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518 Holiday homes in Kissimmee

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Filters applied: Swimming pool (518)

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518 Results  |  
24 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £164 /night

£1146 - £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

18 Photos

Townhouse | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £114 /night

£796 - £1174 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
After vacationing in Windsor Hills with some friends last year, we decided that staying in a townhouse is a much nicer experience than coming back to an impersonal hotel room after a day at the parks. We just bought our vacation home and would like to share it with you.  Amenities include 3  …see more

18 Photos

Townhouse | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £104 /night

£727 - £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

Featured properties

18 Photos

Townhouse | 5 Bedrooms | sleeps 12

5 Nights min stay

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from £140 /night

£976 - £1441 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Best Location in Paradise Palms! Attention to every detail has been put in as we furnished and decorated this townhome. This 5 bedroom 4 bath 2,128 sq feet unit sleeps 12 in style. With 2 king bedrooms, 1 queen bedroom, 1 room with 2 double beds, and 1 twin room there is plenty of room for everyone  …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 | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £164 /night

£1146 - £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

16 Photos

Townhouse | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £104 /night

£727 - £1060 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Come spend your vacation in Orlando in this stylish Emerald Island 3-bedroom, 2-bath town home featuring all of the comforts and amenities of home and then some! With one king, one queen, and two twin beds, this property is perfect for family-size groups, providing plenty of space for everyone to  …see more

21 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £174 /night

£1218 - £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

22 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £200 /night

£1395 - £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 | 6 Bedrooms | sleeps 14

5 Nights min stay

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from £258 /night

£1802 - £2435 / 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 5 bath 3,275 sq feet unit sleeps 14 in style. With 3 king bedrooms, 1 queen bedroom and 4 twin beds, plus a sleeper sofa, there is plenty of room for everyone to spread out and relax after a day out or  …see more

24 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £164 /night

£1146 - £1457 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Gorgeous 4 Bedroom/3bath home in gated Emerald Island Resort, just 5 minutes from Disney Property and 2 minutes from shopping and restaurants. The home has a private screened in pool and spa plus private game room. Emerald Island Resort is located  on 300 acres of conservation.  Amenities include  …see more

24 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £164 /night

£1146 - £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

20 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £164 /night

£1146 - £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 | 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 | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £201 /night

£1404 - £1948 / 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

14 Photos

Townhouse | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £104 /night

£727 - £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

22 Photos

House | 4 Bedrooms | sleeps 10

5 Nights min stay

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from £164 /night

£1146 - £1457 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Brighton floor plan 1816 sqft.4 bedroom 3 bath home (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. The home has 1 king suite, 1 queen  …see more

24 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £201 /night

£1404 - £1948 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Floor Plan (The Barrington II)  2,806  sq. ft. 2 story home with pool (West Facing Pool). 5 bedroom 3.5 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  …see more

16 Photos

Townhouse | 4 Bedrooms | sleeps 10

5 Nights min stay

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from £147 /night

£1028 - £1513 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Floor Plan (The Beach Palm) 1,914 sq. ft. 2 story townhome. 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  …see more

16 Photos

Townhouse | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £104 /night

£727 - £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

16 Photos

Townhouse | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £114 /night

£796 - £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 | 4 Bedrooms | sleeps 10

5 Nights min stay

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from £164 /night

£1146 - £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

16 Photos

Townhouse | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £114 /night

£796 - £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 £200 /night

£1395 - £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

20 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £140 /night

£976 - £1441 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Floor Plan (The Royale Palm) 2,128 sq. ft. 2 story townhome. 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.  …see more

24 Photos

Townhouse | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £114 /night

£796 - £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

16 Photos

Townhouse | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £114 /night

£796 - £1174 / 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

24 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £200 /night

£1395 - £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

14 Photos

Townhouse | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £104 /night

£727 - £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

22 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £140 /night

£976 - £1441 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Floor Plan (The Royale Palm) 2,128 sq. ft.2 story townhome. 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.    …see more

