Air conditioned apartments and villas to rent in Kissimmee

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Kissimmee

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3,580 Holiday homes

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(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 

30

Holiday villa in Kissimmee

Kissimmee / Seasons Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great vacation home!” Thanks for a great vacation experience! The house was neat and clean, with all facilities as advertised. Food and drinks that we found on arrival was a nice touch! Would definitely recommend to others.  …see more

from £134 / night

£884 - £1210 / week

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from £134 / night

(15) Excellent 

29

Kissimmee holiday villa rental

Kissimmee / Seasons Resort

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 110 km
  • Swimming pool
“Great Location, Lovely Villa, Great Pool!” We had an amazing stay at this Villa. The rooms were perfect for our friends and family, it had everything we needed. The pool was lovely and such a nice area outside. Great location, minutes away from a Wal-  …see more

from £109 / night

£722 - £1045 / week

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from £109 / 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

(20) 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 £65 / night

£345 - £675 / week

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from £65 / 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

(5) Very Good 

74

Villa rental in Kissimmee with swimming pool, golf nearby

Kissimmee / Windsor Hills Resort

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Home from home... Fantastic!!” My husband & i stayed here with our teenage daughter & her friend, what a great holiday we all had! The villa was perfect... Centrally located on the 192, really comfortable & stylish with every convenience you could eve  …see more

from £109 / night

£763 / week

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from £109 / night

(8) Excellent 

36

Holiday home rental

Kissimmee / Crescent Lakes

5 13 3 nights min

  • 5 bedrooms
  • Sleeps 13
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Well maintained fully furnished 5 bed 3.5 bath home with 25x15 heated private pool and spa. Private garden overlooking lake. Covered lanai with south facing sundeck and pool furniture. The fabulous sun drenched pool deck and shimmering waters of our private pool offer a  …see more

from £70 / night

£450 - £800 / week

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from £70 / 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 £93 / night

£625 - £763 / week

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from £93 / 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 £161 / night

£1124 / week

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from £161 / night

(11) Excellent 

14

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic Luxury property close to Disney!” We have just returned from a 2 week Holiday to Florida and used this house as our base. The house is located in Kissimee which is an ideal base to visit all the attractions, Disney is about 15 mins, Universa  …see more

from £65 / night

£450 - £500 / week

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from £65 / 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

(25) Excellent 

24

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Location” Great location that is close to restaurants, stores, and Disney World and also very affordable. Our kids loved the pool.  …see more

from £75 / night

£525 - £600 / week

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from £75 / night

(20) Excellent 

24

Holiday townhouse rental

Kissimmee / Encantada Resort

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
“Fantastic accommodation in lovely resort” What a beautiful house, modern and clean with everything you could need. The house is situated in a lovely gated resort and is in a great position near to the communal pools and club house. The owners have tho  …see more

from £95 / night

£640 - £950 / week

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from £95 / 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 £105 / night

£686 - £940 / week

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from £105 / 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

(3) Very Good 

20

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“a good place to relax at the end of an energetic day” Martin's Villa was well equipped and spacious, the pool was screened which helped with privacy. It is on an estate with a mix of residents and some holiday makers and is very convenient for a lar  …see more

from £85 / night

£593 / week

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from £85 / 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 £154 / night

£1073 / week

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from £154 / night

(2) Excellent 

91

Villa accommodation in Kissimmee

Kissimmee / Kissimmee City

5 10 6 nights min

  • 5 bedrooms
  • Sleeps 10
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Fabulous 2 storey home with lots of space for large groups or 2 families, with cable t.v. in every room, wi fi and a games room. The pool & spa area is a great favourite with lots of loungers for relaxing by the pool. Seasons is one of the most sought after communit  …see more

from £100 / night

£675 / week

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from £100 / night

(25) 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 £109 / night

£763 - £875 / week

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from £109 / night

(6) Very Good 

13

Holiday villa with shared pool, golf nearby in Kissimmee

Kissimmee / Windsor Palms

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxury Disney Villa. Close to Disney, Large 6 bedroom villa, private pool with spa, not overlooked, Florida villa, childrens themed rooms, games room, free wifi, gates resort, gated community, Disney Frozen Room, Star Wars Themed room<br />for the perfect family  …see more

from £150 / night

£700 - £800 / week

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from £150 / 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 £150 / night

