Kissimmee apartment or villa with a heated pool | Holiday Lettings

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Kissimmee

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1,246 Holiday homes

Filters applied: Heated pool

(19) Very Good 

17

Holiday villa in Seasons Resort

Kissimmee / Seasons Resort

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • 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
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from £60 / night

£360 - £700 / week

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from £60 / night

91

Villa accommodation in Kissimmee

Kissimmee / Kissimmee City

5 10 6 nights min

  • 5 bedrooms
  • Sleeps 10
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £129 / night

£903 / week

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from £129 / night

(10) 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

from £130 / night

£910 - £1200 / week

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from £130 / night

(56) 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
“Couldn't be anywhere better to stay” As the holiday season is a time for family we decided to have a mini family reunion and renting this Villa was the best thing we did. We were able to cook, use the pool and the kids were always entertain. The house
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from £90 / night

£475 - £725 / week

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from £90 / night

(14) Excellent 

Certificate of Excellence

24

Holiday villa in Doral Woods

Kissimmee / Doral Woods

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Fantastic!” We have just returned from Palm Tree Villa. We stayed there for nearly two weeks and to say we had a fantastic time and enjoyed it there is an understatement. The house is as clean as advertised. It has all the facilities in place to make
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Certificate of Excellence

from £100 / night

£695 - £875 / week

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from £100 / night

(1) Excellent 

34

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

from £77 / night

£539 - £670 / week

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from £77 / night

(45) 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
“Highly recommended - Great place with all you need” Took the family to Disney for a few days in March and found Lee's place on VRBO - first time we use this service. This home is amazing, the whole family loved the pool, hot tub, games room, and over
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from £104 / night

£716 - £885 / week

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from £104 / 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

from £143 / night

£997 / week

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from £143 / night

(32) Excellent 

17

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
“Fantastic! Didn't want to leave!” The best vacation, my family ever had. Two small children ages 6yrs. and 4yrs. loved the kiddie pool.
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from £97 / night

£654 - £708 / week

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from £97 / 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
“Everything we needed and more.” We stayed at this villa for 3 weeks ,with other family members. In total there were 10 of us. The villa was spotlesly clean when we arrived and it was very welcoming. There was a fantastic welcome pack for when we arriv
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from £154 / night

£1039 - £1689 / week

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from £154 / night

(33) 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
“***AWSOME VILLA*** fabulous holiday!” We stayed in this villa for 2 weeks in September and had a fantastic time, we were a family of 8 and everyone of us thoroughly enjoyed every minute. Can't fault anything about this property... It was big enough fo
…see more

from £100 / night

£600 - £700 / week

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from £100 / night

(11) Very Good 

25

Holiday villa in Kissimmee

Kissimmee / Crescent Lakes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“First time rental experience” Exceeded my expectations! Home was clean and well furnished. Great selection of tv channels and wifi service. The experience with management was exceptional and I have already reserved another stay at their properties thi
…see more

from £85 / night

£500 - £612 / week

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from £85 / 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,
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from £154 / night

£1072 / week

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from £154 / night

(9) Excellent 

24

Holiday home in Kissimmee

Kissimmee / Tuscany, Florida

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Wonderful holiday in a fantastic Villa!” This was our second family holiday to Orlando so we had an idea of what we were looking for from a villa and a location close to the parks. We considered a number of possible options before settling on Luce Del
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from £115 / night

£805 - £980 / week

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from £115 / night

(28) Very Good 

18

Kissimmee holiday townhouse rental

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 55 km
  • Swimming pool
“Great location and facilites” This house gave us everything we needed for a great holiday. Clean, well equipped and in a pleasant area. Pools and public areas very well kept. Would recommend for couples and families alike. Six adults would be easily a
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from £46 / night

£322 - £385 / week

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from £46 / night

(25) Very Good 

27

Holiday home in Kissimmee

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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
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from £80 / night

£525 - £1054 / week

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from £80 / night

(29) Excellent 

24

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“FANTASTIC VILLA.....GREAT COMMUNICATION WITH OWNER” Lovely villa, spacious enough for 8 people and fully equipped. The location is lovely too, very quiet, with regular landscaping and nice views. The villa is approximately 2-3 miles from lots of res
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from £90 / night

£650 - £820 / week

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from £90 / night

(4) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Tuscany, Florida

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £54 / night

£380 - £490 / week

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from £54 / night

(26) 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
“A wonderful Vacation Villa” This was our fifth visit to this gated neighborhood (our second visit since September) but our first stay in this villa. We loved it! Everything was perfect. The security system offered an added comfort. The extra large p
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from £104 / night

£727 - £835 / week

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from £104 / night

(3) 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 £150 / night

£997 - £1612 / week

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from £150 / night

(19) 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
“Fantastic!” This was like home from home , clean , beautiful furnished,very relaxing, child friendly, lovely veiws from pool ect, can't wait to go back.
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from £70 / night

£460 - £600 / week

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from £70 / night

(11) 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
“Fab villa” We just returned from a week at the Palm Heaven Villa. The villa is fab and located in the beautiful Terra Verde resort. It is close to the clubhouse and resort pool. The villa itself is very comfortable and has everything you need. The poo
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from £65 / night

