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

Close

View larger map

Also consider

North America Holidays
174603 properties
United States Holidays
130862 properties
Florida Holidays
36317 properties
Central Florida Holidays
16054 properties
Emerald Isle Kissimmee
39 properties
Villas Windsor Hills Resort
20 properties
Kissimmee City
18 properties
Villas Paradise Palms
18 properties
Lindfields
15 properties
Villas Windsor Palms
15 properties
Lake Berkley
15 properties
Cumbrian Lakes
12 properties
Bellavida Resort
12 properties
Terra Verde Resort
12 properties
Compass Bay
8 properties
Doral Woods
8 properties
Villas Coral Cay
6 properties
Villas Formosa Gardens
6 properties
Crescent Lakes
6 properties
Trafalgar Village
6 properties
Villas Orange Lake Resort
5 properties
Encantada Resort
5 properties
Sunset Lakes
5 properties
Seasons Resort
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

16,281 Holiday homes

(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
“Comfy home from home” Situated in great location for my husband and myself. We love to be in central 192 and it must be here, so convenient for shopping and eating etc. peaceful community also. Home was comfy, would stay here again. Had a well equip
…see more

Certificate of Excellence

from £75 / night

£525 / week

Book View

Responds fast!
avg. 23 minutes

from £75 / 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
“FANTASTIC VILLA.....GREAT COMMUNICATION WITH OWNER” Lovely villa, spacious enough for 8 people and fully equipped. The location is lovely too, very quiet, with regular landscaping and nice views. The villa is approximately 2-3 miles from lots of res
…see more

from £80 / night

£575 - £650 / week

Book View

Responds fast!
avg. 2 hours 32 minutes

from £80 / night

(26) 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. 2 hours 0 minutes

from £91 / night

(47) Excellent 

40

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
“Holiday To Remember” A perfect exciting, fantastic holiday with all the family. Family of 6. In the last week 7.Quality time with everyone.Extremely a special and magical holiday to remember.The villa was fabulous and very homely.Perfect from start t
…see more

from £90 / night

£545 - £565 / week

Book View

Responds fast!
avg. 56 minutes

from £90 / night

(58) Excellent 

Certificate of Excellence

42

Westside holiday villa rental

Kissimmee / Westside

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Excellent well equipped villa-very spacious and extremely clean” Well situated for all Disney Parks close to supermarket and several restaurants. We were a party of 7 with 2 children who adored the pool and jacuzzi. We felt the villa was exceptionally
…see more

Certificate of Excellence

from £95 / night

£575 - £900 / week

Book View

Responds fast!
avg. 1 hour 19 minutes

from £95 / night

(15) Very Good 

Certificate of Excellence

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
“Fab villa” We just returned from a week at the Palm Heaven Villa. The villa is fab and located in the beautiful Terra Verde resort. It is close to the clubhouse and resort pool. The villa itself is very comfortable and has everything you need. The poo
…see more

Certificate of Excellence

from £100 / night

£600 - £750 / week

Book View

from £100 / 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
“Just Perfect” My wife and I are regular visitors to the Orlando area and have stayed in several Rental Villas in the past. It was our first time at ‘Ventura Villa’ hopefully not our last, we had a really enjoyable stay. The villa is clean, well fur
…see more

from £80 / night

£550 - £1,054 / week

Book View

from £80 / night

(15) Excellent 

24

Calabria, Orlando holiday villa rental

Kissimmee / Calabria, Orlando

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Just what we wanted. Great space. Great location” Preparation communications from owner was excellent. Group of 10 with no issues at all throughout the stay. Quite and pleasant neighbourhood.
…see more

from £125 / night

£875 / week

Book View

Responds fast!
avg. 3 hours 38 minutes

from £125 / night

(16) Very Good 

Certificate of Excellence

40

Holiday home with swimming pool in Kissimmee

Central Florida / Kissimmee

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Merry christmas” We enjoyed our first ever family vacation over the holiday. The house was beautiful and very close to everything. It was a stress free stay and look forward to staying at this home in the future.
…see more

Certificate of Excellence

from £100 / night

£679 / week

Book View

from £100 / 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
“Fantastic! Definitely going back! Loved it!” I rented this villa for 3 weeks with my fiancée, future brother and sister in law and niece. We had a fantastic holiday and even made a trip down to Miami for 2 days where we got engaged! I think this is a
…see more

from £105 / night

£635 - £825 / week

Book View

Responds fast!
avg. 3 hours 57 minutes

from £105 / night

(13) Excellent 

36

Holiday home rental

Kissimmee / Crescent Lakes

5 13 3 nights min

  • 5 bedrooms
  • Sleeps 13
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £80 / night

