Villas with a pool Kissimmee | Apartments to rent with swimming facilities

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471 Holiday homes

Filters applied: Swimming pool (471)

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

1 / 13

Lakeside Villa - Enchanting Vacation Rental with Hot Tub - Crescent Lakes villa sleeps 16

Kissimmee / Crescent Lakes

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
Luxury villa with 7 bedroom 4 bathroom (2 ensuite) recently refurbished * large south facing pool by lake 8 person spa, lanai *short drive to theme parks * new 60" led hdmi internet tv with cable and lots of channels including sports and soccer. * 1200w home cinema  …see more

from £140 / night

£950 - £1600 / week

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from £140 / night

(9) Excellent 

1 / 24

Charming Home with Gameroom and Hot Tub - Kissimmee villa sleeps 8

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
This is a beautifully furnished vacation home near to all Disney theme parks, several good golf courses and a 5 minute drive from restaurants and shops. The villa sleeps 8 people and has four good sized bedrooms and two bathrooms.The villa is fully equipped with eveythi  …see more

from £84 / night

£648 - £815 / week

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from £84 / night

(12) Excellent 

1 / 41

Beautiful Cane Island Condo with Pool, Sauna & Spa - Cane Island condo sleeps 6

Kissimmee / Cane Island

3 6 5 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 65 km; Swimming pool;
This beautifully furnished 3 bedroom, 2 bathroom property in Cane Island Resort in Kissimmee benefits from a wonderful lakeside setting and is less than 4 miles from the main gates of Disney World. This resort really does benefit from the best of both worlds - far enoug  …see more

from £57 / night

£375 - £527 / week

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from £57 / night

(1) Excellent 

1 / 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
Key info: 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 £76 / night

£493 - £849 / week

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from £76 / night

(4) Very Good 

1 / 19

VIP Villa close to Disney - Lake Berkley villa sleeps 8

Kissimmee / Lake Berkley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Child friendly ;
The villa is situated within Lake Berkley, Kissimmee, one of the most sought after locations for people wanting to rent a villa. For those visiting Disney it is just 5 miles away--approximately 10 minutes drive. All the other major theme parks are also very close by. F  …see more

from £99 / night

£679 - £906 / week

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from £99 / night

1 / 16

Luxury 3 Bed Villa with private pool near Disney21 - Kissimmee house sleeps 6

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Air conditioning;
This is a luxurious 3 bedroom 3 bathroom villa with private pool with conservation view on 5 Star Eagle Pointe Resort, Kissimmee, Orlando. The villa was recently refurbished and now benefits from ceramic tile and wood flooring throughout. The villa is furnished to a v  …see more

from £84 / night

£569 - £679 / week

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from £84 / night

(4) Excellent 

1 / 44

Villa Orlando, Lovely Home with a Pool and WiFi - Kissimmee villa sleeps 6

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
This luxurious Florida vacation home with its own large private heatable south facing swimming pool overlooking a beautiful lake is located in the small tranquil community of Westminster Gardens. Situated in Kissimmee and just 25 minutes from Disney, via Osceola Parkwa  …see more

from £90 / night

£585 / week

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from £90 / night

(1) Excellent 

1 / 70

Scotsman's Retreat - Cumbrian Lakes villa sleeps 10

Kissimmee / Cumbrian Lakes

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: 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

(4) Excellent 

1 / 18

Tropical Beauty 3 Bedroom Villa with WiFi and Game - Kissimmee villa sleeps 6

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Air conditioning;
Tropical Beauty Villa is a tastefully furnished and well maintained pool villa boasting 1800 of air conditioned Floridian Luxury. The accommodation has 3 bedrooms, family bathroom, en-suite with walk in shower and a corner bath tub, fully fitted kitchen. If you love su  …see more

from £60 / night

£425 - £650 / week

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from £60 / night

1 / 22

Central Florida / Kissimmee

4 8 3 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
 …see more

from £107 / night

£743 / week

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from £107 / night

1 / 24

OLAF`S HOLIDAY RETREAT: REFURBISHED VILLA 4B 3BA 4 - Kissimmee villa sleeps 8

Central Florida / Kissimmee

4 8 5 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
4 Bedroom 3 Bathroom Pool Home Villa At Indian Creek Only 10 Minutes From Disney4 Bedrooms, 3 Bathrooms, sleeps 8 people comfortablyOur recently Refurbished Executive Villa with a NEW fitted highly equipped kitchen and appliances and a 45ft screened pool with spa is loc  …see more

