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462 Holiday homes in Kissimmee

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462 Results  |  
12 Photos

Condo | 2 Bedrooms | sleeps 6

5 Nights min stay

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from £84 /night

£587 - £799 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This two bedroom/ two bath condo, with queen sleeper sofa, can accommodate up to six people. This unit has a 1 car garage, and is professionally decorated. To make your stay feel more like home, this unit is equipped with all the latest technologies including: XBOX 360, Nintendo Wii, 3 Flat Screen  …see more

24 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £229 /night

£1597 - £2162 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Located in Windsor Hills, this beautiful home has been furnished and decorated with the utmost attention to every detail so that you can enjoy the luxury of a great vacation rental as well as the comforts of home. With no less than five bedrooms, five baths, and a 2-car garage, this property can  …see more

24 Photos

House | 4 Bedrooms | sleeps 10

5 Nights min stay

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from £189 /night

£1317 - £1693 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
This 4bdrm/3bth house located in a resort style gated community of Windsor Palms offfers 2 king, 1 queen & 2 twin beds. This home has free long distance and has tv's in everyroom. The home also has a private pool & spa. This home sleeps up to 10 persons comfortably. Located just  …see more

Featured properties

18 Photos

Condo | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £95 /night

£659 - £895 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Water & nature views surround this spectacular 3 bedroom 2 bath, 1500 sq.ft. newly furnished and professionally decorated condo. Our Home offers WiFi as well as unlimited local and long distance to more than 60 countries(some restrictions apply), so you can easily share your memories prior to  …see more

14 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £91 /night

£634 - £941 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This beautiful spacious 3bdrm/2/bth condo w/ balcony  located in the resort style gated community of  Windsor Palms is nicely decorated to suit your needs while vacationing.  This condo offers wireless internet. It is located just 3 miles from Disney's gates. The resort also has many amenities  …see more

14 Photos

House | 6 Bedrooms | sleeps 12

5 Nights min stay

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from £259 /night

£1808 - £2445 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
This very modern 6 bedroom 4 bathroom home has been professionally furnished and decorated including beautiful relaxing colors through-out the home with custom window treatments. No expense has been spared with this home which comes with every little item to make your stay ever enjoyable and  …see more

16 Photos

Condo | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £95 /night

£659 - £895 / week

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Key info:

  • Not suitable for children
  • Pets welcome
Welcome to this beautiful Florida vacation condo in Oakwater which was built in 2007. This 3 bedroom, 2 bath condo sleeps 8 and was completely refurnished with new furniture in November 2009. New laminate flooring were installed in the bedrooms in November of 2011. There is a king size bed in the  …see more

24 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £165 /night

£1153 - £1457 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Brighton floor plan- 1816 sq.ft. 4 bedroom 3 bath (1 story) South facing pool Welcome to this elegant, professionally decorated Orlando vacation pool home, located in the beautiful Windsor Palms Resort. This home is absolutely perfect for large family groups. This property features all the comforts  …see more

16 Photos

Townhouse | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £115 /night

£799 - £1174 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
"Disney Hideaway" town-home has a spacious family room to relax in during the day or evening, with a ceramic tiled floor, contemporary-style interior with beautiful decor, cable TV with a DVD player so you can watch your favorite movie with the whole family. If you need to surf the web  …see more

24 Photos

House | 5 Bedrooms | sleeps 12

5 Nights min stay

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from £229 /night

£1597 - £2162 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Welcome to this elegant, and professionally decorated Orlando vacation pool home, located in the beautiful Windsor Hills Resort. Absolutely perfect for large family groups, this property features all the comforts of home and more! Windsor Hills is a gorgeous gated community just 1.5 miles from the  …see more

24 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £229 /night

£1597 - £2162 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
This 2,500 square foot 5B/5B Seville home sleeps 11 and is south facing for year round, all day Florida sun. The fully air conditioned ''dream come true'' home has luxurious tropical furnishings and is professionally decorated throughout. Your every need has been anticipated.  …see more

14 Photos

Townhouse | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £105 /night

£730 - £1060 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
3 bedroom 3 bath townhome Welcome to this elegant, professionally decorated Orlando vacation town home, located in the beautiful Windsor Palms Resort.  This townhome sleeps 6 comfortably in 1 king, 1 queen, and 2 twin sized beds.  It also comes with a full kitchen equipped with microwave, coffee  …see more