£450 - £867 / week

Book View

from £80 / 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
“Excellent villa, definitey recommend” An excellent spacious, well equipped villa. Very well situated for the parks, especially Disney, and very well sited near to route 192 that is very well populated by restaurants and further entertainment. The vill
…see more

from £100 / night

£705 / week

Book View

Responds fast!
avg. 26 minutes

from £100 / night

(18) Excellent 

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

from £85 / night

£595 - £735 / week

Book View

from £85 / night

(19) Excellent 

Certificate of Excellence

28

Doral Woods holiday villa rental

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Marvellous away from it all Villa!” We stayed at Woodland Villa for 5 days and wish it had been much longer. We have been to Florida a dozen times and this is one of the best we have stayed at, It is a little bit away from the US192 but that suited us
…see more

Certificate of Excellence

from £74 / night

£495 - £505 / week

Book View

Responds fast!
avg. 1 hour 56 minutes

from £74 / night

(17) Excellent 

Certificate of Excellence

24

Holiday villa in Doral Woods

Kissimmee / Doral Woods

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Fantastic!” We have just returned from Palm Tree Villa. We stayed there for nearly two weeks and to say we had a fantastic time and enjoyed it there is an understatement. The house is as clean as advertised. It has all the facilities in place to make
…see more

Certificate of Excellence

from £100 / night

£695 - £875 / week

Book View

Responds fast!
avg. 1 hour 23 minutes

from £100 / night

(22) 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
“Fantastic” 1   person found this review helpful Our stay in the villa was incredibly pleased! Zakir, was quick to respond, and very easy to work with.We have stayed in the Orlando/Kissimee area before, but this was our best stay so far. Vill
…see more

from £108 / night

£536 / week

Book View

Responds fast!
avg. 3 hours 55 minutes

from £108 / 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
“As good as it gets” From the first contact with the owner to our last day at the villa was excellent. The villa décor and facilities were just what we hoped for and more. From our location it was only a short trip to the theme parks eating out or shop
…see more

from £72 / night

£500 / week

Enquire View

from £72 / night

(14) 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
“Fantastic House, Resort & Location” Fantastic, clean well maintained villa so near to Disney & Universal. We have just finished 22 days from 27th March to 18th April 2012 in the villa. The resort is idealy located just off of the 192, Wall Mart is
…see more

from £165 / night

£1,155 / week

Book View

Responds fast!
avg. 2 hours 19 minutes

from £165 / night

(3) Excellent 

20

Villa rental in Cumbrian Lakes with swimming pool

Kissimmee / Cumbrian Lakes

5 10 3 nights min

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

from £120 / night

£840 / week

Book View

Responds fast!
avg. 49 minutes

from £120 / night

(14) Excellent 

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

from £110 / night

£650 - £1,210 / week

Book View

Responds fast!
avg. 1 hour 34 minutes

from £110 / night

(24) 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

(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

£570 / week

Book View

from £82 / 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
“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 £65 / night

£450 - £800 / week

Book View

from £65 / night

30

Holiday apartment in Kissimmee

Central Florida / Kissimmee

1 4 4 nights min

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

from £47 / night

£325 / week

Book View

from £47 / night

(34) Very Good 

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
“Well placed, compact townhouse on a secure community at a reasonable price.” We were a couple staying here for five nights to do the theme parks before returning to the UK. It was well positioned for this and we felt it was a secure gated community. I
…see more

from £50 / night

£385 - £420 / week

Book View

Responds fast!
avg. 2 hours 17 minutes

from £50 / night

(14) Very Good 

Certificate of Excellence

22

Holiday villa in Kissimmee

Kissimmee / Terra Verde Resort

5 12 5 nights min

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

Certificate of Excellence

from £93 / night

£650 - £750 / week

Book View

from £93 / night

(1) Excellent 

25

Holiday villa rental

Central Florida / Kissimmee

5 10 4 nights min

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

from £105 / night

£735 / week

Book View

Responds fast!
avg. 35 minutes

from £105 / night

(90) 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
“Excellent Villa, Extremely convenient to Disney, shops, restaurants etc.” This villa is superb. It is a very comfortable home for a holiday stay with three great bedrooms, a large spacious living room, great kitchen and a great pool. The real beauty o
…see more

Certificate of Excellence

from £67 / night

£460 - £600 / week

Book View

Responds fast!
avg. 1 hour 56 minutes

from £67 / night

(17) Excellent 

18

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Superb holiday rental in Kissimmee- Orlando” Fabulous locaction, 10 minutes from all the main attractions with other local amenities on the doorstep. The villa is in a gated community and all I can say is the pictures do not do it justice. The villa i
…see more

from £90 / night

£495 / week

Enquire View

from £90 / night

(43) 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
“Fantastic Villa” This was our first experience of a Florida holiday villa and I think we found the best one first time! Located at the end of a quiet cul-de-sac in the Crescent Lakes community it is the ideal holiday base for those seeking something a
…see more

