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Kissimmee

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833 Holiday homes

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Travellers going to Kissimmee are booking March dates now. Secure your holiday home today and have the perfect trip.

(3) Very Good 

28

Holiday villa with shared pool in Kissimmee

Central Florida / Kissimmee

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This fabulous villa gives our guests a real home from home experience. It is furnished for relaxation with comfy furniture, carpeted floors & it's own private pool that can be heated. Overview of Villa • Private Pool with Lanai • Recently Refurbish  …see more

from £92 / night

£620 - £756 / week

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from £92 / night

(51) Excellent 

60

Villa rental in Kissimmee

Kissimmee / Indian Ridge

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Excellent Location and a Wonderful Home.” Never booked through holiday lettings before so I was a bit nervous however I needn't have been. From the first moment I had contact with the owners of Russel Ridge communications and reassurance have been exc  …see more

from £100 / night

£575 - £700 / week

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from £100 / night

(2) Very Good 

51

Kissimmee holiday apartment rental

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sun Lake amenities include a clubhouse with gym and pool table, a lighted tennis court and a heated spa and a free form pool.<br />We are two miles from Disney and 15 minutes from Sea World, Premium Outlet Malls and 20 minutes from Univers  …see more

from £68 / night

£476 / week

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from £68 / night

(30) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“We'd stay again in a heartbeat !!” Everything about this place was "top shelf". It was sparkling clean and comfortable, with all the amenities one could ask for. Beautifully decorated and thoughtfully equipped, this place completely met our needs an  …see more

from £135 / night

£800 - £995 / week

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from £135 / night

(13) Very Good 

13

Holiday villa with swimming pool in Kissimmee

Kissimmee / Indian Point

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“fantastic and in a good position to explore the area” We have just got back from a wonderful two week stay at this villa.It's spacious and nicely decorated.The pool is a really good size and we used it everyday to cool off after a day at the parks.It'  …see more

from £90 / night

£600 - £680 / week

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from £90 / night

(3) Excellent 

24

Villa rental in Kissimmee

Kissimmee / Lake Berkley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Great Villa, Great Location” We have stayed at Lake Berkley a dozen or so times now and this is probably one of the better villas. Its located in a beautiful gated community overlooking a lake but in an ideal place for access to all the major attracti  …see more

from £90 / night

£575 - £625 / week

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from £90 / night

(7) Very Good 

20

Holiday townhouse in Kissimmee

Kissimmee / Paradise Palms

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
A Beautiful 5* Star 'Spacious', 4 bedroom, 3 bath Vacation home, south Facing Private Pool on a holiday resort with Communal Pool, tennis Courts, Games Room, Sauna, Gym, Card Room. Tiki Bar. 5 Mins from Disney and all the major attractions. Ideal for families  …see more

from £94 / night

£610 - £940 / week

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from £94 / night

(17) Excellent 

27

Holiday villa in Kissimmee

Kissimmee / Formosa Gardens

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Couldn't ask for a nicer place!!” We stayed in the Diamond Villa on our first trip to Disney World and we were blown away with how beautiful this villa was! It was beautifully decorated, spotlessly clean, extremely well equipped and more comfortable t  …see more

from £143 / night

£1000 - £1300 / week

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from £143 / night

(2) Excellent 

28

Holiday villa in Seasons Resort

Kissimmee / Seasons Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Home from home, great value for money.” Having stayed here with my family, plus another family of five in 2013 we tried to rebook the same villa but unfortunately it was fully booked up. We found this villa to have everything we needed and more, beaut  …see more

from £156 / night

£1036 - £1676 / week

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from £156 / night

(13) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“Excellent Villa highly recommend it, great location.” Property was excellent, close to Disney and places to eat. The weather was nice and the complex where the villa was situated was well looked after, nice and clean and staff was pleasant.  …see more

from £148 / night

£1000 - £1450 / week

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from £148 / night

(12) Excellent 

32

Kissimmee / Paradise Palms

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £96 / night

£924 / week

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from £96 / night

(12) Excellent 

51

Apartment rental in Kissimmee

Central Florida / Kissimmee

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Very clean and with everything you need!” The place was big for being an apt, clean, close to everything but quite. The instructions were clear and chris replayed me back an email almost instantly. It was the first time renting a place by internet,  …see more

from £68 / night

£468 / week

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from £68 / night

(12) Very Good 

24

Cumbrian Lakes holiday villa rental

Kissimmee / Cumbrian Lakes

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Great Villa for families” We stayed at this villa with our daughter and my wife's parents. This is a fantastic property for more than one family as there are two master suites as well as a queen room and two twin bedrooms. The best feature is the exte  …see more

from £79 / night

£550 / week

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from £79 / night

(6) Excellent 

21

Trafalgar Village holiday home rental

Kissimmee / Trafalgar Village

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
“Fabulous home away from home” Ten of us stayed in this Villa, consisting 3 children, 2 teenagers and 5 adults. We had plenty of room for all of us as it's such a large property. The Villa was very well equipped with everything we needed and spotlessly  …see more

