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

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Kissimmee

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4,289 Holiday homes

Travellers going to Kissimmee are booking March dates now. Secure your holiday home today and have the perfect trip.

(8) Excellent 

20

Holiday villa letting

Kissimmee / Emerald Isle Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Fully furnished and extensively equipped. Flat screen TV's with DVD players in living room and all bedrooms.  …see more

from £75 / night

£525 - £665 / week

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from £75 / night

(26) 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
“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 pr  …see more

from £61 / night

£425 - £600 / week

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from £61 / night

(6) 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  …see more

from £121 / night

£932 / week

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from £121 / 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
“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  …see more

from £100 / night

£595 - £895 / week

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from £100 / night

(11) Excellent 

24

Villa accommodation in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Home from home.” The villa is in a fantastic location for all the attractions and the gated community is set in an attractive environment. The photos do not do it justice- we were blown away with the space and quality of this lovely villa. It has ho  …see more

from £70 / night

£480 - £595 / week

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from £70 / 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 £150 / night

£1045 / week

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from £150 / night

(17) 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
“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  …see more

from £143 / night

£1000 - £1300 / week

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from £143 / night

(12) Excellent 

51

Apartment rental in Kissimmee

Central Florida / Kissimmee

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Very clean and with everything you need!” The place was big for being an apt, clean, close to everything but quite. The instructions were clear and chris replayed me back an email almost instantly. It was the first time renting a place by internet,  …see more

from £69 / night

£472 / week

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from £69 / night

(17) 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  …see more

from £149 / night

£1045 - £1495 / week

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from £149 / night

(12) Excellent 

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

from £65 / night

£460 / week

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from £65 / night

(38) 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
“Holiday To Remember” A perfect exciting, fantastic holiday with all the family. Family of 6. In the last week 7.Quality time with everyone.Extremely a special and magical holiday to remember.The villa was fabulous and very homely.Perfect from start t  …see more

from £80 / night

£495 - £515 / week

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from £80 / night

(5) Excellent 

24

Holiday villa with swimming pool in Kissimmee

Kissimmee / Cumbrian Lakes

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Cumbrian Lakes is an exclusive gated community with lakes, cycling & walking trails & a kids play area.  …see more

from £100 / night

£700 - £850 / week

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from £100 / night

(12) 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  …see more

from £92 / night

£640 - £700 / week

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from £92 / night

(11) Excellent 

14

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“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  …see more

from £65 / night

£450 - £500 / week

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from £65 / night

(17) 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

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
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) Excellent 

41

Holiday condo with golf nearby in Kissimmee

Kissimmee / Cane Island

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 65 km
  • Swimming pool
“Absolutely Perfect” It was exactly what we expected and more - very nicely furnished, clean and had everything we needed. It was just perfect, the location was close to everything - restaurants, shopping, main attraction parks as long as you have a  …see more

from £77 / night

£480 - £601 / week

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from £77 / 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 £130 / night

£910 - £1200 / week

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from £130 / 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 £158 / night

£1045 - £1690 / week

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from £158 / night

(8) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Oak Island Cove

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
Positioned on Oak Island Cove next to Formosa Gardens, this is one of the most exclusive vacation sub rental divisions in Central Florida. Every amenity is close at hand for a wonderful vacation. No other location boasts a 5 minute journey to Disney World, Orlando. The  …see more

from £133 / night

£925 - £1195 / week

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from £133 / night

(20) 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
“Great villa, everything you need” Villa was spacious, immaculately clean and had everything you could possibly need. Pool kept kids more than occupied, fun gator spotting in the lake behind the house. Easy to get to the main routes to head off to park  …see more

from £107 / night

£750 - £900 / week

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from £107 / night

(2) Very Good 

34

Kissimmee / Crescent Lakes

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £92 / night

£644 / week

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from £92 / night

(20) 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 £65 / night

£345 - £675 / week

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from £65 / 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
“Fantastic! Didn't want to leave!” The best vacation, my family ever had. Two small children ages 6yrs. and 4yrs. loved the kiddie pool.  …see more

from £101 / night

£686 - £742 / week

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from £101 / 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  …see more

from £109 / night

£722 - £1045 / week

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from £109 / night

(9) Excellent 

24

Kissimmee holiday villa rental

Kissimmee / Doral Woods

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Excellent Villa” This was our sixth time in Florida and our third stay at Doral Woods in our third different villa on the estate and it certainly compares very favourably in what is simply a very nice place to stay. Set in a very quiet residential cul  …see more

from £80 / night

£560 - £930 / week

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from £80 / 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

