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Also consider

Emerald Isle Kissimmee
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Lindfields
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Bellavida Resort
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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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Venetian Bay Villages
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Regal Oaks
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2,604 Holiday homes

Filters applied: Non-Smoking property (2,607)

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

(8) Excellent 

14

Stunning Lake View Resort Townhouse - Terra Verde Resort townhouse sleeps 6

Kissimmee / Terra Verde Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This 3 bed townhome has a large patio area with private Hot Tub and lake view. It has recently been upgraded with new paint, tile and wooden flooring. Stainless steel appliances have also been added to the kitchen. There is a dining table to seat 6 and the living area h  …see more

from £80 / night

£560 - £700 / week

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from £80 / night

(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

42

Minion Cove - Windsor Hills Resort condo sleeps 6

Kissimmee / Windsor Hills Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
3 Bedroom 2 Bathroom Condo Sleeps 6 Welcome to Minion Cove, our 3 bedroom 2 bathroom condo located in the beautiful 5 star gated community of Windsor Hills located less than 2 miles from the main gates of Walt Disney World. Windsor Hills is one of the newest and greates  …see more

from £66 / night

£424 - £916 / week

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from £66 / night

(9) Excellent 

24

Palm Tree Villa Florida, 5 Star Review Rating. - Doral Woods villa sleeps 8

Kissimmee / Doral Woods

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Palm Tree Villa Florida, is tucked away in the much sought after location of Doral Woods. This large 4 Bedroom, 3 Bathroom villa, is ideal for making the perfect vacation. This is our own holiday home, so the furnishings are to a high standard, as you can see from the  …see more

from £100 / night

£695 - £875 / week

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from £100 / night

(5) Very Good 

63

GREAT VACATION RESORT HOME CLOSE TO THEME PARKS ! - Coral Cay house sleeps 7

Kissimmee / Coral Cay

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
GREAT LOCATION , CLOSE TO ALL THE PARKS , BARS , SHOPS AND EATERIES .CORAL CAY RESORT OFFERS THE PEACE AND QUIET AFTER A BUSY ORLANDO HOLIDAY AT THE PARKS , RELAX BY THE POOL OF IN THE HOT TUB , WATCH A FILM IN THE CINEMA , PLAY POOL OR VOLLEYBALL IN THIS SAFE QUIET GAT  …see more

from £50 / night

£350 - £630 / week

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from £50 / night

12

Terra Verde Townhouse - Terra Verde Resort townhouse sleeps 8

Kissimmee / Terra Verde Resort

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
This home is located in Terra Verde resort with guarded entry and Clubhouse facilities. The 3 bed townhome is situated in a quiet cul de sac. It has its own Hot Tub and, as it backs on to conservation, the patio area is very private. It also has the advantage of catchin  …see more

from £65 / night

£455 - £840 / week

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from £65 / 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

(10) Very Good 

10

Florida Holiday Villa includes WiFi and Hot Tub - Kissimmee villa sleeps 9

Central Florida / Kissimmee

4 9 4 nights min

  • 4 bedrooms
  • Sleeps 9
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Our villa is situated in the popular community of Indian Point, which is about 15 minutes drive from Disney and close to the other vast array of attractions that Florida has to offer. It is the perfect place to relax by the pool, or come back to after a day at the theme  …see more

from £65 / night

£450 / week

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from £65 / night

(1) Excellent 

20

Encantada Resort 4 bed 3 Bath - Encantada Resort townhouse sleeps 10

Kissimmee / Encantada Resort

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Child friendly
  • Air conditioning
This is the Encantada Resort Condo in a beautiful short term rental development. Heated Pool attached to condo plus resort pool with all amenities. Very close to Disney and all attractions. Includes all kitchen utensils, appliances and washer dryer. Has WiFi and flat sc  …see more

from £97 / night

£616 / week

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from £97 / night

(18) Excellent 

24

Luxurious 6 Bedroom Tink@Bella Villa with Gameroom, Hot Tub, and WiFi - Bellavida Resort house sleeps 13

Kissimmee / Bellavida Resort

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
Tink@Bella... we set out to achieve a truly beautiful and exciting luxurious home, not a basic 'rental villa'. With impressive vital statistics this huge 4184sq ft 6 bedroom, 6 bathroom home is located on a premium lot overlooking a sparkling lake, with a sun drenched,  …see more

from £143 / night

£995 - £1395 / week

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from £143 / night

24

Lake View House - Oak Island Harbor villa sleeps 8

Kissimmee / Oak Island Harbor

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful Villa offers Executive living at affordable prices located at the prestigious Oak Island Harbor a sub division of Formosa Gardens. Oak Island Harbor is the closest sub diversion to Di  …see more

from £116 / night

£808 - £1116 / week

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from £116 / 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 £29 / night

