …see more

22 Photos

Villa | 5 Bedrooms | sleeps 12

Excellent 5/5 

1 night min stay

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from £54 /night

£375 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury Villa with large south facing garden, extended swimming pool and deck ,overlooking a lovely lake and fountain. Cumbrian Lakes is prestigious development of villas very sought after for holidays.  …see more

24 Photos

House | 6 Bedrooms | sleeps 12

Very Good 4.5/5 

3 Nights min stay

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from £102 /night

£711 - £848 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Large spacious well equipped house which is ideally sited in a rpivate gated community 5 minutes from Disney  …see more

22 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £91 /night

£635 - £825 / 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
Brand new luxury rental vacation Villa on the Exclusive Bellavida Resort Orlando. 4 large bedrooms all en-suite. Villa comes complete with games room, internet access Pool and Hot Spa/Jacuzzi and is ideal for small or large families. Furnished to the highest standard. 5 star Luxury villa, you will not be disappointed at this truly charming villa.  …see more

12 Photos

Villa | 4 Bedrooms | sleeps 10

3 Nights min stay

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from £65 /night

£450 - £550 / 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
Luxury Lakeside Villa with South Facing Private Pool with Views over a Lake & Conservation Area only 15mins from the Disney Parks, 5mins. to 192 for Walmart supermarket, shopping & restaurants.  …see more

22 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £117 /night

£817 - £949 / 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
Spoil yourself in this five bedroomed villa with its own private pool and spa. This villa is located in a gated community with playgrounds, tennis, fishing and a gym on site Chill out in our four poster bed or enjoy a relaxing cool drink by the poolside.  …see more

10 Photos

Villa | 4 Bedrooms | sleeps 8

Good 3/5 

7 Nights min stay

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from £65 /night

£454 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 40 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
This luxurious air-conditioned rental villa-pool accommodation is available for your holiday rental bookings set in large grounds overlooking a lake at the rear it can be your dream holiday let.  …see more

23 Photos

Villa | 8 Bedrooms | sleeps 18

Excellent 5/5 

Short stays welcome

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from £429 /night

£3000 - £3670 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 110 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury Home. Sleeps 18. Close to Theme Parks, Shops, Golf & Restaurants 2 miles Disney World. Custom Built Manor. Private, Landscaped Pool. Summer Kitchen & BBQ. Cinema. Games Room w/ Pool Table. Free WiFi Internet. Overlooks Natural Woodland & Lake Located in Formosa Gardens. Gated community. Closest to Disney. Restaurants, shops and bars, golf nearby.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 8

Excellent 5/5 

4 Nights min stay

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from £50 /night

£350 - £395 / 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
Luxury 3 bed villa sleeps 8. Large 30ft fully heated secluded pool. 15mins.drive from Disney. Surrounded by beautiful golf courses  …see more

12 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £72 /night

£500 - £945 / 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
Fabulous 4 bed / 3 bath villa with pool (Heated at extra cost) on Terra Verde resort only 10 mins from Disney and local golf courses.  …see more

10 Photos

Villa | 4 Bedrooms | sleeps 10

4 Nights min stay

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from £84 /night

£586 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Indian Creek -just a 10min drive from the Disney gates and close by to the other main attractions in the theme park capital of the world!  …see more

20 Photos

Townhouse | 4 Bedrooms | sleeps 8

Excellent 5/5 

Short stays welcome

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from £57 /night

£395 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
The townhouse is a modern, beautifully appointed home complete with the space and facilities you need to make your stay a memorable one. The open plan format offers plenty space with separate seating and dining areas and fully equipped kitchen.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £62 /night

£434 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Great location, good price, very clean.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

4 Nights min stay

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from £69 /night

£477 - £635 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Located in a Family friendly community with free use of resort facilities our well-furnished villa with pool and hot tub can comfortably accommodate up to 8 Guests. Less than 15 miles from Walt Disney World.  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 13

Short stays welcome

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from £92 /night

£644 - £784 / 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
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 | 6 Bedrooms | sleeps 13

Very Good 4/5 

7 Nights min stay

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from £100 /night

£700 - £875 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A lifetime of memories in our fantastic and luxurious 6 bedroom villa located in Oak Island Cove, Kissimmee, Florida, just 5 minutes from Disney. This memorable, yet affordable house comprises two floors of comfort and elegance. Our home we enjoy and love. It's where we spend our vacation time relaxing and enjoying Florida sunshine.  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 12

