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50 Holiday homes in Kissimmee

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  • Acadia (2)
  • Bass Lakes Estate (1)
  • Bellavida Resort (1)
  • Chatham Park (1)
  • Crescent Lakes (1)
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  • Cumbrian Lakes (2)
  • Doral Woods (1)
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  • Formosa Gardens (4)
  • Indian Creek (3)
  • Indian Ridge Oaks (1)
  • Kissimmee City (2)
  • Liberty Village (1)
  • Lindfields (1)
  • Oak Island Cove (1)
  • Remington (1)
  • Reunion Resort (1)
  • Seasons Resort (1)
  • Terra Verde Resort (1)
  • The Hamlets (1)
  • Windsor Hills Resort (2)

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Filters applied: Pets allowed (50)

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50 Results  |  
24 Photos

House | 5 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £263 /night

£1838 - £2570 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Reunion Resort, 5 bedroom, spacious living areas, private pool, full home cinema, golf views, membership access, modern kitchen, Grand Master En-suites, The private pool can be heated on request at a separate/additional cost.  …see more

16 Photos

Villa | 4 Bedrooms | sleeps 10

3 Nights min stay

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from £60 /night

£419 - £525 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Disney location with secluded heated pool and King sized Four Poster Bed. This newly renovated property, located in one of the nicest residential communities in Kissimmee, is a great base for any holiday in the area.  …see more

11 Photos

Villa | 2 Bedrooms | sleeps 10

5 Nights min stay

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from £112 /night

£782 - £1085 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
Lovely Villa with loft at Wetgate Vacation Villas - Kissimmee, 5 miles away from Disney and just minutes from Orlando Theme Parks.  …see more

Featured properties

24 Photos

Villa | 5 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £106 /night

£742 - £780 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Completely private pool and spa. Disney is 3 miles about a 5-10 minute drive, Universal & Sea World are about a 15 minute drive, more than 10 fantastic restaurants within 5 minutes drive. Shopping centers and outlets within 20 minutes drive Trip Advisor Certificate of Excellence Award Winners 2014 please see our reviews from previous guests  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 8

Excellent 5/5 

4 Nights min stay

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from £57 /night

£398 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Genuine 3 miles to Disney, over sized heated pool, fully air conditioned throughout, free WiFi, upgraded kitchen appliances, 43 inch HD plasma TV in the lounge with additional TV's in all the bedrooms.  …see more

24 Photos

House | 4 Bedrooms | sleeps 10

Excellent 5/5 

4 Nights min stay

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from £79 /night

£550 - £757 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 76 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Lovely 4 bedroomed villa with south facing heated pool with extensive lake views, perfectly located for all the main attractions. Located in the beautiful recreational golfing community of Remington in Kissimmee. Fully equipped for a perfect vacation. Free WiFi. Very spacious two storey house, beautifully furnished and perfect for all the family.  …see more

21 Photos

Villa | 4 Bedrooms | sleeps 9

Excellent 5/5 

3 Nights min stay

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from £78 /night

£541 - £689 / week

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Key info:

  • Nearest beach 45 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Private pool, 10mls Disney, 17mls Universal, Ground Floor Master, Queen Room, Disney Pixar Cars & Sunny Beach Theme twin rooms, twin beds convert to a king bed, Baby Pack, Games Room, Nintendo Wii +4 controllers, PSII, FREE Wi-Fi, calls, cable TV. Full A/C, ceiling Fans Just 10 miles from Mickey's doorstep, 17 miles from Shamu. 2 miles from The Loop and 2 minutes from Wal*Mart  …see more

21 Photos

Villa | 5 Bedrooms | sleeps 10

Short stays welcome

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from £91 /night

£636 - £1060 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Available all year round Local management team (Contact numbers provided) Secure gated community with coded entry system Private screened pool / patio area Private parking on driveway & limited on-street parking Recently renovated & carpeted upstairs Tiled ground floor Fully fitted kitchen with new appliances New washer & dryer Cable TV in 4 bedroom Stereo in bunk bedroom  …see more

11 Photos

Villa | 2 Bedrooms | sleeps 10

5 Nights min stay

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from £133 /night

£930 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
You will expend a wonderfull time at this villas, as well at the Resort. The Resort offers free transportation to Epcot, Universal, Sea World and Prime Outlets  …see more

18 Photos

Townhouse | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £81 /night

£565 / week

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Key info:

  • Suitable for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
3 bed 2.5 town home 10 minutes from Disney Fantastic resort facilities Safe, gated resort  …see more

16 Photos

Villa | 4 Bedrooms | sleeps 10

3 Nights min stay

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from £84 /night

£586 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
4 bed 3 bath heated pool close to Disney flat screen tv's  …see more

19 Photos

Villa | 6 Bedrooms | sleeps 12

3 Nights min stay

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from £85 /night

£590 - £1110 / week

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Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Luxury 6 bedroom villa on exclusive gated resort with conservation view, private pool and spa, free wifi. Only 15 minutes drive to Disney. This Villa is the perfect place to stay to enjoy your Disney vacation.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

