50 Best Kissimmee Apartments on Holiday Lettings - Vacation rentals

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Kissimmee

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5,112 Vacation rentals

(3) Excellent 

91

Villa accommodation in Kissimmee

Kissimmee / Kissimmee City

5 10 6 nights min

  • 5 bedrooms
  • Sleeps 10
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful 5 bed villa in Kissimmee, Florida, the holiday destination of the world. Just 10 minutes from Disney in one of the most sought after communities in Orlando. Our villa is luxuriously furnished, with its own secluded pool & spa, a fabulous games room and minutes …see more

from $166 / night

$1156 / week

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from $166 / night

(22) Very Good 

17

Vacation villa in Seasons Resort

Kissimmee / Seasons Resort

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to our home on Seasons. It is a St Vincent model built by Park Square Homes and is 2765 Sq. Foot of Executive quality. It is a luxurious 5 Bedroom – 4 Bathroom Villa, which has 2 Master Suites and 3 other Bedrooms - which comfortably sleep 10 with ease, a Privat …see more

from $77 / night

$461 - $896 / week

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from $77 / night

(2) Excellent 

45

Kissimmee Vacation villa accommodation

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A home from home, the British owners spend as much time as possible in the villa themselves. The villa is situated on a large lot and the private south facing heated pool and jacuzzi back onto a wooded area. Pool heating for cooler months is available for an additional …see more

from $110 / night

$770 - $981 / week

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avg. 2 hours 11 minutes

from $110 / night

(24) Excellent 

24

Kissimmee Vacation villa rental

Kissimmee / Lake Berkley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our home is a luxury 4-bedroom, 3-bathroom home with its own private screened pool. The villa is located in Lake Berkley, a peaceful and gated subdivision situated approximately 10 min from the Walt Disney World entrance and is conveniently located for the other theme p …see more

from $90 / night

$621 - $730 / week

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from $90 / night

(59) Excellent 

60

Villa rental in Kissimmee

Kissimmee / Indian Ridge

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxury executive home located at the head of a quiet cul-de-sac on Indian Ridge, 10 mins from the Disney Main Gate. The spacious, air-conditioned accommodation (2000sqft) comprises 4 bedrooms (2 doubles, 2 twin "character" rooms), 2 bathrooms (1 en-suite), 2 lounges (o …see more

from $116 / night

$608 - $928 / week

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from $116 / night

(11) Excellent 

28

Vacation villa in Kissimmee

Kissimmee / Windsor Hills Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This fabulous 5 Bed/5 Bath Executive Villa with Games Room can easily accommodate 10 guests in absolute comfort. Fully air conditioned and with the added luxury of ceiling fans in all rooms the property offers total privacy and space to relax and enjoy your holiday of a …see more

from $167 / night

$1165 - $1536 / week

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avg. 3 hours 25 minutes

from $167 / night

(3) Excellent 

28

Vacation villa in Seasons Resort

Kissimmee / Seasons Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This Kissimmee home offers plenty for all the family – from the jungle-themed kids' TV and entertainment space to the wonderful, sparkling pool overlooking the attractive lake. Plus, it has a good location for access to all of Orlando's amusement parks & attractions. It …see more

from $195 / night

$1295 - $2095 / week

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from $195 / night

(8) Very Good 

40

Vacation home in Kissimmee

Central Florida / Kissimmee

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Ready to have your dream Florida vacation? You're gonna need a dream house! This vacation villa has 4 bedrooms, 3 bathrooms, and is totally teeming with luxury! Get ready to dive into the exclusive community of Hamilton's Reserve, which offers extreme privacy and …see more

from $130 / night

$901 / week

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from $130 / night

(4) Excellent 

24

Vacation 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
This Italian style one storey villa completed in 2008 has 3 bedrooms a family bathroom and shower room. It is located on the sought after Tuscany development and is perfect for a family holiday to Orlando where you can enjoy the wonderful climate and year round sunshin …see more

from $69 / night

$483 - $623 / week

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from $69 / night

(11) Very Good 

25

Vacation villa in Kissimmee

Kissimmee / Crescent Lakes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This vacation home is set in the tranquil and beautiful conservation area of Crescent Lakes. Guests will find a peaceful retreat from the busy theme parks & shopping malls. This spacious home has a fabulous South-facing private pool & children's splash pool. The pool …see more

from $110 / night

$650 - $795 / week

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from $110 / night

(47) Excellent 

91

Vacation villa in Westside

Kissimmee / Westside

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 96 mi
  • Swimming pool
  • Child friendly
La Bella Vita is our newly refurbished Italian-style villa featuring 4 luxury bedrooms and 3.5 bathrooms in the highly desirable Westside community of Calabria and West Tuscany. A perfect location for your family vacation to Disney. It is situated in Kissimmee and jus …see more

