Villas with a pool Kissimmee | Apartments to rent with swimming facilities | Holiday Lettings

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Kissimmee

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3,051 Holiday homes

Filters applied: Swimming pool

(22) 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
“Beautiful villa, great location, perfect for families” Another great stay at seasons villa, just as we remembered! Ideal location for Disney and International Drive. We started to pay the toll to take a slightly quicker and less busy route to Disney e
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from £60 / night

£360 - £700 / week

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from £60 / 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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Responds fast!
avg. 3 hours 50 minutes

from £70 / night

(3) Excellent 

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

(31) Very Good 

23

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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Responds fast!
avg. 3 hours 46 minutes

from £35 / night

(31) 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

(12) Very Good 

24

Cumbrian Lakes holiday villa rental

Kissimmee / Cumbrian Lakes

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Great Villa for families” We stayed at this villa with our daughter and my wife's parents. This is a fantastic property for more than one family as there are two master suites as well as a queen room and two twin bedrooms. The best feature is the exte
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from £100 / night

£550 - £700 / week

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from £100 / 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 £146 / night

£1020 / week

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Responds fast!
avg. 2 hours 41 minutes

from £146 / 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

(59) 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

(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

(3) Excellent 

45

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £87 / night

£607 - £772 / week

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Responds fast!
avg. 2 hours 11 minutes

from £87 / 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 £91 / night

£611 - £745 / week

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from £91 / night

(22) 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
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from £53 / night

£375 - £725 / week

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Responds fast!
avg. 3 hours 56 minutes

from £53 / night

(11) 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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Responds fast!
avg. 3 hours 27 minutes

from £130 / night

(8) Excellent 

21

Trafalgar Village holiday home rental

Kissimmee / Trafalgar Village

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • 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
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from £119 / night

£910 / week

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Responds fast!
avg. 3 hours 38 minutes

from £119 / 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
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from £87 / night

£512 - £626 / week

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from £87 / night

(9) 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 £103 / night

£709 / week

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from £103 / 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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Responds fast!
avg. 1 hour 57 minutes

from £100 / night

(14) 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
“Lovely villa, great service and excellent location for all the Disney parks!” Definitely recommended! From the moment I enquired about the villa, (we dealt directly with the owner) we received excellent service. Booking was easy, and we were supplie
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from £90 / night

£580 - £775 / week

Enquire View

from £90 / night

(24) Excellent 

Certificate of Excellence

59

Holiday townhouse with shared pool in Trafalgar Village

Kissimmee / Trafalgar Village

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“excellent” my wife and two friends stayed here in may for 10 days. one word excellent. the house is only about 25 mins from all the parks. the location is incredibly quiet with onsite security. 3 bedrooms + 3bathrooms a large living area gives plenty
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Certificate of Excellence

from £45 / night

£360 - £840 / week

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Responds fast!
avg. 2 hours 38 minutes

from £45 / night

(2) 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
“Rental” It's beautiful clean home I really enjoyed my stay there!! I will highly recommend this house. This house is complete for stay.
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from £79 / night

£552 - £686 / week

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from £79 / night

(19) Excellent 

28

Villa rental in Kissimmee

Kissimmee / Doral Woods

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“A truly amazing place to stay!” If you are looking at this page, thinking about renting this villa, just do it, you'll have no regrets. We stayed for 3 weeks in July/August and had a fantastic time. It was the perfect villa for us (a family of 2 adul
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from £64 / night

£445 - £525 / week

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Responds fast!
avg. 38 minutes

from £64 / night

(2) 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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Responds fast!
avg. 2 hours 35 minutes

from £105 / night

(30) 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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Responds fast!
avg. 3 hours 34 minutes

from £90 / night

19

Kissimmee holiday villa rental

Kissimmee / Indian Creek

4 8 4 nights min

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

from £134 / night

£932 / week

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from £134 / night

(17) Excellent 

Certificate of Excellence

49

Bungalow rental in Kissimmee

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“Family friendly vacation home with screened in pool...immaculate and exactly as posted!” The home was very clean and had a fully functional and equipped kitchen. The bedrooms were each spacious and had sufficient linens. There is wi-fi and sufficien
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Certificate of Excellence

from £87 / night

£571 - £650 / week

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Responds fast!
avg. 1 hour 42 minutes

from £87 / 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
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from £119 / night

£827 / week

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Responds fast!
avg. 1 hour 31 minutes

from £119 / night

(18) 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
“Absolutely wonderful!” This house is amazing! The pictures do not capture the true beauty of this property. We traveled with 3 families - all ages. There was plenty of room for everyone - bedrooms, kitchen, living room, family room, pool, etc. The
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from £149 / night

£1045 - £1495 / week

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Responds fast!
avg. 3 hours 42 minutes

from £149 / night

(3) Excellent 

100

Holiday home in Kissimmee

Kissimmee / Paradise Palms

4 12 Min stay varies

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

from £95 / night

£662 / week

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Responds fast!
avg. 3 hours 15 minutes

from £95 / night

(13) 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
“We will not be going anywhere else!” This was our second stay at the beautiful villa. Local to all the best restaurants, Wall-Mart and Target for food shops. With only a 15 minute drive we were in the theme parks, International Drive and only 45 minut
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from £90 / night

£495 - £625 / week

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Responds fast!
avg. 3 hours 22 minutes

from £90 / night

(14) Excellent 

Certificate of Excellence

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
“Perfect for couples and families” I stayed here for 9 days with my husband and 5 month old daughter and we had lovely time! My husband and I had previously been to Florida and stayed in a property in Doral Woods so we knew we wanted to be in the same
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Certificate of Excellence

from £65 / night

£460 - £480 / week

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Responds fast!
avg. 1 hour 31 minutes

from £65 / night

(20) Excellent 

25

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
“Perfect Florida home” From the minute we arrived, we loved and enjoyed every minute of our four week stay here. Everything was perfect from the moment we went through the door. The rooms are spacious, comfortable and tastefully decorated. Ove
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from £130 / night

£875 / week

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Responds fast!
avg. 3 hours 29 minutes

from £130 / night

(26) Very Good 

25

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

(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
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from £154 / night

£1020 - £1650 / week

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from £154 / night

(34) 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
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from £100 / night

£600 - £700 / week

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Responds fast!
avg. 1 hour 52 minutes

from £100 / night

(9) 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

(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 £99 / night

£670 - £725 / week

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Responds fast!
avg. 3 hours 53 minutes

from £99 / 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 £159 / night

£1072 - £1743 / week

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from £159 / night

23

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

5 13 Min stay varies

  • 5 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £105 / night

£784 - £994 / week

Enquire View

from £105 / 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 £103 / night

£670 - £918 / week

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from £103 / night

1