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Kissimmee

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603 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.

(24) Very Good 

12

Villa rental in Lindfields with swimming pool

Kissimmee / Lindfields

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“A great place to relax after a busy day at Disney World” We had a wonderful holiday staying at Sunrise Villa in Lindfields Reserve. The villa is lovely, very well equipped for self catering and is as good as it looks in the photos. The pool area is pa  …see more

from £61 / night

£425 - £525 / week

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from £61 / night

(43) Excellent 

39

Westside holiday villa rental

Kissimmee / Westside

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Beautiful villa in an excellent location” I stayed at Disney Davella for one week with my husband and parents. There are two excellent master bedrooms which made it perfect for us (with a bathroom off each) and an extra toilet downstairs as well. Th  …see more

from £90 / night

£595 - £850 / week

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from £90 / night

(26) Very Good 

18

Kissimmee holiday townhouse rental

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 55 km
  • Swimming pool
“Great location and facilites” This house gave us everything we needed for a great holiday. Clean, well equipped and in a pleasant area. Pools and public areas very well kept. Would recommend for couples and families alike. Six adults would be easily a  …see more

from £46 / night

£322 - £364 / week

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from £46 / night

Featured properties

(48) 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

£425 - £700 / week

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from £100 / night

(12) Excellent 

23

Kissimmee holiday villa rental

Kissimmee / Windsor Palms

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Everything you need..and more” Beautiful open plan villa, lots of room, clean, the sofas are really soft and cosy after a day at the parks. The pool was a definate hit with the kids, as was the games room. The gated community was very friendly and h  …see more

from £92 / night

£640 - £700 / week

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from £92 / night

(7) Excellent 

28

Holiday villa in Kissimmee

Kissimmee / Windsor Hills Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Santa Caterina is located in the beautiful Windsor Hills Resort where you can enjoy all the comforts and amenities of home with all the attractions and the social interactions of a First Class Resort.<br />ALL PRICES QUOTED INCLUDE 13% FLORIDA TAXRefundable securi  …see more

from £116 / night

£812 - £1085 / week

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from £116 / night

(23) Excellent 

24

Kissimmee holiday villa rental

Kissimmee / Lake Berkley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic” This holiday was excellent the home was absolutely fab, it was differently home from home The villa we stayed in was pristine and had every little thing you could want and more. It was a pleasure to enter into a home that was spotless. I  …see more

from £70 / night

£485 - £570 / week

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from £70 / 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

(15) Very Good 

18

Kissimmee holiday villa rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“1st time in Florida fantastic stay - lovely villa” This was our first time to florida with 2 small children, we had a lovely time, the villa was clean and had everything we needed for our stay, having the cot and highchair free of use was great. The p  …see more

from £64 / night

£450 - £500 / week

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from £64 / night

(29) Excellent 

20

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“One of the best villas we've stayed in!!!” Lovely house in a very convenient location - 2 minutes from a huge Walmart and numerous restaurants along the 192, 20 minutes to Disney, 35 minutes to Universal and International Drive. House is spacious, we  …see more

from £102 / night

£651 - £748 / week

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from £102 / night

(5) Very Good 

45

Holiday villa rental

Central Florida / Kissimmee

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
Disney location with secluded heated pool and King sized Four Poster Bed.This newly renovated property, located in one of the nicest residential communities in Kissimmee, is a great base for any holiday in the area.  …see more

from £80 / night

£559 - £675 / week

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from £80 / night

(10) Excellent 

18

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Excellent location, peaceful and very well equipped” Easy to find. Had everything we needed and a great place to come back to after busy days at the attractions.  …see more

from £80 / night

£495 - £625 / week

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from £80 / night

(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 £94 / night

£631 - £769 / week

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from £94 / night

(3) Excellent 

16

Holiday villa in Indian Creek

Kissimmee / Indian Creek

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Great Florida Villa in a Perfect Location” Myself & my Family spent a lot of time looking on website at Villas for our Florida Holiday, hoping to find a Good deal with the right location near to all the Attractions and a villa that would be suitabl  …see more

from £122 / night

£854 / week

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from £122 / night

(27) Very Good 

24

Holiday condo with golf nearby in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 106 km
  • Swimming pool
  • Child friendly
“Ideal "near to Disney" condo” Condo had everything we needed at very reasonable price, especially for Christmas period. Owners (Ronald and Pam) very helpful with arrival instructions, directions, etc. Useful local info provided at condo. Good variety  …see more

from £35 / night

£219 - £375 / week

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from £35 / night

(13) Very Good 

17

Holiday villa in Seasons Resort

Kissimmee / Seasons Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Great House, Perfect Location!” House was in great shape. Had everything needed. Pool was perfect. Near everything needed. Shopping, minutes from the theme parks. Payment plan was perfect for people on a budget. Owner very responsive. We hope to rent  …see more

from £60 / night

£360 - £550 / week

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from £60 / night

(16) Excellent 

22

Holiday villa with swimming pool in Bellavida Resort

Kissimmee / Bellavida Resort

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Perfect villa for all the Orlando attractions” Belles Cove is a lovely family home and ideally located for the parks and other attractions The rooms are tastefully decorated and with the benefit of 4 bathrooms presents ideal accommodation for a large  …see more

