Apartments and villas with Wi-Fi available in Kissimmee

Close

View larger map

Also consider

North America Holidays
169169 properties
United States Holidays
120165 properties
Florida Holidays
34992 properties
Central Florida Holidays
13610 properties
Emerald Isle Kissimmee
50 properties
Kissimmee City
29 properties
Villas Windsor Hills Resort
29 properties
Lake Berkley
23 properties
Villas Paradise Palms
20 properties
Cumbrian Lakes
20 properties
Villas Windsor Palms
20 properties
Lindfields
18 properties
Terra Verde Resort
16 properties
Bellavida Resort
14 properties
Crescent Lakes
10 properties
Villas Indian Creek
10 properties
Seasons Resort
10 properties
Venetian Bay Villages
10 properties
Compass Bay
9 properties
Doral Woods
9 properties
Encantada Resort
8 properties
Trafalgar Village
7 properties
Eagle Pointe
7 properties
Regal Oaks
7 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

1,492 Holiday homes

Filters applied: Wi-Fi available (1,492)

Travellers going to Kissimmee are booking March dates now. Secure your holiday home today and have the perfect trip.

8

Townhouse rental in Kissimmee with golf nearby

Kissimmee / Emerald Isle Kissimmee

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Emerald Island has a great location, only minutes from Disney and theres loads of shops and restaurants close by. Our house has a brilliant position right infront of the heated pool and spa and you can just sit on the balcony and chill out after a busy day at the parks  …see more

from £78 / night

£492 / week

Book View

from £78 / 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

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
Philsvillas The Villa is big enough for two families - 4 bedrooms; 2 double each with en-suite facilities and 2 twin rooms with a shared bathroom. With a sofa bed in the living room the villa comfortably accommodates up to 10 people. Bed linen and towels are provided. C  …see more

from £68 / night

£475 - £550 / week

Book View

from £68 / night

Featured properties

(8) Excellent 

14

Holiday townhouse in Kissimmee

Kissimmee / Bellavida Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Fantastic holiday home. Would definatley use again.” What a great holiday. Just home and couldn't wait to review this property. The resort itself is very modern and clean, with a good main pool. It has free internet access within the club house or fre  …see more

Pricing unknown

Enquire View

Pricing unknown

25

Holiday villa in Windsor Palms

Kissimmee / Windsor Palms

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Child friendly
  • Air conditioning
Not all rental villas offer the same degree of comfort and exclusivity, even on the fantastic Windsor Palms Resort.<br />Spacious fully-equipped luxury accommodation.  …see more

from £169 / night

£1185 / week

Book View

from £169 / night

(1) Very Good 

22

Holiday home in Kissimmee

Central Florida / Kissimmee

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Please note we only allow maximum 8 guests to ensure our villa is kept in top condition. A stunning, larger than average, 6 Bed 3.5 Bathroom villa with a fantastic private pool. This villa is located in the 5 stars resort of Lake Berkley. The villa is furnished and main  …see more

from £132 / night

£898 - £1005 / week

Book View

from £132 / night

(6) Excellent 

16

Holiday villa with swimming pool in Kissimmee

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Soon You'll Be Staying at a Individually Designed Luxury 4 Bed villa with all of the home comforts you expect.Our Disney area villa comes with its very own private swimming pool where you can escape all the thrills and spills down the road and have some family time  …see more

from £82 / night

£558 - £1062 / week

Book View

from £82 / 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 £155 / night

£1085 - £1680 / week

Book View

from £155 / night

(21) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Windsor Palms

6 13 5 nights min

  • 6 bedrooms
  • Sleeps 13
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Immaculate - delivers above and beyond ..” An immaculate villa, perfectly presented and equipped with everything you could need. Choosing a villa always comes with a little bit of interpretation but Sundown Palm delivered above and beyond the descrip  …see more

from £190 / night

£1330 / week

Book View

from £190 / 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
Come and stay in our lovely Florida holiday home located right on Disney's doorstep. It's located in the stunning Emerald Island resort, a prestigious gated community. It's beautifully decorated, with enough space to comfortably sleep 6 people.  …see more

from £60 / night

£450 / week

Book View

from £60 / night

42

Holiday home with golf nearby in Kissimmee

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Magical Home in the Perfect Location You'll LOVE! Serendipity at Indian Creek offers you all those extra finishing touches that turn an ordinary home into your very own piece of vacation paradise. ** Totally Private Pool & Hot Tub ** Outdoor Poolside Living S  …see more

