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

Close

View larger map

Also consider

North America Holidays
172375 properties
United States Holidays
128284 properties
Florida Holidays
38862 properties
Central Florida Holidays
16066 properties
Emerald Isle Kissimmee
50 properties
Villas Windsor Hills Resort
29 properties
Kissimmee City
28 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
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

4,883 Holiday homes

(31) 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

(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

20

Cumbrian Lakes holiday villa rental

Kissimmee / Cumbrian Lakes

5 10 Min stay varies

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

from £95 / night

£665 - £940 / week

Book View

Responds fast!
avg. 36 minutes

from £95 / night

(1) Excellent 

29

Kissimmee holiday home rental

Kissimmee / Formosa Gardens

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • 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 £219 / night

£1530 - £2300 / week

Book View

from £219 / 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

(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 £179 / night

£1250 - £1689 / week

Book View

from £179 / 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

11

Holiday apartment in Kissimmee

Central Florida / Kissimmee

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £134 / night

£936 / week

Book View

from £134 / night

(1) Excellent 

5

Holiday villa with shared pool, golf nearby in Kissimmee

Kissimmee / Orange Lake Resort

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Excellent experience” It's a resort within a golf course. Very close to Disney World and other attractions. Staff was very friendly and helpful. Pools are wonderful for the kids. The resort was close to supermarket. It was a wonderful destination for
…see more

from £116 / night

£808 / week

Book View

from £116 / 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

(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

Responds fast!
avg. 1 hour 20 minutes

from £125 / night

20

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 10 4 nights min

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

from £111 / night

£774 / week

Book View

from £111 / night

43

Kissimmee holiday villa rental

Central Florida / Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Child friendly

from £220 / night

£1540 / week

Book View

Responds fast!
avg. 2 hours 26 minutes

from £220 / night

(2) Excellent 

24

Holiday villa in Sunset Lakes

Kissimmee / Sunset Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fabulous villa in fabulous location” Stayed at this villa in September and had a wonderful time. The whole family thoroughly enjoyed themselves and the kids were in the pool virtually every day. The villa overlooks a lake and there are great sunsets.
…see more

from £84 / night

£525 - £695 / week

Book View

from £84 / night

(2) Excellent 

24

Holiday villa accommodation

Kissimmee / Formosa Gardens

8 18 1 night min

  • 8 bedrooms
  • Sleeps 18
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool

from £500 / night

£3480 - £4176 / week

Book View

from £500 / 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

(5) Very Good 

18

Kissimmee holiday villa rental

Kissimmee / Crescent Lakes

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Superb villa” The only fault with this property is that we couldn't stay longer. The booking process went smoothly. The owner was very attentive and answered all of our questions promptly. The villa is in a perfect setting and is fully equipped, clean
…see more

from £90 / night

£575 / week

Book View

Responds fast!
avg. 3 hours 2 minutes

from £90 / night

(31) 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
“Great place for families” Clean, close to everything, fast owner response and supplies all you need. We loved the pool and the tiki bar. Our kids loved the playground, basketball court and tennis court. Disney and Universal are so close. Grocery stor
…see more

Certificate of Excellence

from £70 / night

£450 - £695 / week

Book View

Responds fast!
avg. 1 hour 10 minutes

from £70 / 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

Responds fast!
avg. 3 hours 10 minutes

from £69 / night

14

Holiday home with indoor pool in Kissimmee

Central Florida / Kissimmee

5 10 2 nights min

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

from £110 / night

£770 / week

Book View

from £110 / night

(18) Excellent 

24

Home rental in Bellavida Resort

Kissimmee / Bellavida Resort

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“East 192, Where Tink@Bella waits for Youuuuuuu” The Bella Vida resort is a Great, Gated Community. Where inside awaits the the Fantastic Tink@Bella Villa. Approx 30 mins from Orlando Int. Perfect location for all that awaits you, Disney, Universal,
…see more

