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

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

5,101 Holiday homes

(2) Excellent 

12

Holiday villa in Windsor Palms

Kissimmee / Windsor Palms

4 8 3 nights min

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

from £135 / night

£945 / week

Book View

from £135 / night

(2) Excellent 

24

Holiday home in Kissimmee

Central Florida / Kissimmee

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £172 / night

£1200 - £1800 / week

Book View

from £172 / night

(2) Excellent 

71

Holiday villa with shared pool in Kissimmee City

Kissimmee / Kissimmee City

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect in every way” we have stayed here several times (approx. 10) and every time the house delivers what we expect in a Florida villa. Villa is cleaned to a high standard on arrival, the kitchen has everything you have in your own kitchen at home s
…see more

from £80 / night

£550 / week

Book View

from £80 / night

(1) Very Good 

56

Holiday townhouse in Kissimmee City

Kissimmee / Kissimmee City

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
“Great wee resort” Terra Verde was an immaculately kept resort. Seemed to be 20mins from most big attraction parks. This house was ideal for our family of four and could easily have accommodated 2 more. It was spotlessly clean and the couple of hiccups
…see more

from £75 / night

£525 - £630 / week

Book View

Responds fast!
avg. 1 hour 57 minutes

from £75 / night

(3) Very Good 

81

Holiday home in Oak Island Harbor

Kissimmee / Oak Island Harbor

6 13 4 nights min

  • 6 bedrooms
  • Sleeps 13
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £199 / night

£1389 / week

Book View

from £199 / night

(11) Very Good 

48

Holiday villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

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

from £61 / night

£423 / week

Book View

Responds fast!
avg. 2 hours 41 minutes

from £61 / night

(3) Very Good 

51

Kissimmee holiday apartment rental

Central Florida / Kissimmee

3 6 3 nights min

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

from £68 / night

£473 / week

Book View

Responds fast!
avg. 3 hours 9 minutes

from £68 / night

(4) Very Good 

23

Holiday villa with swimming pool in Kissimmee

Kissimmee / Lindfields

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £85 / night

£595 - £910 / week

Book View

Responds fast!
avg. 1 hour 57 minutes

from £85 / night

(5) Excellent 

Certificate of Excellence

21

Villa rental in Kissimmee

Kissimmee / Indian Ridge

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“great villa with a great pool area” Not far from all the theme parks and a great pool area to chill out after a long day. The villa was in good condition and equipped with all the home comforts you could need for a great holiday
…see more

Certificate of Excellence

from £115 / night

£700 - £895 / week

Book View

from £115 / night

23

Holiday villa in Kissimmee

Kissimmee / Windsor Palms

6 12 Min stay varies

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

from £150 / night

£1050 - £1150 / week

Book View

from £150 / night

(7) Excellent 

24

Holiday villa with golf nearby in Kissimmee

Kissimmee / Bellavida Resort

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • 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 / week

Book View

Responds fast!
avg. 2 hours 3 minutes

from £165 / night

(3) Excellent 

24

Holiday home in Crescent Lakes

Kissimmee / Crescent Lakes

4 8 Min stay varies

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

from £90 / night

£580 - £1000 / week

Book View

from £90 / night

(2) Average 

55

Holiday condo with shared pool in Kissimmee

Kissimmee / Cane Island

2 6 3 nights min

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

from £39 / night

£258 - £473 / week

Book View

Responds fast!
avg. 2 hours 49 minutes

from £39 / night

18

Crescent Lakes holiday villa rental

Kissimmee / Crescent Lakes

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

from £103 / night

£715 - £874 / week

Book View

from £103 / night

(2) Excellent 

29

Holiday villa in Kissimmee

Kissimmee / Seasons Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £118 / night

£826 - £1481 / week

Book View

from £118 / night

(11) Very Good 

75

Holiday villa with shared pool in Kissimmee

Kissimmee / Lake Berkley

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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 £116 / night

£806 / week

Book View

from £116 / night

(27) Very Good 

Certificate of Excellence

56

Holiday home rental

Kissimmee / Lindfields

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 90 km
  • Swimming pool
“Great accommodation” Stayed here for two weeks for our honeymoon. Location of the villa is excellent if visiting the Disney Parks. Clean and tidy, very large living area and bedrooms. Couldn't have asked for anything better.
…see more

Certificate of Excellence

from £50 / night

£350 / week

Book View

Responds fast!
avg. 3 hours 25 minutes

from £50 / night

(20) Excellent 

25

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Swimming pool
“Perfect Florida home” From the minute we arrived, we loved and enjoyed every minute of our four week stay here. Everything was perfect from the moment we went through the door. The rooms are spacious, comfortable and tastefully decorated. Ove
…see more

from £130 / night

£875 / week

Book View

from £130 / night

14

Holiday home with indoor pool in Kissimmee

Central Florida / Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £134 / night

