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

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Kissimmee

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18,199 Holiday homes

(17) Excellent 

30

Kissimmee holiday villa rental

Kissimmee / Windsor Palms

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £96 / night

£700 - £750 / week

Book View

Responds fast!
avg. 3 hours 45 minutes

from £96 / night

(11) Very Good 

Certificate of Excellence

24

Villa rental in Kissimmee

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 £75 / night

£525 / week

Book View

Responds fast!
avg. 26 minutes

from £75 / night

(28) Excellent 

24

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

from £106 / night

£747 / week

Book View

Responds fast!
avg. 48 minutes

from £106 / night

(36) Excellent 

24

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £80 / night

£575 - £650 / week

Book View

Responds fast!
avg. 1 hour 41 minutes

from £80 / night

(45) Very Good 

23

Holiday condo with golf nearby in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 106 km
  • Swimming pool
  • Child friendly

from £45 / night

£245 - £370 / week

Book View

Responds fast!
avg. 3 hours 39 minutes

from £45 / night

(27) Excellent 

Certificate of Excellence

12

Kissimmee holiday villa rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £91 / night

£550 - £750 / week

Book View

Responds fast!
avg. 1 hour 56 minutes

from £91 / night

(50) Excellent 

Certificate of Excellence

41

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

Certificate of Excellence

from £90 / night

£545 - £585 / week

Book View

Responds fast!
avg. 1 hour 20 minutes

from £90 / 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 £55 / night

£380 - £600 / week

Book View

from £55 / night

(92) Excellent 

Certificate of Excellence

25

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

Certificate of Excellence

from £70 / night

£485 - £600 / week

Book View

Responds fast!
avg. 1 hour 47 minutes

from £70 / night

(30) 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

from £105 / night

£635 - £825 / week

Book View

from £105 / night

(18) Very Good 

90

Holiday townhouse in Kissimmee

Kissimmee / Terra Verde Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £100 / night

£600 - £750 / week

Book View

from £100 / night

(20) Very Good 

24

Townhouse rental in Kissimmee

Kissimmee / Regal Oaks

3 6 Min stay varies

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

from £85 / night

£592 / week

Book View

Responds fast!
avg. 2 hours 44 minutes

from £85 / night

(27) Excellent 

21

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

from £72 / night

£500 / week

Book View

from £72 / night

(18) Excellent 

Certificate of Excellence

20

Holiday villa letting

Kissimmee / Emerald Isle Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £85 / night

£595 - £840 / week

Book View

from £85 / night

(25) Excellent 

Certificate of Excellence

19

Villa rental in Kissimmee with swimming pool

Kissimmee / Bellavida Resort

4 8 3 nights min

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

Certificate of Excellence

from £90 / night

£590 / week

Book View

from £90 / night

(2) Excellent 

39

Holiday villa rental

Central Florida / Kissimmee

8 20 4 nights min

  • 8 bedrooms
  • Sleeps 20
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £240 / night

£1,680 / week

Book View

Responds fast!
avg. 2 hours 7 minutes

from £240 / night

(10) Very Good 

14

Kissimmee holiday villa let

Kissimmee / Windsor Hills Resort

6 13 3 nights min

  • 6 bedrooms
  • Sleeps 13
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly

from £174 / night

£1,208 / week

Book View

Responds fast!
avg. 3 hours 59 minutes

from £174 / night

(19) Very Good 

48

Townhouse rental in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 104 km
  • Swimming pool
  • Child friendly

