Kissimmee Villas, Holiday rentals and apartments

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Kissimmee

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4,301 Holiday homes

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

58

Kissimmee holiday home rental

Central Florida / Kissimmee

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Calla Lily is a fabulous Lake front 5 bedroom 3 bathroom pool home in Crescent Lakes in Kissimmee, a fantastic, superbly well cared for community that is situated in a natural conservation area yet it is still close to all that the Orlando/Disney area has to offer to e  …see more

from £184 / night

£1288 / week

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from £184 / night

(5) Excellent 

24

Kissimmee holiday villa rental

Kissimmee / Oak Island Cove

4 10 6 nights min

  • 4 bedrooms
  • Sleeps 10
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Super villa” Great for all age groups - has everything you would ever need - teenagers loved the table tennis plus pool. 8 month old grandaughter had cot, toys high hair. The villa is close to shops & theme parks. Quiet estate with villa overlooking l  …see more

from £100 / night

£700 / week

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from £100 / night

(18) Excellent 

28

Villa rental in Kissimmee

Kissimmee / Doral Woods

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“A truly amazing place to stay!” If you are looking at this page, thinking about renting this villa, just do it, you'll have no regrets. We stayed for 3 weeks in July/August and had a fantastic time. It was the perfect villa for us (a family of 2 adul  …see more

from £64 / night

£445 - £525 / week

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from £64 / night

(26) Excellent 

24

Villa rental in Cumbrian Lakes

Kissimmee / Cumbrian Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Great villa” This is our last day here in Robson's retreat villa. It has been an excellent stay, we have stayed in Cumbrian lakes many times and it's the nicest we have stayed in. Lovely pool, games room. Plenty of room for us all. Great management  …see more

from £110 / night

£750 - £900 / week

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from £110 / 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

(9) Very Good 

75

Holiday villa with shared pool in Kissimmee

Kissimmee / Lake Berkley

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 107 km
  • Swimming pool
“Fantastic Relaxing Retreat from the Orlando Hustle and Bustle” We very much enjoyed our stay in this spacious and secure house. It is situated in a safe and quiet gated community less than half an hour's drive from most of the Orlando theme parks and  …see more

from £98 / night

£686 / week

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from £98 / night

(2) Excellent 

32

Villa rental in Kissimmee with shared pool, golf nearby

Kissimmee / Vista del lago

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
Spacious 3 bedroom/2 bathroom villa. Minutes from all the Disney attractions. Complimentary use of all complex facilities inc 3 great pools, a gym, floodlit tennis courts and a children's park.  …see more

from £50 / night

£350 / week

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from £50 / night

(33) Excellent 

20

Holiday townhouse in Kissimmee

Kissimmee / Regal Oaks

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Family trip” Me and my family stayed at Vic's place. There's no place I would call home like this one. We love it there. Very spacious and clean, Close to fun spot where the kids would just walk there whenever they want.close to plenty of restraunts,s  …see more

from £75 / night

£525 - £650 / week

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from £75 / 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
“Couldn't be anywhere better to stay” As the holiday season is a time for family we decided to have a mini family reunion and renting this Villa was the best thing we did. We were able to cook, use the pool and the kids were always entertain. The house  …see more

from £100 / night

£575 - £700 / week

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from £100 / 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

(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
“Best Florida Villa - by far !!!” We have spent many many weeks at this villa and when it isn't available for our trips to Florida nothing we stay at compares !!! It is a great villa, owned by an owner who cares. Well equipped, south facing, very pri  …see more

from £135 / night

£800 - £995 / week

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from £135 / night

(1) Very Good 

20

Condo rental in Kissimmee with golf nearby

Kissimmee / Kissimmee City

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This spacious 3 bedrooms and 2 bedrooms vacation home includes the Following Amenities: 4 miles to Disney , 1 King Bed, 1 Queen Bed, 2 Twin Beds, COMMUNITY has heated pool, spa, fitness center, theater room, basketball and tennis court and children playground, Complemen  …see more