8 Photos

Townhouse | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £107 /night

£749 - £1091 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
We invite you to enjoy our townhome on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at this beautiful townhome with splash pool. Attention to every detail has been put in as we furnished and  …see more

22 Photos

Townhouse | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £115 /night

£799 - £1174 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Experience a sunny Florida vacation in this 3 bedroom, 3 baths Saddlebrook model which features 1400 sq. ft.  This bedroom sleeps 6 in one king, one queen, and two twin sized beds, and each bedroom has its own private bathroom.  Included in the full sized kitchen are microwave, ice maker, coffee  …see more

24 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £202 /night

£1410 - £1879 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
This five bedroom vacation home comes complete with five bathrooms, full kitchen, and pool. This spacious property will easily accommodate 10 on two king, one queen, and four twin sized beds.  Amenities include a pool, patio, washer/dryer combo, dishwasher, and hot tub.  In addition to this,  …see more

24 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £202 /night

£1410 - £1951 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Welcome to this beautifully furnished home in Kissimmee, Florida. With five bedrooms and three-and-a-half baths, it can accommodate up to ten people easily and features both a private patio and swimming pool. The full kitchen provides you with everything you need to whip up and enjoy a home cooked  …see more

16 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £98 /night

£684 - £988 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Newly decorated and upgraded 1st floor 3 bedroom, 2 bath condo. This home comes with a 42" flat screen TV in the living room with a Playstation 3 game system, flat screen TV's in each of the bedrooms (two 32" and one 24" with DVD). The kitchen comes fully equipped and this condo  …see more

20 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £165 /night

£1153 - £1457 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
This Lovely 4 bedroom/3 bath home is located in gated Windsor Palms just minutes to Disney.   The home features a private swimming pool and spa/jacuzzi with pool heating features.  It also includes a home entertainment DVD combination, play station and TV's in every bedroom.  In addition,  …see more

24 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £165 /night

£1153 - £1457 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Orlando Florida vacation dreamhome, in gated community minutes from Disney and other attractions. 4 bedroom pool/spa home totally professionally redecorated. Flatscreen TVs throughout. 54" in livingroom & master. Gameroom with pool table,ping pong, airhockey, Flatscreen w/playstation.  …see more

24 Photos

House | 6 Bedrooms | sleeps 8

5 Nights min stay

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from £198 /night

£1386 - £1858 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Attention to every detail has been put in as we furnished and decorated this home. This 6 bedroom 4 bath 3,073 sq feet unit sleeps 13 in style. With 2 king bedrooms, 1 queen bedroom, and 4 twin beds, there is plenty of room for everyone to spread out and relax after a day out or to just relax and  …see more

24 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £202 /night

£1410 - £1879 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Relax in this elegant and professionally decorated 5 bedroom/5 bath pool home, located in the beautiful 5 Star, gated community of Windsor Hills, in Kissimmee, Florida--“Kissimmee Castle.” This home has been completely renovated and newly furnished, including the washer and dryer and all new  …see more

20 Photos

House | 5 Bedrooms | sleeps 11

5 Nights min stay

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from £202 /night

£1410 - £1951 / week

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Key info:

  • Not suitable for children
  • No pets allowed
We invite you to enjoy this home on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at this beautiful home with pool & spa located in the Windsor Palms Resort. Attention to every detail has been  …see more

16 Photos

Condo | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £95 /night

£659 - £895 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Welcome to our Florida vacation condo. We invite you to enjoy our great property at Oakwater, built in 2007. This complex is one of the closest to Walt Disney World. I drove from the door to the gates of Disney and it took me 4 ½ minutes. It is also close to plenty of restaurants, shopping and  …see more

24 Photos

House | 4 Bedrooms | sleeps 10

5 Nights min stay

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from £165 /night

£1153 - £1457 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
A 4 bedroom/3 bath home located in the Windsor Palms. This home has 1 king, 1 queen, and 4 twin beds also with many upgrades like TV's in every room, DVD, heatable (Private) pool & spa, sofa sleeper, Internet access. The Palms clubhouse has a fitness center, movie theatre, & game room.  …see more