Very Good 4/5 

7 Nights min stay

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from £86 /night

£600 - £650 / 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
Florida Executive home is a 5 bedroom 3 and 2 half athroom house that can comfortably accommodate more than one family wtih a floor area of approximately 2500sq/ft. The property is south facing with private pool and jacuzzi and overlooks the lake and fountain which illuminates at night. Set in a gated community with conservation area surrounding who could wish for more.  …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
  • Suitable 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

10 Photos

Villa | 6 Bedrooms | sleeps 14

Short stays welcome

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from £128 /night

£891 - £1166 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Emerald Island Lake View is a luxurious villa situated on the prestigious Emerald Island Resort. It is spacious with a separate lounge and a large family room with views over the private pool and large garden. It is furnished and equipped to a very high standard.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

1 night min stay

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from £99 /night

£689 - £742 / 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
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

17 Photos

House | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £67 /night

£467 - £583 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 30 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Terra Verde is an award winning resort close to Walt Disney, Sea World , and all the other thrilling parks. Sunseeker over looks a large fishing lake, is also immaculate and and has wonderful furnishings which makes it a little different to all the others . T The Patio is a wonderful place to relax and maybe have a BBQ and chill in the spa  …see more

13 Photos

Villa | 7 Bedrooms | sleeps 16

3 Nights min stay

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from £144 /night

£1007 - £1696 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
  • Private garden
7 Bedrooms, 4 Bathrooms, Large South facing Pool / Spa Near Disney Theme Parks, Games Room, Wi Fi, 60" Internet TV, DVD, Conservation area, Lake views, Fully equiped kitchen, towels provided, suitable for disabled people, local management company, fishing, gold nearby Lovely views of the lake and It is only a short drive from the main theme parks and many golf courses.  …see more

19 Photos

Villa | 3 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £70 /night

£490 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 110 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Sit back and enjoy one of the best views in Kissimmee! You will be amazed at the view from your pool area. Our vacation rental is a beautiful newly decorated, three bedroom, two bath home that backs on to a lake with a conservation area, lush with wildlife.  …see more

16 Photos

House | 4 Bedrooms | sleeps 10

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
  • Suitable 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

16 Photos

Villa | 5 Bedrooms | sleeps 10

Short stays welcome

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from £129 /night

£901 / 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
F lorida villa with 5 bedrooms, 3 bathrooms, air-conditioned,large south facing private pool/Spa,close to Disney,sea world,universal and restaurants, great shoping at florida mal, Ideal 2 families Travle cot & high chair for babies .  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 16

7 Nights min stay

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from £158 /night

£1100 - £1250 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa in lake Berkley, kissimmee, Florida/. 7 bedroom all with en-suite facilities villa at lake Berkley resort with stunning views across the lake and of the island, peaceful location but only 15 minutes to Disney. Luxury pool seating on extended deck overlooking large pool and spa.  …see more

15 Photos

Villa | 5 Bedrooms | sleeps 11

7 Nights min stay

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from £113 /night

£790 - £819 / 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
Our stunning 5 bedroomed villa has everything that you could need for a wonderful holiday in the Orlando area. Including fully stocked games room, swimming pool and hyrotherapy spa, gas barbeque and a PC will full internet and wifi access. Our stunning Lakeside Villa will make all your Florida dreams come true. We have tried to think of everything that you should possibly need for the perfect vacation and just some of our features are, PC is high-speed Internet access, infrared gas barbecue on our sun terrace area which has extended decking the hydrotherapists bar and applewood has coloured lighting display that looks wonderful litter for Nightswimming.  …see more

11 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £150 /night

£1050 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Affordable LuxuryJust 5 minutes Drive from Walt Disney World's Animal Kingdom This Attractive, two story charming villa provides guests with a home from home in the sun. There's plenty of room to stretch out and relax away from the excitement and bustle of the parks Games room with full size, slate top pool table and air hockey table ~ fun for the kids! Free phone calls  …see more

13 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £54 /night

£377 - £504 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
5 Star luxury at affordable rates, this home from home in Sunny Florida is situated in peaceful surrounding on the edge of Kissimme in a rual setting. Just 10 minutes at normal driving speeds from the world famous Disney Parks. The 5 star luxury is reflected in the quality of the fixtures and fittings, with a host of free items.  …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

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

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

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

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.