Holiday houses for rent in Kissimmee

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Kissimmee

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2,167 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.

(30) Excellent 

23

Holiday home with swimming pool in Oak Island Cove

Kissimmee / Oak Island Cove

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Ideally situated, beautifully kept property with everything you ever need, a home from home!” This was our first family holiday to Florida and the villa absolutely had everything we wanted to enjoy our holiday! Ideally situated with ease if access to  …see more

from £100 / night

£600 - £700 / week

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from £100 / 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 - £730 / week

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from £70 / night

(6) Excellent 

21

Trafalgar Village holiday home rental

Kissimmee / Trafalgar Village

5 12 3 nights min

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min
  • 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 £134 / night

£932 - £955 / week

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from £134 / night

Featured properties

(8) Excellent 

22

Holiday home with shared pool in Kissimmee

Kissimmee / Trafalgar Village

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
The Trafalgar Village community is centred around the luxurious Trafalgar Village Center (or Clubhouse), a 2 minute stroll from the property with amenities that include a man made beach and lagoon, lakes (stocked for fishing), a pool and games arcade room, a 48 seat mov  …see more

from £67 / night

£452 - £702 / week

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from £67 / 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

(8) 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

(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

(23) Very Good 

23

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

£550 - £3395 / week

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from £80 / night

(12) Excellent 

31

Kissimmee / Paradise Palms

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £109 / night

£932 / week

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from £109 / night

30

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
An immaculate, larger than average, 4 Bed 4 Bathroom villa. Built in 2011, all rooms in the villa are spacious and have been furnished and maintained to a very high standard. The villa has a south west facing private pool with an incredible lake view. The villa is spa  …see more

from £101 / night

£678 - £884 / week

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from £101 / night

(2) Very Good 

59

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

 …see more

from £113 / night

£791 / week

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from £113 / night

(14) Very Good 

29

Holiday home in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Superb stay close to Orlando and parks.” My family, together with my parents and sister in law stayed at this villa during the last week of December for 6 days. This was an excellent home, spacious and clean with all the amenities a villa should h  …see more

from £140 / night

£980 - £1400 / week

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from £140 / 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

17

Kissimmee holiday home rental

Central Florida / Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
GREAT LOCATION!! GAMEROOM, 2 MASTER SUITES, PROFESSIONALLY DECORATED!! Property Type: 5 Bedrooms, 4.5 Baths Private Pool Home Floor Area: 2800 sq ft Location: Veranda Palms, Kissimmee, Disney Area Professionally managed and fully furnished vacation home property with Pr  …see more

from £113 / night

£791 / week

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from £113 / night

(7) Very Good 

37

Kissimmee / Terra Verde Resort

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

 …see more

from £73 / night

£509 / week

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from £73 / night

(1) Excellent 

8

Holiday home in Kissimmee

Kissimmee / Lake Marion

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Self-catering condo with communal pool and free WiFi in the property, along with a full set of cable channels<br />Totally Renovated 2 Bed Family Home With Pool & Free Wi-Fi  …see more

from £35 / night

£250 / week

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from £35 / night

57

Central Florida / Kissimmee

6 16 Min stay varies

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £201 / night

£1417 - £1858 / week

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from £201 / 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

(8) Very Good 

49

Home rental in Kissimmee

Kissimmee / Lake Berkley

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“Our stay in Florida was made that much more enjoyable staying here” 995 Lake Berkley Drive, was a great place for us to stay during our recent two week trip to Florida. The estate itself is very impressive, clean and well maintained. A safe and secure  …see more

from £121 / night

£819 - £988 / week

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from £121 / night

16

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
We are ideally located for the numerous Florida attractions including Disney, Universal Studios, and Seaworld. For golfers the townhouse is ideally located with many fantastic courses within easy reach, with the closest being Falcons Fire Golf Club and Celebration Golf  …see more

from £93 / night

£650 / week

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from £93 / night

(32) Excellent 

20

Holiday home in Crescent Lakes

Kissimmee / Crescent Lakes

4 11 3 nights min

  • 4 bedrooms
  • Sleeps 11
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Amazing property!” This property really is as amazing as the photos show! Andy offers great communication before, during and after the stay, and it really is a fantastic place to stay. We visited Universal Studios and Wet'n'Wild and it's about a 20  …see more

