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467 Holiday homes in Kissimmee

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467 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

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

20 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
Enjoy this brand-new resort featuring luxury condominiums! This beautiful gated community is just 1.5 miles (2.5km) from the gates of Walt Disney World. At Oakwater, you're sure to find accommodations to suit your vacation needs. The residences range in size from 1,036 sq. ft. to 1,777 sq. ft.  …see more

Featured properties

22 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
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 five bedrooms and five baths, this property can  …see more

24 Photos

House | 5 Bedrooms | sleeps 12

5 Nights min stay

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from £175 /night

£1221 - £1693 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Barrington lll floor plan 2450 sq. ft 5 bedrooms- 3 baths (2 story) Welcome to this elegant, professionally decorated Orlando vacation pool home, located in the beautiful Windsor Palms Resort. This 5 bedroom, 3.5 baths home has a screened-in pool and spa. The fun game room has a pool table and  …see more

16 Photos

Condo | 2 Bedrooms | sleeps 4

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 beautiful and modern 2 bedroom/ 2 bath condo is located in the brand new gated community of Oakwater, located 1.5 miles from Disney.  This unit can accommodate up to 4 people comfortably with 1 queen and 2 twin sized beds.  Also, this property offers a full kitchen inclusive of coffee maker,  …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
We invite you to enjoy our condo 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 1st floor condo in the Windsor Hills Resort. Attention to every detail has been put in as we  …see more

12 Photos

House | 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
Enjoy your next stay in Florida's sunshine at this beautiful 2 bedroom, 2 bathroom vacation condo with its one queen, two twin, and one sofa beds.  This unit comes with a fully equipped kitchen with stainless steel appliances, wireless internet, cable, and widescreen TV equipped with DVD player.  …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

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

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

16 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
Welcome to this elegant, professionally decorated Orlando vacation condo, located in the beautiful Windsor Palms Resort. This property features all the comforts of home, and more! Windsor Palms is a gorgeous gated community, just minutes from the gates of Walt Disney World. Renting this home gives  …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

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
4 bedroom 3 bath; Luxury house located beautiful gated community just 2.5 miles(4km) from the gates of Walt Disney. The house was recently renovated and well decorated. Master suite with king size bed, TV LCD& master bathroom including a separate shower. 3 others bedrooms; 2 twin,1 queen,1  …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
Floor Plan (The Seville) 2,827 sq. ft. 2 story home with pool and spa. (South 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 home with  …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

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 | 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

24 Photos

Villa | 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
  • Air conditioning
  • No pets allowed
Sunrise Sunset Villa is nestled in the exclusive Winsor Palms community, less than 3 miles from Walt Disney World in Kissimmee, Florida. With 4 bedrooms and 2 bathrooms, this fully air-conditioned, elegant, professionally decorated, luxurious Orlando vacation home is perfect for family groups,  …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

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

20 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
Enjoy your next vacation in this beautiful Florida vacation home.  This property will comfortably sleep 8  in a 3 bedroom, 3 bath home that features one king, one queen, one set of twin sized beds, and a sleeper sofa.  Experience a home-away-from home experience with all the amenities of this home,  …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 | 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

16 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:

  • Not suitable for children
  • No pets allowed
Please feel free to view our new, professionally decorated townhouse. Our amenities include a spacious Townhouse with 3 bedrooms and 3 baths. Each bedroom has its own bathroom, flat screen TV, and Wireless High Speed Internet.  Hair dryer in each bathroom. South facing splash pool in a screened  …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

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

24 Photos

House | 5 Bedrooms | sleeps 12

5 Nights min stay

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from £175 /night

£1221 - £1693 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
2317 sq ft 5 bedroom 3 bath (2 story) Pool home. We invite you to enjoy your next vacation at our luxurious, brand new and beautifully decorated 5 bed/3 bath Home with 28ft pool. Sleeping accommodation features one elegant master suite with 1 king size bed; 2 rooms with queen size beds; two twin  …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

18 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
Come stay in a home away from home! This 3 bedroom, 3 bath townhome, decorated in a tasteful new Florida style, is located a short drive from the airport, just minutes from Disneyworld, SeaWorld, restaurants, shopping, a PGA golf course, and many other activities. The open kitchen and lounge lead  …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

16 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
This 3 Bedroom 3 Bath Townhome is located in the gated resort style Windsor Palms just minutes from disney. The clubhouse offers a game room, movie theatre and complete fitness center. For further enjoyment guest stay active throughout the 3-acre recreation area which includes community pool and  …see more

24 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
All the comforts of home in this 3-bedroom, 3 bath townhome in Windsor Hills. One bedroom and bath downstairs and 2 bedrooms upstairs. This property sleeps 8, 2 in each bedroom and we have a sleeper sofa too. Amenities include fully equipped kitchen, washer/dryer, stereo and DVD player in living  …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

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
Beautiful 3 bedroom, 2 bath, 1,447 sq. ft. condo featuring a "Platinum plus" furniture and appliance package with all the comforts of home including high speed internet. This condo will sleep 6 easily in its one king, one queen, and two twin sized beds.  You'll also experience no lack of  …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
Newly Renovated 5 bedroom, 5 bath property in the 5star gated Windsor Hills community just 5 minutes from Walt Disney World and the surrounding attractions. After an energetic day exploring the sights and sounds of this magical playground you can return home to your own pool and spa area, or relax  …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

24 Photos

House | 7 Bedrooms | sleeps 14

5 Nights min stay

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from £219 /night

£1528 - £1997 / week

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Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
A stylish, warm and homely welcome awaits you in our 7 Bedroom true-luxury 2,827sq.ft holiday villa, complete with extended west facing private heated swimming pool, Jacuzzi and a fully fitted air-conditioned Games Room. Our home can accommodate up to 14 people making it remarkably affordable for  …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
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 home with pool and spa located in the Windsor Hills Resort. Attention to every detail has been put  …see more

21 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £175 /night

£1221 - £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 in this 5 bedroom, 3.5 bathroom vacation home. 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 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

16 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 lovely condo consists of one king bed, one queen bed and two twin beds, all bedrooms equipped with TV and DVD, PlayStation 2, high speed wireless internet access, and fully equipped kitchen. This property features all the comforts of home and a beautiful lakeview. Offering a family-friendly  …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

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

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

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

7 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

1 night min stay

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from £106 /night

£742 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
close to disney close to orlando close to outlets/malls free theater showing about three times a day. Depending on the requirements There can be a 1 bed for 2 couples/ 1bed 1 sofa for family of 2 adults 2 children in a front room at the higher rates. WEEKLY BOOKINGS FROM WEEKEND TO WEEKEND AT DISCOUNTED RATED ONLY.  …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