from $135 / night

$930 - $1150 / week

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Responds fast!
avg. 1 hour 27 minutes

from $135 / night

(14) Excellent 

Certificate of Excellence

24

Vacation villa in Doral Woods

Kissimmee / Doral Woods

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
Palm Tree Villa Florida, is tucked away in the much sought after location of Doral Woods. This large 4 Bedroom, 3 Bathroom villa, is ideal for making the perfect vacation. This is our own holiday home, so the furnishings are to a high standard, as you can see from the …see more

Certificate of Excellence

from $127 / night

$883 - $1112 / week

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Responds fast!
avg. 1 hour 57 minutes

from $127 / night

(2) Excellent 

34

Kissimmee Vacation villa rental

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Villa Betty Boo is on the prestigious Hampton Lakes Community which has a swimming pool, basketball, volleyball and tennis courts for your free use. Hampton Lakes is beautifully landscaped and is a very secure community. Villa Betty Boo has 4 spacious bedrooms and can s …see more

from $100 / night

$700 - $870 / week

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from $100 / night

(18) Excellent 

23

Kissimmee Vacation villa rental

Kissimmee / Bellavida Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Brand new Luxury 6 bedroom with 51/2 bath, fully air-conditioned. It is complete with heated pool and spa on an extended screened- deck area with speaker system, and looks directly onto the lake.With a 'state-of -the -art' alarm system giving you complete peace of min …see more

from $191 / night

$1338 - $1914 / week

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avg. 3 hours 42 minutes

from $191 / night

(9) Excellent 

36

Vacation home rental

Kissimmee / Crescent Lakes

5 13 3 nights min

  • 5 bedrooms
  • Sleeps 13
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Well maintained fully furnished 5 bed 3.5 bath home with 25x15 heated private pool and spa. Private garden overlooking lake. Covered lanai with south facing sundeck and pool furniture. The fabulous sun drenched pool deck and shimmering waters of our private pool offer a …see more

from $102 / night

$604 - $947 / week

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from $102 / night

(31) Very Good 

18

Kissimmee Vacation townhouse rental

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 55 mi
  • Swimming pool
Enjoy the comforts of our 3 bedroom, 2 bathroom town home which will sleep 6. The home was newly built in Jan 2004 and is located on a gated community in Kissimmee (just off the US192) 15 mins from Disney. Wi-Fi internet access provided in the home. On site f …see more

from $59 / night

$413 - $493 / week

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from $59 / night

(19) Excellent 

28

Villa rental in Kissimmee

Kissimmee / Doral Woods

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
********** AMAZING CASTLE IN THE SUN ************* IDYLLIC PLACE TO RELAX AFTER ALL THE FUN OF THE DISNEY MAGIC *** LUXURY VILLA WITH A COMPLETELY PRIVATE SOUTH FACING POOL * 3 Beds, 2 Baths, 2 Lounges.* CABLE TV's, VCR/DVD* GAMES consoles in bedrooms* GAMES ROOM* FULLY …see more

from $82 / night

$570 - $672 / week

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avg. 38 minutes

from $82 / night

(19) Excellent 

24

Vacation villa rental

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 60 mi
  • Swimming pool
Disney Lakeside Villa, fully A/C, plus fans, furnished to a luxury standard, is situated in the beautiful community of Eagle Point. Boasting a south-facing 30ft private pool with stunning views overlooking lake and conservation area where much wildlife can be observed. …see more

from $90 / night

$589 - $768 / week

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avg. 3 hours 50 minutes

from $90 / night

(2) Excellent 

20

Villa rental in Cumbrian Lakes with swimming pool

Kissimmee / Cumbrian Lakes

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful 5 bed home is over 2 levels. The sparkling pool overlooks a lake with conservation beyond and is an idyllic setting for your Kissimmee stay. The bottom level has wooden flooring. Here you can relax on the bold striped sofa and watch the flat screen TV. Th …see more

from $135 / night

$941 - $1344 / week

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avg. 1 hour 30 minutes

from $135 / night

(10) Excellent 

22

Vacation home with shared pool in Kissimmee

Kissimmee / Trafalgar Village

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
The Trafalgar Village community is centred around the luxurious Trafalgar Village Center (or Clubhouse), a 2 minute stroll from the property with amenities that include a man made beach and lagoon, lakes (stocked for fishing), a pool and games arcade room, a 48 seat mov …see more

