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

Close

View larger map

Also consider

North America Holidays
172306 properties
United States Holidays
128195 properties
Florida Holidays
38862 properties
Central Florida Holidays
15933 properties
Emerald Isle Kissimmee
50 properties
Villas Windsor Hills Resort
29 properties
Kissimmee City
27 properties
Villas Paradise Palms
20 properties
Villas Windsor Palms
19 properties
Lake Berkley
19 properties
Cumbrian Lakes
18 properties
Lindfields
17 properties
Bellavida Resort
15 properties
Terra Verde Resort
15 properties
Crescent Lakes
10 properties
Compass Bay
10 properties
Seasons Resort
10 properties
Villas Formosa Gardens
9 properties
Venetian Bay Villages
9 properties
Doral Woods
8 properties
Villas Orange Lake Resort
8 properties
Trafalgar Village
8 properties
Encantada Resort
7 properties
Villas Indian Creek
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

4,832 Holiday homes

(5) Excellent 

27

Holiday villa letting

Kissimmee / Windsor Palms

4 10 3 nights min

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

from £120 / night

£825 / week

Book View

from £120 / night

22

Kissimmee holiday home rental

Central Florida / Kissimmee

4 8 Min stay varies

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

from £93 / night

£647 - £75385 / week

Book View

from £93 / night

(1) Excellent 

31

Holiday home rental

Central Florida / Kissimmee

4 13 4 nights min

  • 4 bedrooms
  • Sleeps 13
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £113 / night

£787 / week

Book View

from £113 / night

(18) Very Good 

19

Townhouse rental in Kissimmee

Kissimmee / Regal Oaks

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Excellent value, good facilities, close to the Disney Parks” The accommodation was excellent value for money. It was more than spacious enough for 2 adults and 2 children, and had good facilities (although it lacked wi-fi, which was sorely missed by s
…see more

from £70 / night

£485 / week

Book View

from £70 / night

(15) Very Good 

Certificate of Excellence

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

Certificate of Excellence

from £66 / night

£450 / week

Book View

from £66 / night

(8) 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

from £75 / night

£525 / week

Book View

from £75 / night

(1) Excellent 

22

Kissimmee holiday villa rental

Kissimmee / Winward Cay

3 8 7 nights min

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

from £50 / night

£350 - £500 / week

Book View

from £50 / night

(1) Excellent 

15

Kissimmee holiday villa rental

Kissimmee / Lake Berkley

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
“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
…see more

from £410 / night

£570 / week

Book View

from £410 / night

38

Holiday home in Kissimmee

Kissimmee / Compass Bay

4 10 3 nights min

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

from £81 / night

£770 / week

Book View

from £81 / 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 £108 / night

£754 - £1094 / week

Book View

from £108 / night

(3) Excellent 

28

Holiday home with golf nearby in Kissimmee

Central Florida / Kissimmee

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £231 / night

£1385 - £1939 / week

Book View

from £231 / night

30

Home rental in Kissimmee

Central Florida / Kissimmee

4 4 Min stay varies

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

from £93 / night

£612 - £808 / week

Book View

from £93 / night

(7) Excellent 

31

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee / Winward Cay

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Spacious villa with everything we needed” I stayed at this villa with my husband and 3 boys aged 13, 10 and 7yrs old. The property was very spacious with a double bedroom and bathroom downstairs which we used, leaving the boys to have loads of roo
…see more

from £66 / night

£460 - £599 / week

Book View

from £66 / night

30

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

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

from £97 / night

£647 - £766 / week

Book View

from £97 / night

(16) Excellent 

28

Holiday villa with golf nearby 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 £118 / night

£825 - £1090 / week

Book View

from £118 / night

40

Holiday home accommodation

Central Florida / Kissimmee

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £115 / night

£803 / week

Book View

from £115 / night

(1) Excellent 

13

Apartment rental in Kissimmee

Kissimmee / Windsor Palms

3 6 5 nights min

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

from £69 / night

£461 / week

Book View

from £69 / night

99

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

7 14 5 nights min

  • 7 bedrooms
  • Sleeps 14
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool

from £245 / night

£1715 / week

Book View

from £245 / night

(2) Very Good 

13

Holiday villa in Kissimmee

Kissimmee / Kissimmee City

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
“Amazing stay, great villa” Had a lovely stay for 2 weeks. Very easy to book and a lot of useful information emailed before and in the villa as well. Brilliant directions- made it a less daunting experience! Villa very clean with plenty of room and s
…see more