from £85 / night

£550 / week

Book View

from £85 / night

(13) Excellent 

22

Holiday home with shared pool in Kissimmee

Kissimmee / Trafalgar Village

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

from £64 / night

£445 - £598 / week

Book View

from £64 / night

(13) 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

£800 - £1,200 / week

Book View

Responds fast!
avg. 2 hours 16 minutes

from £100 / night

(13) Very Good 

50

Holiday villa rental

Kissimmee / Trafalgar Village

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic villa” Was very impressed with the villa. Very spacious and clean. Lots of local amenities and all parks very close by. Situated on a quiet estate and very welcoming would definitely recommend
…see more

from £85 / night

£550 - £700 / week

Book View

Responds fast!
avg. 3 hours 58 minutes

from £85 / night

(11) Excellent 

26

Holiday villa in Formosa Gardens

Kissimmee / Formosa Gardens

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Superb chillout base for a large group visiting the theme parks” As a group of 9 adults and 2 children, we thought it may prove difficult to rent anywhere large enough to accommodate everyone under the same roof, but this house met this need with hono
…see more

from £229 / night

£1,600 - £2,000 / week

Enquire View

from £229 / night

(3) Excellent 

23

Holiday townhouse with golf nearby in Kissimmee

Kissimmee / Fiesta Key

3 8 3 nights min

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

from £61 / night

£379 - £479 / week

Book View

Responds fast!
avg. 1 hour 17 minutes

from £61 / night

(5) Very Good 

24

Holiday villa in Kissimmee

Kissimmee / Tuscany, Florida

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £54 / night

£380 / week

Book View

from £54 / 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
“***AWSOME VILLA*** fabulous holiday!” We stayed in this villa for 2 weeks in September and had a fantastic time, we were a family of 8 and everyone of us thoroughly enjoyed every minute. Can't fault anything about this property... It was big enough fo
…see more

from £93 / night

£650 - £750 / week

Book View

Responds fast!
avg. 1 hour 28 minutes

from £93 / night

(9) Excellent 

Certificate of Excellence

19

Kissimmee holiday villa rental

Kissimmee / Oak Island Cove

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“The Best” Family of 4, 2 teenagers. Have been going to Floruda for almost 20 years, this is by far the best accommodation we have stayed in. Villa has got everything that you need, just been upgraded with outside covered seating area. Oak Island Har
…see more

Certificate of Excellence

from £100 / night

£700 / week

Book View

from £100 / 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 £165 / night

£1,143 / week

Book View

from £165 / night

(8) Excellent 

Certificate of Excellence

32

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

Certificate of Excellence

from £190 / night

£1,250 - £2,143 / week

Book View

from £190 / night

Top Destination reviews

Belle's Cove, Family-Friendly Villa with Gameroom and Hot Tub
Lovely villa

We thoroughly enjoyed our stay at Belles cove. The house had everything we could possibly need even down to icepacks on the freezer. The beds were very comfortable, the rooms were spacious and well equipped and the pool and Jacuzzi were lovely. It was worth heating the pool as we were able to use it even in the evenings when it got cooler. The management company were very quick to respond when we had a small issue and it was sorted the same day, excellent service.see more
Robson's Retreat, Relaxing Vacation Home with a Ba
Perfect accommodation for needed relaxation and family-friendly hom

This home is set up perfectly for a family vacation. Plenty of bedrooms and bathrooms along with a beautiful pool and lanai. Pool and hot tub are comfortable and overlook a lovely wooded area. If you are looking for a place to settle in and enjoy relaxing, this would be the perfect spot. … see more
A hideaway dream - an amazing spacious family home
The home we'd like to have in Florida

We arrived in Florida with high expectations of the house we rented, and not only were they met, they were greatly exceeded. A house that we rented over the internet soon became a home for our 7 week stay. Everything to ensure a great stay was provided for us by the home owner, as well as the property management company. Our favourite time was spent lounging by the beautifully maintained pool overlooking the natural surroudings of the back yard. The house is in a great location near all the amenities we were looking for, especially Walt Disney World. We are looking forward to coming back to Florida and staying here again. We would highly recommend this home to anyone coming to this area.see more
Wyndham Cypress Palms Accommodations - One Bedroom WVR
Overall very good - but be prepared for a disappointment

Good central location, especially for the theme parks. The site is well run, its just a pity that the picture consistently used to advertise this accommodation features a balcony, and the apartment does not have one! Good news - wood floors throughout, bad news - they are not clean, not just dusty, but ingrained dirt. These points downgrade what would have been an excellent stay.see more
Amazing Disney Condo, Pool & Hot tub Onsite
Fantastic apartment in a great location

The apartment has loads of space and is fully kitted out. The pool and clubhouse make all the difference … see more
AFFORDABLE LUXURY WITH AIR CONDITIONED GAMES ROOM
Great villa

This is a great villa, very clean, well equipped and in a nice area, would use again, had no issues. … see more