Villas with a pool Kissimmee | Apartments to rent with swimming facilities

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Also consider

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3,164 Holiday homes

Filters applied: Swimming pool (3,166)

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(1) Excellent 

52

Cumbrian Lakes gated community Villa - Cumbrian Lakes villa sleeps 12

Kissimmee / Cumbrian Lakes

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A Spacious 6 bedroom, 4 1/2 bathroom Vacation Home with private pool for your enjoyment. In the popular gated community of Cumbrian Lakes, only 15 minutes to the entrance to Disney World, 5 minutes more to Seaworld & another 10 minutes to Universal Studios. This home wi  …see more

from £45 / night

£315 / week

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from £45 / night

(4) Very Good 

12

Another Day in Paradise - Cumbrian Lakes villa sleeps 8

Kissimmee / Cumbrian Lakes

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our luxury 4 Bed, 3.5 Bath villa is situated in the exclusive, secure gated community of Cumbrian Lakes. Set in a prime position backing onto a conservation area (over 200 acres) not overlooked, secluded and peaceful. Conveniently situated just off 192 and all it ameni  …see more

from £85 / night

£612 / week

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from £85 / night

(5) Excellent 

68

Ladysvilla, Lovely Vacation Pool Home in the Sun - Kissimmee villa sleeps 8

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 12 km
  • Swimming pool
  • Child friendly
Ladys Villa (Loz and Ady's villa) is our holiday home in the sun, it will sleep up to 8 people, with games room, private screened pool (heated on guest payment). We invite you to share our home. It is ideally situated for the independent traveller, giving easy access  …see more

from £85 / night

£539 - £893 / week

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from £85 / night

(2) Very Good 

20

Villa Sol 5 bedroom luxury villa . - Villasol villa sleeps 12

Kissimmee / Villasol

5 12 3 nights min

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min
  • Nearest beach 96 km
  • Swimming pool
  • Child friendly
A beautifully appointed 5 bedroom, 3 bath luxury family vacation home provides state of the art living, comfort and freedom that cannot be found in a hotel room. The master bedroom has a king size bed, walk in wardrobe, and en-suite with walk in shower, the 2nd and 3rd  …see more

from £100 / night

£600 - £880 / week

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from £100 / night

(9) Excellent 

24

Palm Tree Villa Florida, 5 Star Review Rating. - Doral Woods villa sleeps 8

Kissimmee / Doral Woods

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Palm Tree Villa Florida, is tucked away in the much sought after location of Doral Woods. This large 4 Bedroom, 3 Bathroom villa, is ideal for making the perfect vacation. This is our own holiday home, so the furnishings are to a high standard, as you can see from the  …see more

from £100 / night

£695 - £875 / week

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from £100 / night

(2) Very Good 

20

Legacy Dunes Resort - Legacy Dunes Resort condo sleeps 4

Kissimmee / Legacy Dunes Resort

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This Condo is on the doorstep of Disney, just off 192, In the heart of Kissimmee. From the moment you drive up the entrance road, with its beautiful landscaping, you know you are about to enter a great resort. Legacy Dunes Resort offers a wonderful guest experience. The  …see more

from £77 / night

£539 - £686 / week

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from £77 / night

51

Executive villa nr Disney park - Hamilton's Reserve villa sleeps 8

Kissimmee / Hamilton's Reserve

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 85 km
  • Swimming pool
This luxury home is set in a very quiet residential neighbourhood and within easy reach (15 to 20 minutes) of all the Disney theme and water parks, Universal Studios and Islands of Adventure, Sea World, Legoland, etc. The Buena Vista Shopping Mall is about a 5 minutes  …see more

from £108 / night

£712 - £808 / week

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from £108 / night

(5) Very Good 

74

holiday villa golf nearby WindsorHills Resort - Windsor Hills Resort villa sleeps 10

