Kissimmee Villas, Holiday rentals and apartments

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Kissimmee

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4,180 Holiday homes

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

(2) Average 

30

Holiday villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Family friendly, plenty of room, great location” We stayed here for our very first trip to Disney World with our three teenaged daughters and our young grade-school daughter. We loved the home; it had everything we needed, plenty of space. The three  …see more

from £85 / night

£550 - £660 / week

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from £85 / night

(6) Excellent 

18

Holiday villa in Kissimmee

Kissimmee / Lake Berkley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Excellent living in secure environment for family” Well equipped house for a family, from kitchen, over bedrooms and living area to pool, close to attractions, dining and shopping  …see more

from £100 / night

£695 - £750 / week

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from £100 / night

(2) Excellent 

15

USA East Coast holiday townhouse rental

Kissimmee / Terra Verde Resort

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Resortgated  …see more

from £70 / night

£490 - £665 / week

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from £70 / night

15

Kissimmee holiday townhouse rental

Kissimmee / Fiesta Key

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 123 km
  • Swimming pool
Quiet Location Electronic door locking system (no lost key issue) High Speed Internet Stainless appliance Modern furniture •Beach / lakeside relaxation •Swimming pool •Great for children of all ages •Air conditioning •No pets allowed  …see more

from £100 / night

£635 / week

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from £100 / night

12

Townhouse rental in Kissimmee

Kissimmee / Terra Verde Resort

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
quiet resortUse of all Resort facilities  …see more

from £65 / night

£455 - £840 / week

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from £65 / night

(1) Excellent 

33

USA East Coast holiday villa rental

Kissimmee / Lake Berkley

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“A great base for a family holiday” Having used other villas around Orlando I came across this one as our normal one was booked, I contacted the owner who could not of been more helpfull and booked up our stay. When we arrived at the villa it was a  …see more

from £139 / night

£973 / week

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from £139 / night

57

Central Florida / Kissimmee

6 16 Min stay varies

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

 …see more

from £198 / night

£1395 - £1828 / week

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from £198 / night

(6) Excellent 

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
“Great stay close to all attractions and shopping.” We really enjoyed our stay at Mandyville. The house was very clean. We lucked out on the weather for January and made great use of the pool area. The UV protection on the pool enclosure was great a  …see more

from £75 / night

£485 - £525 / week

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from £75 / night

(3) Very Good 

14

Kissimmee / Venetian Bay Villages

3 6 5 nights min

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

 …see more

from £56 / night

£386 / week

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from £56 / night

(2) Very Good 

100

Holiday villa in USA East Coast

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Secret Key Cove Villa Luxury Award Winning Vacation villa rental, in Orlando, FloridaSet in a Gated CommunityThis 2 story upgraded Villa has, 4 bedrooms, 3 bathrooms, air conditioning and is set in a private location with its own private pool and spa. Emerald Island R  …see more

from £112 / night

£778 - £1129 / week

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from £112 / night

(4) Very Good 

12

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Idyllic base for Orlando holiday” Just got back from this lovely villa where we spent a wonderful two weeks. The owners have made this feel just like home, with everything necessary for a comfortable stay. From the extended pool deck with comfy sunbed  …see more

from £88 / night

£631 / week

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from £88 / 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

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from £100 / night

(1) Very Good 

56

Holiday townhouse in USA East Coast

Kissimmee / Kissimmee City

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
“Great wee resort” Terra Verde was an immaculately kept resort. Seemed to be 20mins from most big attraction parks. This house was ideal for our family of four and could easily have accommodated 2 more. It was spotlessly clean and the couple of hiccups  …see more

from £75 / night

£525 - £630 / week

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from £75 / night

(21) Excellent 

43

Central Florida / Kissimmee

4 10 Min stay varies

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

 …see more

from £63 / night

£337 - £793 / week

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from £63 / night

(5) Excellent 

24

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 72 km
  • Swimming pool

 …see more

from £54 / night

£378 / week

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from £54 / night

(2) Very Good 

14

Villa rental in Kissimmee

Kissimmee / Bellavida Resort

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Set in the beautiful Bellavida Resort with own South West Facing Pool. Close to all attractions including Disney World, Universal Studios and Islands of Adventure. Dining and Shops are in abundance.  …see more

