Kissimmee apartment or villa with a heated pool

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Kissimmee

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1,303 Holiday homes

Filters applied: Heated pool (1,305)

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

(1) Average 

23

Kissimmee holiday townhouse rental

Kissimmee / Venetian Bay Villages

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The unit is situated in a very safe area and very central to the theme parks.(10/15 min.) Close to shops and restaurants.And 20/30 min.drive from Orlando Aiport ( mco ) 90 min.drive to the gulf coastBedrooms: 3 Bedrooms, Sleeps 8, Beds for 6-8Bedroom 1  …see more

from £74 / night

£488 / week

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from £74 / night

32

Villa rental in Oak Island Cove

Kissimmee / Oak Island Cove

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 125 km
  • Swimming pool
  • Child friendly
Vacation home near Disney Secure, safe, tranquil, neighborhood Close to restaurants, shopping outlets etc... Villa close to Disney Private pool Fully equipped home Vacation rental home Kissimmee Florida  …see more

from £135 / night

£883 / week

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from £135 / night

(29) Very Good 

20

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Very peaceful area to vacation.” Very nice home with all the amenities needed for your vacation. Close to all Disney adventures and alot to do nearby in Kissimmee. Lots of shopping near home too. Very clean home. Would not think twice about rentin  …see more

from £105 / night

£732 / week

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from £105 / night

Featured properties

28

Villa rental in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Marriott Retreat - one of the closest 24 hour Guarded Gatehouse Resorts - Less than 3 miles from Disney - Luxury Executive Villa - 5 bedroom, 5.5 Bath, with Private Pool (30 x 14ft) & Spa with Extended Pool Deck area - 8ft slate Pool Table- Credit Cards accept  …see more

from £215 / night

£1505 / week

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from £215 / night

17

Holiday townhouse with shared pool in Kissimmee

Central Florida / Kissimmee

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This 3 bedroom/3 bath townhome is located in the luxurious, gated community of Windsor Hills. You will be only 2.5 miles from the main gate of Walt Disney World. It is within walking distance to the clubhouse which includes a lagoon-style heated pool (with 2-story tall  …see more

from £97 / night

£678 / week

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from £97 / night

20

Kissimmee holiday home rental

Central Florida / Kissimmee

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Awesome 4 Bed home with 3 Baths, newly reformed. Located at Terra Verde Resort, close to 192 and to many restaurants and markets. a few minutes from Disney Parks, only 7 miles away. 15 minutes away from Universal Studios and 15 min away from Outlet Premium, very close t  …see more

from £108 / night

£752 / week

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from £108 / night

31

Central Florida / Kissimmee

7 14 2 nights min

  • 7 bedrooms
  • Sleeps 14
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £179 / night

£1253 / week

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from £179 / night

24

Holiday home in Kissimmee

Central Florida / Kissimmee

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A brand new house furnished to a high standard with a wall mounted TV in each room and 2 large TVs in the lounge and family room. There is a heated private pool and spa over looking a conservation area (heating at an extra cost). Entertainment in house includes table  …see more

from £172 / night

£1200 - £1800 / week

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from £172 / night

(8) Excellent 

19

Kissimmee holiday villa rental

Kissimmee / Creekside

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 110 km
  • Swimming pool
“Great place to stay” Just had a fantastic 2 weeks in this lovely house. It is well equipped, has wifi and great views of the lake and woods at the back. The house is well situated for all the attractions and a Walmart is just up the road, but it is  …see more

Pricing unknown

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Pricing unknown

28

Holiday villa with golf nearby in Kissimmee

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 10 km
  • Swimming pool
  • Child friendly
This was the show model villa in Acadia Estates, it was fully furnished and decorated by an interior designer, with a no limit spending budget, every detail was looked after, this villa has many extras that all the other villas in Acadia will not have, you will feel wel  …see more

from £139 / night

£968 - £1139 / week

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from £139 / night

24

Townhouse rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
Why stay anywhere else when you can get all this within 5 minutes (3 miles) of Disney World Orlando Florida?  …see more

from £90 / night

£570 / week

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from £90 / night

(8) Excellent 

14

Holiday townhouse in Kissimmee

Kissimmee / Bellavida Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Fantastic holiday home. Would definatley use again.” What a great holiday. Just home and couldn't wait to review this property. The resort itself is very modern and clean, with a good main pool. It has free internet access within the club house or fre  …see more