from £77 / night

£458 - £587 / week

Enquire View

from £77 / night

(6) Very Good 

100

Kissimmee holiday home rental

Central Florida / Kissimmee

4 10 6 nights min

  • 4 bedrooms
  • Sleeps 10
  • 6 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Beautiful sunsets and a fabulous vacation home” We choose Star Lake View as we were looking for a nice lakeside view as we were not disappointed. The views of the sunset were gorgeous and we loved spotting all the wild birds. The villa was immacula
…see more

from £90 / night

£585 / week

Book View

from £90 / night

(2) Very Good 

20

Kissimmee holiday villa rental

Kissimmee / Windsor Hills Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
“Lovely villa in a super location” We all thoroughly enjoyed our stay at Harmony Haven with its good standard, spacious accommodation and super swimming pool. We travelled with our children and grandchildren and we all enjoyed the water shoot at th
…see more

from £93 / night

£647 / week

Book View

from £93 / night

(3) 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 - £1050 / week

Book View

from £110 / night

(2) Very Good 

38

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £174 / night

£1770 / week

Book View

from £174 / night

10

Holiday home rental

Central Florida / Kissimmee

3 8 3 nights min

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

from £70 / night

£462 / week

Book View

from £70 / night

(2) Excellent 

50

Holiday home with indoor pool in Kissimmee

Central Florida / Kissimmee

3 8 3 nights min

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

from £74 / night

£512 / week

Book View

from £74 / night

(24) Excellent 

23

Holiday villa with golf nearby in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
“You must stay in this Home” We have stayed at Emerald Island Resort on several occasions because we like the closeness of the location to the main attractions and the safety of the gated community with 24 hour security. So, when looking for a property
…see more

from £135 / night

£945 - £1250 / week

Book View

from £135 / night

(9) Very Good 

24

Holiday home in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 130 km
  • Swimming pool
“Fabulous House, Fabulous Holiday” We loved this house!!! It was spotlessly clean, and the furnishings were of a high standard. The beds were really comfy and the children loved the playroom and pool. Great for two families. It is a great location
…see more

from £62 / night

£434 / week

Book View

from £62 / night

33

Home rental in Kissimmee with swimming pool

Central Florida / Kissimmee

6 10 2 nights min

  • 6 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £170 / night

£1185 / week

Book View

from £170 / 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 £231 / night

£847 - £2059 / week

Book View

from £231 / night

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 £66 / night

£460 - £599 / week

Book View

from £66 / night

(1) Excellent 

25

Holiday villa rental

Central Florida / Kissimmee

5 10 3 nights min

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

from £125 / night

£875 / week

Book View

from £125 / night

(5) Very Good 

Certificate of Excellence

88

Holiday villa in Kissimmee

Kissimmee / Seasons Resort

5 10 4 nights min

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

Certificate of Excellence

from £110 / night

£695 / week

Book View

from £110 / night

19

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 11 1 night min

  • 4 bedrooms
  • Sleeps 11
  • 1 night min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £110 / night

£766 / week

Book View

from £110 / night

(13) Excellent 

18

Holiday villa with golf nearby in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“A fantastic place to stay, would highly recommend!” This is a perfect villa for a family holiday to Orlando! The complex is pristine and very safe. The villa itself had everything you could wish for and more. The owners had thought of everything to ma
…see more

from £180 / night

£1260 - £1925 / week

Book View

from £180 / night

9

Holiday townhouse in Venetian Bay Villages

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

from £74 / night

£512 - £700 / week

Book View

from £74 / night

11

Holiday villa in Indian Point

Kissimmee / Indian Point

4 8 3 nights min

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

from £114 / night

£792 / week

Book View

from £114 / night

23

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £231 / night

£1077 - £2069 / week

Book View

from £231 / night

9

Holiday apartment with shared pool in Kissimmee

Central Florida / Kissimmee

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £104 / night

£725 / week

Book View

from £104 / night

26

Home rental in Kissimmee

Central Florida / Kissimmee

4 8 4 nights min

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

from £106 / night

£742 - £896 / week

Book View

from £106 / night

22

Holiday townhouse with shared pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

3 6 7 nights min

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

from £60 / night

£450 / week

Book View

from £60 / night

1