from £90 / night

£625 / week

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from £90 / night

(13) Excellent 

1 / 28

Luxurious 3 Bedroom Club Cortile Condo with a Balc - Kissimmee condo sleeps 6

Central Florida / Kissimmee

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
Our superb condition 3 bed 2 bath condo has a 6 person maximum occupancy at Club Cortile Resort, a luxury gated resort with a 4,000 sq ft clubhouse, community pool with jacuzzi, tennis court, fitness centre, movie theatre, internet room and kids playground. Perfect loca  …see more

from £38 / night

£266 - £304 / week

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from £38 / night

(6) Very Good 

1 / 22

Scenic Lakeside 4 Bedroom House with WiFi at Regal - Regal Oaks townhouse sleeps 8

Kissimmee / Regal Oaks

4 8 3 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
This spacious lakeside townhouse is situated only 3 miles drom Disney. It is ideal for families or Groups of up to 10 people. The property has a local professional Management Company who ensure guests receive wonderful customer care. This property is in a perfect locati  …see more

from £60 / night

£420 / week

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from £60 / night

(5) Excellent 

1 / 15

Poohs House Kissimmee Villa with a Pool, WiFi, and - Kissimmee villa sleeps 8

Central Florida / Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 65 km; Swimming pool; Child friendly ;
Welcome to our lovely luxury villa in KissimmeeThis is our luxury 3-bedroom, 2 bathroom villa with games room and free wi-fi internet in Kissimmee, Florida.. Start your Florida vacation in Kissimmee and the possibilities are endless..Just a quick drive south of Orlando  …see more

from £60 / night

£425 - £540 / week

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from £60 / night

1 / 24

Mickey's Magic Villa by Emerald Island Rentals - Emerald Isle Kissimmee townhouse sleeps 8

Kissimmee / Emerald Isle Kissimmee

3 8 5 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min stay
Key info: Swimming pool; Child friendly ; Car not necessary;
Our luxurious 1300 sqft, 3 bedroom / 2.5 bath townhouse that sleeps up to 8 is fully air conditioned and very well equipped including a TVs and DVD players in all bedrooms, a PS2 games console for the kids, wireless internet access, free local & national telephone c  …see more

from £84 / night

£531 / week

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from £84 / night

(4) Very Good 

1 / 24

Resort Home (Lake Berkley) Stunning Lake Views - Lake Berkley villa sleeps 8

Kissimmee / Lake Berkley

4 8 7 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
The highlight of this property is the stunning lakeside view from the pool and living areas. But if you tear your eyes away from the view for a while, you'll enjoy comfortably furnished rooms and wonderful resort facilities. A great option for families or couples alik  …see more

from £99 / night

£695 / week

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from £99 / night

(2) Good 

1 / 15

Disney villa w/ pool your Orlando home from home - Kissimmee villa sleeps 8

Central Florida / Kissimmee

3 8 7 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
Our villa offers large open plan Floridean accommodation. Light and breezy with high vaulted ceilings you can get a real sense of space to relax in. With a luxurious American sized en-suite master bedroom, as well as two further good sized rooms, our villa offers real c  …see more

from £65 / night

£450 / week

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from £65 / night

(1) Excellent 

1 / 12

Mickey's Holiday Home - King / King / Queen / Twin - Windsor Palms villa sleeps 8

Kissimmee / Windsor Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 5 km; Swimming pool; Child friendly ;
LESS THAN 10 MINUTES FROM DISNEY ! Luxury villa located in popular 5 star holiday resort " Windsor Palms " ! free high speed WiFi ! CHILD FRIENDLY ! The new system makes salt water swimming in the pool more enjoyable. A chlorine pool has the great disadvantage that the  …see more

from £129 / night

£902 - £1167 / week

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from £129 / night

1 / 24

Lovely Villa Near Disney World - Kissimmee villa sleeps 6

Central Florida / Kissimmee

3 6 3 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 60 km; Swimming pool;
This large 3 bedroom 2 baths house is beautifully furnished and offers anything a traveler will need. Has up to date appliances and a full kitchen. To start you up you will find toilet paper, paper towels, dish washer tablets, laundry detergent, bottles of water in the  …see more

from £83 / night

£531 / week

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from £83 / night

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Stunning townhouse, discounts for 2016 bookings - Kissimmee house sleeps 10