from £120 / night

£924 / week

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from £120 / night

(1) Excellent 

55

Holiday condo with shared pool in Kissimmee

Kissimmee / Cane Island

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Self-catering air-conditioned condo with shared swimming pool, gym and games room.<br />We own three of these condos, one above the other, so if you have a large party you can all stay together.  …see more

from £49 / night

£343 / week

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from £49 / night

(13) Excellent 

44

Holiday villa rental

Kissimmee / Indian Ridge Oaks

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Quick Getaway” We had an unexpected trip to Orlando after booking some cheap flights, we found Tracey's villa and she couldn't have been more helpful. We loved the villa, all the disney touches, even dresses for little princesses and the games in the  …see more

from £75 / night

£515 - £747 / week

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from £75 / night

23

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

5 13 Min stay varies

  • 5 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This new executive villa features state of-the-art living ... 5 bedrooms, 3.5 bathrooms, swimming pool and spa. Cumbrian Lakes is set in a conservation area yet only 5 minutes from shops and restaurants and less than 15 minutes to Disney World.The execut  …see more

from £105 / night

£735 - £980 / week

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from £105 / night

(13) Excellent 

24

Kissimmee holiday villa rental

Kissimmee / Veranda Palms

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 75 km
  • Swimming pool
“Great villa stay in Orlando” My partner and two teenage girls spent just over a week in this lovely villa. It's modern, very clean and has everything you need, with some lovely finishing touches that add to the feeling of luxury. The beds are very com  …see more

from £90 / night

£580 - £750 / week

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from £90 / night

(5) Excellent 

24

Holiday villa with swimming pool in Kissimmee

Kissimmee / Cumbrian Lakes

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Cumbrian Lakes is an exclusive gated community with lakes, cycling & walking trails & a kids play area.  …see more

from £100 / night

£700 - £850 / week

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from £100 / night

23

Holiday villa in Kissimmee

Kissimmee / Windsor Palms

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
6 Bedroom Luxury Villa at Windsor Palms 3 Miles from Disney. Private Pool area with extended decking overlooking beautiful conservation area. 42" flat screen HDTV with cable. Free Wifi Internet. Games room. Gated community. Clubhouse facilities cinema, tennis, gym,  …see more

from £130 / night

£900 - £1150 / week

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from £130 / night

(4) Excellent 

45

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Lovely villa and ideal location” The villa was lovely, very clean and spacious with a great view of the lake behind. It was situated in an ideal location - especially for Disney! Would definitely stay again.  …see more

from £96 / night

£672 / week

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from £96 / night

(5) Very Good 

100

Kissimmee holiday home rental

Central Florida / Kissimmee

4 10 6 nights min

  • 4 bedrooms
  • Sleeps 10
  • 6 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Beautiful sunsets and a fabulous vacation home” We choose Star Lake View as we were looking for a nice lakeside view as we were not disappointed. The views of the sunset were gorgeous and we loved spotting all the wild birds. The villa was immacula  …see more

from £90 / night

£585 / week

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from £90 / night

(17) Excellent 

23

Holiday townhouse in Kissimmee

Kissimmee / Encantada Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic house in a fantastic location” Recently returned from 2 weeks of fun in Florida with our 5 year old daughter. The weather was glorious and the parks brilliant. What topped our holiday was returning everday to our rented home. The home had a  …see more

from £64 / night

£396 - £856 / week

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from £64 / night

(11) Excellent 

24

Calabria, Orlando holiday villa rental

Kissimmee / Calabria, Orlando

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Just what we wanted. Great space. Great location” Preparation communications from owner was excellent. Group of 10 with no issues at all throughout the stay. Quite and pleasant neighbourhood.  …see more

from £152 / night

£1064 / week

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from £152 / night

(6) Excellent 

24

Villa rental in Kissimmee

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great stay close to all attractions and shopping.” We really enjoyed our stay at Mandyville. The house was very clean. We lucked out on the weather for January and made great use of the pool area. The UV protection on the pool enclosure was great a  …see more

from £75 / night

£485 / week

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from £75 / night

(21) Excellent 

59

Holiday townhouse with shared pool in Trafalgar Village

Kissimmee / Trafalgar Village

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“A TRUE home from home” A gorgeous home on lake the complex is clean with fantastic facilities close to parks & restaurants. The home is About 80yds from a beautiful man made beach with volley ball area, my kids loved it there so much so we booked up  …see more

from £100 / night

£360 - £700 / week

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from £100 / night

(17) Excellent 

48

Townhouse rental in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 104 km
  • Swimming pool
  • Child friendly
“Absolutely fabulous -we will rent this villa again next time we go to Forida” There really wasn't anything about this property that disappointed us. It was clean, beautifully decorated and furnished, kitchen had more equipment that we ever used - an  …see more

