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Kissimmee

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1,979 Holiday homes

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

(8) 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

from £130 / night

£910 - £1200 / week

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from £130 / night

(45) 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
“Excellent well equipped villa-very spacious and extremely clean” Well situated for all Disney Parks close to supermarket and several restaurants. We were a party of 7 with 2 children who adored the pool and jacuzzi. We felt the villa was exceptionally  …see more

from £100 / night

£595 - £925 / week

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from £100 / night

(21) 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
“Really nice” Nice house good location, we really liked the option of being able to use the pool at the house or the two large pools by the clubhouse. Would certainly stay again.  …see more

from £100 / night

£680 - £950 / week

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from £100 / night

Featured properties

(10) Very Good 

20

Holiday villa letting

Kissimmee / Emerald Isle Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £75 / night

£525 - £735 / week

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from £75 / night

(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
“A beautiful home in the sun.” We stayed in this lovely villa for two weeks and we honestly could not fault it. The location is very good with easy access to Disney plus the i4 and the 192. There is a Walmart under 2 miles away and a number of great re  …see more

from £65 / night

£455 - £553 / week

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from £65 / night

(28) Excellent 

24

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“FANTASTIC VILLA.....GREAT COMMUNICATION WITH OWNER” Lovely villa, spacious enough for 8 people and fully equipped. The location is lovely too, very quiet, with regular landscaping and nice views. The villa is approximately 2-3 miles from lots of res  …see more

from £90 / night

£630 - £820 / week

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from £90 / night

(27) 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
“Fantastic Villa” This villa is just perfect! Beautifully furnished and has everything you could possibly need for your stay. Kathryn the owner is great, if you have any questions etc....It is situated in a very quiet cup- de-sac and ver secure. The pr  …see more

from £61 / night

£425 - £600 / week

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from £61 / 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

(21) 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
“As good as it gets” From the first contact with the owner to our last day at the villa was excellent. The villa décor and facilities were just what we hoped for and more. From our location it was only a short trip to the theme parks eating out or shop  …see more

from £68 / night

£475 / week

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from £68 / night

(13) 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
“We will not be going anywhere else!” This was our second stay at the beautiful villa. Local to all the best restaurants, Wall-Mart and Target for food shops. With only a 15 minute drive we were in the theme parks, International Drive and only 45 minut  …see more

from £90 / night

£495 - £625 / week

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from £90 / night

(18) 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

(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 - £650 / week

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from £65 / night

(28) 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

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

from £105 / night

£735 - £980 / week

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from £105 / 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
“Great place to stay” Great place to stay, it's a lot bigger than it looks on the photos. The pool is lovely with sun on it from early morning till evening in July. The beds are comfortable, loads of towels available, the BBQ, fridge freezer,microwave  …see more

from £65 / night

£450 - £500 / week

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from £65 / 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
“Geat location” Stayed 23.8.16 to 6.9.16. Great home for 9 people that stayed. Home was clean and well kept. A 10 minute drive to Disney and 20 minutes to Universal and Sea World. Great that there were plenty of extra towels in the cupboard. Washi  …see more

from £143 / night

£1000 - £1300 / week

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from £143 / 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
“A wonderful Vacation Villa” This was our fifth visit to this gated neighborhood (our second visit since September) but our first stay in this villa. We loved it! Everything was perfect. The security system offered an added comfort. The extra large p  …see more

from £108 / night

£756 - £868 / week

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from £108 / 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

from £54 / night

£380 - £490 / week

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from £54 / night

(14) Very Good 

24

Villa accommodation in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Home from home.” The villa is in a fantastic location for all the attractions and the gated community is set in an attractive environment. The photos do not do it justice- we were blown away with the space and quality of this lovely villa. It has ho  …see more

from £70 / night

£480 - £600 / week

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from £70 / night

(8) 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

from £133 / night

£925 - £1195 / week

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from £133 / night

(27) 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 - £371 / week

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from £46 / night

(24) 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
“Home from home!” Beautiful clean villa, well equipped, spacious and extremely relaxing and comfortable. Nice added touches i.e. the games room and security at the gate. The gardens and pool area kept clean and tidy. Fantastic communication from owner  …see more

from £70 / night

£485 - £570 / week

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from £70 / night

(17) Excellent 

23

Kissimmee holiday villa let

Kissimmee / Bellavida Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Absolutely wonderful!” This house is amazing! The pictures do not capture the true beauty of this property. We traveled with 3 families - all ages. There was plenty of room for everyone - bedrooms, kitchen, living room, family room, pool, etc. The  …see more

from £149 / night

£1045 - £1495 / week

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from £149 / 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

(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
“Perfect location for Disney and we couldnt fault the villa which was spacious, clean and well equipped, thank you” We had a wonderful stay in this modern, spacious and well equipped villa which we found to be ideally placed for Disney We also visited  …see more

from £75 / night

£525 - £625 / week

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from £75 / night

(8) 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

from £94 / night

£610 - £930 / week

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from £94 / night

(2) Average 

20

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

6 14 1 night min

  • 6 bedrooms
  • Sleeps 14
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £172 / night

£1204 / week

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from £172 / 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 £110 / night

£760 - £925 / week

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from £110 / night

(13) 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
“Wyndham Palm Way review” Lovely villa, easy to find just off the 192 and easily accommodates 9 people so perfect for a large family holiday. Easy to get to the parks and out for food but you will need a car. Good value for money although it is a li  …see more

from £92 / night

£640 - £700 / week

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from £92 / 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
“Excellent Villa” This was our sixth time in Florida and our third stay at Doral Woods in our third different villa on the estate and it certainly compares very favourably in what is simply a very nice place to stay. Set in a very quiet residential cul  …see more

from £80 / night

£560 - £930 / week

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from £80 / 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

from £148 / night

£1036 / week

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from £148 / night

(16) Very Good 

17

Holiday villa in Seasons Resort

Kissimmee / Seasons Resort

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • 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 - £700 / week

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from £60 / night

(17) 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
“Our stay” Loved it, very clean and had everything we needed. Would definitley recommend, 10 mins from disney 2 mins from shops/ restaurants whilst still being in a very quiet street.  …see more

from £65 / night

£450 - £500 / week

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from £65 / 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

(54) 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 £90 / night

£475 - £725 / week

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from £90 / 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

from £60 / night

£420 - £630 / week

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from £60 / 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
“Excellent” Brilliant home. Well equipped. Great pool deck and jacuzzi. We got the sun all day and found the pool deck very private. The covered patio is good for shade. The location was perfect as close to all the attractions. Good restaurants c  …see more

from £108 / night

£716 - £1036 / week

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from £108 / 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
“Lovely villa, great service and excellent location for all the Disney parks!” Definitely recommended! From the moment I enquired about the villa, (we dealt directly with the owner) we received excellent service. Booking was easy, and we were supplie  …see more

from £90 / night

£580 - £775 / week

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from £90 / 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 £156 / night

£1036 - £1676 / week

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from £156 / night

(20) Excellent 

56

Kissimmee holiday villa rental

Kissimmee / Crescent Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Great villa, everything you need” Villa was spacious, immaculately clean and had everything you could possibly need. Pool kept kids more than occupied, fun gator spotting in the lake behind the house. Easy to get to the main routes to head off to park  …see more

from £107 / night

£750 - £900 / week

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from £107 / night

1