£203 / week

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from £29 / night

(1) Very Good 

47

Central Florida / Kissimmee

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Child friendly
  • Air conditioning

 …see more

from £54 / night

£377 / week

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from £54 / 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

(4) Very Good 

12

Another Day in Paradise - Cumbrian Lakes villa sleeps 8

Kissimmee / Cumbrian Lakes

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our luxury 4 Bed, 3.5 Bath villa is situated in the exclusive, secure gated community of Cumbrian Lakes. Set in a prime position backing onto a conservation area (over 200 acres) not overlooked, secluded and peaceful. Conveniently situated just off 192 and all it ameni  …see more

from £85 / night

£612 / week

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from £85 / 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

(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

(2) Very Good 

18

River Island at Orange Lake - Orange Lake Resort villa sleeps 8

Kissimmee / Orange Lake Resort

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
This family-friendly resort, spanning more than 1,400 acres, is right on the doorstep of Walt Disney World and offers a wide variety of activities on both water and land. Villas, apartments and suites are available.Holiday Inn Club Vacations at Orange Lake Resort featur  …see more

from £171 / night

£1200 / week

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from £171 / night

(3) Excellent 

24

Lakeside Luxury - Crescent Lakes house sleeps 8

Kissimmee / Crescent Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxury 4 bedroom detached family home with pool occupying a very large, private plot on a quiet culdesac offering lots of indoor and outdoor space. The property is situated on a retention lake, the large garden and lakeside position providing privacy on all sides for th  …see more

from £93 / night

£760 - £900 / week

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from £93 / night

(2) Excellent 

24

Oakhill Disney Villa - Kissimmee City villa sleeps 10

Kissimmee / Kissimmee City

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Living AreaOur recently upgraded and spacious lounge is the ideal place to just relax after a hard day at the theme parks! The comfortable lounge benefits from a 42" LCD HD cable television with DVD, video-player, Playstation 2 and a selection of children's vi  …see more

from £110 / night

£549 - £700 / week

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from £110 / 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

(1) Excellent 

22

Cumbrian Lakes Prestige - Cumbrian Lakes villa sleeps 12

Kissimmee / Cumbrian Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
This home has a breath taking view from the pool deck. It overlooks a pretty lake and you may be lucky enough to see deer grazing on the conservation area which lies beyond it. The deck area has been extended so there is also a Hot Tub for you to enjoy. The home itself  …see more

from £120 / night

£840 - £1050 / week

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from £120 / 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

(9) Excellent 

12

192villamagic - Kissimmee villa sleeps 6

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Our luxury villa is situated in Country Creek Estates, just off Highway 192 in Kissimmee. The villa offers a high standard family accommodation and all that you need for a relaxing stay with us in Florida.This air conditioned villa comprising 1650 square ft, is locate  …see more

from £73 / night

£510 - £630 / week

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from £73 / night

(1) Very Good 

24

Stunning Family Friendly Villa with Lake Views - Crescent Lakes villa sleeps 14

Kissimmee / Crescent Lakes

6 14 4 nights min

  • 6 bedrooms
  • Sleeps 14
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 123 km
  • Swimming pool
Thank you for taking the time to look at our beautiful villa, we know you will find everything you need to make your stay a perfect one. Crescent Lakes is a stunning, tranquil community and our villa is set right in the heart of it. Disney World is only a short 15 minut  …see more

from £145 / night

£950 - £1230 / week

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from £145 / night

56

Central Florida / Kissimmee

3 6 2 nights min

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

 …see more

from £70 / night

£447 / week

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from £70 / night

15

Emerald Island Deluxe - Emerald Isle Kissimmee villa sleeps 8

Kissimmee / Emerald Isle Kissimmee

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Car not necessary
Fantastic, four bedroom, three bathroom villa with private pool and spa, located on beautiful Emerald Island Resort which is a gated community very near to all amenities and less than two miles from Disney.Consists open plan living, two separate dining areas, fully fitt  …see more

from £85 / night

£595 / week

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from £85 / night

(2) Very Good 

20

Villa Sol 5 bedroom luxury villa . - Villasol villa sleeps 12

Kissimmee / Villasol

5 12 3 nights min

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min
  • Nearest beach 96 km
  • Swimming pool
  • Child friendly
A beautifully appointed 5 bedroom, 3 bath luxury family vacation home provides state of the art living, comfort and freedom that cannot be found in a hotel room. The master bedroom has a king size bed, walk in wardrobe, and en-suite with walk in shower, the 2nd and 3rd  …see more