Pricing unknown

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Pricing unknown

(1) Excellent 

35

Holiday home rental

Central Florida / Kissimmee

5 11 5 nights min

  • 5 bedrooms
  • Sleeps 11
  • 5 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Can you imagine? You could be at Disney, in just five minutes. ---------------------------------- ♠♠♠ SPACIOUS FAMILY LIVING ♠♠♠ There’s an unwritten rule in Florida: Where there’s sun, play outside! Luckily, ther  …see more

from £150 / night

£1025 - £1625 / week

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from £150 / night

(1) Excellent 

20

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Countryside Manor is a peaceful, exclusive community of just 30 custom built homes all set well apart from one another with large established gardens, with an abundance of pine, oak & palm trees and surrounded by conservation area of protected woodlands and wetlands  …see more

from £143 / night

£1000 / week

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from £143 / night

(1) Excellent 

31

Central Florida / Kissimmee

4 13 Min stay varies

  • 4 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £119 / night

£831 / week

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from £119 / night

(1) Excellent 

29

Kissimmee holiday home rental

Kissimmee / Formosa Gardens

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“An Excellent Choice” We had a wonderful time at Whispering Palms and think it is an excellent choice of villa both for the quality of accommodation and its location. It is large, comfortable and well maintained. We were an extended family group com  …see more

from £219 / night

£1530 - £2300 / week

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from £219 / night

(1) Very Good 

24

Holiday villa in Kissimmee

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

(2) Very Good 

18

Holiday villa with golf nearby in Kissimmee

Central Florida / Kissimmee

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
“Nice Villa, Good Amenities, Very helpful owner.” We booked the above villa on the basis of previous reviews and the fact the owner, Mark, called us and spoke to us in person, answering any questions or emails with speed and efficiency. Mark is very h  …see more

from £79 / night

£550 - £750 / week

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from £79 / night

18

Holiday villa rental

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
Luxury 4 Bed 3 bath villa with pool, spa and games room incorporating air hockey table, football table and pool table. Free International phone calling, Free WifI and free internet streaming for unlimited free movies from Netflix. Two spacious living rooms. Baby goods.  …see more

from £110 / night

£700 - £1070 / week

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from £110 / night

35

Kissimmee holiday villa rental

Central Florida / Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This NEWLY UPGRADED 6 bedrooms 4 bathrooms 3500 sqft luxury home is located in famous Windsor Hill Resort, one of best upscale vacation home resort. This tropical vacation home has everything that you and your family could possibly need for the most magical vacation to  …see more

from £154 / night

£1076 / week

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from £154 / night

85

Holiday villa with swimming pool in Kissimmee

Kissimmee / Sunset Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
5 Bedroom south facing lakeside pool villa in Sunset Lakes just a stones throw from Walt Disney World. Very private pool area yet with beautiful lake and sunset views.  …see more

from £95 / night

£665 - £1000 / week

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from £95 / night

23

Guest house rental in Kissimmee

Central Florida / Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Summary •South Facing Pool overlooks conservation lake and woodland •7 Bed 5.5 bathrooms with 3 Masters 2 Kings 2 Queens 6 Singles Sofa Bed •Closest gated resort to Disney Thank you for visiting Tinkerbells Retreat com ***** Choosing the right villa for  …see more

from £204 / night

£1423 - £2399 / week

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from £204 / night

21

Central Florida / Kissimmee

6 12 2 nights min

  • 6 bedrooms
  • Sleeps 12
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £179 / night

£1253 / week

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from £179 / night

(24) Excellent 

20

Holiday villa with golf nearby in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 13 3 nights min

  • 6 bedrooms
  • Sleeps 13
  • 3 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
“You must stay in this Home” We have stayed at Emerald Island Resort on several occasions because we like the closeness of the location to the main attractions and the safety of the gated community with 24 hour security. So, when looking for a property  …see more

from £163 / night

£1139 / week

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from £163 / night

(13) Excellent 

18

Holiday villa with golf nearby in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“A fantastic place to stay, would highly recommend!” This is a perfect villa for a family holiday to Orlando! The complex is pristine and very safe. The villa itself had everything you could wish for and more. The owners had thought of everything to ma  …see more

from £155 / night

£1085 - £1680 / week

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from £155 / night

15

Kissimmee holiday townhouse rental

Kissimmee / Fiesta Key

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 123 km
  • Swimming pool
Quiet Location Electronic door locking system (no lost key issue) High Speed Internet Stainless appliance Modern furniture •Beach / lakeside relaxation •Swimming pool •Great for children of all ages •Air conditioning •No pets allowed  …see more

