Kissimmee apartment or villa with a heated pool

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1,356 Holiday homes

Filters applied: Heated pool (1,358)

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

(11) Excellent 

69

Luxury Home near Disney and Golf Courses at Fiesta - Fiesta Key townhouse sleeps 8

Kissimmee / Fiesta Key

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 115 km
  • Swimming pool
Our lovely home is in the secure community "Fiesta Key", 15 mins. from Disney & Universal theme parks. Busch Gardens 1h 20m. Daytona Beach 1h 40m. Castillo de San Marcos, 2h 50m. South Beach Miami & Evergaldes, 3h 30m. Key West, 6h 30m. Kennedy Space Center, 1h 15m. Ame  …see more

from £31 / night

£343 - £404 / week

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from £31 / 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

(20) Excellent 

27

Sun Palm - 5 star Disney executive villa. - Windsor Palms villa sleeps 8

Kissimmee / Windsor Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
- The villa has two Master en-suite bedrooms and two further bedrooms with twin beds. These bedrooms share a third bathroom. One of the twin Bedrooms is a Disney themed room. The main bedroom has its own dressing room and has direct access to the pool (via a safety fe  …see more

from £112 / night

£762 - £1154 / week

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from £112 / night

(15) Excellent 

48

Beautiful Kissimmee Townhome at Fiesta Key - WIFI - Kissimmee townhouse sleeps 8

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 104 km
  • Swimming pool
  • Child friendly
Our Orlando Vacation Home, 'CABALLERO' is a beautiful Spanish influenced fully equipped home in the exclusive Fiesta Key Resort - ideally situated within easy reach of all the major Orlando theme parks, attractions, shops and restaurants. Just 20 minutes drive to Disney  …see more

from £42 / night

£294 / week

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from £42 / night

32

Central Florida / Kissimmee

3 6 Min stay varies

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

 …see more

from £61 / night

£426 - £534 / week

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from £61 / night

(8) Very Good 

60

Lovely Lake Berkley Villa with a Gameroom and Hot Tub - Lake Berkley villa sleeps 10

Kissimmee / Lake Berkley

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
South Facing Pool!!!!Luxury 5 Bedroom Villa in Lake Berkley gated communityOne storey villa situated in the prestigious Lake Berkley Resort gated community. South facing pool and spa for all day sun. This is a basic must in Florida. Why go to the sun in order to sit in  …see more

from £100 / night

£600 - £1200 / week

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from £100 / night

(4) Excellent 

98

THE HAVEN IN EMERALD ISLAND RESORT - Emerald Isle Kissimmee house sleeps 8

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 96 km
  • Swimming pool
  • Child friendly
In our house, fell like you are at home, with the comfort of a King suit and an attached bathroom with garden tub and 3 more bed : queen bed and fully attached bathroom and kids rooms with 2 twin beds in each and their own bathroom to share. Enjoy the heated swimming po  …see more

from £77 / night

£539 - £970 / week

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from £77 / night

(10) Very Good 

46

Magical Vacations Pool Villa with A/c'd Games Room - Indian Point villa sleeps 10

Kissimmee / Indian Point

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Indian Point is an attractive and peaceful residential development only ten minutes drive from the Disney World theme parks and centrally located within easy reach of the other Orlando attractions. US192, famous for its glittering array of attractions, restaurants and s  …see more

from £75 / night

£525 - £700 / week

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from £75 / night

19

Kissimmee / Indian Creek

4 8 4 nights min

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

 …see more

from £130 / night

£910 / week

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from £130 / night

(4) Very Good 

22

Florida Jewels - Emerald Isle Kissimmee villa sleeps 10

Kissimmee / Emerald Isle Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
We offer a beautifully furnished villa on Lido Key Drive. It is 1935 Sq ft and has 4 bedrooms 3 bathrooms.A south westerly facing extended pool deck with raised spa and childs safety fence, the pool deck is 40' x 21' with the pool being 26' x 12' wi  …see more

from £90 / night

£630 - £835 / week

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from £90 / night

(5) Excellent 

23

3 Bedroom Villa in Country Creek, Kissimmee - Country Creek villa sleeps 6

Kissimmee / Country Creek

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our beautiful family owned villa is located only 10 mins from WDW and close to many other attractions such as Sea World, Aquatica, Universal Studios and Universal Islands of Adventure. Our home from home is comfortably furnished and equipped with all the amenities to m  …see more

