50 Best Kissimmee Apartments on Holiday Lettings - Vacation rentals

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Kissimmee

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4,435 Vacation rentals

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(20) Excellent 

56

Kissimmee Vacation villa rental

Kissimmee / Crescent Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Our Magnificently Luxurious Spacious 4 bedroom Modern Villa in Crescent Lakes Kissimmee Orlando. Our close to Disney home will make your Florida Vacation complete. There is lots of space to chill out and relax after a hard day at Disney or Universa  …see more

from $133 / night

$930 - $1116 / week

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from $133 / night

(28) Very Good 

24

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 $44 / night

$272 - $465 / week

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from $44 / night

(26) Very Good 

12

Villa rental in Lindfields with swimming pool

Kissimmee / Lindfields

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Sunrise Villa is a luxurious villa close to all major attractions in a quiet, private & gated community in the town of Kissimmee. Our rate is from £400 per week .We are only 25 minutes from the airport & a stones throw away from Walt Disney World Orlando.  …see more

from $76 / night

$527 - $744 / week

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from $76 / night

(6) Excellent 

26

Vacation 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
Set in a third of an acre with extensively landscaped gardens and mature palm trees, this spacious (4.000 sq. ft.) luxury home has been professionally furnished and decorated to the highest of standards and enjoys many upgraded facilities including tiling throughout the  …see more

from $284 / night

$1984 - $2480 / week

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from $284 / night

(12) Excellent 

23

Kissimmee Vacation villa rental

Kissimmee / Windsor Palms

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Windsor Palms is a fabulous resort style community and has all the facilities that you would expect from its 5 star status all completely free when you stay at Disney Paradise. It is one of the closest communities to Disney located along Formosa Gardens Boulevard just  …see more

from $114 / night

$794 - $868 / week

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from $114 / 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 $87 / night

$602 - $707 / week

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from $87 / night

(8) Excellent 

20

Vacation villa rental

Kissimmee / Emerald Isle Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
A luxurious 4 bedroom, 3 bathroom vacation villa features a large private south facing pool and spa with conservation view plus fully air conditioned rooms and tv's and dvd's in living room and all bedrooms. The home is on the superb Emerald Island Resort an  …see more

from $93 / night

$651 - $825 / week

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from $93 / night

(38) 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 $100 / night

$614 - $639 / week

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from $100 / night

(14) Excellent 

41

Vacation condo with golf nearby in Kissimmee

Kissimmee / Cane Island

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 65 mi
  • Swimming pool
This beautifully furnished 3 bedroom, 2 bathroom property in Cane Island Resort in Kissimmee benefits from a wonderful lakeside setting and is less than 4 miles from the main gates of Disney World. This resort really does benefit from the best of both worlds - far enoug  …see more

from $96 / night

$596 - $745 / week

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from $96 / night

(9) Excellent 

24

Kissimmee Vacation villa rental

Kissimmee / Doral Woods

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The exclusive woodland setting of Doral Woods is an excellent place for relaxation and yet is within convenient reach of all the action of Disney, Universal, Sea World and Legoland and the other attractions. Be at one with nature in our unspoilt landscape. You can enjoy  …see more

from $100 / night

$695 - $1154 / week

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from $100 / night

(12) Excellent 

51

Apartment rental in Kissimmee

Central Florida / Kissimmee

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a newly renovated 1500 SF unit with an open floor plan. Well appointed modern furnishings with ceramic and porcelain flooring throughout. This is ideal for allergy sufferers. The three bedrooms contain 1 King, 1 Queen and 2 twin beds, respectively. There are two  …see more

from $85 / night

$585 / week

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from $85 / night

(15) 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  …see more

from $136 / night

$895 - $1296 / week

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from $136 / night

(15) Very Good 

17

Vacation villa in Seasons Resort

Kissimmee / Seasons Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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  …see more

from $75 / night

$447 - $682 / week

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from $75 / night

(29) Excellent 

90

Villa rental in Kissimmee with swimming pool

Kissimmee / Eagle Pointe

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our beautiful villa is located just minutes away from the Disney theme parks and other attractions in Orlando, Florida. For the holiday of a lifetime, a vacation in our villa will provide you with spacious accommodation and your own private, south-facing swimming pool w  …see more

