Kissimmee Villas, Holiday rentals and apartments

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Kissimmee

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4,105 Holiday homes

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

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 £74 / night

£513 / week

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from £74 / night

(18) Excellent 

24

Home rental in Bellavida Resort

Kissimmee / Bellavida Resort

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“East 192, Where Tink@Bella waits for Youuuuuuu” The Bella Vida resort is a Great, Gated Community. Where inside awaits the the Fantastic Tink@Bella Villa. Approx 30 mins from Orlando Int. Perfect location for all that awaits you, Disney, Universal,  …see more

from £143 / night

£995 - £1395 / week

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from £143 / night

(3) Very Good 

14

Kissimmee holiday villa let

Kissimmee / Windsor Hills Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
our beautiful villa at 7764 Teascone Bvld. Windsor Hills Reserve will provide you the best of time on your vacation. You are welcome here to be at your ease. Additional features for the house:- • Games room – Pool, Air hockey, Basketball and Play Station 2.  …see more

from £179 / night

£1220 - £1261 / week

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from £179 / night

Featured properties

33

Home rental in Kissimmee with swimming pool

Central Florida / Kissimmee

6 10 2 nights min

  • 6 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Remarkable 6 Bed home with 5 Baths, located at Bella Vida 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 20 min away from Outlet Premium. Excellent clubhouse with f  …see more

from £179 / night

£1253 / week

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from £179 / 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

26

Holiday townhouse with shared pool in Venetian Bay Villages

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Fabulous fully equipped town home near Disney with free WiFi. Safe, family-friendly gated community with excellent facilities.  …see more

from £58 / night

£406 - £555 / week

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from £58 / night

(2) Excellent 

100

Emerald Isle Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

7 16 5 nights min

  • 7 bedrooms
  • Sleeps 16
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
LUXURY OF THE HIGHEST QUALITY! Large South facing pool plus spa, games room, BBQ and beautiful lake and woodland conservation views. One of the closest to Disney World!  …see more

from £185 / night

£1295 / week

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from £185 / night

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

(1) Excellent 

20

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful 3 bedroom 2 bathroom villa in Kissimmee. This villa has a private screened pool overlooking a lake. Situated in the tranquil community of Eagle Pointe only 15 minutes from Disney. Living Room – Light and airy open plan room overlooking the pool with two  …see more

from £86 / night

£600 - £750 / week

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from £86 / 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 £116 / night

£809 / week

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from £116 / night

9

Central Florida / Kissimmee

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £104 / night

£725 / week

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from £104 / night

(1) Excellent 

22

Villa rental in Kissimmee with swimming pool

Kissimmee / Cumbrian Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
This home has a breath taking view from the pool deck. It overlooks a pretty lake and you may be lucky enough to see deer grazing on the conservation area which lies beyond it. The deck area has been extended so there is also a Hot Tub for you to enjoy. The home itself  …see more

from £99 / night

£693 - £910 / week

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from £99 / night

(1) Excellent 

21

Kissimmee holiday villa rental

Kissimmee / The Hamlets

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Villa's situated in a gated community 6m / 10km from Disney World. Close to Highway 192 with all local amenities & restaurants, Near I-4 interstate and within easy reach of Orlando Int'l Airport . 5 double bedrooms inc'l a downstairs en-suite bedroom.  …see more

from £115 / night

£800 / week

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from £115 / 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

14

Villa rental in Kissimmee

Central Florida / Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Sparkling lakes provide a hospitable habitat for cranes, ospreys and blue heron. Cumbrian Lakes is a peaceful place to come home after a long day at the parks. Yet is so close to all the excitement that makes Central Florida the Number One Tourist destination in the Wor  …see more

from £80 / night

£490 - £725 / week

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from £80 / night

32

Holiday home in Kissimmee

Central Florida / Kissimmee

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This 6 bedroom, 5.5 bathroom house is situated in Terra Verde, Kissimmee. There are 4 master king en suite bedrooms. It has a wonderful west facing pool overlooking a huge lake. The resort offers a beautiful club house with resort manager and concierge, lounges, swimmin  …see more

from £158 / night

£925 - £1481 / week

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from £158 / night

15

Home rental in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Free WI-FI -3 Miles from Disney Private screened swimming pool - Free phone calls within the US, Canada and Puerto Rico - Tastefully furnished - Beautiful 4 bed /3 full bath - Cable TV - Fully appointed kitchenAll linen and towels - DVD player - Child alarmed - Culture  …see more

from £102 / night

£712 / week

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from £102 / night

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Oak Island Harbor

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Oak Island Harbor community is a community that is known and appreciated for its convenient location in the prestigious Formosa Gardens area. Upscale private pool homes in a spectacular and peaceful setting yet close to where everything is going on.  …see more

from £122 / night

£854 - £1179 / week

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from £122 / night

(8) Very Good 

49

Home rental in Kissimmee

Kissimmee / Lake Berkley

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“Our stay in Florida was made that much more enjoyable staying here” 995 Lake Berkley Drive, was a great place for us to stay during our recent two week trip to Florida. The estate itself is very impressive, clean and well maintained. A safe and secure  …see more

from £122 / night

£826 - £996 / week

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from £122 / night

23

Holiday villa in Kissimmee

Kissimmee / Windsor Palms

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
6 Bedroom Luxury Villa at Windsor Palms 3 Miles from Disney. Private Pool area with extended decking overlooking beautiful conservation area. 42" flat screen HDTV with cable. Free Wifi Internet. Games room. Gated community. Clubhouse facilities cinema, tennis, gym,  …see more