from £72 / night

£460 - £680 / week

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from £72 / night

9

Holiday townhouse in Venetian Bay Villages

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Beautiful 3 bedroom home on the popular Venetian Bay in Kissimmee. This is the perfect place to relax after your busy day at the parks. Only 15 minutes from Disney World and great facilities in this gated community makes planning your Florida Vacation easy.The s  …see more

from £76 / night

£532 - £728 / week

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from £76 / night

(5) Excellent 

24

Kissimmee holiday home accommodation

Kissimmee / Lindfields

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Pete and Louise” I felt like I was at home !!!!! Everything I needed and could have forgotten was already there......this place was immaculate! It was close tho so many things to do and shopping as well......I will be back again real soon for sure, th  …see more

from £50 / night

£308 - £325 / week

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from £50 / night

45

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
A home from home, the British owners spend as much time as possible in the villa themselves. The villa is situated on a large lot and the private south facing heated pool and jacuzzi back onto a wooded area. Pool heating for cooler months is available for an additional  …see more

from £68 / night

£476 - £700 / week

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from £68 / night

(7) Very Good 

26

Kissimmee holiday villa rental

Central Florida / Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great Disney Vacation” The house was great but does need some repairs. The ironing board could not be used the leg was broken in half. The living room furniture is very worn and needs to be replaced and when my husband went to open the refrigerator d  …see more

from £72 / night

£504 / week

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from £72 / night

(2) Very Good 

18

Central Florida / Kissimmee

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £80 / night

£555 / week

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from £80 / night

(17) Very Good 

30

Villa rental in Kissimmee with swimming pool

Central Florida / Kissimmee

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic” 1   person found this review helpful Our stay in the villa was incredibly pleased! Zakir, was quick to respond, and very easy to work with.We have stayed in the Orlando/Kissimee area before, but this was our best stay so far. Vill  …see more

from £72 / night

£560 / week

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from £72 / 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

(2) Very Good 

29

Holiday villa in Kissimmee

Kissimmee / Seasons Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Wonderful home. Great location.” One of the nicest homes we have ever rented. The pond behind the house provided lovely views of the sunrise and the walking path around it got well used during our stay. While we encountered a mechanical problem with t  …see more

from £152 / night

£888 - £1481 / week

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from £152 / night

(3) Very Good 

24

Holiday villa in Kissimmee

Kissimmee / Tuscany, Florida

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
One storey villa with 3 bedrooms that can easily accommodate 8 people as there is a sofa bed. Ideally located within easy reach of Disney World and is just minutes from the new West Gate entrance to the Walt Disney World Resort  …see more

from £54 / night

£378 - £490 / week

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from £54 / 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
“Mrs” Just back from a 2 week stay at this villa. It is one of the best we have stayed in. Perfect location, near lots of our favourite restaurants, disney etc. The pool gets sun all day and has loads of outdoor space. The pool and Jacuzzi heat actuall  …see more

from £83 / night

£575 - £625 / week

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from £83 / night

(2) Very Good 

24

Kissimmee holiday home rental

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxury tropical five star resort and house. Close to Disney parks and within range of Florida's west coast beaches.  …see more

from £99 / night

£693 - £910 / week

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from £99 / night

30

Holiday home with golf nearby in Kissimmee

Central Florida / Kissimmee

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Fabulous location for everything the area has to offer. Only 10 minutes from Disney main gates & 20 mins to Universal. Convenient for shops, restaurants and outlets Complex offers heated pool, tennis, basketball, play area, splash pad, volley ball, & other amen  …see more

from £69 / night

£449 - £589 / week

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from £69 / night

52

Holiday villa in Eagle Pointe

Kissimmee / Eagle Pointe

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 115 km
  • Swimming pool
The house is all on one level and has two large separate living/dining areas, a games room and a large pool.  …see more