Kissimmee / Windsor Hills Resort

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Our 4 bedroom / 4 bathroom, newly built vacation home has a beautiful corner lot in the prestigious Windsor Hills Resort and has over 1800 sq ft of living space. Sleeping up to 8 people comfortably, our home boasts 1 king bedroom with ensuite, 1 queen bedroom with ensu  …see more

from £124 / night

£862 / week

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from £124 / night

(6) Very Good 

21

Hideaway Villa - Terra Verde Resort villa sleeps 12

Kissimmee / Terra Verde Resort

5 12 5 nights min

  • 5 bedrooms
  • Sleeps 12
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Hideaway Villa is the perfect choice for the ultimate Disney family holiday - just 10 minutes east of Disney, on the exclusive gated community of Terra Verde. Conveniently located close to Walmart, Medieval Times and Olde Town. Hideaway Villa has 5 bedrooms, all with  …see more

from £97 / night

£679 - £808 / week

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from £97 / night

(7) Excellent 

25

Kissimmee / Lucaya Village

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £70 / night

£747 / week

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from £70 / night

(1) Very Good 

24

Spacious 6 bed/ 5.5bath in BellaVida Resort 220LF - Kissimmee house sleeps 14

Central Florida / Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
Upscale 6 bed 5 1/2 baths home with enclosed pool and spa is the perfect place to relax after a long day at the parks.This beautiful pool home is 6 bedrooms 5 ½ bath, located in the most sought after gated resort community of Bella Vida about 10 miles from Disney World  …see more

from £124 / night

£862 - £1508 / week

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from £124 / night

(20) Excellent 

43

Central Florida / Kissimmee

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £61 / night

£365 - £769 / week

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from £61 / night

55

Beautifully furnished condo 10 minutes from Disney - Cane Island condo sleeps 6

Kissimmee / Cane Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This ground floor apartment is first class. Compare staying here with staying in a Disney Hotel and you will be astonished. Half the price of a 'moderate' Disney Resort but twice as much space as a 'Deluxe' Resort. Not only will you be saving mone  …see more

from £49 / night

£343 / week

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from £49 / night

18

Family Vacation Home near Disney - Crescent Lakes villa sleeps 12

Kissimmee / Crescent Lakes

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Car not necessary
Why stay in a hotel / motel when you can experience a truly spacious accommodation? This villa has 6 bedrooms and 3 bathrooms on two levels. There is a large south facing swimming pool. The rear of the property is not overlooked as it has a high privacy fencing down b  …see more

from £93 / night

£650 - £800 / week

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from £93 / night

(3) Very Good 

16

Villa Orlando Disney Area Rent - Veranda Palms house sleeps 9

Kissimmee / Veranda Palms

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to our beautiful villa situated in Veranda Palms, only 3 minutes away from West Irlo Bronson Memorial Highway. Our home boasts stunning scenery, tranquil surroundings, and a breathtaking lake view. Veranda Palms is ideal for a family vacation. It is located ri  …see more

from £138 / night

£762 - £839 / week

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from £138 / night

(2) Very Good 

14

Bellavida Palms - Bellavida Resort villa sleeps 10

Kissimmee / Bellavida Resort

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Fabulous corner lot with warming decor, making you feel at home as soon as you enter. After a day at the nearby theme parks enjoy the last of the sun by sitting under the lanai which has a south west facing aspect overlooking the 30' lit pool. The home theater syst  …see more

from £104 / night

£720 / week

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from £104 / night

24

Luxury 6 Bedroom, 5.5 Bathroom Villa - Kissimmee villa sleeps 12

Central Florida / Kissimmee

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Won’t it be great to simply relax and not have to worry about a thing? That’s the dream of many people nowadays. But did you know that you can experience this same dream of comfort and relaxation? Yes, when you visit Florida, there is a special place waiting just  …see more

from £185 / night

£1374 - £2020 / week

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from £185 / night

(4) Excellent 

98

THE HAVEN IN EMERALD ISLAND RESORT - Emerald Isle Kissimmee house sleeps 8

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 96 km
  • Swimming pool
  • Child friendly
In our house, fell like you are at home, with the comfort of a King suit and an attached bathroom with garden tub and 3 more bed : queen bed and fully attached bathroom and kids rooms with 2 twin beds in each and their own bathroom to share. Enjoy the heated swimming po  …see more

from £77 / night

£539 - £970 / week

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from £77 / night

(5) Excellent 

98

Kissimmee / Seasons Resort

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 81 km
  • Swimming pool
  • Child friendly