from $86 / night

$551 - $864 / week

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from $86 / night

(8) 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
THE VILLA with it,s fully screened, south facing 30x15ft swimming pool with underwater lighting for evening swimming and has free solar heating with electronic control and electric heating for the winter months. The large deck with sun or shade is equipped with new luxu …see more

from $96 / night

$616 / week

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Responds fast!
avg. 1 hour 39 minutes

from $96 / night

(2) Excellent 

15

Kissimmee Vacation villa accommodation

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 90 mi
  • Swimming pool
Just as the name suggests, Emerald Island Resort is truly a tropical oasis. Nestled within a protected wetland, a unique vacation destination. Emerald Island is located minutes from Walt Disney World and the myriad other resorts and activities that bring millions to Or …see more

from $186 / night

$1295 / week

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Responds fast!
avg. 2 hours 49 minutes

from $186 / night

(19) Excellent 

23

Kissimmee Vacation villa rental

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Doral Woods community is set within a Wildlife Conservation area. The location has a very private and unique semi rural setting in which peace and tranquility are the order of the day. Our recently refurbished Villa is built on an 1/4 acre landscaped plot, our swimmi …see more

from $127 / night

$890 - $1018 / week

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avg. 2 hours 24 minutes

from $127 / night

(22) Excellent 

24

Vacation townhouse rental

Kissimmee / Encantada Resort

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 50 mi
  • Swimming pool
  • Child friendly
THE HOUSE Interior designed 4 bedroomed house, sleeps 8, with (heated) private pool located in the beautiful 5 star Encantada resort. The resort itself is a "Hidden Gem" with the lake-facing property situated just a stone's throw away from the main clubhouse. The …see more

from $127 / night

$864 - $1207 / week

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Responds fast!
avg. 2 hours 57 minutes

from $127 / night

(13) Excellent 

18

Kissimmee Vacation villa rental

Kissimmee / Cumbrian Lakes

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our villa is south west facing, so when you have had a busy day at the theme parks you can relax with a bbq around the pool, with its covered lania & ceiling fan to watch the sun go down. We have a fully fitted Games room,with pool table, foosball, dart board,Xbox, Wi …see more

from $116 / night

$634 - $800 / week

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Responds fast!
avg. 3 hours 22 minutes

from $116 / night

(40) Excellent 

39

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
A stunning property in Kissimmee, Florida with all the home comforts to ensure a truly wonderful vacation. Within 8 minutes drive of Disney Main Gate. LUXURY, STYLE AND COMFORT. Country Creek Estates is a beautiful, well maintained community that offers peace and tranqu …see more

from $109 / night

$647 - $660 / week

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Responds fast!
avg. 45 minutes

from $109 / night

(22) Very Good 

26

Vacation 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
Luxury 3 bed 2 bath villa can sleep 8. Large 30ft fully heated secluded pool. Only 15 minutes from airport & theme parks & 1 hour from Kenedy space centre & cocoa beach. Also 1 hour from Bush Gardens & clearwater beach to the west coast. Surounded by beautiful golf cour …see more

from $68 / night

$477 - $921 / week

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avg. 3 hours 56 minutes

from $68 / night

(14) Excellent 

Certificate of Excellence

28

Doral Woods Vacation villa rental

Kissimmee / Doral Woods

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
- 4 Bedrooms, 2 Queen, 2 Twin. En-suite to Master. Flat screen TV in Master and Queen. - Private heated pool, not overlooked. Within mesh to keep those insects out. - 2 Bathrooms, shower cubicle in en-suite, shower over bath in family bathroom. - Sleeps 8 people. Addit …see more

Certificate of Excellence

from $84 / night

$589 - $615 / week

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Responds fast!
avg. 1 hour 31 minutes

from $84 / night

(24) Excellent 

Certificate of Excellence

59

Vacation townhouse with shared pool in Trafalgar Village

Kissimmee / Trafalgar Village

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
The home is a 3 Bed town home at the Trafalgar Village Resort which is located on Poinciana Boulevard just 10 minutes south of highway 192 and approx 15 – 20 minutes to Disney. The home has been furnished to a very good standard and has a King, and two Queen bedrooms …see more