1 night min stay

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from £93 /night

£650 - £875 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Doral woods executive secluded villa set in an acre of woodland, not overlooked.4 Bedrooms (2 master King Beds), 3.5 Baths. south heated pool and deck area with two lanai's, 59 jet jacuzzi hot tub, BBQ, Games Room, Convenient for attractions. Perfect Honeymoon choice. Relax in comfort and style, this completely secluded 2500sq.ft. home offers exceptional space & comfort .  …see more

20 Photos

Condo | 3 Bedrooms | sleeps 8

Excellent 5/5 

1 night min stay

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from £53 /night

£367 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
Superb spacious three bedroomed condo 4 miles from Disney, excellent golf courses, restaurants and shops Light, airy accommodation with plenty of space and luxurious comfort. Cable TV DVD Internet Free Calls icemaker cooker microwave dishwasher utensils travel cot highchair pets  …see more

15 Photos

Villa | 5 Bedrooms | sleeps 10

1 night min stay

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from £89 /night

£619 - £795 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
Luxurious 5 BED, 3 BATH Spacious Family Villa, conveniently located in Seasons Community, just minutes from the famous 192 & all its attractions - Disney only 10 mins away. Featuring a private pool with a spa, games room to keep the kids entertained & WIFI.  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 16

Excellent 5/5 

1 night min stay

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from £244 /night

£1707 - £1820 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
" This really is the classiest of them all ", Winner of the Best Kissimmee Vacation Rental Home 2011 & 2012, and Rated Excellent, and Recommended by Trip Advisor. Exceptionally luxurious 7 bed, 6 baths, sleeps 16, South Facing, Lake View, Formosa Gardens Villa. Florida Vacation Home,10 minutes from Disney,take a look at the outstanding features this Holiday Home has.  …see more

23 Photos

Townhouse | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £46 /night

£317 - £465 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
This glorious fully furnished townhouse was built in 2005 in the magnificent Key West style. This house features 3 wonderful bedrooms and 2.5 exquisite bathrooms and can house up to 8 people,within the gated community of Fiesta Key. The Villa is close to all the Theme Parks. 10 mins from Disney Land, 30 mins to Universal.  …see more

12 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

3 Nights min stay

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from £76 /night

£530 - £742 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Large pool and spa, only 3 miles to gates of Disney, only 1 mile to shops, restaurants, banks, only 20 mins from Orlando Airport, Winnie the Poo themed twin room. Perfect for families or snow birds. games room, tv's in all rooms.  …see more

16 Photos

Villa | 3 Bedrooms | sleeps 6

Very Good 4/5 

4 Nights min stay

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from £60 /night

£420 - £500 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Executive 3bed/2 bath villa with private pool.Located on one of the most popular rental areas close to all the attractions with Disney just 8 minutes away. Ideal for families & Perfect for Golfers with many courses within 5 minutes drive.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 10

Excellent 5/5 

Short stays welcome

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from £91 /night

£631 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
A wonderful villa, very close to Disney, overlooking beautiful lake, private heated swimming pool, Restaurants and shops close by. Fully air conditioned, 4 large bedrooms, premium cable TV, games console, everything you could want in your home from home.  …see more

17 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

Short stays welcome

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from £108 /night

£750 - £950 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Private villa with private lake views. Villa is not overlooked by other villas. Private pool, jacuzzi, just 10 minutes from Disney, situated in Kissimmee.  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 18

1 night min stay

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from £367 /night

£2566 - £3117 / week

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Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Stunning Family Mansion Villa - Only 2 miles from Disney World. 2/3rds acre PRIVATE garden with GIANT CHESS SET (so much fun!) Private, Heated Pool & Spacious Deck. Cinema. Games Room w/ Pool Table. Gas BBQ, Free WiFi Internet & Calls. Sleeps 18. Newly Refurnished (2014 Located in Formosa Gardens. Closest to Disney World. Restaurants, shops and bars nearby.  …see more

7 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

Short stays welcome

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from £54 /night

£372 - £496 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Spacious and comfortable Villa. Ideal for family holidays and/or long term rent. Personal swimming pool. Great location. Villa With Private Pool Short Walk From Wal-mart And Outdoor Miniature Golf Sleeps 6 (3 Bedrooms)  …see more

8 Photos

Townhouse | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £111 /night

£772 - £1278 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Welcome to this beautiful Saddleback Model (1600 sqft.) 3 bedroom 3 bath townhome (2 story) East facing pool This tranquil but pristine three-bedroom, three-bath vacation townhome provides you with everything you will need for the perfect holiday escape. The first floor has an open floor plan with  …see more

13 Photos

Villa | 7 Bedrooms | sleeps 16

3 Nights min stay

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from £144 /night

£1007 - £1696 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
  • Private garden
7 Bedrooms, 4 Bathrooms, Large South facing Pool / Spa Near Disney Theme Parks, Games Room, Wi Fi, 60" Internet TV, DVD, Conservation area, Lake views, Fully equiped kitchen, towels provided, suitable for disabled people, local management company, fishing, gold nearby Lovely views of the lake and It is only a short drive from the main theme parks and many golf courses.  …see more

