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552 Holiday homes in Kissimmee

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Filters applied: Swimming pool (552)

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552 Results  |  
16 Photos

Villa | 4 Bedrooms | sleeps 10

5 Nights min stay

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from £95 /night

£665 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
This villa is located in a community with a clubhouse that offers its own cinema, beach, volley ball, tennis courts, games room, bar and pool. An abundance of restaurants and shops are conveniently located just a short drive away.  …see more

16 Photos

Villa | 5 Bedrooms | sleeps 10

Short stays welcome

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from £122 /night

£850 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great 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

24 Photos

Villa | 5 Bedrooms | sleeps 12

5 Nights min stay

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from £105 /night

£735 - £1083 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
** 2014 discounts available , up to 30% off ** 5 min from Disney! Windsor Hills 5* Gated Resort. Luxury villa. Private South Facing Pool with Spa. Games Room. Free Wi-fi. Resort amenities: Large heated pool, water slide, movie theatre, children's play area. Cable TV. X-box. Close to Restaurants and Outlet Shops. Daily shuttle buses.  …see more

Featured properties

14 Photos

Villa | 4 Bedrooms | sleeps 10

4 Nights min stay

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from £79 /night

£550 - £800 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Set in the beautiful Bellavida Resort with own South West Facing Pool. Close to all attractions including Disney World, Universal Studios and Islands of Adventure. Dining and Shops are in abundance.  …see more

14 Photos

House | 6 Bedrooms | sleeps 12

1 night min stay

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from £110 /night

£770 - £1120 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Windsor Hills 6 bedroom home Gated community  …see more

17 Photos

Villa | 4 Bedrooms | sleeps 8

4 Nights min stay

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from £79 /night

£550 - £650 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Beautiful 4 bedroom villa with private pool. Refurbished for 2014 to a high standard and situated on the beautiful Lake Berkley resort gated community. The Villa is located approximately10 minutes drive from Disney and 20 minutes from Universal Studios.  …see more

16 Photos

Villa | 4 Bedrooms | sleeps 10

3 Nights min stay

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from £57 /night

£395 - £495 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Disney location with secluded heated pool and King sized Four Poster Bed. This newly renovated property, located in one of the nicest residential communities in Kissimmee, is a great base for any holiday in the area.  …see more

20 Photos

Townhouse | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £80 /night

£560 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Disney, Kissimmee, Windsor Palms. We are premiervacationsflorida, so look us up! We have properties in Sarasota and Kissimmee, and they are listed on Holiday lettings.  …see more

22 Photos

Townhouse | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £61 /night

£425 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
- Sleeps six. - Gated community. - Two swimming pools and spa pools. - Tennis Courts. - Children's play areas. - Gym. - Free Wifi. - Close to Walt Disney World. - Close to Universal Studios. - Close to SeaWorld. - Close to Waterparks. - Close to Orlando Int Airport  …see more

10 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

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from £79 /night

£550 - £750 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Emerald Island Resort, Kissimmee. This prestigious, 5 star, 24 hour manned, gated community, set in 11 acres on a conservation area. Resort community amenities: gated entryway, community pools and spa, sauna, game room, snack bar, cyber cafe with internet access, sand c  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £87 /night

£609 - £884 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Secret Key Cove Villa Luxury Award Winning Vacation villa rental, in Orlando, Florida Set in a Gated Community This 2 story upgraded Villa has, 4 bedrooms, 3 bathrooms, air conditioning and is set in a private location with its own private pool and spa. Emerald Island Resort Emerald Island Resort is a platinum class Orlando vacation Resort community, special  …see more

23 Photos

Villa | 8 Bedrooms | sleeps 17

3 Nights min stay

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from £276 /night

£1926 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • 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