Central Florida / Kissimmee

4 10 3 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
Fabulous location for everything the area has to offer. Only 10 minutes from Disney main gates & 20 mins to Universal. Convenient for shops, restaurants and outlets Complex offers heated pool, tennis, basketball, play area, splash pad, volley ball, & other amenities al  …see more

from £69 / night

£449 - £589 / week

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from £69 / night

(5) Excellent 

1 / 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
Key info: 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

(6) Excellent 

1 / 31

Stunning Executive Family Home - 10 mins Disney - Seasons Resort villa sleeps 13

Kissimmee / Seasons Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
This villa is furnished to a high standard throughout. The bright & spacious rooms provide plenty of room for the whole family. The highlight has to be the lovely south-west-facing pool – the perfect spot to unwind at the end of a long day enjoying Orlando's many  …see more

from £148 / night

£1019 - £1815 / week

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from £148 / night

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Holiday home on Disney's doorstep - Emerald Isle Kissimmee townhouse sleeps 6

Kissimmee / Emerald Isle Kissimmee

3 6 1 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Car not necessary;
Come and stay in our lovely Florida holiday home located right on Disney's doorstep. It's located in the stunning Emerald Island resort, a prestigious gated community. It's beautifully decorated, with enough space to comfortably sleep 6 people. Our except  …see more

from £60 / night

£450 / week

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from £60 / night

(2) Excellent 

1 / 28

Stunning Lake View /Games Room / WiFi /Near Disney - Seasons Resort villa sleeps 14

Kissimmee / Seasons Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
This Kissimmee home offers plenty for all the family – from the jungle-themed kids' TV and entertainment space to the wonderful, sparkling pool overlooking the attractive lake. Plus, it has a good location for access to all of Orlando's amusement parks & attractions.  …see more

from £148 / night

£982 - £1588 / week

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from £148 / night

(8) Excellent 

1 / 57

Florida Gold - Lindfields house sleeps 8

Kissimmee / Lindfields

4 8 7 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
The dream home of a British family. A grand floor plan that is ideal for up to eight guests. Open the patio doors and you will find a serene, secluded sundeck and pool. The whole pool area at the rear of the house is south facing , with a lake to the side for the keen  …see more

from £85 / night

£595 / week

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from £85 / night

(20) Very Good 

1 / 24

Bay Head Villa, Great 3 Bedroom near Golf Courses and Theme Parks - Kissimmee villa sleeps 8

Central Florida / Kissimmee

3 8 7 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
Luxury 3 bed 2 bath villa can sleep 8. Large 30ft fully heated secluded pool. Only 15 minutes from airport & theme parks & 1 hour from Kenedy space centre & cocoa beach. Also 1 hour from Bush Gardens & clearwater beach to the west coast. Surounded by beautiful golf cour  …see more

from £50 / night

£350 - £725 / week

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from £50 / night

(8) Very Good 

1 / 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
Key info: 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

(25) Excellent 

1 / 77

Chris and Sue's Disney Condo - Windsor Palms condo sleeps 7

Kissimmee / Windsor Palms

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Nearest beach 117 km; Swimming pool; Child friendly ;
FREE PHONE CALLS AND WIFILuxurious 3 bedroom/2 bathroom, fully equipped Condo is located in the exclusive gated community of Windsor Palms, Kissimmee, less than 3 miles from Walt Disney World. A perfect location for all that Central Florida has to offer eg The Parks of  …see more

from £63 / night

£390 - £675 / week

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from £63 / night

(3) Excellent 

1 / 24

Resort Villa-Pool & Spa-Lake Berkley-near Disney - Lake Berkley villa sleeps 8

Kissimmee / Lake Berkley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
Stylish vacation home, sleeps 8, with private pool & spa pool. Located in the gated resort of Lake Berkley in Kissimmee with excellent resort amenities for you to enjoy. You are located minutes away from Disney, all attractions, theme parks & there are many restaurant  …see more

