Kissimmee apartment or villa with a heated pool

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Kissimmee

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1,261 Holiday homes

Filters applied: Heated pool

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

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 £216 / night

£1440 - £2080 / week

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from £216 / 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 £159 / night

£1109 / week

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from £159 / night

46

Villa rental in Kissimmee with swimming pool

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
Turn your dreams into reality in our Luxury Holiday Villa just a short distance from the Orlando theme parks.This is Mickey's Retreat, our 3 Bedroom, 2 Bathroom Villa in Kissimmee, Florida. Mickey's Retreat is conveniently situated just a short ten min  …see more

from £96 / night

£640 - £824 / week

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from £96 / night

(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 £72 / night

£480 / week

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from £72 / night

(2) Excellent 

27

Holiday villa in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
“Great rental experience” As the title of the listing states, this villa was only 5 minutes to Disney. We found the description and the pictures to be quite accurate too. The community is well maintained and it is gated which made us feel secure. Also  …see more

from £180 / night

£1840 / week

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from £180 / night

28

Home rental in Kissimmee

Central Florida / Kissimmee

5 11 5 nights min

  • 5 bedrooms
  • Sleeps 11
  • 5 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
After a long day’s walk (or run – thanks, kids!) through Disney, there’s nothing quite like sinking into the warm, inviting bubbles of your very own, very spa. After a theme park marathon, there’s nothing quite like taking a day off for a famil  …see more

from £125 / night

£875 - £1425 / week

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from £125 / night

8

Kissimmee holiday villa rental

Kissimmee / Trafalgar Village

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Easy, friendly booking, very good rates and a fun, peaceful relaxation away from the hustle and bustle of the parks guaranteed.<br />We can boast a remarkable, fast acting local management. A phone call with any problem will be sorted fast.  …see more

from £84 / night

£588 / week

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from £84 / night

(2) Excellent 

28

Holiday townhouse in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 £80 / night

£560 - £880 / week

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from £80 / night

8

Kissimmee holiday villa rental

Central Florida / Kissimmee

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Golf Courses Within a Short Drive  …see more

from £64 / night

£445 - £540 / week

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from £64 / night

(21) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Windsor Palms

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fabulous house” We had a great time at Sundown Palm. The house was beautiful and very roomy. My 6 year old and 2 year old had a great time playing in the play room and in the pool. I would highly recommend. My only regret is not spending more time  …see more

from £190 / night

£1330 / week

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from £190 / night

17

Holiday villa with golf nearby in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
Emerald Island is a gated community and is manned 24 hours a day. There is a club house with a small shop ,games room ,computer room and a gym , there is large pool and tikki bar, where you can enjoy meeting other people. There are shops near by and many very good r  …see more

from £120 / night

£795 - £830 / week

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from £120 / night

(3) Very Good 

14

Kissimmee / Venetian Bay Villages

3 6 5 nights min

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

 …see more

from £55 / night

£381 / week

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from £55 / night

58

Kissimmee holiday home rental

Central Florida / Kissimmee

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Calla Lily is a fabulous Lake front 5 bedroom 3 bathroom pool home in Crescent Lakes in Kissimmee, a fantastic, superbly well cared for community that is situated in a natural conservation area yet it is still close to all that the Orlando/Disney area has to offer to e  …see more

from £184 / night

£1288 / week

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from £184 / 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
“Our Family 4th of July Vacation” I was looking for a place where my family and myself could go to spend time in Florida from where I live in NYC. We chose the perfect location. Check in was simple, directions to the home were easy to understand, and i  …see more

from £100 / night

£695 - £895 / week

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from £100 / night

(7) Excellent 

20

Holiday bungalow with swimming pool, golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
Location. Location. Location! We are close to all amenities within the resort ( volleyball, tennis and basketball courts; putting green, large pool, water slide and jacuzzi ; video games and movie theatre) and we are close to all Disney theme and water parks! Some night  …see more

from £132 / night

£924 / week

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from £132 / night

(1)  

14

Remington holiday villa rental

Kissimmee / Remington

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
A luxury villa with its own extended pool, spa and games room, that adjoins the prestigious Remington Golf Club. Minutes from the Florida Turnpike & Highway 192 that takes you to Disney and Parks.  …see more

from £96 / night

£672 / week

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from £96 / 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

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 £176 / night

£1232 / week

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from £176 / 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 £100 / night

£640 / week

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from £100 / night

30

Home rental in Kissimmee

Central Florida / Kissimmee

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 £90 / night

£796 / week

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from £90 / night

16

Townhouse rental in Venetian Bay Villages with shared pool

Kissimmee / Venetian Bay Villages

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Excellent 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 s  …see more

from £76 / night

£532 - £728 / week

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from £76 / night

(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

11

Holiday villa in Kissimmee

Kissimmee / Formosa Gardens

2 10 7 nights min

  • 2 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Lovely Villa with loft at Wetgate Vacation Villas - Kissimmee, 5 miles away from Disney and just minutes from Orlando Theme Parks.  …see more

from £152 / night

£1064 / week

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from £152 / 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 £141 / night