24 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £164 /night

£1146 - £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

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £201 /night

£1404 - £1948 / 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 10

5 Nights min stay

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from £188 /night

£1314 - £1678 / 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

House | 6 Bedrooms | sleeps 12

5 Nights min stay

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from £258 /night

£1802 - £2435 / 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

24 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £186 /night

£1302 - £1646 / 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 four bedrooms and four baths, this property can accommodate up to  …see more

20 Photos

Townhouse | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £114 /night

£796 - £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

14 Photos

Townhouse | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £114 /night

£796 - £1174 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
This beautifully furnished 3 bed, 3 bath Saddlebrook Townhome features 1390 sq. ft. of living space.  Sleeping accommodations include1 king, 1 queen, 2 twin, and 1 sofa sized beds.  Also, this property comes with a full kitchen boasting an ice maker, coffee maker, microwave, and dishwasher.  Along  …see more

24 Photos

House | 6 Bedrooms | sleeps 8

5 Nights min stay

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from £197 /night

£1379 - £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

14 Photos

Townhouse | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £104 /night

£727 - £1060 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Enjoy this beautiful 3 bedroom, 2.5 bathroom vacation condominium in Kissimee Florida.  It sleeps 6 comfortably in 1 king and 2 queen sized beds.  It also comes with a fully equipped kitchen inclusive of ice maker, coffee maker, microwave, and dishwasher.  There is also access to off-street parking  …see more

24 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £200 /night

£1395 - £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 8

5 Nights min stay

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from £188 /night

£1314 - £1678 / 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

24 Photos

Townhouse | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £161 /night

£1122 - £1656 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Welcome to this beautiful vacation home in Kissimmee, Florida. Featuring four bedrooms, four baths, and a garage, this spacious home has been carefully and lovingly furnished to ensure that you have a comfortable and memorable experience. The full kitchen is equipped with everything you could need  …see more

24 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £164 /night

£1146 - £1457 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Brighton floor plan 1816 sqft. 4 bedroom 2 bath A newly renovated 4 bedroom house with game room just minutes away from Disney and golf courses. 1800 sq ft fully equipped with washer & dryer, dishwasher, all bath towels & bed linens provided. This home can accommodate up to 8 people. Very  …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 £174 /night

£1218 - £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

11 Photos

Villa | 2 Bedrooms | sleeps 10

5 Nights min stay

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from £142 /night

£988 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
You will expend a wonderfull time at this villas, as well at the Resort. The Resort offers free transportation to Epcot, Universal, Sea World and Prime Outlets  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

4 Nights min stay

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from £79 /night

£550 - £725 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 75 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
New 4 Bedroom, 3 Bathroom villa with 30' pool situated on the impressive Veranda Palms gated community. Surrounded by conservation area but located only 6 miles from Walt Disney World, just off US192. 30ft pool, games room, free wi-fi & US calls, HD cable TV.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

Short stays welcome

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from £108 /night

£750 - £972 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Our villa's are on a quiet sub-division ,we have a one acre garden fully fenced and private with a play area and large decking .Our pool is SW facing .Our homes are family owned and finished to a high standard our guests enjoy.We upgrade each visit ,prices are kept low Both villas are private , guests return knowing they have found their perfect villa ,visit our website  …see more

24 Photos

House | 6 Bedrooms | sleeps 12

Excellent 5/5 

5 Nights min stay

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from £121 /night

£847 - £1200 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
This beautifully furnished, air-conditioned executive home is at Emerald Island Resort, the nearest gated community to Disney. With 6 bedrooms, all with TVs, 4 masters with en suites, and 5.5 bathrooms will sleep up to 12 people in spacious, elegantly furnished style. Close to shops and many restaurants  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

3 Nights min stay

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from £80 /night

£559 - £932 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Family accommodation near Orlando. Self-catering accommodation in Florida. Holiday Home near Disney. Disney Dream Villa. Orlando villa with pool Prime location near Disney, also near to local amenities. Private pool/spa in a secure location. Games Room  …see more