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229 Holiday homes in Kissimmee

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229 Results  |  
18 Photos

House | 4 Bedrooms | sleeps 7

5 Nights min stay

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from £43 /night

£297 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
LOCATED DIRECTLY OF THE 192 , WE ARE 30 MINS DRIVE FROM ORLANDO AIRPORT , 30 MINS DRIVE TO DISNEY OR UNIVERSAL AND 1 HOUR FROM THE GREAT MELBOURNE BEACHES . WE ARE WALKING DISTANCE TO WALLMART / ALDI AND LYNX BUS ROUTE THAT CAN TAKE YOU INTO DISNEY ! WHAT COULS BE BETTE  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 10

3 Nights min stay

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from £106 /night

£742 - £1007 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

21 Photos

Villa | 5 Bedrooms | sleeps 12

5 Nights min stay

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from £89 /night

£621 - £742 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
5 Beds,4 Baths. Sleeps 12. AC. Outdoor Pool. Xbox. Wii. PS2. Games Room with Pool Table, Foosball, Air Hockey.  …see more

Featured properties

16 Photos

Villa | 7 Bedrooms | sleeps 16

4 Nights min stay

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from £177 /night

£1235 - £2067 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Summary • South Facing oversized pool and hot tub Spa • Huge 3900 sq ft of living and playing space • Extended 40' deck overlooks lake and woodland • 7 Bed 5.5 bathrooms with 4 Master Suites • So close to Disney you can be there in 6 minutes • 2 King, 2 Queen, en-suite  …see more

23 Photos

Villa | 7 Bedrooms | sleeps 16

1 night min stay

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from £154 /night

£1073 - £1916 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Pamper yourself in this luxury Emerald Island Resort villa located 3 miles to Disney World. Offering outstanding amenities at affordable prices, this luxury villa with private south-facing pool and spa accommodates 16 guests in sheer comfort and luxury in 7 bedrooms. Emerald Island Resort offers many community features and stands above the rest in offering luxurious villas.  …see more

5 Photos

Villa | 2 Bedrooms | sleeps 8

Excellent 5/5 

5 Nights min stay

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from £110 /night

£767 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
It would be hard for you to find a better place at such a price.  …see more

11 Photos

Villa | 2 Bedrooms | sleeps 10

6 Nights min stay

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from £115 /night

£805 - £1118 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • May take pets – please enquire
Villa with loft at Wetgate Vacation Villas - Kissimmee, 5 miles away from Disney and just minutes from Orlando Theme Parks.  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £90 /night

£626 - £909 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

8 Photos

House | 5 Bedrooms | sleeps 12

3 Nights min stay

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from £128 /night

£894 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
Bedding Summary: Bedroom #1: King Bed Bedroom #2: King Bed Bedroom #3: King Bed Bedroom #4: Queen Bed Bedroom #5: (2) Double Beds  …see more

24 Photos

House | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £99 /night

£691 - £928 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
Luxury tropical five star resort and house. Close to Disney parks and within range of Florida's west coast beaches.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

4 Nights min stay

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from £119 /night

£827 - £1038 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Massive pool deck for relaxing, south facing with sun all day. Great look out over a conservation area and not over looked. Super comfort furniture. Formal and informal dining areas plus breakfast bar. 2 x King sized en suite bedrooms. 1 x Queen and 2 x twin rooms. Slate bed pool table and air hockey table within a well equipped games room. Fantastic location.  …see more

24 Photos

House | 5 Bedrooms | sleeps 12

3 Nights min stay

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from £293 /night

£2050 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
From the moment you meet us online, we are with you every step of the way to help make the planning of your dream vacation as easy as possible. We offer our guests a welcome as warm as the sun and the utmost in personal attention.  …see more

17 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £144 /night

£1007 - £1161 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
Close to Disney Parks Secure Gated Entrance Clubhouse 58 seat 3D Movie Theater Nintendo Wii Suite Fitness Room & Gym Billiard Room Video Arcade Lighted Tennis Courts Lighted Basketball Courts Volleyball Courts Children's Play Area Olympic Size Swimming Pool Belle's has won awards 3 Years running 2011,2012 & 2013 for top holiday rental in the Disney area.  …see more

7 Photos

Apartment | 2 Bedrooms | sleeps 8

1 night min stay

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from £76 /night

£530 - £1590 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Orlando Disney. Kissimmee disney. Orlando golf  …see more

12 Photos

Villa | 3 Bedrooms | sleeps 8

Very Good 4/5 

3 Nights min stay

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from £67 /night

£467 - £626 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
South Facing Pool that cannot be overlooked from any direction, Free wi-fi, Games room, Free International calls, 3 TV's including 50'' plasma TV, Smart TV with Free Netflix, Walking Distance to Shops, Restaurants, Attractions and nature park.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 13

Excellent 5/5 

3 Nights min stay

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from £179 /night

£1250 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
6 bedrooms, gated community, Windsor palms, swimming pool, Jacuzzi, Disney, air conditioned, clubhouse  …see more

10 Photos

Townhouse | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £57 /night

£398 - £477 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Close to Disney on great resort with resort pool, clubhouse, gated community, tennis & gym on resort  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

5 Nights min stay

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from £67 /night

£467 - £674 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Indian Ridge Oaks - one of the closest communities to Disney / 4 miles to Disney Maingate - south facing pool 4 bedroom, luxury villa in a superb location genuinely only a few minutes drive from Disney and, more importantly, only 4 sets of traffic lights! ONE OF THE CLOSEST COMMUNITIES TO DISNEY in a peaceful and tranquil setting.  …see more

