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Kissimmee

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288 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.

(48) Excellent 

60

Villa rental in Kissimmee

Kissimmee / Indian Ridge

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Excellent Location and a Wonderful Home.” Never booked through holiday lettings before so I was a bit nervous however I needn't have been. From the first moment I had contact with the owners of Russel Ridge communications and reassurance have been exc  …see more

from £100 / night

£425 - £700 / week

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from £100 / night

(18) Excellent 

56

Kissimmee holiday villa rental

Kissimmee / Crescent Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Just what we needed.” Plenty of room for us all. Easy routes to parks etc. if you are happy to drive in US. House had everything we needed. Pool was perfect.  …see more

from £93 / night

£650 - £900 / week

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from £93 / night

(30) Excellent 

23

Holiday home with swimming pool in Oak Island Cove

Kissimmee / Oak Island Cove

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Ideally situated, beautifully kept property with everything you ever need, a home from home!” This was our first family holiday to Florida and the villa absolutely had everything we wanted to enjoy our holiday! Ideally situated with ease if access to  …see more

from £100 / night

£600 - £700 / week

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from £100 / night

Featured properties

(23) Excellent 

24

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Location” Great location that is close to restaurants, stores, and Disney World and also very affordable. Our kids loved the pool.  …see more

from £75 / night

£525 - £600 / week

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from £75 / night

(3) Very Good 

28

Holiday villa with shared pool in Kissimmee

Central Florida / Kissimmee

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This fabulous villa gives our guests a real home from home experience. It is furnished for relaxation with comfy furniture, carpeted floors & it's own private pool that can be heated. Overview of Villa • Private Pool with Lanai • Recently Refurbish  …see more

from £95 / night

£636 - £775 / week

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from £95 / night

(7) Excellent 

28

Holiday villa in Kissimmee

Kissimmee / Windsor Hills Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Santa Caterina is located in the beautiful Windsor Hills Resort where you can enjoy all the comforts and amenities of home with all the attractions and the social interactions of a First Class Resort.<br />ALL PRICES QUOTED INCLUDE 13% FLORIDA TAXRefundable securi  …see more

from £116 / night

£812 - £1085 / week

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from £116 / night

(19) Very Good 

68

Holiday villa in Kissimmee

Kissimmee / Lindfields

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Thanks” This was a great Vila with everything you needed and in a good area to base yourself, if any c ok militants a bit dated  …see more

from £100 / night

£450 - £540 / week

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from £100 / night

(16) Excellent 

22

Holiday villa with swimming pool in Bellavida Resort

Kissimmee / Bellavida Resort

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Perfect villa for all the Orlando attractions” Belles Cove is a lovely family home and ideally located for the parks and other attractions The rooms are tastefully decorated and with the benefit of 4 bathrooms presents ideal accommodation for a large  …see more

from £105 / night

£635 - £825 / week

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from £105 / night

(36) Excellent 

39

Villa rental in Kissimmee

Central Florida / Kissimmee

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Wonderful place to spend your hollidays with your family” Wonderful villa to stay in a group of 6. The house was well equipped and very good conditions. The location of the house was very convenient (there is a wallmart just 1 mille away and not that  …see more

from £80 / night

£495 - £505 / week

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from £80 / night

(6) Excellent 

26

Holiday villa in Formosa Gardens

Kissimmee / Formosa Gardens

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Superb chillout base for a large group visiting the theme parks” As a group of 9 adults and 2 children, we thought it may prove difficult to rent anywhere large enough to accommodate everyone under the same roof, but this house met this need with hono  …see more

from £218 / night

£1520 - £1983 / week

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from £218 / night

(3) Excellent 

24

Villa rental in Kissimmee

Kissimmee / Lake Berkley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Great Villa, Great Location” We have stayed at Lake Berkley a dozen or so times now and this is probably one of the better villas. Its located in a beautiful gated community overlooking a lake but in an ideal place for access to all the major attracti  …see more

from £90 / night

£575 - £625 / week

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from £90 / night

(24) Excellent 

23

Holiday villa rental

Kissimmee / Veranda Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 84 km
  • Swimming pool
  • Child friendly
“Excellent , pleasant and very convenient .” We enjoyed 8 wonderful days at Villa Nirvana. We were an extended family, a groop of 8 people including teenagers and a baby. All of us wish to emphasize that the time we spent at the villa was wonderful. E  …see more

from £110 / night

£769 - £883 / week

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from £110 / night

(8) Excellent 

14

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
“A HOLIDAY TO REMEMBER” Cumbrian lakes drive is a well appointed 8 bed villa in very pleasant surroundings. We stayed there 4 adults and 2 young children aged 6 & 8 for 2 weeks. It is within easy access of all the parks, the malls etc and only a shor  …see more

