Holiday condos in Kissimmee

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  • United States
  • Florida
  • Central Florida
  • Kissimmee
  • All locations
  • Cane Island (3)
  • Kissimmee City (7)
  • Lake Marion (1)
  • Legacy Dunes Resort (6)
  • Lindfields (2)
  • Oak Island Cove (1)
  • Orange Lake Resort (1)
  • Seasons Resort (1)
  • Westside (1)
  • Windsor Hills Resort (7)
  • Windsor Palms (5)

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187 Holiday homes

Filters applied: Condo (187)

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

(12) Excellent 

41

Beautiful Cane Island Condo with Pool, Sauna & Spa - Cane Island condo sleeps 6

Kissimmee / Cane Island

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 65 km
  • 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 £58 / night

£378 - £531 / week

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from £58 / night

(24) Very Good 

17

Amazing Disney Condo, Pool & Hot tub Onsite - Kissimmee condo sleeps 6

Central Florida / Kissimmee

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Nearest beach 106 km
  • 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 £35 / night

£220 - £330 / week

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from £35 / night

(22) Excellent 

8

Affordable and Luxurious Ground Floor Condo at Cane Island Resort - Cane Island condo sleeps 6

Kissimmee / Cane Island

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 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.This is  …see more

from £50 / night

£350 - £420 / week

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from £50 / night

(13) Excellent 

59

Orlando condo at Legacy Dunes - resort amenities - Legacy Dunes Resort condo sleeps 6

Kissimmee / Legacy Dunes Resort

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 78 km
  • Swimming pool
The Ultimate Family Fun Getaway! 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  …see more

from £45 / night

£300 - £550 / week

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from £45 / night

(2) Very Good 

20

Legacy Dunes Resort - Legacy Dunes Resort condo sleeps 4

Kissimmee / Legacy Dunes Resort

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This Condo is on the doorstep of Disney, just off 192, In the heart of Kissimmee. From the moment you drive up the entrance road, with its beautiful landscaping, you know you are about to enter a great resort. Legacy Dunes Resort offers a wonderful guest experience. The  …see more

from £77 / night

£539 - £686 / week

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from £77 / night

28

Condo at Legacy Dunes - resort amenities - Legacy Dunes Resort condo sleeps 10

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 - £600 / week

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from £60 / night

(27) Excellent 

77

Chris and Sue's Disney Condo - Windsor Palms condo sleeps 7

Kissimmee / Windsor Palms

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 117 km
  • