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  • United States
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  • Coral Cay (5)
  • Crestwynd Bay (1)
  • Crystal Cove Resort (3)
  • Emerald Isle Kissimmee (3)
  • Fiesta Key (1)
  • Formosa Gardens (3)
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  • Indian Point (1)
  • Kissimmee City (2)
  • Lake Berkley (1)
  • Legacy Dunes Resort (1)
  • Liberty Village (3)
  • Lindfields (2)
  • Paradise Palms (3)
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  • The Hamlets (1)
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  • Windsor Hills Resort (4)
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Also consider

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Lindfields
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Terra Verde Resort
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Villas Indian Creek
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Crescent Lakes
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Sunset Lakes
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Compass Bay
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Venetian Bay Villages
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Regal Oaks
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Encantada Resort
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Doral Woods
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Villas Formosa Gardens
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456 Holiday homes

Filters applied: Pets allowed (456)

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

(16) Very Good 

68

Gorgeous Palm Villa with a Pool and free WiFi!! - Lindfields villa sleeps 12

Kissimmee / Lindfields

5 12 1 night min

  • 5 bedrooms
  • Sleeps 12
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxurious Detached Villa- 5 Bedrooms - 3 Baths - (Sleeps 12)Simply the best location! Just a ten-minute drive from the Disney Theme parks but set in the quiet haven of the prestigious Lindfields Estate. This luxury villa sleeps up to 12 people and is beautifully furnish  …see more

from £70 / night

£410 - £495 / week

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from £70 / night

(6) 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 £70 / night

£485 / week

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from £70 / night

(5) Excellent 

55

Windsor Hills,own cinema room, Xbox one, free WiFi - Windsor Hills Resort villa sleeps 14

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Our Villa in Windsor Hills is a BEAUTIFUL custom designed home. Windsor Hills is a secure gated community that has all the amenities of a 5 star hotel or resort, but with the comfort, convenience, and privacy of staying in a high end home. Facilities Air Conditioning F  …see more

from £174 / night

£1212 / week

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from £174 / night

(1) Excellent 

19

4 bed/3bath 5 mins from Disney - Indian Creek villa sleeps 10

Kissimmee / Indian Creek

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This fantastic luxury, 4 bed 3 bath villa has just been totally redecorated to a high standard. With it's private, screened pool, removable child safety fence and large lanai - it's a perfect location to relax after a day at the theme parks or an 18 hole game  …see more

from £80 / night

£641 / week

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from £80 / night

(1) Excellent 

23

Fiesta Key vacation home - Fiesta Key townhouse sleeps 8

Kissimmee / Fiesta Key

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Kitchen- The kitchen is fully-equipped ready to meet your needs. American style fridge/freezer,electric oven,microwave,dishwasher,kettle,coffeemaker etc, Full set of crockery,cutlery and utensils. A true home from home. Master Bedroom-This is the prefect master bedroom  …see more

from £66 / night

£408 - £646 / week

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from £66 / night

16

Luxury 4 bed town house close to Disney parks - Kissimmee house sleeps 8

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 £89 / night

£620 / week

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from £89 / night

(12) Excellent 

34

Funshine Magical Villa with Gameroom and WiFi - Kissimmee City villa sleeps 9

Kissimmee / Kissimmee City

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~ YOUR DREAM VACATION RENTAL IN THE SUNSHINE CAPITAL IS HERE ... COME AND ENJOY: A Beautiful Sun Drenched 4 bedroom 2 storey fully a  …see more

from £100 / night

£666 - £847 / week

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from £100 / night

11

Awesome holiday villa near Disney - Indian Point villa sleeps 8

Kissimmee / Indian Point

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This newly refurbished villa and pool is ideal for Disney and Universal Holidays. It has a Super HD television, and an HD television in the two en-suite bedrooms. The Lanai is in a cage and faces West for warm lazy evenings by the pool after hard days enjoying the parks  …see more

from £114 / night

£792 / week

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from £114 / night

(5) Very Good 

74

holiday villa golf nearby WindsorHills Resort - Windsor Hills Resort villa sleeps 10