Certificate of Excellence

from $58 / night

$461 - $1076 / week

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Responds fast!
avg. 2 hours 39 minutes

from $58 / night

(37) Very Good 

20

Vacation 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
Welcome to our very special lakeside villa. You'll love the feeling of light and space as you enter the vill,with over 3000sq ft of living space this feeling just goes on. The villa is beautifully furnished and presented with lots of luxurious extras that make our villa …see more

from $127 / night

$864 / week

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from $127 / night

(12) Very Good 

62

Coral Cay Vacation home rental

Kissimmee / Coral Cay

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 60 mi
  • Swimming pool
GREAT LOCATION , CLOSE TO ALL THE PARKS , BARS , SHOPS AND EATERIES .CORAL CAY RESORT OFFERS THE PEACE AND QUIET AFTER A BUSY ORLANDO HOLIDAY AT THE PARKS , RELAX BY THE POOL OR IN THE HOT TUB AT THE POOL DECK , WATCH A FILM IN THE CINEMA , PLAY POOL OR VOLLEYBALL IN T …see more

from $75 / night

$525 / week

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Responds fast!
avg. 3 hours 5 minutes

from $75 / night

(22) Excellent 

18

Vacation 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
A beautiful lakeside American Villa with a private pool with wonderful views of the lake, wildlife and woodland area. No back-to-back villas here!. Thousands of £'s spent recently on upgrading the villa with new facilities. The Villa is Located just off Poinciana …see more

from $87 / night

$604 / week

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from $87 / night

(31) Very Good 

23

Vacation condo with golf nearby in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 106 mi
  • Swimming pool
  • Child friendly
A perfect location for all that central Florida has to offer, for Mickey fans, serious shoppers, sun worshippers, delicious dining, space shuttle launches, big thrills and spills, airboat adventures, palm trees and pina-coladas! All in the fantastic Sunshine State! Win …see more

from $45 / night

$279 - $477 / week

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avg. 3 hours 29 minutes

from $45 / night

(9) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Oak Island Cove

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
Positioned on Oak Island Cove next to Formosa Gardens, this is one of the most exclusive vacation sub rental divisions in Central Florida. Every amenity is close at hand for a wonderful vacation. No other location boasts a 5 minute journey to Disney World, Orlando. The …see more

from $170 / night

$1184 - $1530 / week

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from $170 / night

(5) Very Good 

74

Vacation villa in Kissimmee

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our Home is a Modern single 4 home with plenty of space for upto 12 Guests, Its in a Quiet location yet very close to all major Shops like Walmart, Target, K Mart and several Shopping Malls also Restaurants and Fast Food outlets and all the areas Theme Parks. Ful …see more

from $157 / night

$1195 - $1395 / week

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avg. 3 hours 58 minutes

from $157 / night

(13) Excellent 

44

Vacation villa rental

Kissimmee / Indian Ridge Oaks

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
We welcome you to take a look at our villa close to all the magic, yet in a peaceful and tranquil setting. Indian Ridge Oaks - one of the closest communities to Disney / 4 miles to Disney Maingate - south facing pool ***** Luxury villa in a superb location …see more

from $108 / night

$753 - $999 / week

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from $108 / night

(48) Excellent 

21

Vacation villa in Kissimmee

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our villa is set in one acre of private fenced garden with a children's play area and 20 x 30 wood BBQ decking and 28 x 14 private heated pool with spa. Relax on the private sundeck we have plenty of comfy chairs . There is seating for 8 for dining around the pool an …see more

from $167 / night

$1146 - $1274 / week

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Responds fast!
avg. 2 hours 24 minutes

from $167 / night

(16) Excellent 

29

Kissimmee Vacation villa rental

Kissimmee / Seasons Resort

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 110 mi
  • Swimming pool
Wonderful, private vacation home just 10 minutes from Disney World. This property is a stylish vacation rental in the heart of Kissimmee, set on a quiet lakeside development just off the 192 highway. The fantastic games room & south-facing private pool with Jacuzzi mak …see more

from $125 / night

$845 - $1165 / week

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from $125 / night

23

Kissimmee Vacation villa rental

Kissimmee / Cumbrian Lakes

5 13 Min stay varies

  • 5 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This new executive villa features state of-the-art living ... 5 bedrooms, 3.5 bathrooms, swimming pool and spa. Cumbrian Lakes is set in a conservation area yet only 5 minutes from shops and restaurants and less than 15 minutes to Disney World. The execut …see more

from $134 / night

$996 - $1263 / week

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from $134 / night

(24) Very Good 

Certificate of Excellence

36

Vacation 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
Indian Point with gorgeous lake and conservation view from pool. Indian Point, Kissimmee is a beautiful residential community situated within a few minutes drive of the Highway 192, convenient for the Wal-Mart superstore, a large selection of restaurants, and close t …see more

Certificate of Excellence

from $96 / night

$672 - $736 / week

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Responds fast!
avg. 3 hours 47 minutes

from $96 / night

1