Watersports holiday villas and apartments Kissimmee | Holiday Lettings

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Kissimmee

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312 Holiday homes

Filters applied: Water sports

(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

(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

(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

(47) 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
“Outstanding home, just perfect for the guys basketball trip” This home was perfect for our group. We had a few middle age guys visiting Orlando for the NCAA March Madness. A long weekend of playing basketball and watching the college kids play baske
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from £107 / night

£733 - £906 / week

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Responds fast!
avg. 1 hour 27 minutes

from £107 / 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

(47) Excellent 

42

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
“Location! Location!” GREAT LOCATION of the Villa 5 minutes to Publix, 7 minutes to Target or Walmart, 15 from Disney, the house itself it is very comfortable and clean, big pool, all we needed for our vacation. If I had to book again I certainly would
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from £100 / night

£595 - £925 / week

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Responds fast!
avg. 1 hour 0 minutes

from £100 / night

(22) Excellent 

24

Holiday townhouse rental

Kissimmee / Encantada Resort

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
“Really nice” Nice house good location, we really liked the option of being able to use the pool at the house or the two large pools by the clubhouse. Would certainly stay again.
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from £100 / night

£680 - £950 / week

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Responds fast!
avg. 2 hours 57 minutes

from £100 / night

(76) 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” We have been to Orlando several times as a family and location wise this is without doubt the best villa we have stayed at. In fact it is the only one we would stop at again. There's a Walmart at the end of the steeet and plenty of
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from £70 / night

£475 - £590 / week

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Responds fast!
avg. 1 hour 36 minutes

from £70 / 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

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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

(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 18 minutes

from £35 / 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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Responds fast!
avg. 3 hours 38 minutes

from £103 / 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

from £120 / night

£825 / week

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from £120 / night

(10) Excellent 

22

Holiday home with shared pool in Kissimmee

Kissimmee / Trafalgar Village

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

from £67 / night

£430 - £675 / week

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from £67 / 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

(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

(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

13

Villa rental in Kissimmee with shared pool

Central Florida / Kissimmee

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £95 / night

£662 / week

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from £95 / 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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Responds fast!
avg. 3 hours 30 minutes

from £59 / 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

(10) 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

(8) 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
“Excellent place to stay” The communication from booking was excellent, the house was in a great position for all parks and is great for a stay for large groups. I would recommend it to anyone
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from £229 / night

£1600 - £2000 / week

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Responds fast!
avg. 3 hours 27 minutes

from £229 / night

(4) Excellent 

32

Villa rental in Kissimmee with shared pool, golf nearby

Kissimmee / Vista del lago

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £50 / night

£350 / week

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from £50 / night

(2) Excellent 

84

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £111 / night

£772 - £1120 / week

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from £111 / 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

(6) Excellent 

68

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 12 km
  • Swimming pool
  • Child friendly
“Fantastic accommodation, Ladysvilla deserves 10 stars instead of 5!!!!!!!!” This is the second time we have stayed in this villa and I cannot express enough how good it is. It is ideally located for all the attractions and theme parks in Orlando. The
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from £87 / night

£552 - £875 / week

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Responds fast!
avg. 3 hours 56 minutes

from £87 / 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

(24) 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
“Home from home!” Beautiful clean villa, well equipped, spacious and extremely relaxing and comfortable. Nice added touches i.e. the games room and security at the gate. The gardens and pool area kept clean and tidy. Fantastic communication from owner
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from £70 / night

£485 - £570 / week

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from £70 / 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

(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

(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

(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 37 minutes

from £119 / night

(5) Very Good 

18

Kissimmee holiday villa rental

Kissimmee / Crescent Lakes

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Superb villa” The only fault with this property is that we couldn't stay longer. The booking process went smoothly. The owner was very attentive and answered all of our questions promptly. The villa is in a perfect setting and is fully equipped, clean
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from £105 / night

£675 / week

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Responds fast!
avg. 2 hours 46 minutes

from £105 / 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

(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

(9) Excellent 

88

Kissimmee holiday villa rental

Kissimmee / Bellavida Resort

6 14 5 nights min

  • 6 bedrooms
  • Sleeps 14
  • 5 nights min
  • Nearest beach 111 km
  • Swimming pool
  • Child friendly
“Our vacation in Florida 2014” The location of the property was ideally suited for our planned vacation. The size and facilities were extremely good and especially with 6 adults & 4 children it worked perfectly with each family. The kitchen lent itsel
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from £178 / night

£1246 - £1483 / week

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Responds fast!
avg. 1 hour 19 minutes

from £178 / night

(1) Very Good 

20

Condo rental in Kissimmee with golf nearby

Kissimmee / Kissimmee City

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £71 / night

£469 - £611 / week

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Responds fast!
avg. 3 hours 52 minutes

from £71 / night

(23) 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
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from £105 / night

£635 - £825 / week

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Responds fast!
avg. 3 hours 45 minutes

from £105 / night

(19) Very Good 

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
“Geat location” Stayed 23.8.16 to 6.9.16. Great home for 9 people that stayed. Home was clean and well kept. A 10 minute drive to Disney and 20 minutes to Universal and Sea World. Great that there were plenty of extra towels in the cupboard. Washi
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from £143 / night

£1000 - £1300 / week

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Responds fast!
avg. 3 hours 27 minutes

from £143 / night

(27) Excellent 

56

Holiday villa with private swimming pool in Kissimmee

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“On the booking with Steve” Steve has kindly been answering my questions and helped me make my decision to want to stay at his beautiful villa looks stunning
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from £125 / night

£825 - £995 / week

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Responds fast!
avg. 1 hour 23 minutes

from £125 / night