 …see more

from £116 / night

£731 - £1924 / week

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from £116 / night

(11) Excellent 

31

Tennyson Villa in Kissimmee close to Disney - Hamilton's Reserve villa sleeps 10

Kissimmee / Hamilton's Reserve

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 40 km
  • Swimming pool
13% USA Tax Included in price. Luxurious well maintained spacious private 5 bed family villa located in a quiet cul-de-sac no through traffic. Comfortable home from home for a family holiday. Suitable for guests with limited mobility and children welcome.DISNEY main gat  …see more

from £89 / night

£620 - £892 / week

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from £89 / night

(1) Excellent 

22

Cumbrian Lakes Prestige - Cumbrian Lakes villa sleeps 12

Kissimmee / Cumbrian Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
This home has a breath taking view from the pool deck. It overlooks a pretty lake and you may be lucky enough to see deer grazing on the conservation area which lies beyond it. The deck area has been extended so there is also a Hot Tub for you to enjoy. The home itself  …see more

from £120 / night

£840 - £1050 / week

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from £120 / night

9

Venetian Bay II - Venetian Bay Villages townhouse sleeps 6

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Beautiful 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.The spacious  …see more

from £74 / night

£512 - £700 / week

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from £74 / night

(10) Very Good 

10

Florida Holiday Villa includes WiFi and Hot Tub - Kissimmee villa sleeps 9

Central Florida / Kissimmee

4 9 4 nights min

  • 4 bedrooms
  • Sleeps 9
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Our villa is situated in the popular community of Indian Point, which is about 15 minutes drive from Disney and close to the other vast array of attractions that Florida has to offer. It is the perfect place to relax by the pool, or come back to after a day at the theme  …see more

from £65 / night

£450 / week

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from £65 / night

(6) Excellent 

24

The Road to "Mandyville"- Fantastic 3 Bedroom Villa - Kissimmee villa sleeps 6

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
THE VILLA with it,s fully screened, south facing 30x15ft swimming pool with underwater lighting for evening swimming and has free solar heating with electronic control and electric heating for the winter months. The large deck with sun or shade is equipped with new luxu  …see more

from £67 / night

£465 - £525 / week

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from £67 / night

(8) Excellent 

14

Alberto Circle, Fun Vacation House with Pool - Bellavida Resort townhouse sleeps 6

Kissimmee / Bellavida Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Enjoy the fabulous climate and amenities of the Central Florida area without breaking the bank. This is a 3 bedroom townhouse, fully air conditioned, with private pool, conveniently located in the recently completed BellaVida resort in Kissimmee.The property is ideally  …see more

Pricing unknown

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(1) Excellent 

20

Lake view villa Eagle Pointe - Kissimmee villa sleeps 6

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful 3 bedroom 2 bathroom villa in Kissimmee. This villa has a private screened pool overlooking a lake. Situated in the tranquil community of Eagle Pointe only 15 minutes from Disney. Living Room – Light and airy open plan room overlooking the pool with two com  …see more

from £86 / night

£600 - £750 / week

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from £86 / night

(1) Excellent 

10

Lake View - Compass Bay townhouse sleeps 9

Kissimmee / Compass Bay

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 101 km
  • Swimming pool
Location is important and Compass Bay is one of the best, it is situated on the corridor of the 192 which has restaurants, shops and attractions. It is within minutes of the major attractions of Disney, Universal and International Drive. It is a gated community with a l  …see more

from £70 / night

£495 - £580 / week

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from £70 / night

(6) Excellent 

38

Golden Springs Vacation Home with a Pool and Hot Tub - Indian Creek villa sleeps 12

Kissimmee / Indian Creek

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Superb 5 bed 4 bathroom vacation home on Indian CreekNot overlooked with a large pool and hot tub and a removable safety fence to ensure youngsters dont have access if requiredFor those who are more energetic the villa is next to basket ball, tennis courts and a childre  …see more

from £120 / night

£610 - £790 / week

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from £120 / night

42

Minion Cove - Windsor Hills Resort condo sleeps 6

Kissimmee / Windsor Hills Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
3 Bedroom 2 Bathroom Condo Sleeps 6 Welcome to Minion Cove, our 3 bedroom 2 bathroom condo located in the beautiful 5 star gated community of Windsor Hills located less than 2 miles from the main gates of Walt Disney World. Windsor Hills is one of the newest and greates  …see more

from £66 / night

£424 - £916 / week

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from £66 / night

(2) Excellent 

61

Great value for money Townhome near Disney - Venetian Bay Villages house sleeps 6