from £70 / night

£550 - £650 / week

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from £70 / night

24

Elegant Pool/Spa Villa Near Disney - Emerald Isle Kissimmee villa sleeps 16

Kissimmee / Emerald Isle Kissimmee

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
Only 3 miles to Disney, 14 miles to SeaWorld, 17 miles from Universal Studio and easy access to all major theme parks, this lovely 8 bedroom 4.5 bath heated pool/spa villa is located on the prestigious Emerald Island Resort, a beautiful community with 24/7 guarded gate.  …see more

from £231 / night

£1000 - £2405 / week

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from £231 / night

(1) Excellent 

17

5 Bed, 3 Bath,Pool, Spa,Games - Kissimmee villa sleeps 12

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This spacious, five bedroom, three bath, luxury villa with optionally heated private Pool Spa and Games Room with Pool Table, Air Hockey Table and Football Table, is situated on the exclusive EMERALD ISLAND RESORT (The nearest to Disney). It is located just three miles  …see more

from £115 / night

£700 - £1120 / week

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from £115 / night

(6) Excellent 

18

Lighthouse Keys Spa and resort - Kissimmee condo sleeps 8

Central Florida / Kissimmee

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our condo is located in Kissimmee within the community of lighthouse Keys It is constantly in the top two for accommodation in the area on trip advisor. Ultimate in luxury and can sleep 6 comfortably and up to eight. Perfect for family holiday, golf trip. Fifteen minu  …see more

from £115 / night

£762 / week

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from £115 / night

23

Spacious Private Pool/Spa Villa Near Disney - Emerald Isle Kissimmee villa sleeps 17

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Our Spacious 8 bedroom pool/spa villa is located at prestigious Emerald Island Resort, a gated community with 24/7 security guard at gate and only 3 miles away from World Disney. Emerald Island Resort featured with its own clubhouse sauna, fitness center, video games ar  …see more

from £270 / night

£1231 - £2454 / week

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from £270 / night

(1) Excellent 

52

Cumbrian Lakes gated community Villa - Cumbrian Lakes villa sleeps 12

Kissimmee / Cumbrian Lakes

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A Spacious 6 bedroom, 4 1/2 bathroom Vacation Home with private pool for your enjoyment. In the popular gated community of Cumbrian Lakes, only 15 minutes to the entrance to Disney World, 5 minutes more to Seaworld & another 10 minutes to Universal Studios. This home wi  …see more

from £45 / night

£315 / week

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from £45 / night

(8) Very Good 

49

'Nightingale House' Lake Berkley luxury villa - Lake Berkley house sleeps 10

Kissimmee / Lake Berkley

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
This family friendly, roomy and airy house/villa with private (heated) pool is well equipped and stylishly decorated to a very high standard. Local shops and restaurants are just minutes away. Disney, SeaWorld and Universal theme park complexes are all within easy acces  …see more

from £112 / night

£758 - £943 / week

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from £112 / night

23

Disney Magic II Villa by Emerald Island Rentals - Emerald Isle Kissimmee villa sleeps 16

Kissimmee / Emerald Isle Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
For those looking for the ultimate vacation rental experience, this is the right villa! Located in the tropical grounds of Emerald Island Resort near Disney World, this huge 7 bed villa villa offers outstanding amenities at affordable prices for parties of up to 16 gues  …see more

from £174 / night

£1154 - £2154 / week

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from £174 / night

(4) Very Good 

88

Sunny Seasons Vacation Rental with Wireless Internet - Seasons Resort villa sleeps 10

Kissimmee / Seasons Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our Villa is an Executive Luxury 5 bedroom villa sitated on the ever popular Seasons Estate in Kissimmee. Central for all that the fabulous state of Florida has to offer and within ten minutes drive of the Magical experience that is Disney World, Orlando. USA.Packed wit  …see more

from £95 / night

£625 - £840 / week

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from £95 / night

(8) Very Good 

50

Serendipity Florida, Charming Getaway with Wireles - Trafalgar Village villa sleeps 8

Kissimmee / Trafalgar Village

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Less than 15 miles from Walt Disney World, this villa offers a private backyard pool and hot tub (heated on request, fees payable). The 4-bedroom, 4 bathroomed house includes a fully equipped kitchen and spacious bedrooms with flat-screen TVs. Free Wi-Fi is available t  …see more

from £80 / night

£450 - £680 / week

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from £80 / 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