£495 / week

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from £65 / night

(1) Excellent 

20

Villa rental in Cumbrian Lakes with swimming pool

Kissimmee / Cumbrian Lakes

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £105 / night

£735 - £1050 / week

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from £105 / night

(22) Very Good 

36

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £75 / night

£525 - £575 / week

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from £75 / 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

from £80 / night

£475 - £745 / week

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from £80 / night

(28) Excellent 

23

Holiday condo in Kissimmee

Kissimmee / Cane Island

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect size condo and fantastic location. Very clean with all you could need.” Brilliant location close to parks shirt drive away, shops walking distance and short drive to large supermarkets and amenities! Spacious and clean condo with everything yo
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from £65 / night

£455 / week

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from £65 / night

(19) Excellent 

23

Kissimmee holiday villa rental

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Lovely property. Really enjoyed our stay.” I would highly recommend this villa. It was nicely decorated and very clean. The air conditioning and fans kept it nice and cool as well as a dip in the pool which was a really nice size. I found the property
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from £99 / night

£695 - £795 / week

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from £99 / night

(30) Very Good 

24

Holiday condo with golf nearby in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 106 km
  • Swimming pool
  • Child friendly
“Great place to stay” Great location really close to Disney parks. Communication with owners was great with lots of information with directions to condo and everything we needed to know while we were staying in the condo. Clean and modern and great ame
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from £35 / night

£219 - £375 / week

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from £35 / night

(22) 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
“As good as it gets” From the first contact with the owner to our last day at the villa was excellent. The villa décor and facilities were just what we hoped for and more. From our location it was only a short trip to the theme parks eating out or shop
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from £68 / night

£475 / week

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from £68 / night

(4) 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
“Wonderful property!” Our host Lisa Ellis made us feel welcome since before booking. I had a couple of questions when searching for the perfect place to stay and she answered them very quickly. Once I booked we stayed in constant communication which ma
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from £100 / night

£654 - £897 / week

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from £100 / night

(7) Very Good 

40

Holiday home in Kissimmee

Central Florida / Kissimmee

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Would recommend” Beautiful home, my family and I enjoyed every bit of it. Very spacious, listed as 4 bedrooms also has a loft so it's more like 5, we had a whole room we never used and everyone was comfortable. In a great area for shopping markets and
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from £100 / night

£693 / week

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from £100 / night

(12) Very Good 

62

Coral Cay holiday home rental

Kissimmee / Coral Cay

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“A Nice Stay!!!!” We really loved it and we wish if we would have stayed. Beautiful scenic, nice backyard overlooking the lake. The pool was nice with a hot pool
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from £59 / night

£413 / week

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from £59 / night

(2) Excellent 

70

Holiday villa letting

Kissimmee / Cumbrian Lakes

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 114 km
  • Swimming pool

from £95 / night

£665 - £875 / week

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from £95 / night

(21) 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
“I would return to this villa anytime” location was great, attractions within easy reach, restaurants and shops within easy reach, very clean villa with plenty of everything, pool was clean and inviting, loved it.
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from £65 / night

£450 - £500 / week

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from £65 / night

(45) 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
“Excellent well equipped villa-very spacious and extremely clean” Well situated for all Disney Parks close to supermarket and several restaurants. We were a party of 7 with 2 children who adored the pool and jacuzzi. We felt the villa was exceptionally
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from £100 / night

£595 - £925 / week

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from £100 / night

(15) Excellent 

29

Kissimmee holiday villa rental

Kissimmee / Seasons Resort

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 110 km
  • Swimming pool
“Excellent” Brilliant home. Well equipped. Great pool deck and jacuzzi. We got the sun all day and found the pool deck very private. The covered patio is good for shade. The location was perfect as close to all the attractions. Good restaurants c
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from £97 / night

£650 - £897 / week

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from £97 / night

(3) Excellent 

61

Kissimmee holiday villa rental

Kissimmee / Windsor Hills Resort

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 64 km
  • Swimming pool
“Luxury in the sun” Home from home - if home had all these mod cons and a heated pool outside the lounge and a games room in the garage. Great location for Disney assuming you have a car. Plenty of local restaurants and easy run to NASA. Onsite centr
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from £115 / night

£690 - £1350 / week

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from £115 / night

(1) Excellent 

24

Lake Berkley holiday villa rental

Kissimmee / Lake Berkley

5 10 4 nights min

  • 5 bedrooms
  • Sleeps 10
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £123 / night

£860 / week

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from £123 / night

(37) Excellent 

62

Holiday villa in Kissimmee

Kissimmee / Lindfields

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Mrs” EXCELLENT...doesn't do it justice. Great location Great accommodation Great facilities Would have liked to have stayed longer. A lot of thought and care has gone into making this your home for your stay. Disney is easy to access.... food shops
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from £80 / night

£550 - £675 / week

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from £80 / 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

from £89 / night

£597 - £727 / week

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from £89 / night

1