from $81 / night

$565 - $686 / week

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from $81 / night

(30) Excellent 

23

Vacation home with swimming pool in Oak Island Cove

Kissimmee / Oak Island Cove

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sun Quest Villa is located on the small and peaceful community of Oak Island Cove. The property is an exceptionally spacious and luxuriously decorated 5 bedroom 4 bathroom home with fully screened private pool and hot tub. Oak Island Cove is one of the closest and most  …see more

from $124 / night

$744 - $868 / week

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from $124 / night

(20) Very Good 

17

Vacation villa in Kissimmee City

Kissimmee / Kissimmee City

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
A 3 bedroomed villa which sleeps 6. Approximately 3 miles Disney. Own screened swimming pool with large decking area with gas barbecue with patio furniture and loungers. The villa inside is decorated with blinds and window pelmets. 3 TV's all with cable, VCR and  …see more

from $81 / night

$428 - $837 / week

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from $81 / night

(30) Excellent 

62

Vacation villa in Kissimmee

Kissimmee / Lindfields

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This villa has a fantastic large pool with jacuzzi hot tub backing on to a lovely lake and forest. The pool is not overlooked so you will not find excited children spoiling your peaceful evenings ! The location could not be better - just ten minutes to Disney - cl  …see more

from $100 / night

$651 - $837 / week

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from $100 / night

(8) 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 $164 / night

$1147 - $1482 / week

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from $164 / night

(15) Very Good 

18

Kissimmee Vacation villa rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our villa is furnished to the highest standard and has the WOW factor. The villa has recently been tiled from the Great Room to the Living Room and new carpets in all the bedrooms.From the large hallway it opens up to the large Great room with wall to wall mirrors g  …see more

from $81 / night

$558 - $620 / week

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from $81 / night

(20) Very Good 

68

Vacation villa in Kissimmee

Kissimmee / Lindfields

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxurious Detached Villa- 5 Bedrooms - 3 Baths - (Sleeps 12)Simply the best location! Just a ten-minute drive from the Disney Theme parks but set in the quiet haven of the prestigious Lindfields Estate. This luxury villa sleeps up to 12 people and is beautifully  …see more

from $124 / night

$558 - $670 / week

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from $124 / night

(7) 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 $162 / night

$1129 - $1488 / week

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from $162 / night

(11) Excellent 

24

Villa accommodation in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Our villa is situated just 10 minutes from Disney and all its attractions and 5 minutes to shops and restaurants.Private heated pool fully screened and safety fence.Open plan lounge and formal dining area Fully fitted kitchen making preparing meals and snack  …see more

from $87 / night

$596 - $738 / week

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from $87 / night

(16) Excellent 

27

Vacation villa with swimming pool in Kissimmee

Kissimmee / Indian Ridge

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
The villa is air conditioned, carpeted and ceramic floor tiled to a very high standard with a family room/dining area, front games room . There are ceiling fans in all rooms for your added comfort. The south facing pool is solar heated and totally enclosed in mesh scree  …see more

from $93 / night

$651 - $775 / week

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from $93 / night

(26) 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 $58 / night

$400 - $461 / week

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from $58 / night

(12) Excellent 

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

from $81 / night

$558 - $596 / week

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from $81 / night

(5) Excellent 

24

Vacation villa with golf nearby in Kissimmee

Kissimmee / Bellavida Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Visit our owner website at the bottom of the page to view our 360 degree walk-through video: This is a a beautiful Mediterranean style property which has been designed, built and decorated to be the amongst the best. With 6 bedrooms and 5 1/2 bathrooms this is the per  …see more

from $205 / night

$1433 - $1606 / week

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from $205 / night

(7) Very Good 

20

Vacation townhouse in Kissimmee

Kissimmee / Paradise Palms

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Paradise Palms is situated in one of the best area's in Kissimmee, only minutes from Disney, Universal Studios, Island of Adventure and sea world. With its terrific shopping malls and fantasic restaurants this is the place to stay.Only a Couple of minutes w  …see more

