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

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Kissimmee

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2,878 Holiday homes

Filters applied: Swimming pool

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

(29) Excellent 

90

Villa rental in Kissimmee with swimming pool

Kissimmee / Eagle Pointe

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Comfortable villa in good location” We stayed for 4 nights to attend the Mecum Auto auction. The villa was spacious ,clean and reasonable to rent. Accessible to all Orlando attractions. Travelers need to bring everything, paper goods, coffee, cream  …see more

from £65 / night

£455 - £553 / week

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from £65 / 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 £65 / night

£450 - £500 / week

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from £65 / night

(27) Excellent 

20

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Awesome!!!” Firstly, I would like to thank Donna for being her, Donna is an amazing person she is quick to respond to any problems or queries. Villa is located close to Disney parks. Although we did not do Disney we did do other parks which was appr  …see more

from £83 / night

£575 - £625 / week

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from £83 / 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

(24) Excellent 

23

Holiday condo in Kissimmee

Kissimmee / Cane Island

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Beautiful condo in a great location” The condo at cane island is absolutely wonderful. We were delighted with the choice we made having spent hours trawling the Internet before booking. Everywhere was sparkling clean and absolutely beautifully decorat  …see more

from £65 / night

£455 / week

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from £65 / 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

(24) Very Good 

27

Holiday home in Kissimmee

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Just Perfect” My wife and I are regular visitors to the Orlando area and have stayed in several Rental Villas in the past. It was our first time at ‘Ventura Villa’ hopefully not our last, we had a really enjoyable stay. The villa is clean, well fur  …see more

from £80 / night

£525 - £1054 / 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

(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

(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

(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

(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

(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

(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

(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 £90 / night

£495 - £625 / week

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from £90 / 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

(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 

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 £121 / night

£847 / week

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from £121 / night

(22) 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

(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

(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

(4) Very Good 

40

Holiday home in Kissimmee

Central Florida / Kissimmee

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Would recommend” Beautiful home, my family and I enjoyed every bit of it. Very spacious, listed as 4 bedrooms also has a loft so it's more like 5, we had a whole room we never used and everyone was comfortable. In a great area for shopping markets and  …see more

from £105 / night

£726 / week

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from £105 / 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

(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

(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

24

Lake Berkley holiday villa rental

Kissimmee / Lake Berkley

5 10 4 nights min

  • 5 bedrooms
  • Sleeps 10
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Lake Berkley is a private gated community - a veritable oasis ! Located just off the busy and action packed Highway 192 with its array of shops, entertainment & restaurants, Lake Berkley offers the perfect location for that holiday of a lifetime in the Sunshine Stat  …see more

from £123 / night

£860 / week

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from £123 / 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

(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

(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 £65 / night

£400 - £863 / week

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from £65 / night

(43) Excellent 

21

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
“As good as it gets...” When we arrived at the villa we were blown away, It was clean, well presented and extremely modern...and most definitely had the WOW factor!! Everyone in our party were excited and more so on seeing the terrific pool and huge g  …see more

from £130 / night

£895 - £995 / week

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from £130 / 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

(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

(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

(6) Excellent 

15

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly
“This was a great place to stay.” This house was a great place and was not far from Disney. It was a very nice and spacious house. The pool was nice also.  …see more

from £60 / night

£425 - £595 / week

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from £60 / night

(11) Very Good 

20

Holiday villa with indoor pool in Paradise Palms

Kissimmee / Paradise Palms

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic villa and resort in good location for attractions” Stayed in the villa for 2 weeks. There were 10 of us yet the villa was so roomy. Very comfortable and modern with all you could need. The paradise palms resort is also excellent. Great  …see more

from £202 / night

£1412 - £1694 / week

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from £202 / night

(12) Excellent 

22

Kissimmee holiday villa let

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Super Villa in a super location,” A perfect location for us just a couple of minutes from Kissimmee, Everything you need is there, pool, hot tub, games room, WiFi and as it's English owned it even has a kettle ! (Most Florida Villas don't). Clear i  …see more

from £80 / night

£559 / week

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from £80 / night

(4) Excellent 

44

Holiday villa with golf nearby in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Very nice villa in a quiet and peaceful area.” The villa was very tidy and well maintained. The location was excellent, being very close to a supermarket and to Kissimmee. It was also an ideal location for all the excellent theme parks. We certainly w  …see more

from £95 / night

£585 - £595 / week

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from £95 / night

(9) Very Good 

63

Coral Cay holiday home rental

Kissimmee / Coral Cay

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“A Nice Stay!!!!” We really loved it and we wish if we would have stayed. Beautiful scenic, nice backyard overlooking the lake. The pool was nice with a hot pool  …see more

from £59 / night

£413 / week

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from £59 / 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

(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