from £89 / night

£620 / week

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from £89 / night

(3) Excellent 

24

Holiday home in Crescent Lakes

Kissimmee / Crescent Lakes

4 8 6 nights min

  • 4 bedrooms
  • Sleeps 8
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Large Deck and Lanaii ,private pool not overlooked .Tiled floors all rooms except Family room  …see more

from £90 / night

£580 - £748 / week

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from £90 / night

10

Holiday home rental

Central Florida / Kissimmee

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Near Disney and all the parks , very close to lots of shopping and restaurant's . Great choice of golf course 's ,and guaranteed lots of sunshine .Only 30 minute drive from Orlando International Airport.. The complex has security 24 / 7 , and no problem wi  …see more

from £73 / night

£484 / week

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from £73 / night

29

Kissimmee holiday home rental

Central Florida / Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A stunning, larger than average, 5 Bed 4 Bathroom villa with a beautiful view of the conservation area at the rear as background of our private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard. The villa is located  …see more

from £109 / night

£746 - £1045 / week

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from £109 / night

(4) Very Good 

100

Kissimmee holiday home rental

Central Florida / Kissimmee

4 10 6 nights min

  • 4 bedrooms
  • Sleeps 10
  • 6 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Beautiful sunsets and a fabulous vacation home” We choose Star Lake View as we were looking for a nice lakeside view as we were not disappointed. The views of the sunset were gorgeous and we loved spotting all the wild birds. The villa was immacula  …see more

from £90 / night

£585 / week

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from £90 / 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

(2) Excellent 

61

Holiday home in Venetian Bay Villages

Kissimmee / Venetian Bay Villages

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Why stay in a hotel when you can have all the comforts of your own home away from home in our beautiful new townhome in a dream location, close to the theme parks and the attractions of Orlando and Central Florida.Our home is clean, comfortable and just where you ne  …see more

from £60 / night

£385 / week

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from £60 / night

(7) Excellent 

25

Kissimmee / Lucaya Village

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £93 / night

£783 / week

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from £93 / night

(6) Excellent 

24

Holiday home in Kissimmee

Kissimmee / Tuscany, Florida

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Wonderful holiday in a fantastic Villa!” This was our second family holiday to Orlando so we had an idea of what we were looking for from a villa and a location close to the parks. We considered a number of possible options before settling on Luce Del  …see more

from £115 / night

£805 - £980 / week

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from £115 / night

(1) Excellent 

18

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £107 / night

£746 / week

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from £107 / 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 £202 / night

£1412 - £2299 / week

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from £202 / 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 £137 / night

£955 / week

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from £137 / 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

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 £89 / night

£605 - £722 / week

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from £89 / night

(2) Excellent 

53

Kissimmee holiday home rental

Central Florida / Kissimmee

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Funtastic Retreat - 8 Bedroom Villa Getaway! You cannot beat this amazing 8 bedroom luxury pool home at Central Florida's newest and most exciting luxury resort in the Walt Disney World area! Your guests will love choosing their own perfect bedroom from the 2 grou  …see more

from £343 / night

£1936 - £3388 / week

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from £343 / 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 £210 / night

£1468 / week

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from £210 / night

(3) Very Good 

92

Cumbrian Lakes holiday home rental

Kissimmee / Cumbrian Lakes

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“This place is amazing” We stayed here for a week after a tiring but fun road trip and as a base station for the theme parks! It was exactly what we needed for a group of 7 friends! Good location for the parks, lovely area and amazing view of the sunse  …see more

from £195 / night

£1365 / week

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from £195 / night

22

Kissimmee holiday home rental

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Spacious single storey pool home located in the heart of Kissimmee, just minutes to 192 where many restaurants, banks, shopping plazas and supermarkets are located. A short drive and you are at Walt Disney World Gates, 20 minutes from Universal & Island of Adventure  …see more

from £97 / night

£678 - £79033 / week

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from £97 / night

25

Home rental in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 93 km
  • Swimming pool
  • Child friendly
Mickey's Ritz at Veranda Palms is a private vacation home providing spacious accommodation with luxury, upgraded contemporary furnishings. The home has 4 bedrooms, 3 bathrooms, a large pool + spa , a west facing pool deck with fabulous pool furniture, and a fully f  …see more

from £104 / night

£723 - £949 / week

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from £104 / night

(3) Excellent 

100

Kissimmee / Paradise Palms

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 103 km
  • Swimming pool
  • Child friendly

 …see more

from £97 / night

£678 / week

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from £97 / night