17 Photos

Townhouse | 4 Bedrooms | sleeps 8

1 night min stay

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from £54 /night

£375 - £500 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Our townhouse on the Regal Oaks at Old Town resort is in an ideal location, Old Town has much to offer with its shops, bars, fairground attractions, with its own childrens fair are. You can also be catapulted 365 feet into the air by the human slingshot Every Thursday evening there is a motorbike cruise, on Saturdays, there is a weekly classic car cruise  …see more

6 Photos

Villa | 4 Bedrooms | sleeps 8

Short stays welcome

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from £68 /night

£475 - £675 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Luxury 4 bedroom villa with south facing pool and spa. Air conditioned throughout, great location just 5 minutes from Walt Disney World. Indian Ridge is a quiet residential community, yet just minutes from theme parks, shops and restaurants  …see more

12 Photos

House | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £83 /night

£575 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
4 bedrooms, 3.5 bathrooms, sleeps 10  …see more

20 Photos

Villa | 8 Bedrooms | sleeps 17

2 Nights min stay

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from £213 /night

£1491 - £1864 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa, Private Pool, Spa, Sleep 19, Resort Clubhouse, Kitchen, Game room, Xbox360, Heated Pool, BBQ Grill, 8 Bedrooms, 4.5 Bathrooms, Free WIFI, Cable TV, Game Room, Near Disney  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £90 /night

£630 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Private Pool, games room, conservation area view from the pool in a gated and safe community. Great location from Disney and close to shops and restaurants.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £68 /night

£475 - £680 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Our luxury Florida villa by the lake is a 4 bedroom/2 bathroom villa with its own private pool overlooking a beautiful lake in Kissimmee just minutes from Walt Disney World and the rest of Central Florida's many attractions. The house is all on one level and has two large separate living/dining areas, a games room and a large pool.  …see more

24 Photos

House | 6 Bedrooms | sleeps 14

1 night min stay

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from £162 /night

£1131 - £1500 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
Spacious Home Private Pool High End Resort Minutes from Disney Free WIFI  …see more

17 Photos

Villa | 7 Bedrooms | sleeps 16

3 Nights min stay

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from £129 /night

£898 - £1426 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
The location of Chadwick Manor really is ideal,as it is just south of the popular Highway 192 that has hundreds of shops and an excellent range of good restaurants barely 5 minutes drive from our villa, less than 5 miles from Walt Disney World homes, about 10 -15 minute Optional extras: pool heat, cribs/travel cots, wifi/international calls, early access, late departure  …see more

22 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £95 /night

£665 - £875 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 114 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
5 bedrooms;3 en suites bathrooms; private pool and spa; optional pool heating; Home Cinema; Fully air conditioned games room; south west facing pool; freeWiFi and high speed internet access; all bedrooms have flat screen cable TVs; free local and international calls All towels and linen provided; free floor safe;  …see more

8 Photos

Condo | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £50 /night

£350 - £665 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
3 bed, 2 bath luxury apartment. 4 heated outdoor pools with jacuzzis. Tropical style setting, in quiet and spacious grounds. Free wifi. Nearest international airport is Orlando (35 mins) or Tampa (1hr 10 mins). Car hire is essential.  …see more

14 Photos

House | 7 Bedrooms | sleeps 14

1 night min stay

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from £176 /night

£1230 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
7 bedroom Emerald Island  …see more

13 Photos

House | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £80 /night

£560 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This is an awesome 4 bed 3 bath private pool home in the popular gated golf community  …see more

10 Photos

Villa | 4 Bedrooms | sleeps 10

1 night min stay

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from £60 /night

£420 - £700 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
3 Bathrooms Bathroom 1 - toilet , tub , shower Bathroom 2 - toilet , combination tub/shower Bathroom 3 - toilet , combination tub/shower 4 Bedrooms, Sleeps 10 Bedroom 1 - 1 queen Bedroom 2 - 1 queen Bedroom 3 - 2 twin/ single Bedroom 4 - 2 twin/ single  …see more

