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Kissimmee

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828 Holiday homes

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

(2) Very Good 

100

Holiday villa in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Secret Key Cove Villa Luxury Award Winning Vacation villa rental, in Orlando, FloridaSet in a Gated CommunityThis 2 story upgraded Villa has, 4 bedrooms, 3 bathrooms, air conditioning and is set in a private location with its own private pool and spa. <br />Emer  …see more

from £113 / night

£791 - £1147 / week

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from £113 / night

21

Holiday villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Location: Emerald Island Resort, Kissimmee Central West, Kissimmee, Central-Disney-Orlando Area, Florida, USA View MapHI SPEED INTERNET,POOL/SPA EXT/DECKING,GAMESROOM,THEMED BEDROOMS,FREE USA CALLSAccommodations: , 4 Bedrooms, 3 Baths (Sleeps 8)Welco  …see more

from £101 / night

£666 - £968 / week

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from £101 / 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

(6) Excellent 

75

Holiday villa rental

Kissimmee / Kissimmee City

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Luxurious, spaceous secluded villa” Excellent location to all amenities. Villa exceptionally equipped with luxurious facilities. Didn't want to leave !!  …see more

from £109 / night

£767 - £964 / week

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from £109 / 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 £137 / night

£955 / week

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from £137 / night

(5) Excellent 

27

Holiday villa letting

Kissimmee / Windsor Palms

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
4 bed villa near Disney, FREE wifi, private pool and jacuzzi,air con, 2 bathrooms, 220 channel hdtv's, PS3, Xbox360, Windsor Palms Resort, secure gated community with communal pool, tiki bar, playground, sports courts, gym, games room, cinema, shop, bike/dvd/bbq re  …see more

from £120 / night

£825 / week

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from £120 / 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 £138 / night

£960 - £1130 / week

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from £138 / night

(21) Excellent 

27

Holiday villa with golf nearby in Kissimmee

Kissimmee / Windsor Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 68 km
  • Swimming pool
  • Child friendly
“A magical Christmas vacation” A very clean and comfortable villa, with a beautifully heated pool. The games room was good fun and the owner was very helpful and easy to deal with. Windsor Palms is a good location with easy access to Disney - for a s  …see more

from £117 / night

£799 - £1209 / week

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from £117 / 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

(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

(1) Excellent 

20

Holiday villa in Kissimmee

Kissimmee / Lake Berkley

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
Villa in lake Berkley, kissimmee, Florida/. 7 bedroom all with en-suite facilities villa at lake Berkley resort with stunning views across the lake and of the island, peaceful location but only 15 minutes to Disney.<br />Luxury pool seating on extended deck overlo  …see more

from £157 / night

£1100 / week

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from £157 / 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 £237 / night

£1654 / week

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from £237 / night

23

Holiday villa in Kissimmee

Kissimmee / Terra Verde Resort

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
This superb luxury vacation pool home with 6 bedrooms, 5.5 bathrooms and straight forward fully inclusive pricing has everything that you could possibly need for the perfect holiday.  …see more

from £125 / night

£875 - £1295 / week

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from £125 / 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 £162 / night

£1130 / week

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from £162 / night

(1) Very Good 

19

Holiday apartment with shared pool in Kissimmee

Kissimmee / Windsor Palms

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This gorgeous Kissimmee 3 bedroom vacation rental home, is only 20 minutes drive from Orlando International airport, and is without a doubt, a home away from home. Comfortably sleeping 6 and fully equipped with towels, bedlinen, washer, dryer (highchair and travel cot a  …see more

from £64 / night

£446 / week

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from £64 / 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 £113 / night

£726 - £746 / week

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from £113 / 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 £182 / night

£1855 / week

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from £182 / 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 £134 / night

£875 / week

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from £134 / 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

