Kissimmee Villas, Holiday rentals and apartments

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Kissimmee

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4,230 Holiday homes

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

(1) Excellent 

32

Villa rental in Kissimmee with shared pool, golf nearby

Kissimmee / Vista del lago

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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

£455 / week

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from £50 / night

20

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Villa, Private Pool, Spa, Sleep 19, Resort Clubhouse, Kitchen, Game room, Xbox360, Heated Pool, BBQ Grill, 8 Bedrooms, 4.5 Bathrooms, Free WIFI, Cable TV, Game Room, Near Disney  …see more

from £276 / night

£1260 - £2512 / week

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from £276 / night

9

Holiday townhouse in USA East Coast

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 £75 / night

£524 - £717 / week

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from £75 / night

84

Holiday villa rental

Central Florida / Kissimmee

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This luxury 4 bedroom and 3 bathroom villa is located in the established community of Oak Island Cove. This location is probably one of the closest to Disney World's' main gate and within walking distance ( 5 mins) to shopping and the many great restaurants situated on  …see more

from £95 / night

£599 - £875 / week

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from £95 / night

(1) Excellent 

43

Holiday townhouse in Kissimmee

Central Florida / Kissimmee

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Nearest beach 114 km
  • Swimming pool
  • Child friendly
This is a luxurious stunning spacious modern 3 bedroom, 2.5 Bathroom Townhouse two-storey. As you enter the home you are greeted by light, bright and airy open feel of the home is the perfect base for a relaxing, stress free vacation, situated by a 3-acre lake view from  …see more

from £75 / night

£525 / week

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from £75 / night

(5) Excellent 

24

Holiday villa with swimming pool in Kissimmee

Kissimmee / Cumbrian Lakes

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Cumbrian Lakes is an exclusive gated community with lakes, cycling & walking trails & a kids play area.  …see more

from £100 / night

£700 - £1050 / week

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from £100 / 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 - £525 / week

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from £75 / night

23

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £78 / night

£546 - £767 / week

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from £78 / night

24

Holiday villa in Kissimmee

Kissimmee / Rolling Hills at Formosa

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The house has four bedrooms, two bathrooms and its own pool. It is located just a few minutes' drive from all of Florida's attractions: Disney World, Universal Studios, Splendid China, Sea World etc. It is the ideal starting point for day trips to the Atlantic coast or  …see more

from £79 / night

£546 - £672 / week

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from £79 / 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 £36 / night

£252 / week

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from £36 / night

(2) Excellent 

16

Holiday villa in USA East Coast

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 £119 / night

£827 / week

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from £119 / night

(3) Very Good 

43

Holiday villa rental

Kissimmee / Emerald Isle Kissimmee

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This luxurious 4 bed/3 bath villa is located on the prestigious Emerald Island Resort just 5 minutes from Disney and 2 mins from shops and restaurants. We are 30 mins drive from Orlando International Airport and under 1 hour from Sanford Airport.  …see more

from £70 / night

£490 - £610 / week

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from £70 / night

23

USA East Coast holiday villa rental

Kissimmee / Emerald Isle Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Emerald Island Resort offers many community features and stands above the rest in offering luxurious villas.  …see more

from £178 / night

£1182 - £2205 / week

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from £178 / night

(6) Very Good 

12

Holiday villa rental

Kissimmee / Lindfields

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Large property, sleeps eight fully equipped kitchen with ice making fridge. Large enclosed pool, games room, Linen and towels provided. 10 minutes drive from Disney and close to main attractions. Basic supplies for cleaning.  …see more

from £60 / night

£420 - £525 / week

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from £60 / night

(3) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Kissimmee City

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Indian Ridge Oaks is a quiet, sought after development with a lovely mix of local Floridian families and rental properties. The villa is not near any main roads to be bothered by traffic noise but near to the theme parks and interstates to make this a fantastic location  …see more

from £110 / night

£549 - £700 / week

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from £110 / night

(18) Excellent 

24

Home rental in USA East Coast

Kissimmee / Bellavida Resort

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“East 192, Where Tink@Bella waits for Youuuuuuu” The Bella Vida resort is a Great, Gated Community. Where inside awaits the the Fantastic Tink@Bella Villa. Approx 30 mins from Orlando Int. Perfect location for all that awaits you, Disney, Universal,  …see more

from £143 / night

£995 - £1395 / week

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from £143 / night

(2) Excellent 

20

Holiday townhouse in Kissimmee

Kissimmee / Encantada Resort

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Child friendly
  • Air conditioning
Nice resort very close to Disney World.  …see more

from £99 / night

£630 / 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 amenities al  …see more

from £69 / night

£449 - £589 / week

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from £69 / night

(3) Excellent 

21

Villa rental in Kissimmee

Kissimmee / Indian Ridge

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our private south facing pool is solar heated and enclosed within a 6ft high fenced garden with a forested area to the rear providing total privacy. The pool is fully screened and equipped with a range of upholstered poolside furniture and a lanai for shade. All doors  …see more

from £115 / night

£685 - £900 / week

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from £115 / night

32

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Delightful townhouse with 4 bedrooms and 3 bathrooms, located just 10 minutes from Disney Parks! This lovely home has a large living space. If you are looking for the perfect base for your Florida holiday, then look no further than this amazing 4 bedroom home. Set on th  …see more

from £87 / night

£607 / week

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from £87 / night

(20) Excellent 

21

Holiday bungalow with shared pool in USA East Coast

Kissimmee / Vista del lago

3 7 4 nights min

  • 3 bedrooms
  • Sleeps 7
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We would not stay anywhere else in Orlando” This is our second stay here and the Owners are more than helpful with any query you have and will go out of their way to ensure your stay is the best it can possibly be. The Villa is fully kitted out with  …see more

