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

Close

View larger map

Also consider

North America Holidays
171038 properties
United States Holidays
127247 properties
Florida Holidays
36887 properties
Central Florida Holidays
14949 properties
Emerald Isle Kissimmee
43 properties
Kissimmee City
21 properties
Villas Windsor Hills Resort
20 properties
Villas Paradise Palms
19 properties
Lindfields
15 properties
Villas Windsor Palms
15 properties
Lake Berkley
14 properties
Cumbrian Lakes
13 properties
Terra Verde Resort
13 properties
Bellavida Resort
12 properties
Compass Bay
8 properties
Doral Woods
8 properties
Trafalgar Village
7 properties
Villas Formosa Gardens
6 properties
Villas Orange Lake Resort
6 properties
Villas Coral Cay
6 properties
Crescent Lakes
6 properties
Crystal Cove Resort
5 properties
Seasons Resort
5 properties
Sunset Lakes
5 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

15,363 Holiday homes

(2) Excellent 

31

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £100 / night

£700 - £1,016 / week

Book View

from £100 / night

30

Holiday home with golf nearby in Kissimmee

Central Florida / Kissimmee

4 10 3 nights min

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

from £69 / night

£449 - £589 / week

Book View

from £69 / night

(46) Excellent 

62

Holiday villa in Kissimmee

Kissimmee / Lindfields

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 65 km
  • Swimming pool
“Vacation at Otters Lake Villa” My husband and I really enjoyed our stay at Otters Lake Villa. The Villa is private and located in a very quiet community and only minutes away from all amenities and a short drive to all the theme parks. It had a large
…see more

from £86 / night

£600 - £700 / week

Book View

from £86 / night

(4) Excellent 

45

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Lovely villa and ideal location” The villa was lovely, very clean and spacious with a great view of the lake behind. It was situated in an ideal location - especially for Disney! Would definitely stay again.
…see more

from £87 / night

£605 / week

Enquire View

from £87 / night

(13) Excellent 

Certificate of Excellence

34

Holiday home with swimming pool in Paradise Palms

Kissimmee / Paradise Palms

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 141 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £86 / night

£497 - £849 / week

Book View

Responds fast!
avg. 3 hours 1 minutes

from £86 / night

(27) Excellent 

33

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
“Don't hesitate, it's lovely!” About to take our 8th Florida villa holiday we approached Dot who was helpful and prompt to reply. Knowing what a superb,convenient and safe location Cumbrian Lakes is we booked up. On arrival we were delighted with the v
…see more

from £75 / night

£485 - £600 / week

Book View

Responds fast!
avg. 2 hours 10 minutes

from £75 / night

(1)  

24

Holiday villa in Kissimmee

Kissimmee / Emerald Isle Kissimmee

7 16 3 nights min

  • 7 bedrooms
  • Sleeps 16
  • 3 nights min
  • Swimming pool
  • Air conditioning

from £140 / night

£980 / week

Book View

from £140 / night

(2) Excellent 

18

Kissimmee holiday apartment rental

Central Florida / Kissimmee

4 8 3 nights min

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

from £72 / night

£504 / week

Book View

from £72 / night

(13) Very Good 

75

Holiday villa with shared pool in Kissimmee

Kissimmee / Lake Berkley

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 107 km
  • Swimming pool
“Fantastic Relaxing Retreat from the Orlando Hustle and Bustle” We very much enjoyed our stay in this spacious and secure house. It is situated in a safe and quiet gated community less than half an hour's drive from most of the Orlando theme parks and
…see more

from £105 / night

£731 / week

Book View

from £105 / night

(1) Excellent 

20

Holiday villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £216 / night

£792 - £1,935 / week

Book View

from £216 / night

(1) Excellent 

13

Villa rental in Kissimmee with shared pool

Central Florida / Kissimmee

4 10 3 nights min

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

from £94 / night

£572 / week

Book View

from £94 / night

(10) Excellent 

Certificate of Excellence

48

Apartment rental in Kissimmee with shared pool

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Certificate of Excellence

from £62 / night

£428 / week

Book View

from £62 / night

(9) Excellent 

43

Holiday townhouse in Kissimmee

Central Florida / Kissimmee

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Nearest beach 114 km
  • Swimming pool
  • Child friendly
“Perfect !!!!!” This property was recommended to us by friends and I'm glad to say it delivered on every level for us as a base whilst on holiday in Florida. Spotlessly clean inside and out , easily housed our family of five ( three of which teenagers)
…see more

from £85 / night

£625 / week

Book View

Responds fast!
avg. 2 hours 26 minutes

from £85 / night

(3) Average 

12

Kissimmee holiday townhouse rental

Kissimmee / Terra Verde Resort

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning

from £60 / night

£385 / week

Book View

from £60 / night

24

Emerald Isle Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £216 / night

£864 - £1,890 / week

Book View

from £216 / night

(13) Excellent 

33

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 £105 / night

£735 - £1,127 / week

Book View

Responds fast!
avg. 2 hours 26 minutes

from £105 / night

(4) Very Good 

19

Villa rental in Kissimmee with swimming pool

Kissimmee / Emerald Isle Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £110 / night