from £130 / night

£900 - £1150 / week

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from £130 / night

29

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 90 km
  • Child friendly
  • Air conditioning
"The Hunnypot" at Fiesta Key, Kissimmee, Florida, Exclusive, tranquil gated community, 10 minutes drive from Disney World entrance, Free wifi, Hot tub. "The Hunnypot" is a 4 bedroom, beautifully furnished home which sleeps 8/10 people, situated in a  …see more

from £61 / night

£427 - £700 / week

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from £61 / night

(16) Excellent 

28

Holiday villa with golf nearby 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 Bed, 3.5 Bath ~ Fabulous Vacation Home ~ Sleeps 12 guests + InfantsJust 5 mins drive from Walt Disney Private South Facing Pool with Beautiful Lake View ~ Quiet Location Yet Close To AmenitiesBright, Modern Villa in a Great LocationGreat for Families/group<br />  …see more

from £118 / night

£825 - £1090 / week

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from £118 / night

(1) Excellent 

17

Holiday villa rental

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
5 Bed, 3 Bath Luxury Villa, Pool, Spa, Games Room, Free In-House Wireless Internet - Emerald Island Resort. Ideal location,3 miles from Disney, one mile shops, Restaurants, mini golf, supermarkets and a medical centre. Internet streaming for Netflix etc Baby facilities  …see more

from £115 / night

£725 - £1120 / week

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from £115 / 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 £108 / night

£752 / week

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from £108 / night

26

Home rental in Kissimmee

Central Florida / Kissimmee

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
We have owned this villa for 8 years and we maintain it to high standards. The Pool Decking has been extended which gives greater poolside space together with longer sunshine hours on the deck.The villa is ideally situated for all the attractions and is close to Walmart  …see more

from £100 / night

£700 - £896 / week

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from £100 / night

(3) Very Good 

16

Holiday home with swimming pool in Veranda Palms

Kissimmee / Veranda Palms

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic villa and location” Stayed at this villa for two weeks and highly recommend it. It was clean, spacious and ideally located for Orlando airport and all the theme parks. Would definitely stay there again, the owner and management team were ver  …see more

from £146 / night

£805 - £887 / week

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from £146 / 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 £98 / night

£650 - £838 / week

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from £98 / 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 £86 / night

£598 / week

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from £86 / night

(2) Very Good 

13

Villa rental in Kissimmee with shared pool, golf nearby

Kissimmee / Orange Lake Resort

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Nice accommodation and location.” 20 minutes to theme parks. 10 minutes to super market. 30 minutes to outlet shops. Easy to find on Sat Nav and no hassles with traffic. Lacking a few kitchen utensils, but nothing worth fussing over.  …see more

from £171 / night

£1200 / week

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from £171 / 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

25

Holiday villa in Kissimmee

Kissimmee / Veranda Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 104 km
  • Swimming pool
  • Child friendly
Mickey’s Ritz at Veranda Palms is a private vacation home providing spacious accommodation with luxury, upgraded contemporary furnishings. The home has 4 bedrooms, 3 bathrooms, a large pool (30ft x 15ft) + spa, a south west facing pool deck with fabulous pool furn  …see more

from £105 / night

£729 - £957 / week

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from £105 / night

45

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
A home from home, the British owners spend as much time as possible in the villa themselves. The villa is situated on a large lot and the private south facing heated pool and jacuzzi back onto a wooded area. Pool heating for cooler months is available for an additional  …see more

from £70 / night

£484 - £712 / week

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from £70 / night

22

Holiday villa with golf nearby in Lindfields

Kissimmee / Lindfields

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
disneykidsdkingdom 4 bed & 3 bath pool villa, We are situated in the quiet Lindfields residential area of kissimmee florida, yet only a few minutes from Disney parks &the Interstate 4 & 417 which are the main roads to all the universal attractions and the a  …see more

from £114 / night

£732 - £753 / week

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from £114 / night

19

Holiday villa in Kissimmee

Central Florida / Kissimmee

7 16 7 nights min

  • 7 bedrooms
  • Sleeps 16
  • 7 nights min
  • Child friendly
There are four key features that make the Emerald Villa a fantastic 7 bedroom holiday home for a real family occasion: The pool area – spacious deck area, planting, privacy, lake view, plenty of chairs and loungers, waterfall feature The beds – pillow-top be  …see more

from £239 / night

£1667 / week

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from £239 / night

(10) Excellent 

20

Bellavida Resort holiday villa rental

Kissimmee / Bellavida Resort

6 14 1 night min

  • 6 bedrooms
  • Sleeps 14
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
“5 star villa - everything you need for the holiday of a lifetime” This was our third visit to Orlando and was way beyond our expectations. The villa was amazing. Spacious, luxurious and well equipped with everything you need for a relaxing holiday.  …see more

from £160 / night

£1087 / week

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from £160 / 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

(3) Excellent 

100

Kissimmee / Paradise Palms

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 103 km
  • Swimming pool
  • Child friendly

 …see more

from £98 / night

£683 / week

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from £98 / night

43

Kissimmee holiday villa rental

Central Florida / Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Child friendly
Welcome to our Luxury Home from Home set within the beautiful gated community resort of ‘Windsor at Westside’. Our vacation home sits on a large site which is not overlooked in this brand new resort that has quickly become one of the most desired location  …see more

from £220 / night

£1500 - £1600 / week

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from £220 / night

(54) Excellent 

23

Holiday villa in Crescent Lakes

Kissimmee / Crescent Lakes

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Beyond our expectations” This was our first villa rental in USA. It exceeded our expectations, a spacious modern villa well appointed, washer , tumble dryer, TV in all rooms, dishwasher, games room with full size pool table, air hockey etc, and a love  …see more

from £90 / night

£575 - £690 / week

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from £90 / night

(1) Excellent 

41

Kissimmee / Kissimmee City

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

 …see more

from £94 / night

£610 - £1118 / week

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from £94 / night