(21) 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  …see more

from £50 / night

£350 - £725 / week

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from £50 / 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
“***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

(28) 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
“Ideal "near to Disney" condo” Condo had everything we needed at very reasonable price, especially for Christmas period. Owners (Ronald and Pam) very helpful with arrival instructions, directions, etc. Useful local info provided at condo. Good variety  …see more

from £35 / night

£219 - £375 / week

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from £35 / night

(15) 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

(20) 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  …see more

from £65 / night

£450 - £475 / week

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from £65 / night

(5) Excellent 

24

Holiday villa with golf nearby in Kissimmee

Kissimmee / Bellavida Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Comfortable, smart, spacious, well equipped villa.” We stayed as two family groups comprising 8 Adults and 2 kids. The accommodation was flexibly arranged and everyone could find there own space when they wanted it. The villa's own pool and hot tub w  …see more

from £165 / night

£1155 - £1295 / week

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from £165 / night

(26) 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 - £371 / week

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from £46 / 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  …see more

from £70 / night

£485 - £570 / week

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from £70 / 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
“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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from £229 / night

(20) 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

(3) Excellent 

45

Kissimmee holiday townhouse rental

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
4 Bedrooms / 3 bathrooms - ground floor comprising covered entrance porch, entrance foyer, kitchen, dining area, great room, covered terrace, ground floor double bedroom with bathroom. Stairs leading to - First floor comprising master bedroom with walk in wardrobes and  …see more

from £60 / night

£420 - £560 / week

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from £60 / night

(68) 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
“Perfect spot” We have hired this villa before and the location is what we like.We do not like the hustle and bustle of International drive so this villa adj to the US102 is ideal for us.Located at Bass road its a 2 minute drive to a mega Walmart and a  …see more

from £70 / night

£475 - £590 / week

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from £70 / night

(25) 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
“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  …see more

from £75 / night

£525 - £600 / week

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from £75 / night

Top Destination reviews

Vista Lago
It was perfect, we had everything we needed ....

Family vacation with small children and grandparents, the villa was perfect, we had everything we needed and everything was to a really high standard. Lovely and clean, it really made our holiday. The pool and deck area was a huge hit with the kids … see more
Disney Lakeside Villa with WiFi and a Pool, Kissimmee
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
Sundown Palm
Fabulous house

We had a great time at Sundown Palm. The house was beautiful and very roomy. My 6 year old and 2 year old had a great time playing in the play room and in the pool. I would highly recommend. My only regret is not spending more time at the house. … see more
Sunseeker House
Golf vacation in beautiful surroundings

Terre Verde Resort is a beautiful resort with a luxurious club house with all amenities, pool, pool-bar, fitness center surrounding i relatively large pond. Nice playground. Short distance (15 min) to Disney and a surplus of golf courses nearby. Th … see more
Sun Palm - 5 star Disney executive villa.
What a fantastic experience from start to finish!

The house was beautiful and well taken care of. The pool was very nice and even had things to use in the pool. The outside furniture was nice to relax in by the pool. The rooms were all very nice and spacious. Everything was provided that we needed a … see more
Bella Casa our luxury villa (hot tub, pool & wifi)
Comfortable, smart, spacious, well equipped villa.

We stayed as two family groups comprising 8 Adults and 2 kids. The accommodation was flexibly arranged and everyone could find there own space when they wanted it. The villa's own pool and hot tub were great after a busy day in the parks. There is a … see more