Kissimmee Villas, Holiday rentals and apartments

Close

View larger map

Also consider

North America Holidays
178701 properties
United States Holidays
129085 properties
Florida Holidays
36466 properties
Central Florida Holidays
13599 properties
Emerald Isle Kissimmee
54 properties
Kissimmee City
31 properties
Villas Windsor Hills Resort
31 properties
Lake Berkley
24 properties
Villas Paradise Palms
23 properties
Cumbrian Lakes
21 properties
Villas Windsor Palms
21 properties
Lindfields
18 properties
Terra Verde Resort
16 properties
Bellavida Resort
16 properties
Villas Indian Creek
13 properties
Crescent Lakes
12 properties
Compass Bay
10 properties
Venetian Bay Villages
10 properties
Doral Woods
9 properties
Sunset Lakes
9 properties
Regal Oaks
8 properties
Encantada Resort
8 properties
Trafalgar Village
8 properties
Villas Formosa Gardens
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

4,226 Holiday homes

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

(1) Excellent 

84

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
Skc 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. The luxury Skc VillaNow with  …see more

from £111 / night

£772 - £1120 / week

Book View

from £111 / 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 £87 / night

£626 / week

Book View

from £87 / night

(6) Very Good 

17

Holiday villa in USA East Coast

Central Florida / Kissimmee

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 106 km
  • Swimming pool
  • Child friendly
“Lovely Villa, well placed” Villa was clean & spacious. Pool was lovely & clean with nice garden view. Mostly quiet neighbourhood. Very close to 192 with all the restaurants & shopping. Ian was easy to contact & kept in touch throughout the stay. Pool  …see more

from £65 / night

£450 / week

Book View

from £65 / night

15

Home rental in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Free WI-FI -3 Miles from Disney Private screened swimming pool - Free phone calls within the US, Canada and Puerto Rico - Tastefully furnished - Beautiful 4 bed /3 full bath - Cable TV - Fully appointed kitchenAll linen and towels - DVD player - Child alarmed - Culture  …see more

from £99 / night

£689 / week

Book View

from £99 / night

(5) Excellent 

43

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee / Winward Cay

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic villa and excellent location..” When visiting this fabulous villa I was very impressed with the layout and the pool area, much larger than expected. there was lots of additional equipment in the kitchen area. On arrival we were greeted with  …see more

from £66 / night

£460 - £640 / week

Book View

from £66 / night

16

Central Florida / Kissimmee

4 8 2 nights min

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

 …see more

from £99 / night

£689 / week

Book View

from £99 / night

31

Central Florida / Kissimmee

7 14 2 nights min

  • 7 bedrooms
  • Sleeps 14
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £174 / night

£1213 / week

Book View

from £174 / night

(1) Excellent 

38

Holiday apartment in Kissimmee

Kissimmee / Windsor Palms

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Minutes from Disney World Free Wi-fi Economic rental Resort Amenities Full Equiped Kichen  …see more

from £48 / night

£430 - £612 / week

Book View

from £48 / night

(14) Excellent 

25

Kissimmee holiday home rental

Kissimmee / Windsor Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic Villa, Perfect Location for Disney etc., Food & Shopping” It was a very straightforward process booking 'Mickey's Clubhouse', questions were answered very promptly by the owners - the whole process was quick, efficient and informative.The vi  …see more

from £108 / night

£750 - £850 / week

Enquire View

from £108 / 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

Book View

from £60 / night

34

Holiday home in Kissimmee

Central Florida / Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
Free WIFI 10 minutes from Disney Fully Equipped Home Private Enclosed Pool  …see more

from £79 / night

£552 / week

Book View

from £79 / night

27

Holiday townhouse in Kissimmee

Kissimmee / Kissimmee City

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
This townhome with 3 bedrooms and 2/5 bathrooms, is located in the attractive gated community, Compass Bay, only few min. from Disney. Nearby are also restaurants, shopping outlets, golf courses and a Walmart-store. The house is elegantly furnished, with all the kitchen  …see more

from £63 / night

£441 / week

Book View

from £63 / night

(1) Excellent 

17

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
You will feel it the moment you pass the entry gates to this beautiful new community. A sense of peace and harmony with nature. Pleasing street-scapes are lined with ancient oak trees, giving shade as well as a taste of Florida's natural beauty. Sparkling lakes pro  …see more

from £108 / night

£750 / week

Enquire View

from £108 / 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

Book View

from £70 / night

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
Spacious villa with private pool (Optional heating if required). 3 bedrooms plus queen sofa bed in the lounge means 8 people can sleep comfortably. Covered lanai area for relaxing and dining by the pool. Games room with pool, ping-pong and electronic darts. Situated in  …see more

from £50 / night

£350 - £500 / week

Book View

from £50 / night

24

Townhouse rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Why stay anwhere else when you can get all this within 5 minutes (3 miles) of Disney World Orlando Florida?  …see more

from £87 / night

£552 / week

Book View

from £87 / 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 £101 / night

£706 - £926 / week

Book View

from £101 / night

(2) Very Good 

59

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

 …see more

from £79 / night

£552 / week

Book View

from £79 / night

85

Holiday villa with swimming pool in Kissimmee

Kissimmee / Sunset Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
5 Bedroom south facing lakeside pool villa in Sunset Lakes just a stones throw from Walt Disney World. Very private pool area yet with beautiful lake and sunset views.  …see more