9 Photos

Townhouse | 3 Bedrooms | sleeps 8

4 Nights min stay

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from £72 /night

£501 - £652 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Brilliant 3 Bed 2.5 Bath Town Home, Private Pool in Beautiful Bella Vida Resort, only 8 minutes to Disney and the community neighbors a Walmart Supercenter for added convenience! You are only moments from Orlando International Airport and right off the Hwy 192.  …see more

12 Photos

Villa | 5 Bedrooms | sleeps 10

4 Nights min stay

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from £147 /night

£1029 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Guests also have access and use to the community clubhouse which also has a pool and large area for sunbathing.  …see more

10 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

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from £96 /night

£671 - £738 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Cumbrian Lakes is a gated community and is sought after because of its tranquil setting and proximity to Disney. It has four lovely lakes,a children's area, various jogging trails and open spaces. It offers quick and easy access to Walt Disney World and all major attra  …see more

10 Photos

House | 5 Bedrooms | sleeps 11

2 Nights min stay

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from £180 /night

£1257 - £1940 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • 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 and spa located in the Windsor Palms Resort. Att  …see more

17 Photos

House | 7 Bedrooms | sleeps 14

2 Nights min stay

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from £195 /night

£1363 - £1982 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • 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 m  …see more

15 Photos

House | 6 Bedrooms | sleeps 14

2 Nights min stay

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from £231 /night

£1616 - £2404 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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 spr  …see more

8 Photos

Condo | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £74 /night

£515 - £760 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • 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 i  …see more

11 Photos

Condo | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £99 /night

£688 - £1055 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
A beautiful spacious condo located in a new-gated community. This 3 bedroom, 2.5 bathrooms, Full Kitchen and Dinning is only a half-mile from Disney. It has a large Clubhouse with a Gym, Pool and Spa, Children's Splash Area, Basketball and Volleyball Court.  …see more

10 Photos

House | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £99 /night

£688 - £1055 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Thank you for taking the time to look at our Florida vacation home. For your comfort and enjoyment, we are proud to offer you our town home which features brand new furniture and equipment which was bought in March 2012 which can accommodate up to 8 people. Avail  …see more

7 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £80 /night

£557 - £928 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This beautifully decorated 3bdrm/2bth condo sleeps up to 8 persons located in a resort style gated communtiy just 3 min. away from disney is perfect for a small family looking to have a great time in the surroundings of many wonderful ammenities such as access to commun  …see more

14 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £180 /night

£1257 - £1940 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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. Mast  …see more

8 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £84 /night

£582 - £886 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • 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 lak  …see more

9 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £99 /night

£688 - £1055 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • 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 kin  …see more

10 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £87 /night

£604 - £970 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This vacation condominium will comfortably sleep 6 with 1 King-size and 4 Single beds. Each bedroom has a TV with VCR/DVD player. The amenities of this condo include access to off-street parking, a hot tub, pool, and tennis courts. Also, the cheerful Galley kitchen is f  …see more

8 Photos

Condo | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £84 /night

£582 - £886 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • 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 r  …see more

11 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £179 /night

£1249 - £1856 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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 bath  …see more

8 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £84 /night

£582 - £886 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This beautiful 3 bedroom/ 2 bath condo is located in the brand new gated community of Oakwater. The condo consists of one king bed, one queen bed, two twin beds, game cube, Internet access, patio, and a fully equipped kitchen. This unit can comfortably accommodate up to  …see more

6 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £84 /night

£582 - £886 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • 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, ic  …see more

10 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £99 /night

£688 - £1055 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • 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  …see more

15 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £179 /night

£1249 - £1856 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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 vaca  …see more

14 Photos

House | 5 Bedrooms | sleeps 12

2 Nights min stay

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from £179 /night

£1249 - £1856 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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  …see more

6 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £87 /night

£604 - £970 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • 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  …see more

7 Photos

Condo | 2 Bedrooms | sleeps 6

2 Nights min stay

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from £74 /night

£515 - £760 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This immaculate 2story condo has screened-balcony with beautiful view of both the lake and climate-controlled pool with Jacuzzi, next to clubhouse, containing gymnasium. Condo has its own garage for storage and protects your car (with shade) from the elements. Kitchen i  …see more

8 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £84 /night

£582 - £886 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This beautiful 3 bedroom/ 2 bath condo is located in the beautiful gated community of Oakwater, located 1.5 miles from Disney. The 4,000 sq. clubhouse features a lagoon-style pool, tennis courts volleyball courts, basketball courts, and attraction shuttle. This n  …see more

10 Photos

House | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £147 /night

£1025 - £1434 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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  …see more

14 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £87 /night

£604 - £970 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • 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&  …see more

11 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

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from £147 /night

£1025 - £1434 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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. T  …see more

6 Photos

Condo | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £70 /night

£490 - £802 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This lavishly furnished 2bdrm/2bth condo is located in the gated resort style community of Windsor Palms. This condo will sleep 4 comfortably in 1 queen and 2 twin sized beds. This property also comes with a full kitchen complete with coffee maker, microwave, ice maker,  …see more

16 Photos

House | 5 Bedrooms | sleeps 12

2 Nights min stay

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from £205 /night

£1434 - £2151 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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, a game room  …see more

13 Photos

House | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £147 /night

£1025 - £1434 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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 a  …see more

8 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £80 /night

£557 - £928 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • 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 Di  …see more

14 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £205 /night

£1434 - £2151 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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 y  …see more

Orlando Kissimmee is a great location for a family holiday, with easy access to Florida's big attractions - Disney World, Busch Gardens and Universal Studios. There are also rides through the Florida Everglades and plenty of children-friendly activities to keep everyone happy. The area has some excellent beaches, amongst them Clearwater Beach and Daytona Beach.