Kissimmee / Windsor Hills Resort

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Our 4 bedroom / 4 bathroom, newly built vacation home has a beautiful corner lot in the prestigious Windsor Hills Resort and has over 1800 sq ft of living space. Sleeping up to 8 people comfortably, our home boasts 1 king bedroom with ensuite, 1 queen bedroom with ensu  …see more

from £124 / night

£862 / week

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from £124 / night

(2) Excellent 

24

Home with 4 Bed/3 Baths at Berkley Resort 1204CL - Kissimmee house sleeps 8

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
Kissimmee vacation rental home in a beautiful gated community with 4 bedrooms, 3 Full Bathrooms, Private Pool with Lanai, Outdoor Shower, Patio Furniture & a lovely lake view.Big Screen TV, High Speed Internet, Games Room and full size Pool Table. TVs in 3 bedrooms,  …see more

from £87 / night

£604 - £1363 / week

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from £87 / night

(2) Very Good 

48

Florida Pearl, Beautiful Vacation Home with Wireless Internet - Indian Creek villa sleeps 10

Kissimmee / Indian Creek

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located just 3 miles west of Disney's main entrance, the Florida Pearl is in the Indian Creek subdivision. This single story house has 5 bedrooms, 3 bathrooms, a large pool/spa and games room.The home sleeps 10 plus 2 babies in perfect comfort. A king bed in the ma  …see more

from £90 / night

£630 / week

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from £90 / night

19

Wonderful 6 beds, 3 ½ baths Cumbriam Lakes 4826CL - Kissimmee house sleeps 12

Central Florida / Kissimmee

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Air conditioning
  • Ask about pets
Wonderful 6 beds, 3 ½ baths vacation home, approximately 3,282 square feet, with enclosed pool. The perfect place to relax after a long day at the parks.This beautiful pool home is located in the Cumbrian Lakes area of Kissimmee resort community located approx. 12 mi  …see more

from £108 / night

£754 - £1239 / week

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from £108 / night

(1) Very Good 

24

Spacious 6 bed/ 5.5bath in BellaVida Resort 220LF - Kissimmee house sleeps 14

Central Florida / Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
Upscale 6 bed 5 1/2 baths home with enclosed pool and spa is the perfect place to relax after a long day at the parks.This beautiful pool home is 6 bedrooms 5 ½ bath, located in the most sought after gated resort community of Bella Vida about 10 miles from Disney World  …see more

from £124 / night

£862 - £1508 / week

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from £124 / night

24

Frozen Bedrom. Closest to Disney 6BR/4BA Pool/spa - Windsor Hills Resort villa sleeps 14

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Spread out and enjoy your very own sunny six bedroom, four bathroom villa in Windsor Hills Resort. Best of all, it is only two miles to Walt Disney World!NO REAR NEIGHBOURS! To ensure your privacy, we chose a premium location that overlooks a natural area, not another h  …see more

from £177 / night

£1154 - £2000 / week

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from £177 / night

37

Luxury Detached Villa with Private Pool - Kissimmee villa sleeps 8

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Fantastic villa set on a beautiful lakeside plot overlooking a conservation area. Extended, south facing pool deck provides a place to relax and enjoy a swim in your own private pool. Enjoy free wi-fi, and free calls within the US. Property is situated just south of Hig  …see more

from £65 / night

£425 - £530 / week

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from £65 / night

13

3bed/2bath Home in Resort Bella Vida 1020LF - Kissimmee house sleeps 10

Central Florida / Kissimmee

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Child friendly
This wonderful townhome has 3 bed and 2 1/2 bath and can accommodates up to 10 people.Imagine you and your family relaxing by your private pool with your favorite cocktail or join in at the fantastic resort pool and spa. For those with energy to spare, work out in the w  …see more