(6) Very Good 

21

Hideaway Villa - Terra Verde Resort villa sleeps 12

Kissimmee / Terra Verde Resort

5 12 5 nights min

  • 5 bedrooms
  • Sleeps 12
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Hideaway Villa is the perfect choice for the ultimate Disney family holiday - just 10 minutes east of Disney, on the exclusive gated community of Terra Verde. Conveniently located close to Walmart, Medieval Times and Olde Town. Hideaway Villa has 5 bedrooms, all with  …see more

from £97 / night

£679 - £808 / week

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from £97 / night

(1) Excellent 

13

Villa near Disney Florida w.Pool from $623/wk - Kissimmee City villa sleeps 8

Kissimmee / Kissimmee City

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
Disney Vacation Home Rentals -3Beds 2 baths Villa with Heated Pool $89-$109US/Night. .Located near Disney, this modern 3 Bed Room, 1400 square foot bungalow holds all the amenities that you would expect to have a wonderful relaxing vacation. This home features Master b  …see more

from £77 / night

£480 - £587 / week

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from £77 / night

(7) Excellent 

44

Gorgeous Vacation Home with WiFi, on Yellow Lantana Ln - Encantada Resort townhouse sleeps 10

Kissimmee / Encantada Resort

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Newly and Professionally Furnished 4 bedroom 3 bath town home with lake view, next to club house.This Entire Property has been Professionally updated and decorated and a short walk to the club house.This beautiful affordable townhouse has just been newly and professiona  …see more

from £93 / night

£620 - £754 / week

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from £93 / night

25

Mickeys Ritz at Veranda Palms - Veranda Palms villa sleeps 8

Kissimmee / Veranda Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 104 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 (30ft x 15ft) + spa, a south west facing pool deck with fabulous pool furnitur  …see more

from £99 / night

£690 - £905 / week

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from £99 / night

(1) Excellent 

20

Captain Hook's Haven in Paradise Palms Resort - Paradise Palms townhouse sleeps 10

Kissimmee / Paradise Palms

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
First floor consists of 892 sf with hallway, bathroom, king size bedroom, living room with dining area and a luxurious kitchen. Second floor has 888 sf including 3 bedrooms, 2 full bathrooms, washroom with washer and dryer and closet in the hallway for linens. The patio  …see more

from £77 / night

£500 - £862 / week

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from £77 / night

(8) Excellent 

14

Alberto Circle, Fun Vacation House with Pool - Bellavida Resort townhouse sleeps 6

Kissimmee / Bellavida Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Enjoy the fabulous climate and amenities of the Central Florida area without breaking the bank. This is a 3 bedroom townhouse, fully air conditioned, with private pool, conveniently located in the recently completed BellaVida resort in Kissimmee.The property is ideally  …see more

Pricing unknown

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(12) Very Good 

55

863 Assembly Court - Kissimmee townhouse sleeps 6

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in the upscale Reunion Resort, Carriage Pointe is an exclusive Luxury Townhouse Community adjacent to the 17th Hole Reunion Golf Course. This gated community, only 10 minutes from Disney and close to other theme parks. This 3 bedroom townhouse comfortably sleeps  …see more

from £70 / night

£490 - £560 / week

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from £70 / night

28

Condo at Legacy Dunes - resort amenities - Legacy Dunes Resort condo sleeps 10

Kissimmee / Legacy Dunes Resort

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 150 km
  • Swimming pool
Newly refurbished 4 bedroom/2 bathroom 1400 sq ft condo with screened balcony and view over the lawn to the children's playground and lake. Fantastic place for a large family or group vacation in Orlando! near all the attractions. Would suit the extended family with 2 d  …see more

from £60 / night

£400 - £600 / week

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from £60 / night

(7) Excellent 

22

4 bedroom home, south facing private pool - Cumbrian Lakes villa sleeps 8

Kissimmee / Cumbrian Lakes

4 8 6 nights min

  • 4 bedrooms
  • Sleeps 8
  • 6 nights min
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly
The villa has 4 bedrooms and 3 1/2 bathrooms, arranged to sleep 8 in comfort. The villa benefits from an oversized pie shaped plot with a south facing pool looking out to conservation woodland. The pool area, which is not overlooked, provides maximum daily exposure t  …see more