14 Photos

Condo | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £98 /night

£684 - £988 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Luxuriously appointed 3 bedroom, 2 bath top floor unit in the beautiful Windsor Hills resort that sleeps 6 comfortably. This elegantly decorated Kissimmee vacation condo is located in a gorgeous gated community just 5 minutes from the gates of the Magic Kingdom. This 1,247 sq ft condo has a  …see more

14 Photos

Townhouse | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £105 /night

£730 - £1060 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Welcome to this upgraded and newly decorated very spacious 3 bedroom, 3 bathroom Townhouse with its own private splash pool that overlooks a peaceful park-like area. For a small fee the pool can be heated for you. For your enjoyment and comfort we have flat screen TVs in each of the bedrooms as  …see more

16 Photos

Condo | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £98 /night

£684 - £988 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Luxury condo with an idyllic setting – this is one of the few residences in Windsor Hills with a direct lake view – you can enjoy watching the sunset over the lake from the balcony. Professionally decorated, the interior is luxurious with top of the range furnishings and fittings. It is spacious,  …see more

24 Photos

House | 6 Bedrooms | sleeps 14

5 Nights min stay

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from £225 /night

£1575 - £2115 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Located in Windsor Hills, this beautiful, two-story home has been furnished and decorated with the utmost attention to every detail so that you can enjoy the luxury of a great vacation rental as well as the comforts of home. With no less than six bedrooms, a sofa bed, and four baths, this property  …see more

17 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £95 /night

£659 - £895 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This beautiful 3 bedroom/ 2 bath condo is located in the brand new gated community of Oakwater, located 1.5 miles from Disney. It sleeps 6 comfortably with 1 king, 1 queen, and 2 twin sized beds.  It also comes with a full kitchen inclusive of coffee maker, microwave, ice maker, and dishwasher.   …see more

24 Photos

Villa | 4 Bedrooms | sleeps 10

5 Nights min stay

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from £215 /night

£1504 - £1904 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Villa La Dolce Vita is new 4 bedroom/4 bathroom Luxury Home that sleeps up to 10 people. Our villa is located in the new five star ***** Windsor Hills Reserve Gated Community, the newest, most luxurious and closest private home resort community to Walt Disney World. We are located less than 2 miles  …see more

18 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £111 /night

£777 - £1081 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This beautiful 3 bedroom/ 2.5 bath condo is located in the brand new gated community of Oakwater, located 1.5 miles from Disney. The 4,000 sq. clubhouse features a lagoon-style pool, tennis courts volleyball courts and basketball courts. Condo consists of one king bed, one queen bed, two twin beds,  …see more

14 Photos

Condo | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £98 /night

£684 - £988 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This beautifully decorated 3-bedroom, 2-bath condo is an ideal vacation spot in Orlando for the family or large groups with all the comforts and conveniences of home and then some! One king, one queen, two twins, and a sofa bed provide plenty of room for everyone to relax comfortably in style.  …see more

24 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £202 /night

£1410 - £1951 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Welcome to this elegant, professionally decorated Orlando vacation pool home, located in the beautiful Windsor Palms Resort. This property features all the comforts of home, and more! Private backyard with beautiful Florida Sunsets, a large pool with spa. The home sleeps 12 and offers an amazing  …see more

24 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £189 /night

£1317 - £1693 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Welcome to this elegant, professionally decorated Orlando vacation pool home, located in the beautiful Windsor Palms Resort. This home is absolutely perfect for large family groups. This property features all the comforts of home, and more! Windsor Palms is a gorgeous gated community, just minutes  …see more

16 Photos

Townhouse | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £115 /night

£799 - £1174 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Welcome to this beautiful Saddleback Model (1600 sqft.) 3 bedroom 3 bath townhome (2 story) East facing pool This tranquil but pristine three-bedroom, three-bath vacation townhome provides you with everything you will need for the perfect holiday escape. The first floor has an open floor plan with  …see more

24 Photos

House | 5 Bedrooms | sleeps 12

5 Nights min stay

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from £202 /night

£1410 - £1879 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Floor Plan (The Seville)  2,336 sq. ft. 2 story home with pool and spa (South-West facing pool). We invite you to enjoy our home on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at this beautiful  …see more

12 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £98 /night

£684 - £988 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This is a new 1st floor condo in beautiful Windsor Hills, where there is privacy near the end of the building. It is decorated with the premium Catalina package. The home comes with wireless internet, a playstation II, 2 DVD players. There is a 32" TV in the living room and 2 additional TV&  …see more