from £95 / night

£665 - £995 / week

Book View

from £95 / night

(2) Excellent 

24

USA East Coast holiday home rental

Kissimmee / Lindfields

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our villa is magnificent, fully furnished and equipped to the highest standards with air conditioning and ceiling fans. It has a master bedroom with an en-suite, 3 further double bedrooms and a main bathroom, towels and bed linen are provided. It has a spacious  …see more

from £61 / night

£425 - £500 / week

Enquire View

from £61 / 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

Book View

from £172 / night

(3) Excellent 

24

Holiday home in USA East Coast

Kissimmee / Crescent Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Large Deck and Lanaii ,private pool not overlooked .Tiled floors all rooms except Family room  …see more

from £93 / night

£760 - £900 / week

Book View

from £93 / night

(12) Excellent 

44

Holiday villa rental

Kissimmee / Indian Ridge Oaks

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Quick Getaway” We had an unexpected trip to Orlando after booking some cheap flights, we found Tracey's villa and she couldn't have been more helpful. We loved the villa, all the disney touches, even dresses for little princesses and the games in the  …see more

from £70 / night

£490 - £747 / week

Book View

from £70 / night

(1) Very Good 

20

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 105 km
  • Swimming pool
“Clean & Comfortable Family Friendly Villa” We thoroughly enjoyed our stay at this villa and found it to be well equipped and in a great position. It was easy to travel to any of the main attractions and has tons of shops and restaurants on its doorste  …see more

from £111 / night

£772 / week

Book View

from £111 / night

(6) Excellent 

73

Central Florida / Kissimmee

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £79 / night

£552 / week

Book View

from £79 / 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

Book View

from £66 / 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 £237 / night

£1024 - £2078 / week

Book View

from £237 / 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 £91 / night

£540 - £812 / week

Book View

from £91 / 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

Book View

from £135 / night

(3) Average 

48

Kissimmee holiday villa rental

Kissimmee / Indian Creek

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“The perfect florida villa” This was our second visit to Florida pearl and yet again it didnt disappoint! It was lovely to be back! Florida pearl is in a fantastic location for visiting all the disney theme parks,just a 5 min drive away. Also close by  …see more

from £90 / night

£630 / week

Book View

from £90 / 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 £79 / night

£910 / week

Book View

from £79 / night

(1) Excellent 

57

Home rental in Kissimmee

Kissimmee / Oak Island Harbor

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This luxury 4 bedroom and 3 bathroom villa is located in the established community of Oak Island Cove. This location is probably one of the closest to Disney World's' main gate and within walking distance ( 5 mins) to shopping and the many great restaurants si  …see more

from £205 / night

£1434 / week

Book View

from £205 / night

17

Holiday villa with shared pool, golf nearby in Kissimmee

Kissimmee / Orange Lake Resort

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
Family Fun in the Heart of Orlando, Florida. Shop, dine, play, golf—we've got everything you need for the vacation of a lifetime. And right next door to Walt Disney World® Resort and Animal Kingdom! Luxuriously decorated villas for your comfort.Superb base for Walt  …see more

from £171 / night

£950 - £1000 / week

Book View

from £171 / night

(1) Excellent 

64

Holiday villa in USA East Coast

Kissimmee / Lindfields

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
One of the closest villas to Disney - 5.7 miles to Walt Disney World's Main Gate!Sunny south west facing poolOptional pool heating - recommended October to AprilPool and patio lightingCovered lanaiPrivate fenced gardenFree use of computer with high speed internet  …see more

from £92 / night

£644 / week

Book View

from £92 / night

20

Holiday villa with golf nearby in USA East Coast

Kissimmee / Lake Berkley

5 12 5 nights min

  • 5 bedrooms
  • Sleeps 12
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Five large bedrooms which can sleep 12 persons comfortably. Some with an en-suite bathroom. Lovely peaceful, quiet 'home from home'.Short drive to Disney World attractions and Shopping Mall and Supermarket.BBQ on request.  …see more

from £110 / night

£770 - £980 / week

Enquire View

from £110 / night

(1) Excellent 

55

Kissimmee holiday villa rental

Kissimmee / Lake Berkley

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Loved it so much” Just spent 2 weeks in this villa, loved it so much! Many happy memories of a great holiday, we are definitely looking into coming again. Slept 6 more then comfortably and the pool is in a great position, gets a few hours sunlight bu  …see more

from £90 / night

£550 - £785 / week

Book View

from £90 / night

43

USA East Coast holiday villa rental

Central Florida / Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Child friendly
Welcome to our Luxury Home from Home set within the beautiful gated community resort of ‘Windsor at Westside’. Our vacation home sits on a large site which is not overlooked in this brand new resort that has quickly become one of the most desired locations in the  …see more

from £220 / night

£1500 - £1600 / week

Book View

from £220 / night

8

Holiday home in Kissimmee

Kissimmee / Lake Marion

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Self-catering condo with communal pool and free WiFi in the property, along with a full set of cable channelsTotally Renovated 2 Bed Family Home With Pool & Free Wi-Fi  …see more

from £35 / night

£250 / week

Book View

from £35 / 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

Book View

from £169 / night

6

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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 - £750 / week

Book View

from £68 / night