from £60 / night

£400 - £575 / week

Book View

Responds fast!
avg. 2 hours 0 minutes

from £60 / night

(37) Very Good 

Certificate of Excellence

18

Kissimmee holiday townhouse rental

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 55 km
  • Swimming pool

Certificate of Excellence

from £55 / night

£385 - £420 / week

Book View

Responds fast!
avg. 2 hours 44 minutes

from £55 / night

(27) 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

from £65 / night

£450 - £800 / week

Enquire View

from £65 / night

(6) Very Good 

23

Holiday villa with swimming pool in Kissimmee

Kissimmee / Lindfields

4 10 3 nights min

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

from £100 / night

£700 / week

Book View

Responds fast!
avg. 1 hour 52 minutes

from £100 / night

(4) Excellent 

33

Kissimmee holiday home rental

Central Florida / Kissimmee

3 8 Min stay varies

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

from £80 / night

£717 / week

Book View

Responds fast!
avg. 2 hours 19 minutes

from £80 / night

(28) Very Good 

23

Holiday villa in Kissimmee City

Kissimmee / Kissimmee City

3 6 Min stay varies

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

from £60 / night

£375 - £465 / week

Enquire View

from £60 / night

(8) Very Good 

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

from £110 / night

£695 / week

Book View

Responds fast!
avg. 2 hours 8 minutes

from £110 / night

(2) Excellent 

11

Kissimmee holiday townhouse rental

Kissimmee / Compass Bay

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 101 km
  • Swimming pool

from £90 / night

£635 / week

Book View

Responds fast!
avg. 2 hours 33 minutes

from £90 / night

(12) Excellent 

Certificate of Excellence

30

Kissimmee holiday villa let

Kissimmee / Lindfields

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £70 / night

£445 - £595 / week

Book View

Responds fast!
avg. 2 hours 2 minutes

from £70 / night

(23) Very Good 

30

Villa rental in Kissimmee with swimming pool

Central Florida / Kissimmee

3 6 5 nights min

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

from £114 / night

£566 / week

Book View

Responds fast!
avg. 3 hours 15 minutes

from £114 / night

(15) Excellent 

44

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

from £110 / night

£800 - £1,039 / week

Book View

Responds fast!
avg. 2 hours 38 minutes

from £110 / night

(45) 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

from £85 / night

£550 / week

Book View

from £85 / night

(44) 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

Certificate of Excellence

from £90 / night

£630 - £770 / week

Book View

Responds fast!
avg. 50 minutes

from £90 / night

(42) Very Good 

12

Villa rental in Lindfields

Kissimmee / Lindfields

3 8 Min stay varies

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

from £65 / night

£455 - £630 / week

Book View

from £65 / night

(13) Excellent 

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

from £100 / night

£800 - £1,200 / week

Book View

Responds fast!
avg. 2 hours 5 minutes

from £100 / night

42

Condo rental in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

3 6 3 nights min

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

from £90 / night

£629 / week

Book View

Responds fast!
avg. 3 hours 1 minutes

from £90 / night

30

Home rental in Kissimmee with swimming pool

Central Florida / Kissimmee

4 8 4 nights min

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

from £84 / night

£584 / week

Book View

from £84 / night

(15) Excellent 

Certificate of Excellence

25

Holiday villa in Kissimmee

Kissimmee / Kissimmee City

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £120 / night

£650 - £1,210 / week

Book View

Responds fast!
avg. 1 hour 34 minutes

from £120 / night

(35) Excellent 

23

Holiday condo in Kissimmee

Kissimmee / Cane Island

2 6 5 nights min

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

from £65 / night

£455 / week

Book View

Responds fast!
avg. 34 minutes

from £65 / night

(39) Excellent 

23

Holiday home with swimming pool in Oak Island Cove

Kissimmee / Oak Island Cove

5 10 Min stay varies

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

from £93 / night

£650 - £750 / week

Book View

from £93 / night

(28) Very Good 

25

Holiday home in Kissimmee

Central Florida / Kissimmee

4 10 3 nights min

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

from £80 / night

£550 - £1,054 / week

Book View

from £80 / night

(25) Excellent 

24

Kissimmee holiday villa rental

Kissimmee / Lake Berkley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £71 / night

£495 - £600 / week

Book View

from £71 / night

(1) Very Good 

20

Condo rental in Kissimmee with golf nearby

Kissimmee / Kissimmee City

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool

from £68 / night

£476 - £642 / week

Book View

Responds fast!
avg. 2 hours 42 minutes

from £68 / night

Top Destination reviews

TERRA VERDE TOWNHOUSE 3BR / 2.5 BATH
Lovely house, perfect place to stay for all the family q