from £100 / night

£600 - £880 / week

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from £100 / night

13

DISNEY'S DOORSTEP - BEAUTIFUL FAMILY HOME - Kissimmee City house sleeps 9

Kissimmee / Kissimmee City

4 9 5 nights min

  • 4 bedrooms
  • Sleeps 9
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
We take great pride in the level of accommodation and service we offer to our guests. The house is maintained to the highest standards, and we go to great lengths to ensure that it is always spotlessly clean and welcoming for arriving guests.The house has four bedrooms  …see more

from £170 / night

£847 / week

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from £170 / night

28

The Marriott Retreat - Emerald Isle Kissimmee villa sleeps 10

Kissimmee / Emerald Isle Kissimmee

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Emerald Island Resort is surrounded by a conservation area and encompasses over 300 acres with 11 heavily wooded acres right in the middle of the community. As you pass through the 24 hour guarded gatehouse the playful dolphin fountains welcome you to this unique resort  …see more

from £172 / night

£1200 - £1350 / week

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from £172 / night

17

Villa Aqua Orlando - Kissimmee villa sleeps 12

Central Florida / Kissimmee

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Enjoy your family vacation at our family owned, luxury 5-bed 5-bath Villa Aqua with private pool and spa at the Windsor Hills resort near to Walt Disney World in Orlando, Florida. Relax in the comfort of our luxury villa with five bedrooms, a games room and all the conv  …see more

from £143 / night

£997 / week

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from £143 / night

(2) Excellent 

17

Villa Sunshine - 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
Our spacious Villa Sunshine (approx. 2200 sq. ft.) offers our guests immaculate accommodations filled with fine amenities and quality upgrades. Our formal living and dining rooms greet you as you enter our home. You'll enjoy a king sized master en suite and twins them  …see more

from £97 / night

£674 - £924 / week

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from £97 / night

(7) Excellent 

48

Emerald Magic Villa by Emerald Island Rentals - Emerald Isle Kissimmee villa sleeps 14

Kissimmee / Emerald Isle Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
A 6 bed/5.5 bath villa in Emerald Island Resort offering outstanding amenities such as an air-conditioned game room and a south-facing pool/spa.With 4 king master suites and 2 themed kids rooms, this villa can accommodate up to 14 in sheer luxury. The large pool and spa  …see more

from £185 / night

£1304 - £2154 / week

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from £185 / night

46

Perfect Home @ Disney - Kissimmee condo sleeps 7

Central Florida / Kissimmee

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome home dear ! ! ! A perfect home@Disney within amazing community, location and spacious rooms. First of all, Location & Community ! Our condo is within a famous Windsor Palm Resort Community, which is often viewed as one of the best resorts in the area. Yo  …see more

from £57 / night

£314 - £393 / week

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from £57 / night

(2) Excellent 

70

Scotsman's Retreat - Cumbrian Lakes villa sleeps 10

Kissimmee / Cumbrian Lakes

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 114 km
  • Swimming pool
Scotsman's Retreat is a beautiful and quiet 2 storey 5 bedroom house house on Cumbrian Lakes which is a relatively new gated community build in a conservation area and, as the names suggests, based around 3 large lakes. The villa is situated in an ideal location  …see more

from £95 / night

£665 - £875 / week

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from £95 / night

8

Emerald Island Gem Near Disney - Emerald Isle Kissimmee house sleeps 12

Kissimmee / Emerald Isle Kissimmee

5 12 3 nights min

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Holiday Lettings Special: Free Pool Heat October through May (Spa heat is always free).Be sure to click the link below to the homeowner's site for more details, a floorplan, more pictures and lots more information. (below where it says 'CLICK HERE - Disney Vac  …see more

from £130 / night

£910 / week

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from £130 / night

14

Terra Verde 4 bed Villa - Kissimmee villa sleeps 8

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

(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 

20

Gorgeous Lake Berkley Villa with Jacuzzi, in Kissimme - Lake Berkley villa sleeps 16

Kissimmee / Lake Berkley

7 16 7 nights min

  • 7 bedrooms
  • Sleeps 16
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
A 7 bed 71/2 bathroom luxury villa. With everything you require for a wonderful holidayt stay. pool seating on extended deck overlooking large pool and spa. The villa has the best views on the entire resort overlooking the island. Illuminated pool for evening use, outdo  …see more

from £157 / night

£1100 / week

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from £157 / night

(1) Excellent 

20

Luxury 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
  • Swimming pool
  • Child friendly
  • Air conditioning
Only 3 miles to Disney, 15 miles to SeaWorld, 17 miles from Universal Studio and easy access to all major theme parks, shipping center, restaurants, this lovely 8 bedroom 4.5 bath heated pool/spa villa is located on the prestigious Emerald Island Resort, a beautiful com  …see more

from £231 / night

£1077 - £2454 / week

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from £231 / night

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