from £102 / night

£651 / week

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from £102 / night

42

Holiday home with golf nearby in Kissimmee

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Magical Home in the Perfect Location You'll LOVE! Serendipity at Indian Creek offers you all those extra finishing touches that turn an ordinary home into your very own piece of vacation paradise. ** Totally Private Pool & Hot Tub ** Outdoor Poolside Living S  …see more

from £322 / night

£2049 - £2903 / week

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from £322 / night

38

Kissimmee / Compass Bay

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £86 / night

£598 / week

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from £86 / night

(1) Excellent 

21

Lake Berkley holiday villa rental

Kissimmee / Lake Berkley

6 12 5 nights min

  • 6 bedrooms
  • Sleeps 12
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
*5 Star Rated Accommodation***Over 34 Guest Reviews*** NO BOOKING FEE ! *24hr Guarded and Gated Resort just minutes from Disney World *5 Person Luxury Hot Tub with coloured perimeter lighting *The BEST view on Lake Berkley **In the Centre of the 14 acre Natural Sprin  …see more

from £175 / night

£1225 / week

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from £175 / night

(2) Excellent 

24

Lindfields holiday home rental

Kissimmee / Lindfields

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our villa is magnificent, fully furnished and equipped to the highest standards with air conditioning and ceiling fans. It has a master bedroom with an en-suite, 3 further double bedrooms and a main bathroom, towels and bed linen are provided. It has a spacious  …see more

from £72 / night

£425 - £500 / week

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from £72 / night

24

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee / Windsor Palms

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Massive pool deck for relaxing, south facing with sun all day. Great look out over a conservation area and not over looked.Super comfort furniture. Formal and informal dining areas plus breakfast bar.2 x King sized en suite bedrooms. 1 x Queen and 2 x twin rooms.<br  …see more

from £165 / night

£1150 / week

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from £165 / night

23

Holiday home in Kissimmee

Central Florida / Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Summary • South Facing Pool overlooking conservation lake and woodland • 7 Bed 5.5 bathrooms with 3 Master Suites 2 Kings 2 Queens 6 Singles • Closest gated community to Disney Thank you for visiting Tinkerbells Retreat com ***** Choosing the right vill  …see more

from £204 / night

£1423 - £2318 / week

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from £204 / night

(1) Excellent 

40

Central Florida / Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £204 / night

£1342 - £1667 / week

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from £204 / night

8

Holiday home in Kissimmee

Kissimmee / Emerald Isle Kissimmee

5 12 3 nights min

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Bedding Summary: Bedroom #1: King BedBedroom #2: King BedBedroom #3: King BedBedroom #4: Queen BedBedroom #5: (2) Double Beds  …see more

from £138 / night

£962 / week

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from £138 / night

(3) Excellent 

11

Holiday hotel apartment in Kissimmee

Kissimmee / Compass Bay

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Air conditioning
“Near Disney, Good Price, Beautiful Place” We would stay again. we stayed here and drove to SeaWorld 3 days. very convenient. liked the fact it was a block off the main road. liked where it was near Fun Town for the kids, go cart track walking distan  …see more

from £105 / night

£748 / week

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from £105 / night

(3) Average 

15

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • 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

(31) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Really comfortable and relaxing stay, a quality holiday home.” We stayed here over Christmas and New Year. There were 8 family members - ample room for all and we still had a spare bedroom. The pool area was lovely and the villa location was great.  …see more

from £100 / night

£695 - £895 / week

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from £100 / night

24

Holiday villa in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Spread out and enjoy a sunny six bedroom, four bathroom villa in Windsor Hills Resort. Best of all, it is only two miles to Walt Disney World! FROZEN Themed BedroomNO REAR NEIGHBOURS! To ensure your privacy, our pool overlooks a natural area, not another house!<br /&  …see more

from £220 / night

£1464 - £2114 / week

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from £220 / night

37

Central Florida / Kissimmee

6 14 3 nights min

  • 6 bedrooms
  • Sleeps 14
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £161 / night

£1127 / week

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from £161 / night

(2) Excellent 

28

Holiday townhouse in Kissimmee

Central Florida / Kissimmee

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
Lakeview, 4 bedroom 3 bathroom luxury townhouse, with private heated pool and resort facilities. Proximity to great Clubhouse with lobby/reception, snack bar, all-year heated pools, training facilites and gameroom. 10 min drive to Orlando attractions and 15 minute dri  …see more

from £82 / night

£570 - £895 / week

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from £82 / night