13 Photos

Apartment | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £45 /night

£311 - £435 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Walk to shops, restaurants and supermarkets. We are 5 minutes from Disney and 20 minutes from Universal. Fully equipped kitchen and washer/dryer with free WIFI. Free parking.  …see more

22 Photos

Townhouse | 4 Bedrooms | sleeps 10

5 Nights min stay

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from £65 /night

£453 - £566 / week

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Key info:

  • Nearest beach 97 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
We are located Close to all the Walt Disney World Parks, Sea World, Discovery Cove, Aquatica Water Park, Universal Studios/Islands of Adventure, Gatorland Park, LEGOLand-Florida, Medieval Times and many other Orlando attractions. Venetian Bay Village is a Gated Resort Community with a Private Lake, a Recreation/Fitness Center & 4 Pools.  …see more

11 Photos

Condo | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £50 /night

£350 - £539 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Self-catering air-conditioned condo with shared swimming pool, gym and games room. We own three of these condos, one above the other, so if you have a large party you can all stay together.  …see more

18 Photos

Condo | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £65 /night

£453 - £727 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Internet Connection - Telephone - Cable/Satellite - Multiple TV's - linen/towels provided - Coffeemaker-vacation home rentals-luxury-modern-holiday villa-free wifi-central air/heat Living Area: 1,202 SqFt - Lot Size: 1,202 SqFt  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

4 Nights min stay

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from £77 /night

£535 - £700 / week

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Key info:

  • Nearest beach 104 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Brand new for 2011. Only 4 miles to Disney. 4 bedroom, 3 bathroom luxury villa with modern contemporary furnishings. Games room, pool + spa. Cable, wireless internet.  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 10

3 Nights min stay

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from £100 /night

£700 - £975 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Luxury 4 Bed 3 bath villa with pool, spa and games room incorporating air hockey table, football table and pool table. Free International phone calling, Free WifI and free internet streaming for unlimited free movies from Netflix. Two spacious living rooms. Baby goods.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £85 /night

£591 - £1119 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Oak Island Harbor community is a community that is known and appreciated for its convenient location in the prestigious Formosa Gardens area. Upscale private pool homes in a spectacular and peaceful setting yet close to where everything is going on.  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

3 Nights min stay

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from £111 /night

£777 - £1926 / week

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Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Disney World, Universal Studio, SeaWorld, Resort, Private Heated Pool, Spa, WIFI, Game room, Internet, Cable TVs 3 miles to Disney 14 miles to SeaWorld 17 miles to Universal. Minutes to Super Market and Restaurants  …see more

22 Photos

Villa | 4 Bedrooms | sleeps 9

3 Nights min stay

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from £80 /night

£559 - £702 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
disneykidsdkingdom 4 bed & 3 bath pool villa, We are situated in the quiet Lindfields residential area of kissimmee florida, yet only a few minutes from Disney parks &the Interstate 4 & 417 which are the main roads to all the universal attractions and the airports. There are 4 bedrooms sleeping 9 people (2 master suites) and there are 2 cots and 3 bathrooms  …see more

15 Photos

Villa | 3 Bedrooms | sleeps 8

4 Nights min stay

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from £61 /night

£422 - £515 / week

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Key info:

  • Nearest beach 65 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Our villa in Windward Cay is in the best location for the Theme parks and all the Malls. The coast is an easy 45 minute drive away and we have provided a large cooler box for you to fill and relax on the beach...Recently updated to a very high standard....  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 16

5 Nights min stay

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from £134 /night

£932 - £1926 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
3 Miles from Disney in Emerald Island resort ~ Air-conditioned game room with pool table, air hockey, foosball and large screen TV ~ 7 bedrooms, 4.5 bathrooms ~ 2 Master suites with King size beds ~ Large south-facing pool and spa - Themed kids bedrooms NOTE: We prefer Sat-Sat bookings. All variations are considered by owner, so please ask.  …see more