£770 - £1,050 / week

Book View

Responds fast!
avg. 38 minutes

from £110 / night

(4) Very Good 

35

Holiday townhouse rental

Kissimmee / Windsor Hills Resort

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Perfect 'home from home' with great location” This townhouse has a ‘home from home’ feel to it, very clean and well equipped with all the essentials and we were ready to start our holiday right away. Overall, it is spacious and the bedrooms are a good
…see more

from £82 / night

£572 / week

Book View

from £82 / night

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Oak Island Harbor

4 8 5 nights min

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

from £129 / night

£900 / week

Book View

from £129 / night

(70) Excellent 

27

Villa rental in Kissimmee

Kissimmee / Windsor Palms

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £154 / night

£1,076 - £1,795 / week

Book View

from £154 / night

(10) Very Good 

13

Holiday villa with shared pool, golf nearby in Kissimmee

Kissimmee / Windsor Palms

6 14 4 nights min

  • 6 bedrooms
  • Sleeps 14
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £175 / night

£720 / week

Book View

Responds fast!
avg. 3 hours 38 minutes

from £175 / night

(36) Excellent 

Certificate of Excellence

77

Holiday condo with golf nearby in Kissimmee

Kissimmee / Windsor Palms

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 117 km
  • Swimming pool
  • Child friendly
“Excellent accommodation” I was nervous not using a tour operator but Sue's communication really reassured me. On arrival was easy and the accommodation was to a great high standard. Located in Kissimmee but a short distance to where we wanted
…see more

Certificate of Excellence

from £68 / night

£450 - £680 / week

Book View

Responds fast!
avg. 1 hour 7 minutes

from £68 / night

40

Holiday home in Kissimmee

Central Florida / Kissimmee

4 12 3 nights min

  • 4 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £123 / night

£862 / week

Book View

from £123 / night

22

Holiday villa with golf nearby in Lindfields

Kissimmee / Lindfields

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £98 / night

£647 - £828 / week

Book View

from £98 / night

(2) Excellent 

9

Holiday villa rental

Central Florida / Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £68 / night

£460 - £650 / week

Book View

Responds fast!
avg. 2 hours 34 minutes

from £68 / night

11

Holiday villa in Kissimmee

Kissimmee / Formosa Gardens

2 10 7 nights min

  • 2 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £121 / night

£842 / week

Book View

from £121 / night

(7) Excellent 

44

Holiday villa with golf nearby in Kissimmee

Central Florida / Kissimmee

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Very nice villa in a quiet and peaceful area.” The villa was very tidy and well maintained. The location was excellent, being very close to a supermarket and to Kissimmee. It was also an ideal location for all the excellent theme parks. We certainly w
…see more

from £85 / night

£595 / week

Book View

Responds fast!
avg. 3 hours 46 minutes

from £85 / night

(1) Excellent 

4

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £68 / night

£460 - £650 / week

Book View

Responds fast!
avg. 2 hours 34 minutes

from £68 / night

(13) 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

from £59 / night

£413 / week

Book View

Responds fast!
avg. 3 hours 6 minutes

from £59 / night

(5) Very Good 

Certificate of Excellence

34

Holiday villa in Crescent Lakes

Kissimmee / Crescent Lakes

4 8 4 nights min

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

Certificate of Excellence

from £82 / night

£574 / week

Book View

from £82 / night

(3) Excellent 

100

Holiday home in Kissimmee

Kissimmee / Paradise Palms

4 12 3 nights min

  • 4 bedrooms
  • Sleeps 12
  • 3 nights min
  • Nearest beach 103 km
  • Swimming pool
  • Child friendly

from £86 / night

£600 / week

Book View

Responds fast!
avg. 3 hours 40 minutes

from £86 / night

29

Holiday home letting

Central Florida / Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 90 km
  • Child friendly
  • Air conditioning

from £101 / night

£705 - £1,023 / week

Book View

from £101 / night

(5)  

20

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

6 14 3 nights min

  • 6 bedrooms
  • Sleeps 14
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £172 / night

£1,204 / week

Book View

from £172 / night

44

Holiday home with golf nearby in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly

from £93 / night

£650 / week

Book View

Responds fast!
avg. 2 hours 40 minutes

from £93 / night

(2) Very Good 

18

Holiday villa with shared pool, golf nearby in Orange Lake Resort

Kissimmee / Orange Lake Resort

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
“Perfect family spot.” At the time of our check in our wonderful vacation began. The villa was classically appointed. Everything was spotless and functional. The lush landscape was a fitting tropical backdrop for the winding river. All common a
…see more

from £171 / night

£1,200 / week

Book View

from £171 / night

11

Villa rental in Kissimmee

Central Florida / Kissimmee

2 10 7 nights min

  • 2 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £146 / night

£1,018 / week

Book View

from £146 / night

17

Holiday villa with shared pool, golf nearby in Kissimmee

Kissimmee / Orange Lake Resort

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

from £171 / night

£950 / week

Book View

from £171 / night

32

Villa rental in Oak Island Cove

Kissimmee / Oak Island Cove

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 125 km
  • Swimming pool
  • Child friendly

from £133 / night

£925 / week

Book View

Responds fast!
avg. 50 minutes

from £133 / night

(7) Excellent 

Certificate of Excellence

66

Holiday townhouse in Kissimmee

Central Florida / Kissimmee

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £72 / night

£504 - £648 / week

Book View

Responds fast!
avg. 1 hour 2 minutes

from £72 / night

(1) Excellent 

29

Kissimmee holiday home rental

Kissimmee / Formosa Gardens

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“An Excellent Choice” We had a wonderful time at Whispering Palms and think it is an excellent choice of villa both for the quality of accommodation and its location. It is large, comfortable and well maintained. We were an extended family group com
…see more

from £210 / night

£800 - £2,130 / week

Book View

from £210 / night