from £131 / night

£789 - £978 / week

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from £131 / night

(3) Very Good 

81

Holiday home in Oak Island Harbor

Kissimmee / Oak Island Harbor

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
This home is spotlessly presented and is decorated beautifully with exquisitive furniture.  …see more

from £208 / night

£1456 / week

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from £208 / night

14

Central Florida / Kissimmee

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £115 / night

£801 / week

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from £115 / night

23

Holiday home in Kissimmee

Central Florida / Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Summary • South Facing Pool overlooking conservation lake and woodland • 7 Bed 5.5 bathrooms with 3 Master Suites 2 Kings 2 Queens 6 Singles • Closest gated community to Disney Thank you for visiting Tinkerbells Retreat com ***** Choosing the right vill  …see more

from £200 / night

£1400 - £2280 / week

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from £200 / 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 £160 / night

£1115 / week

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from £160 / night

(8) Very Good 

22

Holiday villa in Kissimmee

Kissimmee / Terra Verde Resort

5 12 5 nights min

  • 5 bedrooms
  • Sleeps 12
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
5 Beds,4 Baths. Sleeps 12. AC. Outdoor Pool. Xbox. Wii. PS2. Games Room with Pool Table, Foosball, Air Hockey.  …see more

from £101 / night

£706 - £840 / week

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from £101 / night

(12) Excellent 

37

Villa rental in Kissimmee with swimming pool

Kissimmee / Kissimmee City

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
“One word to sum up this villa...... PERFECT !!!” Choosing a villa was quite a hard task to ensure that the whole family enjoyed their vacation in Florida. It needed to be centrally located to all the main parks, be furnished to a good standard & have  …see more

from £113 / night

£752 - £920 / week

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from £113 / 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

(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

24

Holiday home in Kissimmee

Central Florida / Kissimmee

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A brand new house furnished to a high standard with a wall mounted TV in each room and 2 large TVs in the lounge and family room. There is a heated private pool and spa over looking a conservation area (heating at an extra cost). Entertainment in house includes table  …see more

from £172 / night

£1200 - £1800 / week

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from £172 / night

24

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee / Windsor Palms

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Massive pool deck for relaxing, south facing with sun all day. Great look out over a conservation area and not over looked.Super comfort furniture. Formal and informal dining areas plus breakfast bar.2 x King sized en suite bedrooms. 1 x Queen and 2 x twin rooms.<br  …see more

from £162 / night

£1132 / week

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from £162 / night

(7) Very Good 

17

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 106 km
  • Swimming pool
  • Child friendly
“Lovely Villa, well placed” Villa was clean & spacious. Pool was lovely & clean with nice garden view. Mostly quiet neighbourhood. Very close to 192 with all the restaurants & shopping. Ian was easy to contact & kept in touch throughout the stay. Pool  …see more

from £65 / night

£450 / 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
“Fantastic!” We Stayed at Doral Woods villa in May 16. The villa is equipped with everything you need and is spotlessly clean. Beautiful pool & garden the best villa we have ever stayed in! Highly recommend also the owners are so helpful and attentive  …see more

from £130 / night

£895 - £995 / week

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from £130 / night

(9) Very Good 

24

Holiday home in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 130 km
  • Swimming pool
“Fabulous House, Fabulous Holiday” We loved this house!!! It was spotlessly clean, and the furnishings were of a high standard. The beds were really comfy and the children loved the playroom and pool. Great for two families. It is a great location  …see more

from £165 / night

£825 - £1255 / week

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from £165 / night

40

Central Florida / Kissimmee

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £136 / night

£947 / week

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from £136 / night

17

Kissimmee holiday home rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a luxurious 3 bedroom 3 bathroom villa with private pool with conservation view on 5 Star Eagle Pointe Resort, Kissimmee, Orlando. The villa was recently refurbished and now benefits from ceramic tile and wood flooring throughout. The villa is furnished to a v  …see more

from £88 / night

£600 - £716 / week

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from £88 / night