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

23

Emerald Isle Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
Emerald Island Resort offers many community features and stands above the rest in offering luxurious villas. Why stay anywhere else when you can rent this luxury villa within 5 minutes (3 miles) of Disney World Orlando Florida? Deal with us, the owners direct and save  …see more

from £202 / night

£1210 - £1855 / week

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from £202 / 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 £65 / night

£455 - £628 / week

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from £65 / 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 £120 / night

£725 - £1120 / week

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from £120 / night

(2) Excellent 

71

Holiday villa with shared pool in Kissimmee City

Kissimmee / Kissimmee City

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect in every way” we have stayed here several times (approx. 10) and every time the house delivers what we expect in a Florida villa. Villa is cleaned to a high standard on arrival, the kitchen has everything you have in your own kitchen at home s  …see more

from £70 / night

£450 - £495 / week

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from £70 / night

(11) Excellent 

23

Holiday villa in Hamilton's Reserve

Kissimmee / Hamilton's Reserve

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 40 km
  • Swimming pool
“excellent spacious well equipped holiday villa and close to parks” Had a lovely two weeks here. There were 6 adults and we never felt cramped. Nice pool area and a large games room. Close to many restaurants etc and easy to get to all parks etc. Lovel  …see more

from £98 / night

£685 - £1240 / week

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from £98 / 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

(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 £200 / night

£1400 / week

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from £200 / night

(58) Excellent 

20

Holiday villa with golf nearby in Kissimmee

Kissimmee / Formosa Gardens

7 22 4 nights min

  • 7 bedrooms
  • Sleeps 22
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“This place is heaven!!” Close to all the attractions yet private enough to give you relaxation!!! Can't wait to book here again!! The owners were very easy to work with and very patient with us!!! Thanks again for renting to us!!!  …see more

from £320 / night

£2238 / week

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from £320 / 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 £153 / night

£1067 / week

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from £153 / 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 £81 / night

£565 - £888 / week

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from £81 / night

(1) Excellent 

21

Kissimmee holiday villa rental

Kissimmee / Lake Berkley

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
7 Bed. 5 Bath Lakeside Villa. Private Pool/24Hr Spa, Gameroom, Lightening WIFI/ Sat. Nav, 5 King beds- 7 mins to Disney. Childs Paradise Stunning Views, Tranquil surroundings on safe gated and guarded Top Resort. Close to all attractions, restaurants and, designer shop  …see more

from £185 / night

£1250 - £1936 / week

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from £185 / 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

(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

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 £97 / night

£645 - £831 / week

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from £97 / 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

(1) Excellent 

24

Holiday villa accommodation

Kissimmee / Formosa Gardens

8 18 1 night min

  • 8 bedrooms
  • Sleeps 18
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
St. George's Manor is the flagship villa of 4 luxurious vacation homes by St. George's Villas - our small, family-run villa rental business. We own all of our villas so we can guarantee you the best service with an unmatched passion for making your holiday the  …see more

from £500 / night

£3480 - £4176 / week

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from £500 / night

(1) Excellent 

55

Kissimmee holiday villa rental

Kissimmee / Lake Berkley

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Loved it so much” Just spent 2 weeks in this villa, loved it so much! Many happy memories of a great holiday, we are definitely looking into coming again. Slept 6 more then comfortably and the pool is in a great position, gets a few hours sunlight bu  …see more

from £90 / night

£550 - £785 / week

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from £90 / night

17

Kissimmee holiday villa rental

Central Florida / Kissimmee

6 13 5 nights min

  • 6 bedrooms
  • Sleeps 13
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Child friendly
Windsor Hills Luxury Lake View Villa, Free Wifi, Games Rooms, Themed Disney Rooms,Close to Disney Tax included, Bedroom, Bunk Bed, Child Friendly Private Pool Spa No rear neighbors, free high speed wifi, free international calls pool table, foosball, air hockey , bbq&  …see more

from £175 / night

£1225 / week

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from £175 / 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

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 £89 / night

£565 / week

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from £89 / night