from £108 / night

£743 / week

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from £108 / night

(3) Excellent 

61

Kissimmee holiday villa rental

Kissimmee / Windsor Hills Resort

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 64 km
  • Swimming pool
“Luxury in the sun” Home from home - if home had all these mod cons and a heated pool outside the lounge and a games room in the garage. Great location for Disney assuming you have a car. Plenty of local restaurants and easy run to NASA. Onsite centr  …see more

from £115 / night

£690 - £1350 / week

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from £115 / night

19

Holiday apartment with shared pool in Kissimmee

Kissimmee / Windsor Palms

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This gorgeous Kissimmee 3 bedroom vacation rental home, is only 20 minutes drive from Orlando International airport, and is without a doubt, a home away from home. Comfortably sleeping 6 and fully equipped with towels, bedlinen, washer, dryer (highchair and travel cot a  …see more

from £63 / night

£439 / week

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from £63 / night

27

Home rental in USA East Coast

Central Florida / Kissimmee

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A stunning, larger than average, 4 Bed 3-end townhouse with a beautiful view of the conservation area at the rear as backdrop to our private pool. The house is split over two floors which makes it ideally beneficial for accommodating 2 families. The sitting room has  …see more

from £80 / night

£790 / week

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from £80 / night

25

Home rental in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 93 km
  • Swimming pool
  • Child friendly
Mickey's Ritz at Veranda Palms is a private vacation home providing spacious accommodation with luxury, upgraded contemporary furnishings. The home has 4 bedrooms, 3 bathrooms, a large pool + spa , a west facing pool deck with fabulous pool furniture, and a fully fitted  …see more

from £102 / night

£712 - £934 / week

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from £102 / night

(6) Excellent 

23

Central Florida / Kissimmee

3 8 3 nights min

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

 …see more

from £55 / night

£362 / week

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from £55 / night

17

Holiday townhouse with shared pool in Kissimmee

Central Florida / Kissimmee

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This 3 bedroom/3 bath townhome is located in the luxurious, gated community of Windsor Hills. You will be only 2.5 miles from the main gate of Walt Disney World. It is within walking distance to the clubhouse which includes a lagoon-style heated pool (with 2-story tall  …see more

from £95 / night

£662 / week

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from £95 / night

(1) Excellent 

20

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
You don't need a magic wand or a secret potion to have a dream holiday of a life time . . . . . . All you need is Magic Villa!!!And as Magic Villa is only 10 minutes' drive from Disney the location is magic too!  …see more

from £135 / night

£945 - £1204 / week

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from £135 / night

(3) Very Good 

16

Holiday home with swimming pool in USA East Coast

Kissimmee / Veranda Palms

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic villa and location” Stayed at this villa for two weeks and highly recommend it. It was clean, spacious and ideally located for Orlando airport and all the theme parks. Would definitely stay there again, the owner and management team were ver  …see more

from £143 / night

£786 - £866 / week

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from £143 / night

25

Holiday villa in USA East Coast

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.Spacious fully-equipped luxury accommodation.  …see more

from £169 / night

£1185 - £1635 / week

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from £169 / 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
Tinkerbells Short Version advert details Summary • South Facing oversized pool and Spa with 40’ deck overlooks lake and woodland • 7 Bed 5.5 bathrooms with 4 Master Suites 2 Kings 2 Queens 6 Singles Sofa Bed • Closest gated resort to Disney Thank you for visi  …see more

from £199 / night

£1389 - £2262 / week

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from £199 / night

(5) Excellent 

31

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee / Winward Cay

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Lovely villa in great location” Villa as described clean and modern. Pool heating made water a pleasure to swim in. Owner Marie very helpful and responsive via email. Whilst she is based in England has a friend who came around to help solve a few mino  …see more

from £66 / night

£460 - £630 / week

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from £66 / night

24

Holiday home in Kissimmee

Central Florida / Kissimmee

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A brand new house furnished to a high standard with a wall mounted TV in each room and 2 large TVs in the lounge and family room. There is a heated private pool and spa over looking a conservation area (heating at an extra cost). Entertainment in house includes table  …see more