from £324 / night

£2066 - £2927 / week

Book View

from £324 / night

22

Holiday condo with shared pool in Kissimmee

Central Florida / Kissimmee

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
GREAT VACATION CONDO VILLA 2 BEDROOM WITH 2 ENSUITE BATH IN ORLANDO FLORIDA. THIS UNIT IS APPROX 10 MINS FROM DISNEY WORLD. THIS UNIT HAS A LOCK OUT WHICH CAN BE CONVERTED INTO TWO SEPARATE SUITES. SUITE IS FULLY FURNISHED WITH LINENS COOKING UTENSILS AND CUTLERY. FR  …see more

from £141 / night

£984 / week

Book View

from £141 / night

(31) 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
“Really comfortable and relaxing stay, a quality holiday home.” We stayed here over Christmas and New Year. There were 8 family members - ample room for all and we still had a spare bedroom. The pool area was lovely and the villa location was great.  …see more

from £100 / night

£695 - £895 / week

Enquire View

from £100 / night

24

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee / Windsor Palms

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Massive pool deck for relaxing, south facing with sun all day. Great look out over a conservation area and not over looked.Super comfort furniture. Formal and informal dining areas plus breakfast bar.2 x King sized en suite bedrooms. 1 x Queen and 2 x twin rooms.<br  …see more

from £166 / night

£1160 / week

Book View

from £166 / night

20

Cumbrian Lakes holiday villa rental

Kissimmee / Cumbrian Lakes

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
Quiet Relaxing getaway but close enough to Disney and Theme Parks when you want to go  …see more

from £90 / night

£630 - £665 / week

Book View

from £90 / night

(24) Excellent 

20

Holiday villa with golf nearby in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 13 3 nights min

  • 6 bedrooms
  • Sleeps 13
  • 3 nights min
  • 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 £164 / night

£1148 / week

Book View

from £164 / night

(1)  

14

Remington holiday villa rental

Kissimmee / Remington

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
A luxury villa with its own extended pool, spa and games room, that adjoins the prestigious Remington Golf Club. Minutes from the Florida Turnpike & Highway 192 that takes you to Disney and Parks.  …see more

from £99 / night

£689 / week

Book View

from £99 / night

(1) Excellent 

31

Central Florida / Kissimmee

4 13 Min stay varies

  • 4 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £120 / night

£838 / week

Book View

from £120 / night

(54) Excellent 

23

Holiday villa in Crescent Lakes

Kissimmee / Crescent Lakes

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Beyond our expectations” This was our first villa rental in USA. It exceeded our expectations, a spacious modern villa well appointed, washer , tumble dryer, TV in all rooms, dishwasher, games room with full size pool table, air hockey etc, and a love  …see more

from £90 / night

£575 - £690 / week

Enquire View

from £90 / night

58

Kissimmee holiday home rental

Central Florida / Kissimmee

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Calla Lily is a fabulous Lake front 5 bedroom 3 bathroom pool home in Crescent Lakes in Kissimmee, a fantastic, superbly well cared for community that is situated in a natural conservation area yet it is still close to all that the Orlando/Disney area has to offer to e  …see more

from £189 / night

£1320 / week

Book View

from £189 / night

(1) Excellent 

40

Central Florida / Kissimmee

6 14 Min stay varies

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

 …see more

from £205 / night

£1353 - £1681 / week

Book View

from £205 / night

(3) Average 

15

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our villa offers large open plan Floridean accommodation. Light and breezy with high vaulted ceilings you can get a real sense of space to relax in. With a luxurious American sized en-suite master bedroom, as well as two further good sized rooms, our villa offers real c  …see more

from £65 / night

£450 / week

Book View

from £65 / night

(2) Very Good 

18

Holiday villa with golf nearby in Kissimmee

Central Florida / Kissimmee

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
“Nice Villa, Good Amenities, Very helpful owner.” We booked the above villa on the basis of previous reviews and the fact the owner, Mark, called us and spoke to us in person, answering any questions or emails with speed and efficiency. Mark is very h  …see more

from £79 / night

£550 - £750 / week

Book View

from £79 / night

(3) Excellent 

17

Holiday home with golf nearby in Kissimmee

Kissimmee / Terra Verde Resort

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 30 km
  • Swimming pool
“Golf vacation in beautiful surroundings” Terre Verde Resort is a beautiful resort with a luxurious club house with all amenities, pool, pool-bar, fitness center surrounding i relatively large pond. Nice playground. Short distance (15 min) to Disney a  …see more

from £70 / night

£490 / week

Book View

from £70 / night

(5) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Lindfields

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Home from Home. Great Location. Perfect.” The Villa was everything we dreamed of for our first family holiday in Florida. First impressions were just as we expected, Directions to villa were spot on. Swimming pool was fab with inflatables included. Ho  …see more