from $117 / night

$757 - $1166 / week

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from $117 / night

(20) Excellent 

24

Vacation townhouse rental

Kissimmee / Encantada Resort

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 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  …see more

from $118 / night

$794 - $1178 / week

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from $118 / night

(25) Excellent 

24

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
Welcome to our 4 bed single storey air conditioned home in Rolling Hills, Kissimee. It is just 10 mins (real time) to Disney Main Gate. It is situated on a part residential, part visitors estate, with lake views at the rear, in a quiet neighbourhood, close to Fo  …see more

from $93 / night

$651 - $744 / week

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from $93 / night

(29) Excellent 

20

Kissimmee Vacation villa accommodation

Central Florida / Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated in a quiet, well established residential area (Indian Point) our 5 bedroom villa easily accommodates 2 large families. There are 2 large master bedrooms with ensuites, 3 more bedrooms and a further bathroom. Outside space comprises a large private heated swimm  …see more

from $125 / night

$851 - $920 / week

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from $125 / night

(2) 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 min  …see more

from $124 / night

$837 / week

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from $124 / night

(5) Excellent 

28

Vacation home rental

Kissimmee / Emerald Isle Kissimmee

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 50 mi
  • Swimming pool
This home has it all !! *Newly Installed Granite kitchen worktops* Our 3,400sqft beautifully decorated Villa is a Luxurious 5 star, 7 bedroom, 5 Bath home, a Private Screened-in South Facing Pool and Jacuzzi with a beautiful view over a lake and preserve, (no homes beh  …see more

from $200 / night

$1394 / week

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from $200 / night

(5) Very Good 

45

Vacation villa rental

Central Florida / Kissimmee

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
Whether you wish to hit the Theme Parks, go shopping at the Florida Mall or along International Drive, play some fantastic golf, or simply relax by the pool, this home is exactly what you are looking for. It is fully licensed and professionally managed through a conveni  …see more

from $100 / night

$694 - $837 / week

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from $100 / night

(24) Excellent 

23

Vacation condo in Kissimmee

Kissimmee / Cane Island

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Cane Island is a luxurious gated resort featuring impressive amenities. Our Condo is located on the ground floor, it is a 2 bedroomed condo that is perfectly accessible for both wheelchairs and pushchairs, everything is on a level so there are no steps or ramps.  …see more

from $81 / night

$565 / week

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from $81 / night

(20) Very Good 

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

from $87 / night

$558 - $713 / week

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from $87 / night

(3) Very Good 

28

Vacation villa with shared pool in Kissimmee

Central Florida / Kissimmee

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This fabulous villa gives our guests a real home from home experience. It is furnished for relaxation with comfy furniture, carpeted floors & it's own private pool that can be heated. Overview of Villa • Private Pool with Lanai • Recently Refurbish  …see more

from $116 / night

$775 - $946 / week

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from $116 / night

(17) 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 pe  …see more

from $185 / night

$1296 - $1854 / week

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from $185 / night

(11) Excellent 

24

Calabria, Orlando Vacation villa rental

Kissimmee / Calabria, Orlando

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
My Disney Villa a new villa within the exclusive Calabria community. The 5 bedrooms and 4.5 bathrooms have been finished to a very high standard and the villa offers all the amenities for your perfect holiday. The house overlooks conservation land, an enviable location  …see more

from $191 / night

$1331 / week

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from $191 / night

(67) Excellent 

24

Vacation 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 mi
  • Swimming pool
Orlando Florida is the perfect holiday destination for all ages with sunshine all year round. It hosts the world's greatest theme parks and most, including Disney World, are very conveniently located to our villa within 15 minutes drive. Beautiful beaches are only  …see more

from $87 / night

$589 - $732 / week

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from $87 / night

(17) Excellent 

22

Vacation 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
The villa benefits from its own private pool, with a shallow end perfect for the children. Leading from the living room is a spacious patio with stunning conservation views, furnished with a table and chairs to enable you to dine al fresco.The villa is  …see more

from $131 / night

$788 - $1023 / week

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from $131 / night