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Kissimmee

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

(18) Very Good 

17

Holiday villa in Kissimmee City

Kissimmee / Kissimmee City

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Magnificent Accomadation” We arrived for our stay of 2 weeks after travelling for 20 hours, we found the place easily everything was as described, the only disappointment my girls had was the pool was cold , however it soon warmed up after a couple o  …see more

from £49 / night

£299 - £550 / week

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from £49 / night

(9) Excellent 

24

Kissimmee holiday villa rental

Kissimmee / Doral Woods

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Home away from home!” We thoroughly enjoyed the villa with all of its amenities. Clearly this was equipped with children in mind. Our 2, 8 and 10 year-olds found things to do for the entire stay. Naturally the pool was number one, but they found plent  …see more

from £74 / night

£470 - £1260 / week

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from £74 / night

(13) Very Good 

17

Holiday villa in Seasons Resort

Kissimmee / Seasons Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Great House, Perfect Location!” House was in great shape. Had everything needed. Pool was perfect. Near everything needed. Shopping, minutes from the theme parks. Payment plan was perfect for people on a budget. Owner very responsive. We hope to rent  …see more

from £60 / night

£360 - £550 / week

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from £60 / night

Featured properties

(5) Excellent 

28

Holiday home rental

Kissimmee / Emerald Isle Kissimmee

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
“Super Spring Break” My family spent the week of April 7 - 14, 2012 at "Jewel In The Crown", which is located in Emerald Island Resort. This is our sixth trip to Orlando and one of the best times we've had!!! Our "home away from home" was comfortable,  …see more

from £162 / night

£1133 / week

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from £162 / night

55

Holiday condo with shared pool in Kissimmee

Kissimmee / Cane Island

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Self-catering air-conditioned condo with shared swimming pool, gym and games room.<br />We own three of these condos, one above the other, so if you have a large party you can all stay together.  …see more

from £49 / night

£343 / week

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from £49 / night

(17) Excellent 

23

Holiday townhouse in Kissimmee

Kissimmee / Encantada Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic house in a fantastic location” Recently returned from 2 weeks of fun in Florida with our 5 year old daughter. The weather was glorious and the parks brilliant. What topped our holiday was returning everday to our rented home. The home had a  …see more

from £66 / night

£403 - £870 / week

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from £66 / night

(10) Excellent 

18

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Excellent location, peaceful and very well equipped” Easy to find. Had everything we needed and a great place to come back to after busy days at the attractions.  …see more

from £80 / night

£495 - £625 / week

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from £80 / night

(23) Excellent 

8

Holiday condo in Kissimmee

Kissimmee / Cane Island

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Beautiful condo in a great location” The condo at cane island is absolutely wonderful. We were delighted with the choice we made having spent hours trawling the Internet before booking. Everywhere was sparkling clean and absolutely beautifully decorat  …see more

from £50 / night

£350 - £420 / week

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from £50 / night

(7) Very Good 

20

Holiday townhouse in Kissimmee

Kissimmee / Paradise Palms

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
A Beautiful 5* Star 'Spacious', 4 bedroom, 3 bath Vacation home, south Facing Private Pool on a holiday resort with Communal Pool, tennis Courts, Games Room, Sauna, Gym, Card Room. Tiki Bar. 5 Mins from Disney and all the major attractions. Ideal for families  …see more

from £94 / night

£610 - £940 / week

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from £94 / night

(21) Very Good 

26

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“very homely” Excellent location Close to airport.all parks and amenities. Would recommend this villa to anybody. Equipped with everything. Home from Home  …see more

from £50 / night

£350 - £725 / week

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from £50 / night

23

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

5 13 1 night min

  • 5 bedrooms
  • Sleeps 13
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This new executive villa features state of-the-art living ... 5 bedrooms, 3.5 bathrooms, swimming pool and spa. Cumbrian Lakes is set in a conservation area yet only 5 minutes from shops and restaurants and less than 15 minutes to Disney World.The execut  …see more

from £105 / night

£735 - £980 / week

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from £105 / night

(14) Very Good 

29

Holiday home in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Superb stay close to Orlando and parks.” My family, together with my parents and sister in law stayed at this villa during the last week of December for 6 days. This was an excellent home, spacious and clean with all the amenities a villa should h  …see more

from £140 / night

£980 - £1400 / week

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from £140 / night

(17) Excellent 

24

Holiday villa letting

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“Had a great time at this Villa” We arrived to a clean, well kept villa. We unloaded our luggage and ran over to the nearby Wal-Mart to get some food etc. It was very convenient having a Wal-Mart near by (as well as several restaurants). The pool was  …see more

