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35 Holiday homes in Kissimmee

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  • All suburbs
  • Bass Lakes Estate (1)
  • Chatham Park (1)
  • Crescent Lakes (1)
  • Cumbrian Lakes (2)
  • Doral Woods (1)
  • Fiesta Key (1)
  • Formosa Gardens (3)
  • Indian Creek (3)
  • Kissimmee City (2)
  • Liberty Village (2)
  • Lindfields (2)
  • Oak Island Cove (1)
  • Orange Lake Resort (1)
  • Remington (1)
  • Reunion Resort (9)
  • Seasons Resort (1)
  • Terra Verde Resort (1)
  • Windsor Hills Resort (1)

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Filters applied: Pets allowed (35)

35 Results  |  
16 Photos

Villa | 4 Bedrooms | sleeps 10

3 Nights min stay

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from £64 /night

£446 - £509 / 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

24 Photos

House | 4 Bedrooms | sleeps 10

Excellent 5/5 

4 Nights min stay

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from £79 /night

£550 - £716 / 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

5 Photos

Villa | 2 Bedrooms | sleeps 8

Excellent 5/5 

5 Nights min stay

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from £110 /night

£767 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
It would be hard for you to find a better place at such a price.  …see more

Featured properties

11 Photos

Villa | 2 Bedrooms | sleeps 10

6 Nights min stay

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from £115 /night

£805 - £1118 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • May take pets – please enquire
Villa with loft at Wetgate Vacation Villas - Kissimmee, 5 miles away from Disney and just minutes from Orlando Theme Parks.  …see more

23 Photos

Villa | 4 Bedrooms | sleeps 9

Excellent 5/5 

1 night 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

17 Photos

Villa | 5 Bedrooms | sleeps 10

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

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

7 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

Short stays welcome

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from £61 /night

£424 - £530 / 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

24 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

1 night min stay

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from £100 /night

£695 - £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

19 Photos

Villa | 6 Bedrooms | sleeps 12

3 Nights min stay

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from £85 /night

£590 - £1100 / 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

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
  • Car not necessary
  • 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

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 Please see our website at http://www.aladdinsoasiskissimmee.com  …see more

24 Photos

House | 5 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £245 /night

£1715 - £2650 / 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 | 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

15 Photos

Villa | 5 Bedrooms | sleeps 10

1 night min stay

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from £89 /night

£619 - £749 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

24 Photos

Villa | 3 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £53 /night

£371 / 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

14 Photos

Townhouse | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £46 /night

£319 - £479 / 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.  …see more

17 Photos

Villa | 3 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £70 /night

£490 - £550 / 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
A larger then average luxury 3 bedroomed private Villa with own heated Pool, 10minutes from Disney main gate and all main attractions. Recently spent $000's on upgrading it .. Free Wi-Fi. New Furniture, Bathrooms, Bedrooms, Pool re-lined, New Fully fitted Kitchen. Internet access - free Wi -Fi  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 10

Excellent 5/5 

Short stays welcome

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from £85 /night

£595 / 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

24 Photos

Villa | 9 Bedrooms | sleeps 18

Short stays welcome

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from £356 /night

£2491 - £3032 / 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
NEWLY RENOVATED Family Mansion - 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. Located in Formosa Gardens. Closest to Disney. Restaurants, shops and bars nearby.  …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
  • Car not necessary
  • 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

9 Photos

Villa | 4 Bedrooms | sleeps 10

3 Nights min stay

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from £79 /night

£553 - £882 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Beautiful single storey villa with 4 bedrooms and 3 bathrooms in the community of Indian Creek 10 minutes from Disney. Luxurious furnishings with Wi-Fi, private pool and BBQ.  …see more

11 Photos

Townhouse | 3 Bedrooms | sleeps 8

Short stays welcome

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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

11 Photos

Condo | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £128 /night

£891 / week

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Key info:

  • Nearest beach 80 km
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Reunion Resort is a Five Star exclusive development just 15 minutes drive from Walt Disney World . Whether you have spent a long day at the theme parks or enjoyed a round of golf on one of the 3 signature courses, you will struggle to find a better place to relax.  …see more

12 Photos

Condo | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £96 /night

£668 / week

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Key info:

  • Nearest beach 80 km
  • Suitable for over 5s only
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Reunion Resort is a Five Star exclusive development just 15 minutes drive from Walt Disney World . Whether you have spent a long day at the theme parks or enjoyed a round of golf on one of the 3 signature courses, you will struggle to find a better place to relax.  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

Min stay varies

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from £303 /night

£2120 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Huge traditional American home. 4 bedrooms and 5 bathrooms. Huge master suite with ensuite bathroom. Fabulous pool and spa with golf course views. Use of Reunion facilities including water parks and scenic gardens.  …see more

24 Photos

Condo | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £128 /night

£891 / week

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Key info:

  • Nearest beach 80 km
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Reunion Resort is a Five Star exclusive development just 15 minutes drive from Walt Disney World . Whether you have spent a long day at the theme parks or enjoyed a round of golf on one of the 3 signature courses, you will struggle to find a better place to relax.  …see more

20 Photos

House | 4 Bedrooms | sleeps 10

3 Nights min stay

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from £206 /night

£1442 / week

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Key info:

  • Nearest beach 80 km
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Reunion Resort is a Five Star exclusive development just 15 minutes drive from Walt Disney World . Whether you have spent a long day at the theme parks or enjoyed a round of golf on one of the 3 signature courses, you will struggle to find a better place to relax.  …see more

19 Photos

Condo | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £128 /night

£891 / week

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Key info:

  • Nearest beach 80 km
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Reunion Resort is a Five Star exclusive development just 15 minutes drive from Walt Disney World . Whether you have spent a long day at the theme parks or enjoyed a round of golf on one of the 3 signature courses, you will struggle to find a better place to relax.  …see more

20 Photos

Townhouse | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £96 /night

£668 / week

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Key info:

  • Nearest beach 80 km
  • Suitable for over 5s only
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Reunion Resort is a Five Star exclusive development just 15 minutes drive from Walt Disney World . Whether you have spent a long day at the theme parks or enjoyed a round of golf on one of the 3 signature courses, you will struggle to find a better place to relax.  …see more

20 Photos

Condo | 3 Bedrooms | sleeps 8

3 Nights min stay

Add to shortlist

from £128 /night

£891 / week

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Key info:

  • Nearest beach 80 km
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Reunion Resort is a Five Star exclusive development just 15 minutes drive from Walt Disney World . Whether you have spent a long day at the theme parks or enjoyed a round of golf on one of the 3 signature courses, you will struggle to find a better place to relax.  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 10

Excellent 5/5 

3 Nights min stay

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from £105 /night

£735 - £1247 / 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
Luxury villa fitted to the highest possible standard, with extended south-south-east private pool overlooking garden then conservation land offering privacy. 5 miles to Disney and minutes to the 194 with its shops, resturants and attractions. Beds can be 'themed' with Disney Princess or Toy Story if required. Brand new games room  …see more

11 Photos

Villa | 2 Bedrooms | sleeps 10

5 Nights min stay

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from £137 /night

£958 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

10 Photos

House | 5 Bedrooms | sleeps 10

1 night min stay

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from £112 /night

£783 - £872 / 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 £105 /night

£735 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

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.