Horse riding holiday villas and apartments Kissimmee | Holiday Lettings

Close

View larger map

Also consider

North America Holidays
167796 properties
United States Holidays
122620 properties
Florida Holidays
36979 properties
Central Florida Holidays
14834 properties
Emerald Isle Kissimmee
49 properties
Villas Windsor Hills Resort
27 properties
Kissimmee City
26 properties
Villas Paradise Palms
20 properties
Villas Windsor Palms
18 properties
Lake Berkley
18 properties
Lindfields
17 properties
Cumbrian Lakes
17 properties
Terra Verde Resort
15 properties
Bellavida Resort
14 properties
Crescent Lakes
10 properties
Compass Bay
10 properties
Seasons Resort
9 properties
Villas Orange Lake Resort
8 properties
Doral Woods
8 properties
Trafalgar Village
8 properties
Venetian Bay Villages
8 properties
Encantada Resort
7 properties
Villas Formosa Gardens
7 properties
Eagle Pointe
6 properties

Kissimmee

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

323 Holiday homes

Filters applied: Horse riding

(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
…see more

from £60 / night

£360 - £700 / week

Book View

from £60 / 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

Book View

Responds fast!
avg. 2 hours 49 minutes

from £145 / 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
…see more

from £64 / night

£445 - £525 / week

Book View

Responds fast!
avg. 38 minutes

from £64 / 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
…see more

Certificate of Excellence

from £100 / night

£695 - £875 / week

Book View

Responds fast!
avg. 1 hour 57 minutes

from £100 / 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 £104 / night

£715 / week

Book View

from £104 / 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
…see more

from £59 / night

£413 / week

Book View

Responds fast!
avg. 3 hours 5 minutes

from £59 / 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

Book View

Responds fast!
avg. 3 hours 25 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
…see more

from £120 / night

£917 / week

Book View

Responds fast!
avg. 3 hours 38 minutes

from £120 / 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
…see more

from £99 / night

£695 - £795 / week

Book View

Responds fast!
avg. 2 hours 24 minutes

from £99 / 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 £155 / night

£1028 - £1663 / week

Book View

from £155 / 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
…see more

from £105 / night

£635 - £825 / week

Book View

Responds fast!
avg. 3 hours 45 minutes

from £105 / 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

Book View

from £99 / night

(48) Excellent 

21

Holiday villa in Kissimmee

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic!” We Stayed at Doral Woods villa in May 16. The villa is equipped with everything you need and is spotlessly clean. Beautiful pool & garden the best villa we have ever stayed in! Highly recommend also the owners are so helpful and attentive
…see more

from £130 / night

£895 - £995 / week

Book View

Responds fast!
avg. 2 hours 24 minutes

from £130 / 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
…see more

from £125 / night

£825 - £995 / week

Book View

Responds fast!
avg. 1 hour 25 minutes

from £125 / 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

Book View

from £95 / 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

Book View

from £67 / night

(5) Excellent 

28

Holiday home rental

Kissimmee / Emerald Isle Kissimmee

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
“Super Spring Break” My family spent the week of April 7 - 14, 2012 at "Jewel In The Crown", which is located in Emerald Island Resort. This is our sixth trip to Orlando and one of the best times we've had!!! Our "home away from home" was comfortable,
…see more

from £156 / night

£1089 / week

Book View

Responds fast!
avg. 3 hours 38 minutes

from £156 / 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
…see more

from £143 / night

£1000 - £1300 / week

Book View

Responds fast!
avg. 3 hours 25 minutes

from £143 / 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
…see more

from £70 / night

£475 - £590 / week

Book View

Responds fast!
avg. 1 hour 49 minutes

from £70 / 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
…see more

from £86 / night

£547 - £868 / week

Book View

Responds fast!
avg. 3 hours 56 minutes

from £86 / night

(26) Excellent 

23

Holiday villa rental

Kissimmee / Veranda Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 84 km
  • Swimming pool
  • Child friendly
“A wonderful Vacation Villa” This was our fifth visit to this gated neighborhood (our second visit since September) but our first stay in this villa. We loved it! Everything was perfect. The security system offered an added comfort. The extra large p
…see more