£984 / week

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from £141 / 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 £96 / night

£667 / week

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from £96 / 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 £160 / night

£1120 / week

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from £160 / night

(7) Excellent 

19

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 6 nights min

  • 4 bedrooms
  • Sleeps 8
  • 6 nights min
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly
“Excellent property and very helpful owners” This house is excellent and very well maintained. It had all the amenities / facilities we needed and in good working order. Very comfortable and easy to relax after long days at the theme parks. Julie and M  …see more

from £95 / night

£570 - £630 / week

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from £95 / night

10

Holiday home rental

Central Florida / Kissimmee

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Near Disney and all the parks , very close to lots of shopping and restaurant's . Great choice of golf course 's ,and guaranteed lots of sunshine .Only 30 minute drive from Orlando International Airport.. The complex has security 24 / 7 , and no problem wi  …see more

from £72 / night

£480 / week

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from £72 / night

(1) Very Good 

20

Kissimmee holiday villa rental

Kissimmee / Windsor Hills Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
“Lovely villa in a super location” We all thoroughly enjoyed our stay at Harmony Haven with its good standard, spacious accommodation and super swimming pool. We travelled with our children and grandchildren and we all enjoyed the water shoot at th  …see more

from £96 / night

£672 / week

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from £96 / night

11

Holiday home with indoor pool in Kissimmee

Central Florida / Kissimmee

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Very nice 2 Bed home with 2,5 Baths, located at Encantada Resort, close to 192 and to many restaurants and markets. a few minutes from Disney Parks, only 3 miles away. 15 minutes away from Universal Studios and 20 min away from Outlet Premium. Excellent clubhouse with f  …see more

from £72 / night

£504 / week

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from £72 / night

35

Holiday home with swimming pool in Kissimmee

Central Florida / Kissimmee

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Wonderful 4 Bed townhome with 3 Baths, located at Paradise Palms Resort, close to 192 and to many restaurants and markets. a few minutes from Disney Parks, only 3 miles away. 15 minutes away from Universal Studios and 20 min away from Outlet Premium. Excellent clubhouse  …see more

from £106 / night

£740 / week

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from £106 / night

(15) Excellent 

21

Holiday villa with golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic villa, great location!” Dunestone is a very smart, spacious and well-positioned villa in a great gated community. So close to Disney and only mins from the I-4 allowing easy access to all of Orlando's attractions. The owners were a pleasure  …see more

from £155 / night

£1085 - £1680 / week

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from £155 / night

20

Holiday home rental

Kissimmee / Lake Berkley

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
A PERFECT LOCATION FOR A DISNEY VACATION. 10 minutes from Disney, 2 minutes from the buzzing 192 with Wal-mart, Restaurants, Shopping malls etc yet a world away on the Prestigious Lake Berkley Resort in one of the envious positioned villas on the resort overlooking  …see more

from £125 / night

£800 / week

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from £125 / 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 £200 / night

£1400 - £2360 / week

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from £200 / night

(1) Excellent 

15

Kissimmee holiday villa rental

Kissimmee / Lake Berkley

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
“FABULOUS all round” Villa location excellent , pool area fantastic , Lake Views Stunning , wildlife & Bird Watching Endless enjoyment The Best of Furniture & Soft Furnishing through out And the Owners a joy to deal with If you think the PHOTOS  …see more

from £410 / night

£570 / week

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from £410 / 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 £200 / night

£1400 - £2280 / week

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from £200 / night

19

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 11 1 night min

  • 4 bedrooms
  • Sleeps 11
  • 1 night min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
Bass Lake Estates is a small, Beautifully maintained community, and is one of the closest to Orlando's main attractions. It is a mature development of detached pool homes with a Glorious large natural lake,which attract many varieties of fish and wildlife. Relaxing  …see more

from £114 / night

£796 / week

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from £114 / night

16

Central Florida / Kissimmee

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £132 / night

£924 / week

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from £132 / night

(1) Very Good 

22

Holiday home in Kissimmee

Central Florida / Kissimmee

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Please note we only allow maximum 8 guests to ensure our villa is kept in top condition. A stunning, larger than average, 6 Bed 3.5 Bathroom villa with a fantastic private pool. This villa is located in the 5 stars resort of Lake Berkley. The villa is furnished and main  …see more

from £128 / night

£876 - £980 / week

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from £128 / night

(1)  

8

Townhouse rental in Kissimmee with golf nearby

Kissimmee / Emerald Isle Kissimmee

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Emerald Island has a great location, only minutes from Disney and theres loads of shops and restaurants close by. Our house has a brilliant position right infront of the heated pool and spa and you can just sit on the balcony and chill out after a busy day at the parks  …see more

from £76 / night

£480 / week

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from £76 / night