from £90 / night

£630 - £795 / week

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from £90 / night

(24) Very Good 

12

Villa rental in Lindfields with swimming pool

Kissimmee / Lindfields

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“A great place to relax after a busy day at Disney World” We had a wonderful holiday staying at Sunrise Villa in Lindfields Reserve. The villa is lovely, very well equipped for self catering and is as good as it looks in the photos. The pool area is pa  …see more

from £61 / night

£425 - £525 / week

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from £61 / night

(2) Excellent 

15

Kissimmee holiday villa accommodation

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 90 km
  • Swimming pool
Minutes from Disney, emerald island resort, 4 bed, not overlooked, private heated pool & spa, 3 bath, games area, free broadband, resort facilities.  …see more

from £151 / night

£1053 / week

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from £151 / night

(16) Excellent 

27

Holiday villa in Kissimmee

Kissimmee / Formosa Gardens

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Couldn't ask for a nicer place!!” We stayed in the Diamond Villa on our first trip to Disney World and we were blown away with how beautiful this villa was! It was beautifully decorated, spotlessly clean, extremely well equipped and more comfortable t  …see more

from £121 / night

£847 - £1100 / week

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from £121 / night

(23) Excellent 

24

Kissimmee holiday villa rental

Kissimmee / Lake Berkley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic” This holiday was excellent the home was absolutely fab, it was differently home from home The villa we stayed in was pristine and had every little thing you could want and more. It was a pleasure to enter into a home that was spotless. I  …see more

from £70 / night

£485 - £570 / week

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from £70 / night

(8) Excellent 

36

Holiday home rental

Kissimmee / Crescent Lakes

5 13 3 nights min

  • 5 bedrooms
  • Sleeps 13
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Well maintained fully furnished 5 bed 3.5 bath home with 25x15 heated private pool and spa. Private garden overlooking lake. Covered lanai with south facing sundeck and pool furniture. The fabulous sun drenched pool deck and shimmering waters of our private pool offer a  …see more

from £70 / night

£450 - £940 / week

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from £70 / night

(43) Excellent 

39

Westside holiday villa rental

Kissimmee / Westside

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Beautiful villa in an excellent location” I stayed at Disney Davella for one week with my husband and parents. There are two excellent master bedrooms which made it perfect for us (with a bathroom off each) and an extra toilet downstairs as well. Th  …see more

from £90 / night

£595 - £850 / week

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from £90 / night

(3) Excellent 

16

Holiday villa in Indian Creek

Kissimmee / Indian Creek

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Great Florida Villa in a Perfect Location” Myself & my Family spent a lot of time looking on website at Villas for our Florida Holiday, hoping to find a Good deal with the right location near to all the Attractions and a villa that would be suitabl  …see more

from £123 / night

£861 / week

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from £123 / night

(67) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Bass Lakes Estate

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“Excellent location, beautiful and comfortable villa.” It was our first time not staying at a hotel. Don't think we'll stay at one again. Being at this house was just perfect for us. Very comfortable and close to everything. Would surely go back!  …see more

from £70 / night

£475 - £590 / week

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from £70 / night

(13) Excellent 

24

Kissimmee holiday villa rental

Kissimmee / Veranda Palms

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 75 km
  • Swimming pool
“Great villa stay in Orlando” My partner and two teenage girls spent just over a week in this lovely villa. It's modern, very clean and has everything you need, with some lovely finishing touches that add to the feeling of luxury. The beds are very com  …see more

from £90 / night

£580 - £750 / week

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from £90 / night

(43) Excellent 

91

Holiday villa in Westside

Kissimmee / Westside

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 96 km
  • Swimming pool
  • Child friendly
“Excellent villa and facilities” The Villa was as describes, nice quiet location, easy access to parks. Facilities really nice, was handy to have a guest food pack - especially if you are on a late flight. Very nice patio furniture - much nicer than  …see more

from £105 / night

£725 - £925 / week

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from £105 / night

(15) Very Good 

18

Kissimmee holiday villa rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“1st time in Florida fantastic stay - lovely villa” This was our first time to florida with 2 small children, we had a lovely time, the villa was clean and had everything we needed for our stay, having the cot and highchair free of use was great. The p  …see more

from £64 / night

£450 - £500 / week

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from £64 / night

(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

(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

(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

(29) Excellent 

20

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“One of the best villas we've stayed in!!!” Lovely house in a very convenient location - 2 minutes from a huge Walmart and numerous restaurants along the 192, 20 minutes to Disney, 35 minutes to Universal and International Drive. House is spacious, we  …see more

from £103 / night

£656 - £755 / week

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from £103 / 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

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

(2) Excellent 

91

Villa accommodation in Kissimmee

Kissimmee / Kissimmee City

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Fabulous 2 storey home with lots of space for large groups or 2 families, with cable t.v. in every room, wi fi and a games room. The pool & spa area is a great favourite with lots of loungers for relaxing by the pool. Seasons is one of the most sought after communit  …see more

from £90 / night

£600 / week

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from £90 / 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

(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 £160 / night

£1062 - £1718 / week

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from £160 / 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

(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

(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

(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