Kissimmee / Venetian Bay Villages

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Why stay in a hotel when you can have all the comforts of your own home away from home in our beautiful new townhome in a dream location, close to the theme parks and the attractions of Orlando and Central Florida.Our home is clean, comfortable and just where you need t  …see more

from £60 / night

£385 / week

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from £60 / night

37

1308 Caribe Suite - Kissimmee condo sleeps 6

Central Florida / Kissimmee

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
Condo 1308 is based in the Caribe Cove Resort. Our luxurious condo with ample amenities will comfort you, making Caribe Cove a great place to retreat to for a long-awaited vacation. Caribe Cove Resort is perfect for your vacation and holidays. Condo 1308 features abou  …see more

from £91 / night

£637 / week

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from £91 / night

(5) Excellent 

23

3 Bedroom Villa in Country Creek, Kissimmee - Country Creek villa sleeps 6

Kissimmee / Country Creek

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our beautiful family owned villa is located only 10 mins from WDW and close to many other attractions such as Sea World, Aquatica, Universal Studios and Universal Islands of Adventure. Our home from home is comfortably furnished and equipped with all the amenities to m  …see more

from £70 / night

£550 - £650 / week

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from £70 / night

(1) Excellent 

24

St Georges Manor - Formosa Gardens villa sleeps 18

Kissimmee / Formosa Gardens

8 18 1 night min

  • 8 bedrooms
  • Sleeps 18
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
St. George's Manor is the flagship villa of 4 luxurious vacation homes by St. George's Villas - our small, family-run villa rental business. We own all of our villas so we can guarantee you the best service with an unmatched passion for making your holiday the best it c  …see more

from £500 / night

£3480 - £4176 / week

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from £500 / night

(2) Excellent 

24

8606 Primrose Drive - Lindfields house sleeps 8

Kissimmee / Lindfields

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our villa is magnificent, fully furnished and equipped to the highest standards with air conditioning and ceiling fans. It has a master bedroom with an en-suite, 3 further double bedrooms and a main bathroom, towels and bed linen are provided. It has a spacious lounge,  …see more

from £61 / night

£425 - £500 / week

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from £61 / night

(6) Very Good 

56

DisneyDream Orlando Florida - Kissimmee apartment sleeps 6

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This is your luxury 3 bedroom 2 bathroom holiday home located in ' the 'VILLAS OF SOMERSET' complex, a quiet leafy location very central to every theme park in the Orlando area. Use all the facilities on the complex, Heated pool, Jacuzzi/hot tub, Sundeck,Clubhouse, G  …see more

from £49 / night

£343 - £549 / week

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from £49 / night

(5) Excellent 

16

Sunrose Villa, 4 Bedroom Home with WiFi and Pool - Eagle Pointe villa sleeps 8

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
When on holiday if you what to retain a bit of independence then a stay in your very own Villa is a perfect way to do it. Our Disney area villa comes with its very own private swimming pool where you can escape all the thrills and spills down the road and have some quie  …see more

from £70 / night

£485 - £1077 / week

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from £70 / night

28

Central Florida / Kissimmee

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £174 / night

£1212 - £1831 / week

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from £174 / night

24

Frozen Bedrom. Closest to Disney 6BR/4BA Pool/spa - Windsor Hills Resort villa sleeps 14

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Spread out and enjoy your very own sunny six bedroom, four bathroom villa in Windsor Hills Resort. Best of all, it is only two miles to Walt Disney World!NO REAR NEIGHBOURS! To ensure your privacy, we chose a premium location that overlooks a natural area, not another h  …see more

from £177 / night

£1154 - £2000 / week

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from £177 / night

(7) Very Good 

24

Disney Villa, Emerald Island - Emerald Isle Kissimmee house sleeps 8

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 130 km
  • Swimming pool
Had a major refurbishment completed in last 3 years, including new furniture throughout, new tile flooring throughout, granite work surfaces and new appliances in this 2005 Emerald Island Resort, Kissimmee, pool home. Located 3 miles from Disney World main gate, and eas  …see more

from £165 / night

£825 - £1255 / week

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from £165 / night

11

Awesome holiday villa near Disney - Indian Point villa sleeps 8

Kissimmee / Indian Point

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This newly refurbished villa and pool is ideal for Disney and Universal Holidays. It has a Super HD television, and an HD television in the two en-suite bedrooms. The Lanai is in a cage and faces West for warm lazy evenings by the pool after hard days enjoying the parks  …see more

from £114 / night

£792 / week

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from £114 / night

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