from £143 / night

£995 - £1395 / week

Enquire View

from £143 / night

23

Holiday home in Kissimmee

Central Florida / Kissimmee

7 16 Min stay varies

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

from £193 / night

£1347 - £2193 / week

Book View

from £193 / 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

(2) 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
“FANTASTIC!” I would highly recommend this 3 bedroom townhouse with heated pool. It was everything and more when we arrived. The outdoor pool was perfect for the kids and the park in the back yard was great to have them play frisbee and soccer. The loc
…see more

from £88 / night

£616 / week

Book View

from £88 / night

24

Townhouse rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £85 / night

£539 / week

Book View

Responds fast!
avg. 52 minutes

from £85 / night

(2) Very Good 

13

Villa rental in Kissimmee with shared pool, golf nearby

Kissimmee / Orange Lake Resort

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Nice accommodation and location.” 20 minutes to theme parks. 10 minutes to super market. 30 minutes to outlet shops. Easy to find on Sat Nav and no hassles with traffic. Lacking a few kitchen utensils, but nothing worth fussing over.
…see more

from £132 / night

£924 / week

Book View

from £132 / night

20

Kissimmee holiday home rental

Central Florida / Kissimmee

4 10 2 nights min

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

from £102 / night

£711 / week

Book View

from £102 / 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

£375 - £725 / week

Book View

from £50 / 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 £76 / night

£532 / week

Book View

from £76 / night

(3) Excellent 

11

Holiday hotel apartment in Kissimmee

Kissimmee / Compass Bay

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Air conditioning
“Near Disney, Good Price, Beautiful Place” We would stay again. we stayed here and drove to SeaWorld 3 days. very convenient. liked the fact it was a block off the main road. liked where it was near Fun Town for the kids, go cart track walking distan
…see more

from £100 / night

£708 / week

Book View

Responds fast!
avg. 1 hour 29 minutes

from £100 / night

11

Holiday villa in Kissimmee

Kissimmee / Formosa Gardens

2 10 Min stay varies

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

from £170 / night

£1024 / week

Book View

from £170 / night

8

Kissimmee holiday villa rental

Central Florida / Kissimmee

3 8 7 nights min

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

from £64 / night

£445 - £540 / week

Book View

from £64 / night

(15) Excellent 

21

Holiday villa with golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic villa, great location!” Dunestone is a very smart, spacious and well-positioned villa in a great gated community. So close to Disney and only mins from the I-4 allowing easy access to all of Orlando's attractions. The owners were a pleasure
…see more

from £180 / night

£1260 - £1925 / week

Book View

from £180 / night

56

Holiday apartment with shared pool in Kissimmee

Central Florida / Kissimmee

3 6 2 nights min

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

from £70 / night

£447 / week

Book View

from £70 / night

(2) Excellent 

37

Holiday townhouse 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 £77 / night

£539 - £770 / week

Book View

Responds fast!
avg. 1 hour 19 minutes

from £77 / night

24

Holiday villa in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £208 / night

£1385 - £2000 / week

Book View

Responds fast!
avg. 3 hours 47 minutes

from £208 / night

17

Kissimmee holiday villa rental

Central Florida / Kissimmee

6 13 5 nights min

  • 6 bedrooms
  • Sleeps 13
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Child friendly

from £175 / night

£1225 / week

Book View

from £175 / night

37

Kissimmee holiday home rental

Central Florida / Kissimmee

6 14 3 nights min

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

from £153 / night

£1067 / week

Book View

from £153 / night

(33) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Our Family 4th of July Vacation” I was looking for a place where my family and myself could go to spend time in Florida from where I live in NYC. We chose the perfect location. Check in was simple, directions to the home were easy to understand, and i
…see more

from £107 / night

£745 - £895 / week

Enquire View

from £107 / night

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Oak Island Harbor

4 8 Min stay varies

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

from £116 / night

£808 - £1116 / week

Book View

from £116 / night

1