from £95 / night

£570 - £630 / week

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from £95 / night

(6) Excellent 

24

The Road to "Mandyville"- Fantastic 3 Bedroom Villa - Kissimmee villa sleeps 6

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
THE VILLA with it,s fully screened, south facing 30x15ft swimming pool with underwater lighting for evening swimming and has free solar heating with electronic control and electric heating for the winter months. The large deck with sun or shade is equipped with new luxu  …see more

from £67 / night

£465 - £525 / week

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from £67 / night

(2) Very Good 

29

The Seasons Villa, lake view and 4 master bedrooms - Seasons Resort villa sleeps 13

Kissimmee / Seasons Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
This luxury villa has all you need to enjoy a family vacation. You can sit at the pool or in the spa and watch the wildlife on the lake. There are no rear neighbours to worry about here. There is plenty of living space to spread out and relax in the lounge or take it ea  …see more

from £139 / night

£815 - £1481 / week

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from £139 / night

(4) Excellent 

24

Lazy Lake Villa, Cumbrian Lakes, Kissimmee - Cumbrian Lakes villa sleeps 10

Kissimmee / Cumbrian Lakes

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to our newly refurbished family 5 bedroom villa, situated in the exclusive Gated Community of Cumbrian Lakes.We have designed our villa with family and relaxation in mind5 bedrooms including Master bedroom with en-suite & balcony over looking the pool &  …see more

from £100 / night

£700 - £1050 / week

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from £100 / night

18

Family Vacation Home near Disney - Crescent Lakes villa sleeps 12

Kissimmee / Crescent Lakes

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Car not necessary
Why stay in a hotel / motel when you can experience a truly spacious accommodation? This villa has 6 bedrooms and 3 bathrooms on two levels. There is a large south facing swimming pool. The rear of the property is not overlooked as it has a high privacy fencing down b  …see more

from £93 / night

£650 - £800 / week

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from £93 / night

(7) Very Good 

26

7 Bed Executive Lakeside Villa with pool/games rm - Kissimmee villa sleeps 16

Central Florida / Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This recently refurbished luxury Villa is now available for bookings. This luxury villa will sleep up to 16 people and yet provides plenty of space. There are seven bedrooms and four bathrooms.This is an ideal location for your vacation.It has all the facilities you wil  …see more

from £70 / night

£485 / week

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from £70 / night

40

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £130 / night

£910 / week

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from £130 / night

(27) Very Good 

20

Indian Point Villa includes Wireless Internet and Gameroom - Kissimmee villa sleeps 10

Central Florida / Kissimmee

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Our home is a private owned Villa with games room , Pool and Hot-Tub/Spa in Florida, it is fully air conditioned with four bedrooms and two bathrooms, it is located in the community of Indian Point mainly to woods about 15 minutes from the Walt Disney theme parks and cl  …see more

from £87 / night

£604 - £693 / week

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from £87 / night

(6) Very Good 

56

DisneyDream Orlando Florida - Kissimmee apartment sleeps 6

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This is your luxury 3 bedroom 2 bathroom holiday home located in ' the 'VILLAS OF SOMERSET' complex, a quiet leafy location very central to every theme park in the Orlando area. Use all the facilities on the complex, Heated pool, Jacuzzi/hot tub, Sundeck,Clubhouse, G  …see more

from £49 / night

£343 - £549 / week

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from £49 / night

(7) Very Good 

75

Lake Berkley Family 5BR/3B SOUTH facing pool - Lake Berkley villa sleeps 10

Kissimmee / Lake Berkley

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 107 km
  • Swimming pool
Our luxury family villa is situated within the well established, prestigious Lake Berkley Community, perfectly located just off the US 192. This central, yet private location, within 16 minutes of Disney is also within strolling distance of local bars, restaurants and s  …see more

from £94 / night

£658 / week

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from £94 / night

(3) Excellent 

30

Chris and Elaine's Florida Home, Near Disney - Lindfields villa sleeps 6

Kissimmee / Lindfields

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Larger than average! -- Oversize heated pool fenced for privacy! -- Free wireless internet! -- Free long distance & overseas telephone calls! Our home is situated at Lindfields, a peaceful development to the west of Kissimmee, very close to the Disney Parks - very conv  …see more

from £65 / night

£410 - £595 / week

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from £65 / night

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