from £89 / night

£620 - £1024 / week

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from £89 / night

16

Home with heated pool by Disney Parks 851LF - Kissimmee house sleeps 8

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Air conditioning
  • Ask about pets
Delightful townhouse with 4 bedrooms and 3 bathrooms, located just 10 minutes from Disney Parks! This lovely home has a large living space with 1,856sq. A large east facing heated pool with sizes of 26x13' and a 6' depth with a lake view in the back.If you are  …see more

from £100 / night

£700 - £1224 / week

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from £100 / night

20

Amazing 6 bed home in beautiful Bella Vida 4584ML - Kissimmee house sleeps 12

Central Florida / Kissimmee

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Ask about pets
Amazing 6 bedroom vacation rental located in the prestigious BellaVida Resort. The villa features 2 traditionally decorated living rooms, a large open plan fully equipped kitchen with a breakfast bar with seating for up to 3 people, a dining area, a games room with a l  …see more

from £173 / night

£1207 - £1842 / week

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from £173 / night

16

Venetian Bay Townhome - Venetian Bay Villages townhouse sleeps 8

Kissimmee / Venetian Bay Villages

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Excellent 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 spacious  …see more

from £74 / night

£512 - £700 / week

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from £74 / night

(2) Very Good 

35

Central Florida / Kissimmee

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Car not necessary

 …see more

from £74 / night

£493 / week

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from £74 / night

(1) Excellent 

21

5 bedroom Villa, with pool, in Kissimmee, Florida. - The Hamlets villa sleeps 10

Kissimmee / The Hamlets

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Villa's situated in a gated community 6m / 10km from Disney World. Close to Highway 192 with all local amenities & restaurants, Near I-4 interstate and within easy reach of Orlando Int'l Airport . 5 double bedrooms inc'l a downstairs en-suite bedroom.  …see more

from £108 / night

£750 - £1000 / week

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from £108 / night

11

Westgate Vacation Villas - Formosa Gardens villa sleeps 10

Kissimmee / Formosa Gardens

2 10 Min stay varies

  • 2 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Very comfortable villa with loft, located on Westgate Vacation Villas Resort - Kissimmee, minutes away from all Orlando Theme parks. The villa has a king size bed, 2 double beds, 2 Twin Beds in the Loft and a Queen Sleeper Sofa in the living area. It also has a Fully Eq  …see more

from £185 / night

£1089 - £1231 / week

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from £185 / night

11

Westgate Vacation Villas - Formosa Gardens villa sleeps 10

Kissimmee / Formosa Gardens

2 10 7 nights min

  • 2 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This is a really spacious loft villa that feature a king-size bed in the master bedroom with private bathroom and jetted tub, two double beds in the second bedroom, second bathroom with shower/tub combination, two twin beds in the loft, queen sleeper sofa in the separat  …see more

from £150 / night

£1050 / week

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from £150 / night

(57) Excellent 

20

Trip Advisor - Award Winning Villa for Three Years - Formosa Gardens villa sleeps 22

Kissimmee / Formosa Gardens

7 22 4 nights min

  • 7 bedrooms
  • Sleeps 22
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
WOW!! Even the other villa owners say this about our home, If you are looking for the best go no further. This is strictly for you sun-seekers, as apart from visiting the Mouse; the sun after all is another great reason to visit Florida. This home has a elegantly shaped  …see more

from £305 / night

£2135 / week

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from £305 / night

78

4 Bed/4Bath At The Beautiful Windsor Hills 7718CS - Kissimmee house sleeps 8

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
This lovely 4 Bedroom home is located at Windsor Hills Resort, which is a gated community with a security gate that is guarded 24 hours per day only 2 miles from Disney, 20 minutes from Universal Studios theme park and Sea World. Great beaches are just an hour awayThere  …see more

from £118 / night

£824 - £1266 / week

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from £118 / night

24

Luxury Vacation Home in Florida 4574ML - Kissimmee house sleeps 12

Central Florida / Kissimmee

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Air conditioning
  • Ask about pets
Upscale 6 bedrooms, 5 1/2 baths home with enclosed pool and spa is the perfect place to relax after a long day at the parks.This beautiful pool home is located in the most sought after gated resort community of BellaVida; located 9 miles from Disney World.This home will  …see more