18 Photos

House | 4 Bedrooms | sleeps 10

1 night min stay

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from £77 /night

£539 - £882 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Hot Tub/Jacuzzi Television Satellite or cable TV DVD Player  …see more

12 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

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from £89 /night

£623 - £826 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Sunset Lakes is a small gated community located right in the heart of Disneys most desirable area  …see more

17 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

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from £101 /night

£707 - £938 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Heated Pool Satellite or cable TV DVD Player Television  …see more

13 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £83 /night

£581 - £784 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Heated Pool DVD Player VCR Television Satellite or cable TV  …see more

8 Photos

House | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £83 /night

£581 - £784 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Heated Pool Television Satellite or cable TV VCR  …see more

13 Photos

House | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £89 /night

£623 - £875 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Private Pool Heated Pool Shared outdoor pool (unheated) VCR DVD Player Television Satellite or cable TV  …see more

10 Photos

House | 4 Bedrooms | sleeps 10

1 night min stay

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from £77 /night

£539 - £889 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access DVD Player Satellite or cable TV Shared outdoor pool (unheated)  …see more

11 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £83 /night

£581 - £784 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Private Pool Shared outdoor pool (unheated) Heated Pool VCR Satellite or cable TV Television DVD Player  …see more

18 Photos

House | 6 Bedrooms | sleeps 14

2 Nights min stay

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from £113 /night

£791 - £1092 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Heated Pool Private Pool Television Satellite or cable TV DVD Player  …see more

16 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £77 /night

£539 - £889 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Shared outdoor pool (unheated) atellite or cable TV Television DVD Player VCR  …see more

22 Photos

House | 4 Bedrooms | sleeps 8

2 Nights min stay

Add to shortlist

from £101 /night

£707 - £938 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Intern Private Pool Shared outdoor pool (unheated) VCR Satellite or cableTV DVD Player Television  …see more

19 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £113 /night

£791 - £1092 / week

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Key info:

  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Private Pool VCR Television DVD Player Satellite or cable TV  …see more

17 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £77 /night

£539 - £889 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Shared outdoor pool (unheated) Hot Tub/Jacuzzi VCR Satellite or cable TV Television DVD Player  …see more

13 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £56 /night

£389 - £516 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
Internet Access Private Pool Heated Pool VCR Television DVD Player  …see more

14 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £83 /night

£581 - £777 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Private Pool Satellite or cable TV DVD Player Television VCR  …see more

8 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £95 /night

£665 - £882 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Heated Pool Private Pool Shared outdoor pool (unheated)  …see more

15 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £77 /night

£539 - £882 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Shared outdoor pool (unheated) Satellite or cable TV DVD Player Television  …see more

14 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £101 /night

£707 - £931 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Heated Pool Private Pool Television VCR Satellite or cable TV DVD Player  …see more

13 Photos

House | 4 Bedrooms | sleeps 10

1 night min stay

Add to shortlist

from £77 /night

£539 - £882 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Shared outdoor pool (unheated) Satellite or cable TV DVD Player Television  …see more

11 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £89 /night

£623 - £826 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Private Pool Heated Pool Stereo or CD player Television Satellite or cable TV  …see more

24 Photos

Townhouse | 2 Bedrooms | sleeps 8

1 night min stay

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from £70 /night

£484 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Enjoy an amazing, family friendly Central Florida vacation right in the heart of Orlando's world famous theme parks and attractions! At Westgate Town Center, you'll discover a world where luxury accommodations and a variety of special resort amenities combine to create an unforgettable vacation experience  …see more

24 Photos

House | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £96 /night

£672 - £686 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • Pets welcome
Audez Tropical Haven is the perfect Florida getaway  …see more

10 Photos

House | 5 Bedrooms | sleeps 10

1 night min stay

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from £109 /night

£760 - £847 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Casa no condomínio Cubrian Lakes para até 10 pessoas, bela vista para o lago. Agradável experiência em família de passar alguns dias próximo ao mágico mundo da Disney. 5 quartos, um suíte , 3 banheiros, cozinha completa, piscina aquecida e internet wi-fi. Seja bem vindo  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 12

4 Nights min stay

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from £102 /night

£713 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
  • Private garden
VILLA 5 CHAMBRES 3 SALLES DE BAIN GAME ROOM PISCINE SPA BONUS ROOM ORDINATEUR FOURNI PS2 ET JEUX FOURNIS WIFI TELE DANS TOUTES LES CHAMBRES IDEALE POUR LES FAMILLES NOMBREUSES OU GROUPE SITUEE A 10 MIN DES PARCS DISNEY  …see more

11 Photos

Townhouse | 3 Bedrooms | sleeps 8

Min stay varies

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from £106 /night

£742 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Luxury 3 bed home with private pool in The Luxury Windsor Hill's Resort only 1.5 miles from Disney World  …see more

Orlando Kissimmee is a great location for a family holiday, with easy access to Florida's big attractions - Disney World, Busch Gardens and Universal Studios. There are also rides through the Florida Everglades and plenty of children-friendly activities to keep everyone happy. The area has some excellent beaches, amongst them Clearwater Beach and Daytona Beach.