£934 / week

Book View

from £134 / night

(13) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“Excellent Villa highly recommend it, great location.” Property was excellent, close to Disney and places to eat. The weather was nice and the complex where the villa was situated was well looked after, nice and clean and staff was pleasant.
…see more

from £130 / night

£840 - £1450 / week

Book View

from £130 / night

(2) Excellent 

22

Villa rental in Kissimmee with swimming pool

Kissimmee / Cumbrian Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

from £100 / night

£700 - £910 / week

Book View

Responds fast!
avg. 1 hour 57 minutes

from £100 / night

(1) Very Good 

19

Holiday apartment with shared pool in Kissimmee

Kissimmee / Windsor Palms

3 6 Min stay varies

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

from £79 / night

£550 / week

Book View

from £79 / night

20

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £235 / night

£860 - £2179 / week

Book View

from £235 / night

(8) Excellent 

43

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee / Winward Cay

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fabulous pool” Beauitiful, clean villa with an open floor plan. Located in a very quiet neighborhood. Great pool.Pool toys in garage. Well stocked with everything you need. Sheets, bath towels, kitchen towels and towels for the pool use. Air condition
…see more

from £66 / night

£460 - £650 / week

Book View

Responds fast!
avg. 1 hour 30 minutes

from £66 / night

(12) Excellent 

Certificate of Excellence

16

Villa rental in Kissimmee

Kissimmee / Indian Creek

4 8 Min stay varies

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

Certificate of Excellence

from £100 / night

£700 - £1100 / week

Book View

from £100 / night

(10) Excellent 

Certificate of Excellence

27

Kissimmee holiday villa rental

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Swimming pool

Certificate of Excellence

from £125 / night

£875 - £1073 / week

Book View

from £125 / 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

(7) Excellent 

98

Home rental in Kissimmee with indoor pool

Kissimmee / Emerald Isle Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 96 km
  • Swimming pool
  • Child friendly
“Perfect” This villa was excellent (exactly as advertised). The location was great being only 10-15 minutes from Walt Disney World. It was perfectly positioned for shopping too, Walmart was only a few minutes away. The kids loved their bedrooms and
…see more

from £80 / night

£556 - £828 / week

Book View

Responds fast!
avg. 2 hours 5 minutes

from £80 / night

(18) Excellent 

14

Holiday townhouse in Kissimmee

Kissimmee / Encantada Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic house in a fantastic location” Recently returned from 2 weeks of fun in Florida with our 5 year old daughter. The weather was glorious and the parks brilliant. What topped our holiday was returning everday to our rented home. The home had a
…see more

from £64 / night

£393 - £849 / week

Book View

Responds fast!
avg. 2 hours 2 minutes

from £64 / night

6

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 10 7 nights min

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

from £79 / night

£550 / week

Book View

from £79 / night

(2) Excellent 

11

Kissimmee holiday townhouse rental

Kissimmee / Compass Bay

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 101 km
  • Swimming pool

from £90 / night

£635 - £730 / week

Book View

from £90 / night

(33) Excellent 

Certificate of Excellence

90

Villa rental in Kissimmee with swimming pool

Kissimmee / Eagle Pointe

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“A beautiful home in the sun.” We stayed in this lovely villa for two weeks and we honestly could not fault it. The location is very good with easy access to Disney plus the i4 and the 192. There is a Walmart under 2 miles away and a number of great re
…see more

Certificate of Excellence

from £65 / night

£455 - £553 / week

Book View

Responds fast!
avg. 2 hours 11 minutes

from £65 / night

16

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 2 nights min

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

from £92 / night

£639 / week

Book View

Responds fast!
avg. 41 minutes

from £92 / 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

(2) Very Good 

100

Holiday villa in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 8 5 nights min

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

from £111 / night

£772 - £1120 / week

Book View

from £111 / night

(4) Excellent 

24

Holiday villa with golf nearby in Kissimmee

Kissimmee / Remington

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
“Great vacation” We had a great holiday . The villa is lovely and very spacious. All home comforts and more. There were 7 of us and we had plenty of room (could comfortably sleep 10). The location is ideal for parks and shopping malls with just a short
…see more

from £75 / night

£525 - £910 / week

Book View

from £75 / night

(3) Very Good 

59

Holiday home with indoor pool in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

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

from £112 / night

£778 / week

Book View

Responds fast!
avg. 2 hours 10 minutes

from £112 / night

(3) Very Good 

15

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 8 7 nights min

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

from £72 / night

£500 - £630 / week

Book View

from £72 / night

12

Townhouse rental in Kissimmee

Kissimmee / Terra Verde Resort

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £65 / night

£455 - £840 / week

Book View

Responds fast!
avg. 1 hour 57 minutes

from £65 / night

(4) Very Good 

12

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Idyllic base for Orlando holiday” Just got back from this lovely villa where we spent a wonderful two weeks. The owners have made this feel just like home, with everything necessary for a comfortable stay. From the extended pool deck with comfy sunbed
…see more

from £87 / night

£626 / week

Book View

from £87 / night

1