from £95 / night

£665 / week

Book View

from £95 / night

33

Holiday apartment in Kissimmee

Central Florida / Kissimmee

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
This condo is situated on Legacy Dunes resort at Kissimmee. Resort amenities include a tropical style swimming pool with fountains, a further swimming pool (both with sun loungers), a clubhouse with games room, a cafe, a bar, a gym and fitness center, tennis courts, bas  …see more

from £63 / night

£417 / week

Book View

from £63 / night

11

Central Florida / Kissimmee

1 4 7 nights min

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

 …see more

from £136 / night

£952 / week

Book View

from £136 / night

26

Kissimmee holiday home rental

Central Florida / Kissimmee

3 6 6 nights min

  • 3 bedrooms
  • Sleeps 6
  • 6 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Our townhouse is situated on one of Orlando's most beautiful gated resort communities, Terra Verde Resort & Spa. Currently rated as one of the top 5 resorts in Kissimmee by Trip Advisor The resort is 30 minutes from Orlando International Airport, 15 minutes fro  …see more

from £70 / night

£490 / week

Book View

from £70 / night

(2) Excellent 

27

Holiday villa in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
“Great rental experience” As the title of the listing states, this villa was only 5 minutes to Disney. We found the description and the pictures to be quite accurate too. The community is well maintained and it is gated which made us feel secure. Also  …see more

from £188 / night

£1917 / week

Book View

from £188 / 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 £106 / night

£755 / week

Book View

from £106 / night

37

Central Florida / Kissimmee

6 14 3 nights min

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

 …see more

from £163 / night

£1137 / week

Book View

from £163 / night

17

Kissimmee holiday home rental

Central Florida / Kissimmee

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Very nice 4 Bed home with 2 Baths, located at Windsor Palms Resort, close to 192 and to many restaurants and markets. a few minutes from Disney Parks, only 3 miles away. 15 minutes away from Universal Studios and 20 min away from Outlet Premium. Excellent clubhouse with  …see more

from £109 / night

£758 / week

Book View

from £109 / night

11

Home accommodation in Kissimmee with indoor pool

Central Florida / Kissimmee

2 3 2 nights min

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Very nice 2 Bed home with 2,5 Baths, located at Encantada Resort, close to 192 and to many restaurants and markets. a few minutes from Disney Parks, only 3 miles away. 15 minutes away from Universal Studios and 20 min away from Outlet Premium. Excellent clubhouse with f  …see more

from £82 / night

£574 / week

Book View

from £82 / night

30

Central Florida / Kissimmee

3 8 2 nights min

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

 …see more

from £91 / night

£632 / week

Book View

from £91 / night

(21) Excellent 

21

Villa rental in Sunset Lakes

Kissimmee / Sunset Lakes

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 104 km
  • Swimming pool
“Excellent house and location” Fantastic house with excellent views over the lake Great location with a massive choice of eating out options close by  …see more

from £100 / night

£700 - £840 / week

Book View

from £100 / night

31

Central Florida / Kissimmee

4 8 2 nights min

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

 …see more

from £109 / night

£758 / week

Book View

from £109 / night

20

Holiday villa in Kissimmee

Central Florida / Kissimmee

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
his vacation home was renovated recently. We put lots of efforts to keep our house at the top of the line. We sincerely welcome all of our guests and feel honor to have your unforgettable memories in our house. It has 3 King Bedrooms, 2 Queen bedrooms, 6 Twin Beds in 3  …see more

from £188 / night

£1065 - £2213 / week

Book View

from £188 / night

22

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
COMPASS BAY(TripHouse10) offers the best options for you that are looking for comfort, safety, comfort and pleasure on your Orlando, Florida vacation. Here you can select the best accommodation for your stay, always focusing on your well-being and your family. In additi  …see more

from £60 / night

£594 - £2572 / week

Book View

from £60 / night

37

Holiday home with swimming pool in Kissimmee

Central Florida / Kissimmee

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated on the beautiful gated Lake Berkley Resort, our luxury 4 bed villa has a west facing pool deck overlooking a tranquil lake, ideal for relaxing after a days out in the theme parks or one of the many shopping malls. Sleeping 8 people in comfort with 4 bedrooms: 1  …see more

from £85 / night

£595 / week

Book View

from £85 / night

(58) Excellent 

20

Holiday villa with golf nearby in Kissimmee

Kissimmee / Formosa Gardens

7 22 4 nights min

  • 7 bedrooms
  • Sleeps 22
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“This place is heaven!!” Close to all the attractions yet private enough to give you relaxation!!! Can't wait to book here again!! The owners were very easy to work with and very patient with us!!! Thanks again for renting to us!!!  …see more

from £325 / night

£2275 / week

Enquire View

from £325 / night