from £90 / night

£575 - £625 / week

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from £90 / night

1 / 24

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

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

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

from £175 / night

£1137 - £1970 / week

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from £175 / night

1 / 9

Venetian Bay II - Venetian Bay Villages townhouse sleeps 6

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Suitable for children age 5+; Air conditioning;
Beautiful 3 bedroom home on the popular Venetian Bay in Kissimmee. This is the perfect place to relax after your busy day at the parks. Only 15 minutes from Disney World and great facilities in this gated community makes planning your Florida Vacation easy.The spacious  …see more

from £72 / night

£504 - £690 / week

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from £72 / night

(9) Excellent 

1 / 28

Doral Woods Woodland Villa - Doral Woods villa sleeps 8

Kissimmee / Doral Woods

4 8 4 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
- 4 Bedrooms, 2 Queen, 2 Twin. En-suite to Master. Flat screen TV in Master and Queen. - Private heated pool, not overlooked. Within mesh to keep those insects out. - 2 Bathrooms, shower cubicle in en-suite, shower over bath in family bathroom. - Sleeps 8 people. Addit  …see more

from £65 / night

£450 - £475 / week

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from £65 / night

1 / 27

4 Bed 3 Bath house, near Disney, private pool BV5 - Kissimmee house sleeps 4

Central Florida / Kissimmee

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Air conditioning;
A stunning, larger than average, 4 Bed 3-end townhouse with a beautiful view of the conservation area at the rear as backdrop to our private pool. The house is split over two floors which makes it ideally beneficial for accommodating 2 families. The sitting room has  …see more

from £75 / night

£754 / week

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from £75 / night

(1) Excellent 

1 / 8

Villa in Florida - Kissimmee villa sleeps 10

Central Florida / Kissimmee

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Not suitable for children;
The villa is situated 20 minutes from Orlando International Airport. In the Buenaventura Boulevard area. It is in a cul de sac of 6 houses. The villa backs onto a lake, which you can fish in. All fishing equipment is at the house.The house has a games room, with a pool  …see more

from £72 / night

£500 / week

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from £72 / night

(4) Excellent 

1 / 27

Mickey's Magical Manor at WIndsor Palms Resort - Windsor Palms villa sleeps 10

Kissimmee / Windsor Palms

4 10 3 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
Beautiful 4 bedroom, 2 bath luxury villa in a private gated community with 24 hr.security, just 2.5 miles from Disney. Private 15x30ft built-in pool & jacuzzi with cushioned loungers and table/chairs/parasol, pool toys and inflatables. Preferred cable TV with on dem  …see more

from £100 / night

£685 / week

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from £100 / night

(8) Very Good 

1 / 25

South Facing Pool/Kiddies splash pool/Near Disney - Crescent Lakes villa sleeps 6

Kissimmee / Crescent Lakes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Air conditioning;
A peaceful retreat from the theme parks. This attractive home has a fabulous private pool & children's splash pool. The pool is south facing & is very private at the rear. The pool deck offers plenty of space for guests to enjoy & you can retreat from the midday sun u  …see more

from £79 / night

£535 - £585 / week

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from £79 / night

1 / 22

Central Florida / Kissimmee

3 6 3 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
 …see more

from £107 / night

£743 / week

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from £107 / night

(7) Excellent 

1 / 25

Kissimmee / Lucaya Village

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
 …see more

from £68 / night

£735 - £841 / week

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from £68 / night

(1) Very Good 

1 / 8

Pet Friendly Wonderful Disney Villa & Pool - Oak Island Cove villa sleeps 8

Kissimmee / Oak Island Cove

4 8 3 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Not suitable for children;
Pet Friendly!! Beautifully Furnished 4 Bedroom 3 Bath with Private Pool and enclosed Lanai!Our luxury villa is located just 1.5 miles from the main gate of Walt Disney World, Orlando, Florida at Oak Island Cove Community. You will enjoy the peaceful and tranquil surroun  …see more

from £103 / night

£663 / week

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from £103 / night

(16) Excellent 

1 / 20

Solaz365 - Luxury Rental Home in Kissimmee - Bellavida Resort villa sleeps 12

Kissimmee / Bellavida Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
Solaz365 ~~~ Watch our exciting new VIDEO - go to our website and enjoy! ~~~ Welcome to Solaz365, our wonderful holiday home, a place to relax 365 days of the year. If you don't say "WOW" the minute you walk through the door, we will be amazed! The house was built in  …see more

from £175 / night

£1225 / week

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from £175 / night

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