from £162 / night

£1131 - £1697 / week

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from £162 / night

18

Townhome in Terra Verde Resort! 111PB - Kissimmee house sleeps 10

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Air conditioning
  • Ask about pets
This Beautiful townhome has 4 bed and 3 Bath that can accommodates up to 10 people.Relax by your private pool with your favorite cocktail or join in at the fantastic resort pool and spa. For those with energy to spare, work out in the well equipped fitness center or hav  …see more

from £87 / night

£604 - £1077 / week

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from £87 / night

67

Luxurious Reunion Home - 5 Bed 5 Bath - 768DM - Kissimmee house sleeps 10

Central Florida / Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Air conditioning
  • Ask about pets
* Brand-new home* This lovely 5-bedroom, 5.5-bathroom vacation home is located in the Fairway Ridge North section of Reunion® Resort's Westside community and offers breathtaking views of the 8th hole of The Tradition™ golf course by Jack Nicklaus.This spacious h  …see more

from £253 / night

£1765 - £2860 / week

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from £253 / night

(26) Excellent 

14

Central Florida / Kissimmee

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £66 / night

£458 / week

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from £66 / night

19

Central Florida / Kissimmee

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets

 …see more

from £100 / night

£700 - £1562 / week

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from £100 / night

9

Central Florida / Kissimmee

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Ask about pets

 …see more

from £70 / night

£485 / week

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from £70 / night

18

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £93 / night

£647 / week

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from £93 / night

(39) Excellent 

100

Central Florida / Kissimmee

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 124 km
  • Swimming pool
  • Child friendly

 …see more

from £74 / night

£443 / week

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from £74 / night

16

Central Florida / Kissimmee

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

 …see more

from £207 / night

£1449 - £2122 / week

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from £207 / night

(2) Very Good 

15

Central Florida / Kissimmee

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £54 / night

£366 / week

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from £54 / night

21

Central Florida / Kissimmee

4 12 3 nights min

  • 4 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £61 / night

£426 / week

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from £61 / night

26

Central Florida / Kissimmee

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Nearest beach 116 km
  • Swimming pool
  • Child friendly

 …see more

from £77 / night

£462 / week

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from £77 / night

100

Central Florida / Kissimmee

8 20 1 night min

  • 8 bedrooms
  • Sleeps 20
  • 1 night min
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £215 / night

£1461 / week

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from £215 / night

15

Central Florida / Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

from £88 / night

£614 - £1314 / week

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from £88 / night

(6) Excellent 

21

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £77 / night

£462 / week

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from £77 / night

Top Destination reviews

One of the closest communities to Disney!
Close to Disney, a villa that caters for everyone!

We stayed here with our 8 year old in July 2016. From the time we booked to the time we returned Tracey (the owner) could not have been more helpful. Emails responded to promptly, very thoughtful communication and information throughout. We arr … see more
holiday villa golf nearby WindsorHills Resort
Lovely villa

Very good if you are visiting Disney parks they are very close by. The villa was in a very nice neighbourhood also it was well maintained. Also the security gates made us feel very secure. Slightly further away from International Drive area but … see more
Lovely Kissimmee Home with Gameroom and Pool
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 homely touches,oth … see more
DORAL WOODS SECLUDED VILLA
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 private, safe with a real florida f … see more
Tuscany Private Villa Rental with Terrace in Kissimmee
Great villa

Lovely quiet area, this villa was just what we wanted. it was clean and spacious and the game room kept the kids entertained. Would definitely stay here again. … see more
Disney Lakeside Villa with WiFi and a Pool, Kissimmee
Fantastic!

This was like home from home , clean , beautiful furnished,very relaxing, child friendly, lovely veiws from pool ect, can't wait to go back. … see more

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