from £107 / night

£745 - £855 / week

Book View

Responds fast!
avg. 1 hour 27 minutes

from £107 / night

(1) Excellent 

24

Lake Berkley holiday villa rental

Kissimmee / Lake Berkley

5 10 4 nights min

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

from £123 / night

£860 / week

Book View

from £123 / night

(40) 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 £85 / night

£505 - £515 / week

Book View

Responds fast!
avg. 45 minutes

from £85 / night

(6) Excellent 

Certificate of Excellence

24

Kissimmee holiday home accommodation

Kissimmee / Lindfields

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Ideal clean and well maintained ideally placed property” Everything went smoothly upon arrival. Followed the directions from my email and arrived with no problems at all. The house is lovely and clean and has plenty of space for everyone. There's a fo
…see more

Certificate of Excellence

from £50 / night

£335 - £350 / week

Book View

Responds fast!
avg. 2 hours 34 minutes

from £50 / 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
…see more

from £68 / night

£475 / week

Enquire View

from £68 / 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 £92 / night

£616 - £750 / week

Book View

from £92 / night

(11) Excellent 

26

Holiday villa in Hamilton's Reserve

Kissimmee / Hamilton's Reserve

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 40 km
  • Swimming pool
“Brilliant villa - perfect place for the perfect holiday” Stayed at the villa as part of a group of 4 adults and 4 children, aged from 4-9. Villa was everything we had hoped it would be and more. Photos did not do it justice. The size of the pla
…see more

from £124 / night

£869 - £1560 / week

Book View

from £124 / 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

Book View

Responds fast!
avg. 1 hour 31 minutes

from £65 / 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

Book View

from £85 / 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

Book View

Responds fast!
avg. 3 hours 25 minutes

from £229 / 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

Book View

Responds fast!
avg. 3 hours 50 minutes

from £70 / night

(13) Excellent 

Certificate of Excellence

22

Kissimmee holiday villa let

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Super Villa in a super location,” A perfect location for us just a couple of minutes from Kissimmee, Everything you need is there, pool, hot tub, games room, WiFi and as it's English owned it even has a kettle ! (Most Florida Villas don't). Clear i
…see more

Certificate of Excellence

from £87 / night

£606 / week

Book View

Responds fast!
avg. 3 hours 53 minutes

from £87 / night

(1) Very Good 

22

Holiday townhouse in Kissimmee

Kissimmee / Encantada Resort

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £96 / night

£667 / week

Book View

from £96 / 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
…see more

from £90 / night

£580 - £775 / week

Enquire View

from £90 / night

(1) Excellent 

52

Holiday villa in Eagle Pointe

Kissimmee / Eagle Pointe

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 115 km
  • Swimming pool

from £118 / night

£707 - £978 / week

Book View

Responds fast!
avg. 2 hours 41 minutes

from £118 / night

(9) 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

from £133 / night

£925 - £1195 / week

Book View

from £133 / 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
…see more

from £53 / night

£375 - £725 / week

Book View

Responds fast!
avg. 3 hours 56 minutes

from £53 / night

(14) Excellent 

23

Kissimmee holiday home rental

Kissimmee / Windsor Palms

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic Villa, Perfect Location for Disney etc., Food & Shopping” It was a very straightforward process booking 'Mickey's Clubhouse', questions were answered very promptly by the owners - the whole process was quick, efficient and informative.The vi
…see more

from £115 / night

£875 / week

Enquire View

from £115 / 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

Book View

from £95 / 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
…see more

Certificate of Excellence

from £45 / night

£360 - £840 / week

Book View

Responds fast!
avg. 2 hours 39 minutes

from £45 / night

1