£1045 / week

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from £150 / 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 £121 / night

£932 / week

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from £121 / 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

(15) Excellent 

19

Villa rental in Kissimmee

Kissimmee / Bellavida Resort

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Lots of space and nice pool” We travelled with two children (9&10) plus two teenagers and everybody enjoyed our stay! Plenty of room for everybody, own swimming pool and jaguzzi plus communal pool. Short (15-20 min) drive to the amusement parks. Sever  …see more

from £90 / night

£590 / week

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from £90 / night

(68) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Bass Lakes Estate

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“Excellent location, beautiful and comfortable villa.” It was our first time not staying at a hotel. Don't think we'll stay at one again. Being at this house was just perfect for us. Very comfortable and close to everything. Would surely go back!  …see more

from £70 / night

£475 - £590 / week

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from £70 / night

(4) Very Good 

12

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Idyllic base for Orlando holiday” Just got back from this lovely villa where we spent a wonderful two weeks. The owners have made this feel just like home, with everything necessary for a comfortable stay. From the extended pool deck with comfy sunbed  …see more

from £89 / night

£642 / week

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from £89 / night

(18) Excellent 

24

Holiday villa letting

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“Had a great time at this Villa” We arrived to a clean, well kept villa. We unloaded our luggage and ran over to the nearby Wal-Mart to get some food etc. It was very convenient having a Wal-Mart near by (as well as several restaurants). The pool was  …see more

from £65 / night

£440 - £550 / week

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from £65 / 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

(3) Excellent 

45

Kissimmee holiday townhouse rental

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
4 Bedrooms / 3 bathrooms - ground floor comprising covered entrance porch, entrance foyer, kitchen, dining area, great room, covered terrace, ground floor double bedroom with bathroom. Stairs leading to - First floor comprising master bedroom with walk in wardrobes and  …see more

from £60 / night

£420 - £560 / week

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from £60 / 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

£350 - £450 / week

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from £50 / night

(20) Very Good 

36

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Indian Point with gorgeous lake and conservation view from pool.Indian Point, Kissimmee is a beautiful residential community situated within a few minutes drive of the Highway 192, convenient for the Wal-Mart superstore, a large selection of restaurants, and close t  …see more

from £70 / night

£450 - £575 / week

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from £70 / night

(12) 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

84

Kissimmee holiday villa rental

Central Florida / Kissimmee

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our luxury family villa is situated within the well established, prestigious Lake Berkley Community, perfectly located just off the US 192, behind Medieval Times. This central, yet private location, within 10 minutes of Disney is also within strolling distance of the Wa  …see more

from £117 / night

£819 - £836 / week

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from £117 / night

(23) Very Good 

56

Holiday home rental

Kissimmee / Lindfields

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 90 km
  • Swimming pool
“Great accommodation” Stayed here for two weeks for our honeymoon. Location of the villa is excellent if visiting the Disney Parks. Clean and tidy, very large living area and bedrooms. Couldn't have asked for anything better.  …see more

from £50 / night

£350 / week

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from £50 / night

(19) Very Good 

20

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Swimming pool
“Dream home, brilliant location, very clean and well equipped.” From the first contact on enquiry to arriving back home 2 weeks later, the whole renting process and communication was outstanding, our family, 3 adults and 4 children aged 3,10,11 and16 a  …see more

from £130 / night

£875 / week

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from £130 / night

24

Holiday villa in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
An amazing family friendly villa in a gated community, a large home from home that has something for all the family! Come explore what our villa has to offer, whilst also exploring the world of Disney only minutes away!  …see more

from £85 / night

£595 - £735 / week

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from £85 / 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 £69 / night

£472 / week

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from £69 / night

(15) Excellent 

49

Bungalow rental in Kissimmee

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“Family friendly vacation home with screened in pool...immaculate and exactly as posted!” The home was very clean and had a fully functional and equipped kitchen. The bedrooms were each spacious and had sufficient linens. There is wi-fi and sufficien  …see more

from £89 / night

£585 - £666 / week

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from £89 / night

(3) 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 £158 / night

£1045 - £1690 / week

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from £158 / night