18 Photos

Townhouse | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £115 /night

£799 - £1174 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Lovely, 3 bedroom /3bath two-story townhome can sleep 6 comfortably. Bedding includes one King-size, one queen-size and 2 single beds. 36" TV in living area w/ VCR and DVD player. TV's in each bedroom with DVD players. Town home has splash pool located out back which can be heated upon  …see more

24 Photos

House | 5 Bedrooms | sleeps 12

5 Nights min stay

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from £202 /night

£1410 - £1879 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Located in Windsor Hills, this beautiful, two-story home with a fantastic view of the lake has been furnished and decorated with the utmost attention to every detail so that you can enjoy the luxury of a great vacation rental as well as the comforts of home. With no less than five bedrooms and five  …see more

24 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £98 /night

£684 - £988 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Ideally located ground floor condo with pool and clubhouse just across the street and the outdoor amenities in back. Master bedroom has a queen size bed and a 32" flatscreen TV. There is a private bath off the master. Second bedroom has a queen bed and a 24" flatscreen TV/DVD combo. Third  …see more

24 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £165 /night

£1153 - £1457 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
This 4 bdrm/3 bth home is located in the Windsor Palms. Home has 1 king, 1 queen, 4 twin beds. Home also has many upgrades like tv's in everyroom, dvd, vcr, patio furniture, heatable pool & spa. The Palms clubhouse has a fitness center, movie theatre, & gameroom. Outside there are  …see more

13 Photos

Apartment | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £43 /night

£297 - £461 / 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

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
  • Great 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

21 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

1 night min stay

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from £198 /night

£1386 - £1964 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Luxury 6 bedroom private villa with private pool, games room in the world renowned gated community of Windsor Hills Resort just 2 miles from the gated of Walt Disney World in Kissimmee, Orllando Florida  …see more

17 Photos

Villa | 6 Bedrooms | sleeps 14

Very Good 4.5/5 

5 Nights min stay

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from £83 /night

£578 - £795 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
6 bedroom, 4 bathroom villa with pool which sleeps up to 14 people, free high speed internet. Located in a quiet residential area just minutes from highway 192 with many restaurants, bars and shops close by. 15 minute drive from Disney.  …see more

16 Photos

Townhouse | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £68 /night

£470 - £566 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Excellent 3 bedroom home on the popular Venetian Bay in Kissimmee. This is the perfect place to relax after your busy day at the parks. Only 15 minutes from Disney World and great facilities in this gated community makes planning your Florida Vacation easy.  …see more

21 Photos

Townhouse | 4 Bedrooms | sleeps 8

Excellent 5/5 

5 Nights min stay

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from £63 /night

£435 - £483 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Terra Verde is a secure gated resort developed around beautiful lake.Townhouse with private swimming pool. The Clubhouse is just a short walk where you can enjoy swimming in the community pool, shoot some basketball or try out the fitness suite then relax in the sauna. Close to Clubhouse, Close to shopping areas, Walmart and publix, Golf courses nearby, Horseriding.  …see more

12 Photos

Villa | 4 Bedrooms | sleeps 8

4 Nights min stay

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from £99 /night

£692 - £1084 / week

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Key info:

  • Nearest beach 5 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Disney World ( 10 minutes ) Special Pool Heater Salt Water Pool Safety Fence 2 en-suite master bedrooms Themed bedrooms High chair , Stroller , Car seats , Crib Fan cooled Lanai Close to Clubhouse All linnen and Towels included Gameroom BBQ Multi Color Pool Light  …see more

17 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

7 Nights min stay

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from £61 /night

£425 - £575 / 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
Fabulous vacation home sleeps 8 in comfort with lake views and a south facing pool with spa. Oak Island Harbor subdivision is part of the Formosa Gardens estate and is minutes from Disney. Quality fittings, wi-fi, and HD TV will make your vacation one to remember. Pool-side toilet and outside shower.  …see more

14 Photos

Villa | 4 Bedrooms | sleeps 10

Excellent 5/5 

5 Nights min stay

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from £64 /night

£446 - £557 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Large property, sleeps ten, fully equipped kitchen with ice making fridge. Large enclosed pool, games room, Linen and towels provided. 10 minutes drive from Disney and close to main attractions.  …see more