from £172 / night

£1200 - £1800 / week

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from £172 / night

(6) Excellent 

75

Holiday villa rental

Kissimmee / Kissimmee City

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Luxurious, spaceous secluded villa” Excellent location to all amenities. Villa exceptionally equipped with luxurious facilities. Didn't want to leave !!  …see more

from £108 / night

£754 - £941 / week

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from £108 / night

8

USA East Coast holiday villa rental

Central Florida / Kissimmee

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Golf Courses Within a Short Drive  …see more

from £64 / night

£445 - £540 / week

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from £64 / night

46

Villa rental in Kissimmee with swimming pool

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
Turn your dreams into reality in our Luxury Holiday Villa just a short distance from the Orlando theme parks.This is Mickey's Retreat, our 3 Bedroom, 2 Bathroom Villa in Kissimmee, Florida. Mickey's Retreat is conveniently situated just a short ten min  …see more

from £92 / night

£544 - £818 / week

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from £92 / night

(3) Very Good 

12

Holiday home rental

Kissimmee / Emerald Isle Kissimmee

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Crystal Cove Gem is located in the fabulous Emerald Island Resort the nearest gated community to from Disney World.Only 3 miles from Disney World  …see more

from £50 / night

£700 / week

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from £50 / night

(1) Excellent 

22

Villa rental in Kissimmee with swimming pool

Kissimmee / Cumbrian Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
This home has a breath taking view from the pool deck. It overlooks a pretty lake and you may be lucky enough to see deer grazing on the conservation area which lies beyond it. The deck area has been extended so there is also a Hot Tub for you to enjoy. The home itself  …see more

from £99 / night

£693 - £910 / week

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from £99 / night

(21) Excellent 

27

Holiday villa with golf nearby in Kissimmee

Kissimmee / Windsor Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“A magical Christmas vacation” A very clean and comfortable villa, with a beautifully heated pool. The games room was good fun and the owner was very helpful and easy to deal with. Windsor Palms is a good location with easy access to Disney - for a s  …see more

from £116 / night

£786 - £1190 / week

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from £116 / night

(23) Very Good 

75

Central Florida / Kissimmee

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 61 km
  • Swimming pool
  • Child friendly

 …see more

from £54 / night

£715 / week

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from £54 / night

(11) Excellent 

31

Kissimmee / Paradise Palms

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £80 / night

£917 / week

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from £80 / night

(1) Excellent 

20

Holiday villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Disney, Spacious, Safe, Gated, Guarded, Luxury, Heated Pool, Spa, Game room, Kitchen, Free WIFI, Free phone Call, Clubhouse, Gym, Sauna 8 Bedroom, Dinning Room, Children's room, private pool and Spa, Xbox 360, Emerald Island, Close to everywhereEmerald Island Resor  …see more

from £239 / night

£1032 - £2095 / week

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from £239 / night

28

Kissimmee holiday home rental

Central Florida / Kissimmee

6 12 2 nights min

  • 6 bedrooms
  • Sleeps 12
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Very nice 6 Bed home with 6 Baths, located at Veranda Palms Resort, close to 192 and to many restaurants and markets. a 10 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 £175 / night

£1223 / week

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from £175 / night

35

Holiday villa in Kissimmee

Central Florida / Kissimmee

7 16 3 nights min

  • 7 bedrooms
  • Sleeps 16
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Mickey's Family Funhouse has 7 bedrooms, 5 bathrooms, this villa is the perfect place to sip your morning coffee or enjoy breakfast. Lay back in the private screened in pool area on one of many cushioned loungers.Great Location:Disney Funhouse 's vaca  …see more

from £207 / night

£1445 / week

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from £207 / night

28

USA East Coast holiday condo rental

Kissimmee / Legacy Dunes Resort

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 150 km
  • Swimming pool
Newly refurbished 4 bedroom/2 bathroom 1400 sq ft condo with screened balcony and view over the lawn to the children's playground and lake. Fantastic place for a large family or group vacation in Orlando! near all the attractions. Would suit the extended family with 2 d  …see more

from £60 / night

£400 - £550 / week

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from £60 / night