23 Photos

Townhouse | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £46 /night

£317 - £466 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
This glorious fully furnished townhouse was built in 2005 in the magnificent Key West style. This house features 3 wonderful bedrooms and 2.5 exquisite bathrooms and can house up to 8 people,within the gated community of Fiesta Key. The Villa is close to all the Theme Parks. 10 mins from Disney Land, 30 mins to Universal.  …see more

20 Photos

Condo | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £47 /night

£327 - £466 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Spacious condo 4 miles to Disney. This condo was built in 2007 and has recently updated do it has all the modern amenities. This is a home away from home that you can relax and enjoy after a long day at the attractions. The kitchen is fully equipped.  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

1 night min stay

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from £58 /night

£400 - £475 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Highly desirable executive villa is situated within the exclusive Seasons resort. Just off the famous Highway 192.This villa is adjacent to Medieval Times and a ten minute stroll to a 'Super Walmart' The villa is less than 15 minutes from Walt Disney World. Villa with private south facing heated pool. Close to Disney and other parks.  …see more

23 Photos

Villa | 7 Bedrooms | sleeps 16

1 night min stay

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from £379 /night

£2650 - £3650 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Best Price Huge 7 Bedroom Reunion Resort Vacation Home-Breathtaking views-Movie Theatre & Games Room!!!  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 23

4 Nights min stay

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from £1572 /night

£11000 - £12500 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
The largest rental home in the Orlando/Disney area with 9 beautiful bedrooms, 2 family rooms, 2 kitchens, library, dining room, home cinema room, gym, poker room, 2 bar areas and a huge pool with hot tub....  …see more

13 Photos

Villa | 2 Bedrooms | sleeps 8

1 night min stay

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from £107 /night

£746 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
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

12 Photos

House | 5 Bedrooms | sleeps 12

5 Nights min stay

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from £108 /night

£750 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
5 bedrooms, 4 bathrooms, homes sleeps 12 people  …see more

22 Photos

Villa | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £62 /night

£430 / week

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Key info:

  • Nearest beach 106 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
LOCAL SUPERMARKETS , DINING IS ONLY A FEW MINUTES DRIVE NEAREST THEME PARK ( DISNEY LAND ) IS ONLY 10 - 15 MINUTES DRIVE UNIVERSAL STUDIOS AND SEAWORLD ARE ABOUT 20 MINUTES AWAY NASA IS AN HOUR AWAY AS IS THE ATLANTIC COAST, THE GULF OF MEXICO IS AN HOUR AND A HALF LOCALLY WE HAVE A LARGE COMMUNITY POOL,TENNIS AND BASKET BALL COURT,HIKING TRAILS,FISHING AND OF COURSE GOLF  …see more

15 Photos

Villa | 4 Bedrooms | sleeps 8

4 Nights min stay

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from £109 /night

£761 - £1044 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 90 km
  • Swimming pool
  • Great 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

24 Photos

Villa | 7 Bedrooms | sleeps 16

5 Nights min stay

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from £203 /night

£1415 - £2155 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
LUXURY OF THE HIGHEST QUALITY! Large South facing pool plus spa, games room, BBQ and beautiful lake and woodland conservation views. One of the closest to Disney World!  …see more

12 Photos

House | 5 Bedrooms | sleeps 12

5 Nights min stay

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from £95 /night

£665 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
5 Beds and 4.5 bathrooms, sleeps 12 (4 poster Bed) 20 mins from Disney  …see more

13 Photos

Apartment | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £50 /night

£350 - £450 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Beautiful resort appartment close to Disney. 3bedroom, 2 bathroom Swimming pool, tennis, basket ball, gym, games room  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

5 Nights min stay

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from £418 /night

£2926 - £3955 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Brand new 5 bedroom home with swimming pool, spa, games room and home cinema. Situated on the Golf course....  …see more

9 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £90 /night

£625 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
4 BED 2 BATH POOL HOME 10 MINS FROM DISNEY  …see more

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