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141 Holiday homes in Kissimmee

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  • Bass Lakes Estate (2)
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  • Venetian Bay Villages (3)
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  • Windsor Hills Resort (4)
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141 Results  |  
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
  • Great for children of all ages 5
  • 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

House | 4 Bedrooms | sleeps 8

Excellent 5/5 

1 night min stay

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from £88 /night

£610 - £1103 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 130 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
Located 3 miles from Disney World main gate, and easy reach of all Orlando attractions. Sleeps 8; comprising of 4 bedrooms, (2 en-suites) and 3 full bathrooms. . Private south facing heated pool and spa + games room and free Wi-Fi, Flat screen TV's in all bedrooms.  …see more

18 Photos

Villa | 2 Bedrooms | sleeps 8

Excellent 5/5 

1 night min stay

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from £182 /night

£1272 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Family Fun in the Heart of Orlando, Florida. Shop, dine, play, golf—we've got everything you need for the vacation of a lifetime. And right next door to Walt Disney World® Resort and Animal Kingdom! Luxuriously decorated villas for your comfort. Superb base for Walt Disney World and Golfing holidays.  …see more

Featured properties

22 Photos

Villa | 6 Bedrooms | sleeps 13

Excellent 5/5 

1 night min stay

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from £150 /night

£1045 - £1595 / 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
Luxury 6 bed. 51/2 bath.Professionally interior-designed villa, full view down lake, with heated-pool,spa, fountains,TV in all rooms,Gated resort.15 Minutes from Disney. walk 2 shops,Golf course 5 minutes.State of the art security system.Crib/playpen & stroller/buggie, Pool/spa heating is an optional extra,(min.5 days)& charged @ $30 p/day,. BBQ may be rented locally.  …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
  • Great for children of all ages 5
  • 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

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
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • 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

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
  • Great for children of all ages 5
  • 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

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
  • Great for children of all ages 5
  • 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

15 Photos

House | 6 Bedrooms | sleeps 13

Excellent 5/5 

7 Nights min stay

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from £101 /night

£701 - £1761 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Wow factor Extra large saline pool South facing deck and slide THX Cinema, with leather tiered seating Smart Tv's Quite location conservation view. Games room, cycles Most comfortable beds Full size bbq outside kitchen Lots of extras not included in other rental homes Book early to avoid disappointment. Holiday periods are extremely busy, so dont delay.  …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
  • Great for children of all ages 5
  • 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

24 Photos

House | 6 Bedrooms | sleeps 13

Excellent 5/5 

7 Nights min stay

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from £143 /night

£999 - £1395 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
We set out to achieve a truly beautiful and exciting luxurious home, not a basic 'rental villa'. With impressive vital statistics this huge 4184sq ft 6 bedroom, 6 bathroom home overlooking a sparkling lake, with a sun drenched south facing pool and spa is perfect! Check out our availability calendar we are booking up fast...book now while you can!  …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
  • Great for children of all ages 5
  • 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

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
  • Great for children of all ages 5
  • 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

17 Photos

House | 3 Bedrooms | sleeps 8

Excellent 5/5 

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
  • Great for children of all ages 5
  • 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

24 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £128 /night

£895 - £1095 / 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
3 D Cinema room with luxury seating . Pool & Spa privacy Water slide /OUTDOOR TV. Unrivalled games room Wurlitzer Jukebox Electric scooters Playstation 3 consoles . iphone docking stations . BBq Baby/toddler cot/bumpers and safety items Fishing equipment bikes Games room - air conditioned Fishing lake next door to villa All bedrooms -large screen TV /PS3/ipod docking  …see more

22 Photos

Villa | 6 Bedrooms | sleeps 14

1 night min stay

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from £101 /night

£704 - £960 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
This superb luxury vacation pool home with 6 bedrooms, 5.5 bathrooms and straight forward fully inclusive pricing has everything that you could possibly need for the perfect holiday.  …see more

12 Photos

Villa | 4 Bedrooms | sleeps 10

3 Nights min stay

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from £68 /night

£475 - £595 / 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
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 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
  • Great for children of all ages 5
  • 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

Villa | 6 Bedrooms | sleeps 13

Very Good 4/5 

7 Nights min stay

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from £106 /night

£742 - £928 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

24 Photos

Villa | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £64 /night

£445 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Great location, good price, very clean.  …see more

10 Photos

Villa | 4 Bedrooms | sleeps 8

4 Nights min stay

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from £86 /night

£600 - £667 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

24 Photos

Villa | 5 Bedrooms | sleeps 12

Very Good 4/5 

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
  • Great for children of all ages 5
  • 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

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
  • Great for children of all ages 5
  • 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

20 Photos

Townhouse | 4 Bedrooms | sleeps 8

Excellent 5/5 

Short stays welcome

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from £71 /night

£495 - £650 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages 5
  • 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 | 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
  • Great for children of all ages 5
  • 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

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
  • Great for children of all ages 5
  • 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

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
  • Great for children of all ages 5
  • 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

15 Photos

Villa | 5 Bedrooms | sleeps 11

7 Nights min stay

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from £116 /night

£809 - £839 / 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
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

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
  • Great for children of all ages 5
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • 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

12 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £76 /night

£530 - £1002 / 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
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

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
  • Great for children of all ages 5
  • 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

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
  • Great for children of all ages 5
  • 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

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
  • Great for children of all ages 5
  • 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

10 Photos

Villa | 4 Bedrooms | sleeps 10

Short stays welcome

Add to shortlist

from £64 /night

£446 / 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
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

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
  • Great for children of all ages 5
  • 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

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

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

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

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

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.