from £65 / night

£440 - £550 / week

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from £65 / night

(5) Excellent 

24

Kissimmee holiday home accommodation

Kissimmee / Lindfields

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Pete and Louise” I felt like I was at home !!!!! Everything I needed and could have forgotten was already there......this place was immaculate! It was close tho so many things to do and shopping as well......I will be back again real soon for sure, th  …see more

from £50 / night

£308 - £325 / week

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from £50 / night

(2) Excellent 

28

Holiday villa in Seasons Resort

Kissimmee / Seasons Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Home from home, great value for money.” Having stayed here with my family, plus another family of five in 2013 we tried to rebook the same villa but unfortunately it was fully booked up. We found this villa to have everything we needed and more, beaut  …see more

from £159 / night

£1053 - £1704 / week

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from £159 / night

(9) Very Good 

50

Holiday villa rental

Kissimmee / Trafalgar Village

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Located in a Family friendly community with free use of resort facilities our well-furnished villa with pool and hot tub can comfortably accommodate up to 8 Guests. Less than 15 miles from Walt Disney World.<br />Pool & Spa Heat is available at an additional  …see more

from £85 / night

£520 - £680 / week

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from £85 / night

(29) Excellent 

90

Villa rental in Kissimmee with swimming pool

Kissimmee / Eagle Pointe

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Comfortable villa in good location” We stayed for 4 nights to attend the Mecum Auto auction. The villa was spacious ,clean and reasonable to rent. Accessible to all Orlando attractions. Travelers need to bring everything, paper goods, coffee, cream  …see more

from £65 / night

£455 - £553 / week

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from £65 / night

42

Condo rental in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Windsor Hills is perhaps the finest resort community in the Disney area. With world famous theme parks and attractions just minutes away, a stay here will create family memories to last a lifetime.  …see more

from £89 / night

£627 - £968 / week

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from £89 / night

(6) Excellent 

21

Trafalgar Village holiday home rental

Kissimmee / Trafalgar Village

5 12 3 nights min

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
“Fabulous home away from home” Ten of us stayed in this Villa, consisting 3 children, 2 teenagers and 5 adults. We had plenty of room for all of us as it's such a large property. The Villa was very well equipped with everything we needed and spotlessly  …see more

from £135 / night

£940 - £962 / week

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from £135 / night

(19) Very Good 

20

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Swimming pool
“Dream home, brilliant location, very clean and well equipped.” From the first contact on enquiry to arriving back home 2 weeks later, the whole renting process and communication was outstanding, our family, 3 adults and 4 children aged 3,10,11 and16 a  …see more

from £130 / night

£875 / week

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from £130 / night

(30) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“We'd stay again in a heartbeat !!” Everything about this place was "top shelf". It was sparkling clean and comfortable, with all the amenities one could ask for. Beautifully decorated and thoughtfully equipped, this place completely met our needs an  …see more

from £135 / night

£800 - £995 / week

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from £135 / night

(12) Excellent 

12

Kissimmee holiday villa rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
•40ft lake view pool with sunshine on deck from 10am till sunset•Within 30 minutes for ALL parks,Orlando airport and the Florida Mall•Prime lake view and privacy •24 hour Walmart and loads of restaurants and shops close by• Returning guests year  …see more

from £73 / night

£510 - £630 / week

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from £73 / night

(2) Very Good 

20

Kissimmee holiday townhouse accommodation

Kissimmee / Paradise Palms

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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 £82 / night

£529 - £911 / week

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from £82 / night

(2) Very Good 

18

Central Florida / Kissimmee

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £81 / night

£564 / week

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from £81 / night

(12) Excellent 

19

Villa rental in Kissimmee

Kissimmee / Bellavida Resort

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Lots of space and nice pool” We travelled with two children (9&10) plus two teenagers and everybody enjoyed our stay! Plenty of room for everybody, own swimming pool and jaguzzi plus communal pool. Short (15-20 min) drive to the amusement parks. Sever  …see more

from £90 / night

£590 / week

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from £90 / night

(23) Very Good 

23

Holiday home in Kissimmee

Central Florida / Kissimmee

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Just Perfect” My wife and I are regular visitors to the Orlando area and have stayed in several Rental Villas in the past. It was our first time at ‘Ventura Villa’ hopefully not our last, we had a really enjoyable stay. The villa is clean, well fur  …see more

from £80 / night

£550 - £1054 / week

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from £80 / night

(20) Excellent 

18

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic, wonderful location and wonderful villa” This is a great villa. The owners are easy to deal with and friendly. The area is great and the villa is a good size. It is 4 bedrooms, 2 doubles and 2 twins and has loads of space, all the amenities  …see more