I stayed here with my family, 5 of us in total including 2 young children. What a lovely place. The townhouse is great for a family. Spacious downstairs area with open plan kitchen and living room. Separate toilet and utility room. 3 spacious bedrooms with comfy beds. The garden looks out towards the lake which is a very nice view, lots of different birds to see which my kids loved! The hot tub was nice to have too. You are just around the corner from the resort pool and clubhouse. Nice play park there too with some outdoor games also. The tiki bar at the pool is handy for a drink or snacks. The resort is fab and very clean, tidy and quiet. Couldn’t fault anything and would definitely visit again. The home owners are very friendly and helpful and very easy to contact. Regarding location, we were a 30 minute drive to Disney World and a little less to Universal. There is a Walmart less than 5 minutes away and you’re very close to the main strip where there are lots of restaurants and cafes etc.see more
Lakefront, Gated 4 Br/3 Ba, sleep 10, 5 miles to Disney, Free WiFi/Cable TV -09
Easter Family holiday April 2018

House was lovely and clean, very spacious and plenty of room for the 5 of us. Everything provided for our basic needs.. Could do with a couple of repairs such as the blinds as we couldn’t fully open to let the light in.. but apart from that we loved staying there... Pool area nice and quiet with beds/umbrellas provided Waffle House and Wendy’s at the end of the road if in need for a quick snack.. Target is the nearest supermarket and slightly cheaper than Walmart. Close to all parks... Kissamee old town is great to visit for a day/evening off from the parks... Would definitely recommend to friends and family...see more
Free Pool Heat and Total Privacy - The Private Retreat, Minutes from Disney
Disney Break

Stayed for one week with our family and found that the villa was ideal for us. The property has everything you would expect and is of a high standard. Beautiful pool area and very private. The location to the Disney parks is brilliant, Animal Kingdom only 10mins drive, others not much more. … see more
Veranda Palms Villa
Fantastic well located villa

We stayed in this villa in April 18. From the moment I contacted the owner Russell, he was quick to respond, really helpful and answered all my questions. There were 3 adults and 2 kids and there was more then enough room at the villa. It is really Spacious and clean and really well located. 2 mins up the road you get to Applebee’s just on the corner of 192. We had the pool heated which was great, it makes such a difference. It’s secure and the pool at the club house it good for a visit for the kids. We are planning to go back next Easter and we will be contacting Russell to re book. I cannot fault this place it was perfect for us and our boys loved the games room.see more
Robson's Retreat, Relaxing Vacation Home with a Ba
Look no further, this home is all you need for your ideal Florida vacation home

We are seasoned veterans of Florida, having been going 2-3 times a year for the past 25 years. In that time we have bought, owned our own Florida home and sold it again and in between not having our own home we have always rented villas for our stay. We have stayed in various villas and locations over the years so have seen a multitude peoples differing ideas of what makes the dream holiday home. I can say without a shadow of doubt, that this one has been the best we have stayed in. Starting with the location, it's close enough to the parks and restaurants that you won't spend a great deal of your holiday time driving, but out of the way enough not to be bothered by the sound of traffic while you relax around the pool. The house itself is situated on a gated community that contains holiday rental homes as well as families, which is always a good sign. The house contains absolutely everything that you could need during your stay. As we have spent so much time in Florida over the years we aren't out all day everyday (like most families would be) so we spent a great deal of time in the home, the best compliment I can pay the home is that it was exactly that, a home, our home for the 3 weeks we were there and it felt like it. Would I recommend this home to my friends, definitely, would I book this home again, absolutely. The location, the woodland environment, the home all perfect for your Florida holiday.see more
Whispering Palms, Stunning Kissimmee Rental Home, twenty minutes Disney.
Absolutely excellent

The house was well situated and extremely well furnished and we will be contacted the owner to book next year. … see more