from £45 / night

£315 - £363 / week

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from £45 / night

16

USA East Coast holiday condo rental

Kissimmee / Legacy Dunes Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Gorgeous fully furnished 4 bed 2 bath corporate rental apartment Orlando, FLLocation: Legacy DunesAbsolutely gorgeous, 4-bed, 2-bath condo located in the fabulous Resort Style privately gated community of Legacy Dunes. It comes fully furnished to accommodate 8 persons v  …see more

from £75 / night

£475 - £850 / week

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from £75 / night

(7) Very Good 

24

Holiday home in USA East Coast

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

(3) Excellent 

30

Kissimmee holiday villa let

Kissimmee / Lindfields

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“The Perfect home in the Perfect location” The only word to describe this beautiful well maintained home is 'wow' I would say it was like a home from home, only much better. Everything has been thought of to ensure a comfortable stay. The pool is super  …see more

from £65 / night

£410 - £595 / week

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from £65 / 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 £113 / night

£789 / week

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from £113 / night

(2) Excellent 

17

Kissimmee holiday villa rental

Kissimmee / Lake Berkley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
We proudly present our Executive Villa located at the “Lake Berkley USA” Kissimmee, Florida. All on one floor. Convenient for guests with disabilities, elderly guests and guests with young children. Our Villa has been fully furnished to cater for all your needs. Th  …see more

from £79 / night

£591 - £749 / week

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from £79 / night

25

Home rental in Kissimmee with swimming pool

Central Florida / Kissimmee

4 6 2 nights min

  • 4 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Very nice 4 Bed home with 3 Baths, located at Windsor Palms Resort, close to 192 and to many restaurants and markets. a few minutes from Disney Parks, only 3 miles away. 15 minutes away from Universal Studios and 20 min away from Outlet Premium. Excellent clubhouse with  …see more

from £104 / night

£728 / week

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from £104 / night

11

Holiday villa in USA East Coast

Kissimmee / Indian Point

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Fabulously refurbished villa with four bedrooms and three bathrooms, and also a poll. It is close to Disney, Universal, Seaworld. The Orlando Eye, Downtown Kissimmee, and Disney Marketplace.  …see more

from £116 / night

£811 / week

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from £116 / night

(9) Excellent 

24

Holiday villa in USA East Coast

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) Very Good 

23

Holiday villa with swimming pool in Kissimmee

Kissimmee / Lindfields

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Lindfield is one of the closest areas to Disney  …see more

from £85 / night

£595 - £735 / week

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from £85 / night

14

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
This 4 Bedroom 3 Bathroom home, in the well sought after Terra Verde Resort ,in Kissimmee, is a very spacious villa. Ideal for two families to share as there are two Master Bedrooms and 2 sitting areas. The two twin bedrooms share a Jack and Jill bathroom.There is also  …see more

from £100 / night

£700 - £910 / week

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from £100 / night

(3) Very Good 

12

Holiday home rental

Kissimmee / Emerald Isle Kissimmee

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Crystal Cove Gem is located in the fabulous Emerald Island Resort the nearest gated community to from Disney World.Only 3 miles from Disney World  …see more

from £50 / night

£700 / week

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from £50 / 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

(9) Excellent 

88

Kissimmee holiday villa rental

Kissimmee / Bellavida Resort

6 14 5 nights min

  • 6 bedrooms
  • Sleeps 14
  • 5 nights min
  • Nearest beach 111 km
  • Swimming pool
  • Child friendly
“Our vacation in Florida 2014” The location of the property was ideally suited for our planned vacation. The size and facilities were extremely good and especially with 6 adults & 4 children it worked perfectly with each family. The kitchen lent itsel  …see more

from £170 / night

£1186 - £1571 / week

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from £170 / night

(1) Excellent 

49

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
~HUGE SECLUDED WATERFRONT VILLA~ Absolute privacy ~ Large pool deck surrounded by native plants and not overlooked Extended pool deck with luxury furniture ~ Large lanai for al fresco dining Fabulous pool and relaxing spa Fish from the end of our garden  …see more

from £125 / night

£895 - £1565 / week

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from £125 / night

(7) Excellent 

48

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Exceeded Expectations” We just got back (May 2013) from a stay at Emerald Magic 6 bedroom villa at Emerald Island Resorts and had a wonderful stay. The house was even better then expected when we arrived. Nice welcoming touches everywhere. Lots of tow  …see more

from £189 / night

£1339 - £2205 / week

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from £189 / night

(4) Excellent 

23

Holiday villa in USA East Coast

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Spacious House” The house was great very spacious and all 12 of us enjoyed it very much. The downside of getting to a property after being delayed for over 2 hours was it was late at night and other properties we had rented before left us a welcome  …see more

from £158 / night

£1103 / week

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from £158 / 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 £104 / night

£728 / week

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from £104 / night

21

Holiday home in Kissimmee

Central Florida / Kissimmee

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A stunning, larger than average, 6 Bed 3.5 Bathroom villa with a fantastic private pool. This villa is located in the 5 stars resort of Lake Berkley. The villa is furnished and maintained to a very high standard. The villa is spaciously arranged over two levels, makin  …see more

from £126 / night

£863 - £965 / week

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from £126 / night

(6) Excellent 

18

Condo rental in USA East Coast

Central Florida / Kissimmee

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Top rated in trip advisor condo 10 mins away for Disney currently voted 2 in whole area. Spacious, quality nothing better  …see more

from £118 / night

£780 / week

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from £118 / night