from £61 / night

£425 - £450 / week

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from £61 / night

(2) Very Good 

51

Kissimmee holiday apartment rental

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sun Lake amenities include a clubhouse with gym and pool table, a lighted tennis court and a heated spa and a free form pool.<br />We are two miles from Disney and 15 minutes from Sea World, Premium Outlet Malls and 20 minutes from Univers  …see more

from £70 / night

£488 / week

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from £70 / night

(10) Very Good 

90

Holiday townhouse in Kissimmee

Kissimmee / Terra Verde Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Very nice, we'll situated resort.” The home was very nice. Furnishings were nice and kitchen had everything we needed to cook with. Home appeared to be well maintained and the owner was a pleasure to deal with. My family highly recommends this hom  …see more

from £65 / night

£400 - £495 / week

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from £65 / night

(11) Excellent 

24

Calabria, Orlando holiday villa rental

Kissimmee / Calabria, Orlando

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Just what we wanted. Great space. Great location” Preparation communications from owner was excellent. Group of 10 with no issues at all throughout the stay. Quite and pleasant neighbourhood.  …see more

from £155 / night

£1082 / week

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from £155 / night

(6) Very Good 

13

Holiday villa with shared pool, golf nearby in Kissimmee

Kissimmee / Windsor Palms

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxury Disney Villa. Close to Disney, Large 6 bedroom villa, private pool with spa, not overlooked, Florida villa, childrens themed rooms, games room, free wifi, gates resort, gated community, Disney Frozen Room, Star Wars Themed room<br />for the perfect family  …see more

from £150 / night

£700 - £800 / week

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from £150 / night

(7) Excellent 

23

Kissimmee holiday villa rental

Kissimmee / Country Creek

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our beautiful family owned villa is located only 10 mins from WDW and close to many other attractions such as Sea World, Aquatica, Universal Studios and Universal Islands of Adventure. Our home from home is comfortably furnished and equipped with all the amenities to m  …see more

from £85 / night

£560 - £665 / week

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from £85 / night

(10) Excellent 

28

Doral Woods holiday villa rental

Kissimmee / Doral Woods

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“It was just GREAT!” Large heated pool, large and clean rooms! Everything was as promised in the description! Ideal family holiday with guaranteed comfort! To Disney 25 Minutes, Universal 35 Minutes :-)  …see more

from £65 / night

£450 - £480 / week

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from £65 / night

(16) Excellent 

23

Kissimmee holiday villa let

Kissimmee / Bellavida Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Very vice decorated big villa in a great area” A lovely big villa, all amenities and very nicely decorated inside. Good size pool with sun from morning to evening and overlooking the resort lake. The resort has a paved path around the lake which is ni  …see more

from £149 / night

£1045 - £1495 / week

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from £149 / night

(13) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“Excellent Villa highly recommend it, great location.” Property was excellent, close to Disney and places to eat. The weather was nice and the complex where the villa was situated was well looked after, nice and clean and staff was pleasant.  …see more

from £148 / night

£1000 - £1450 / week

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from £148 / night

(4) Excellent 

30

Kissimmee holiday villa let

Kissimmee / Lindfields

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“The Perfect home in the Perfect location” The only word to describe this beautiful well maintained home is 'wow' I would say it was like a home from home, only much better. Everything has been thought of to ensure a comfortable stay. The pool is super  …see more

from £70 / night

£445 - £595 / week

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from £70 / 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

(23) Very Good 

56

Holiday home rental

Kissimmee / Lindfields

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 90 km
  • Swimming pool
“Great accommodation” Stayed here for two weeks for our honeymoon. Location of the villa is excellent if visiting the Disney Parks. Clean and tidy, very large living area and bedrooms. Couldn't have asked for anything better.  …see more

from £50 / night

£350 / week

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from £50 / night

(6) Excellent 

31

Holiday villa in Kissimmee

Kissimmee / Seasons Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Amazing family home” Perfect family home to use with a large family (13 of us) plenty of space for all, home from home. A lovely pool with safety fence around which was excellent as we had a 2year old.very clean. Excellent location with resturants ne  …see more

from £159 / night

£1094 - £1948 / week

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from £159 / night

(5) Excellent 

24

Holiday villa with swimming pool in Kissimmee

Kissimmee / Cumbrian Lakes

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Cumbrian Lakes is an exclusive gated community with lakes, cycling & walking trails & a kids play area.  …see more

from £100 / night

£700 - £850 / week

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from £100 / night