Villas in Kissimmee and Holiday rentals - Holiday Lettings - Holiday Rentals Kissimmee

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Kissimmee

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4,851 Holiday homes

(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

(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 

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

(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 29 minutes

from £35 / 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 £145 / night

£1012 / week

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Responds fast!
avg. 2 hours 49 minutes

from £145 / 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

(2) 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 £86 / night

£602 - £766 / week

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Responds fast!
avg. 2 hours 11 minutes

from £86 / night

(24) Very Good 

Certificate of Excellence

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

Certificate of Excellence

from £75 / night

£525 - £575 / week

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Responds fast!
avg. 3 hours 47 minutes

from £75 / night

(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 

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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Responds fast!
avg. 2 hours 24 minutes

from £99 / 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

(4)  

20

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

6 14 1 night min

  • 6 bedrooms
  • Sleeps 14
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £172 / night

£1204 / week

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from £172 / 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

(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

(8) Excellent 

55

Holiday villa with golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £188 / night

£1313 / week

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from £188 / 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 £87 / night

£512 - £626 / week

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from £87 / 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

(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
…see more

from £46 / night

£322 - £385 / week

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from £46 / night

13

Venetian Bay Villages holiday townhouse rental

Kissimmee / Venetian Bay Villages

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £80 / night

£500 / week

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from £80 / night

(14) Excellent 

23

Kissimmee holiday villa rental

Kissimmee / Windsor Palms

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Wyndham Palm Way review” Lovely villa, easy to find just off the 192 and easily accommodates 9 people so perfect for a large family holiday. Easy to get to the parks and out for food but you will need a car. Good value for money although it is a li
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from £93 / night

£650 - £700 / week

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Responds fast!
avg. 2 hours 30 minutes

from £93 / 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 39 minutes

from £45 / 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

(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

(13) Excellent 

44

Holiday villa rental

Kissimmee / Indian Ridge Oaks

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Close to Disney, a villa that caters for everyone!” We stayed here with our 8 year old in July 2016. From the time we booked to the time we returned Tracey (the owner) could not have been more helpful. Emails responded to promptly, very thoughtful
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from £84 / night

£588 - £780 / week

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from £84 / 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

(7) Excellent 

18

Condo rental in Kissimmee

Central Florida / Kissimmee

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £117 / night

£774 / week

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Responds fast!
avg. 3 hours 59 minutes

from £117 / night

(37) Very Good 

20

Holiday home in Crescent Lakes

Kissimmee / Crescent Lakes

4 11 3 nights min

  • 4 bedrooms
  • Sleeps 11
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Amazing property!” This property really is as amazing as the photos show! Andy offers great communication before, during and after the stay, and it really is a fantastic place to stay. We visited Universal Studios and Wet'n'Wild and it's about a 20
…see more

from £99 / night

£675 / week

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from £99 / 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

from £150 / night

£700 - £800 / week

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Responds fast!
avg. 1 hour 59 minutes

from £150 / 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
…see more

from £229 / night

£1600 - £2000 / week

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Responds fast!
avg. 3 hours 25 minutes

from £229 / 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 £153 / night

£1012 - £1637 / week

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from £153 / night

(8) 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
…see more

from £102 / night

£704 / week

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from £102 / night

(10) 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

from £95 / night

£575 - £900 / week

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from £95 / 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 25 minutes

from £130 / 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

(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

(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
…see more

Certificate of Excellence

from £65 / night

£460 - £480 / week

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Responds fast!
avg. 1 hour 31 minutes

from £65 / 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.
…see more

from £70 / night

£460 - £600 / week

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Responds fast!
avg. 3 hours 50 minutes

from £70 / night

85

Holiday villa with swimming pool in Kissimmee

Kissimmee / Sunset Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £95 / night

£665 - £1000 / week

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Responds fast!
avg. 1 hour 22 minutes

from £95 / night

(10) 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
“Fantastic villa” Was very impressed with the villa. Very spacious and clean. Lots of local amenities and all parks very close by. Situated on a quiet estate and very welcoming would definitely recommend
…see more

from £85 / night

£520 - £550 / week

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from £85 / night

(23) Very Good 

Certificate of Excellence

10

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

4 9 4 nights min

  • 4 bedrooms
  • Sleeps 9
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £65 / night

£450 / week

Book View

Responds fast!
avg. 1 hour 43 minutes

from £65 / night

Top Destination reviews

Robson's Retreat, Relaxing Vacation Home with a Ba
Brilliant stay loved this villa 5☆☆

When we arrived after a long flight we were welcomed with a beautiful villa,in a gated community so easy to find and looks amazing, everything was clean and the kitchen had had new appliances which look brilliant, we didn't cook much but it had eve … see more
NEW LISTING! Newly Renovated-Private Pool-Gated Resort-Near DISNEY!!
Exceptional Stay

This was my first time renting a house while in Florida and I was not disappointed. The house was very clean and had everything we needed. Preparing and cooking meals was a breeze as everything was provided. (pots, pans, dishes) Our teenage childre … see more
Spacious 4bdr 3bth townhome with private pool
Wonderful!!!

The property was great! There was plenty of room for my family and I and we loved the pool! Everything was clean on arrival and good instructions were given prior to our arrival so we had no problems with getting into the resort or the villa. We hope … see more
Sunrise Villa Florida
Fantastic Villa

This villa is just perfect! Beautifully furnished and has everything you could possibly need for your stay. Kathryn the owner is great, if you have any questions etc....It is situated in a very quiet cup- de-sac and ver secure. The price of this vill … see more
Detached Villa with WiFi, Tennis Court, and Pool
Great place to stay

Great place to stay, it's a lot bigger than it looks on the photos. The pool is lovely with sun on it from early morning till evening in July. The beds are comfortable, loads of towels available, the BBQ, fridge freezer,microwave and oven are massive … see more
The Lake House
FABULOUS all round

Villa location excellent , pool area fantastic , Lake Views Stunning , wildlife & Bird Watching Endless enjoyment The Best of Furniture & Soft Furnishing through out And the Owners a joy to deal with If you think the PHOTOS on the site are Go … see more
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