from £105 / night

£635 - £825 / 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

(18) Very Good 

17

Holiday villa in Kissimmee City

Kissimmee / Kissimmee City

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Magnificent Accomadation” We arrived for our stay of 2 weeks after travelling for 20 hours, we found the place easily everything was as described, the only disappointment my girls had was the pool was cold , however it soon warmed up after a couple o  …see more

from £49 / night

£320 - £550 / week

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from £49 / night

(7) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Oak Island Cove

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
Positioned on Oak Island Cove next to Formosa Gardens, this is one of the most exclusive vacation sub rental divisions in Central Florida. Every amenity is close at hand for a wonderful vacation. No other location boasts a 5 minute journey to Disney World, Orlando. The  …see more

from £95 / night

£665 - £945 / week

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from £95 / night

(24) Excellent 

23

Holiday villa rental

Kissimmee / Veranda Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 84 km
  • Swimming pool
  • Child friendly
“Excellent , pleasant and very convenient .” We enjoyed 8 wonderful days at Villa Nirvana. We were an extended family, a groop of 8 people including teenagers and a baby. All of us wish to emphasize that the time we spent at the villa was wonderful. E  …see more

from £110 / night

£769 - £883 / week

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from £110 / night

(9) Excellent 

24

Kissimmee holiday villa rental

Kissimmee / Doral Woods

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Home away from home!” We thoroughly enjoyed the villa with all of its amenities. Clearly this was equipped with children in mind. Our 2, 8 and 10 year-olds found things to do for the entire stay. Naturally the pool was number one, but they found plent  …see more

from £74 / night

£470 - £1260 / week

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from £74 / 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

(20) Excellent 

18

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic, wonderful location and wonderful villa” This is a great villa. The owners are easy to deal with and friendly. The area is great and the villa is a good size. It is 4 bedrooms, 2 doubles and 2 twins and has loads of space, all the amenities  …see more

from £61 / night

£425 - £450 / week

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from £61 / night

(16) 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 £121 / night

£847 - £1100 / week

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from £121 / 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 £82 / night

£529 - £911 / week

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from £82 / night

(11) Very Good 

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 £70 / night

£476 / week

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from £70 / night

(14) Excellent 

41

Holiday condo with golf nearby in Kissimmee

Kissimmee / Cane Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 65 km
  • Swimming pool
“Excellent Accommodation and Ideal Location” This accommodation was excellent it was very clean, spacious, well maintained and had absolutely everything needed in order to make it a real home from home. The added bonus of free internet access definite  …see more

from £70 / night

£444 - £606 / week

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from £70 / night

(13) Excellent 

60

Holiday condo rental

Kissimmee / Legacy Dunes Resort

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 78 km
  • Swimming pool
“Exactly as expected.” As we usually have a larger party and rent a 4-5 bed villa, I was a little concerned about taking on a smaller unit, but there was no need to worry. The condo is perfectly sized for 2-4 people to share in comfort. Being ground fl  …see more

from £50 / night

£300 - £450 / week

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from £50 / night

(2) Excellent 

15

Kissimmee holiday villa accommodation

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 90 km
  • Swimming pool
Minutes from Disney, emerald island resort, 4 bed, not overlooked, private heated pool & spa, 3 bath, games area, free broadband, resort facilities.  …see more

from £151 / night

£1053 / week

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from £151 / night

(43) Excellent 

91

Holiday villa in Westside

Kissimmee / Westside

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 96 km
  • Swimming pool
  • Child friendly
“Excellent villa and facilities” The Villa was as describes, nice quiet location, easy access to parks. Facilities really nice, was handy to have a guest food pack - especially if you are on a late flight. Very nice patio furniture - much nicer than  …see more

from £105 / night

£725 - £925 / week

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from £105 / night

(16) Excellent 

27

Holiday villa with swimming pool in Kissimmee

Kissimmee / Indian Ridge

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“Brilliant place to visit” We have been this place 2 years on the run and booked to go again this year, there are no faults what so ever and they are lovely people to rent off very helpful. the villa itself is stunning, decorated up to a very high stan  …see more

from £75 / night

£525 - £625 / week

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from £75 / 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

(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

(6) Excellent 

26

Holiday villa in Formosa Gardens

Kissimmee / Formosa Gardens

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Superb chillout base for a large group visiting the theme parks” As a group of 9 adults and 2 children, we thought it may prove difficult to rent anywhere large enough to accommodate everyone under the same roof, but this house met this need with hono  …see more

from £218 / night

£1520 - £1983 / week

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from £218 / 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

(5) Excellent 

28

Holiday home rental

Kissimmee / Emerald Isle Kissimmee

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
“Super Spring Break” My family spent the week of April 7 - 14, 2012 at "Jewel In The Crown", which is located in Emerald Island Resort. This is our sixth trip to Orlando and one of the best times we've had!!! Our "home away from home" was comfortable,  …see more

from £162 / night

£1133 / week

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from £162 / night

(10) Excellent 

28

Doral Woods holiday villa rental

Kissimmee / Doral Woods

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“It was just GREAT!” Large heated pool, large and clean rooms! Everything was as promised in the description! Ideal family holiday with guaranteed comfort! To Disney 25 Minutes, Universal 35 Minutes :-)  …see more

from £65 / night

£450 - £480 / week

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from £65 / night

42

Condo rental in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Windsor Hills is perhaps the finest resort community in the Disney area. With world famous theme parks and attractions just minutes away, a stay here will create family memories to last a lifetime.  …see more

from £89 / night

£627 - £968 / week

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from £89 / 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