from £53 / night

£375 - £525 / week

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from £53 / night

(11) Very Good 

46

Villa rental in Indian Point with shared pool

Kissimmee / Indian Point

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Outstanding Villa - Real Home from Home” Superb villa - really clean, airy and well-decorated with a lovely pool and patio area. Plenty of room for everyone in the 4 bedrooms & especially liked having 3 bathrooms to make leaving for the parks much qui  …see more

from £66 / night

£460 - £690 / week

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from £66 / night

(4) Excellent 

30

Kissimmee holiday villa let

Kissimmee / Lindfields

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“The Perfect home in the Perfect location” The only word to describe this beautiful well maintained home is 'wow' I would say it was like a home from home, only much better. Everything has been thought of to ensure a comfortable stay. The pool is super  …see more

from £70 / night

£445 - £595 / week

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from £70 / night

(2) Very Good 

20

Kissimmee holiday townhouse accommodation

Kissimmee / Paradise Palms

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
First floor consists of 892 sf with hallway, bathroom, king size bedroom, living room with dining area and a luxurious kitchen. Second floor has 888 sf including 3 bedrooms, 2 full bathrooms, washroom with washer and dryer and closet in the hallway for linens. The patio  …see more

from £80 / night

£520 - £896 / week

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from £80 / night

(8) Excellent 

14

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
“A HOLIDAY TO REMEMBER” Cumbrian lakes drive is a well appointed 8 bed villa in very pleasant surroundings. We stayed there 4 adults and 2 young children aged 6 & 8 for 2 weeks. It is within easy access of all the parks, the malls etc and only a shor  …see more

from £90 / night

£630 - £795 / week

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from £90 / night

(10) Excellent 

24

Holiday villa in Doral Woods

Kissimmee / Doral Woods

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic!” We have just returned from Palm Tree Villa. We stayed there for nearly two weeks and to say we had a fantastic time and enjoyed it there is an understatement. The house is as clean as advertised. It has all the facilities in place to make  …see more

from £100 / night

£695 - £875 / week

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from £100 / night

(13) Excellent 

12

Kissimmee holiday villa rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
•40ft lake view pool with sunshine on deck from 10am till sunset•Within 30 minutes for ALL parks,Orlando airport and the Florida Mall•Prime lake view and privacy •24 hour Walmart and loads of restaurants and shops close by• Returning guests year  …see more

from £73 / night

£510 - £630 / week

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from £73 / night

(9) Very Good 

50

Holiday villa rental

Kissimmee / Trafalgar Village

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Located in a Family friendly community with free use of resort facilities our well-furnished villa with pool and hot tub can comfortably accommodate up to 8 Guests. Less than 15 miles from Walt Disney World.<br />Pool & Spa Heat is available at an additional  …see more

from £85 / night

£520 - £680 / week

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from £85 / night

(20) Very Good 

68

Holiday villa in Kissimmee

Kissimmee / Lindfields

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Thanks” This was a great Vila with everything you needed and in a good area to base yourself, if any c ok militants a bit dated  …see more

from £100 / night

£450 - £540 / week

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from £100 / night

(17) Very Good 

10

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

4 9 4 nights min

  • 4 bedrooms
  • Sleeps 9
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Executive style four bedroom, two bathroom Villa in Kissimmee. Very close to Disney and Universal theme parks. Private garden, with heated pool and Jacuzzi.  …see more

from £65 / night

£450 / week

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from £65 / night

(6) Very Good 

45

Holiday villa with golf nearby in Indian Creek

Kissimmee / Indian Creek

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Fantastic well equipped/maintained villa in a perfect location close to everything, will definitely be back” We chose this villa as it was well equipped and in a location we knew well, we found a lot of villas can be a bit of a drive away from anythin  …see more

from £110 / night

£750 - £1200 / week

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from £110 / night

(18) Excellent 

51

Villa rental in Kissimmee

Kissimmee / Villasol

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 55 km
  • Swimming pool
Clubhouse, tennis court, boat dock, children's play area, basketball, nature walks, communal pool & spa.  …see more

from £99 / night

£693 / week

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from £99 / night

(14) Very Good 

29

Holiday home in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Superb stay close to Orlando and parks.” My family, together with my parents and sister in law stayed at this villa during the last week of December for 6 days. This was an excellent home, spacious and clean with all the amenities a villa should h  …see more

from £140 / night

£980 - £1400 / week

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from £140 / night

(5) Excellent 

27

Holiday villa letting

Kissimmee / Windsor Palms

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
4 bed villa near Disney, FREE wifi, private pool and jacuzzi,air con, 2 bathrooms, 220 channel hdtv's, PS3, Xbox360, Windsor Palms Resort, secure gated community with communal pool, tiki bar, playground, sports courts, gym, games room, cinema, shop, bike/dvd/bbq re  …see more

from £120 / night

£825 / week

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from £120 / night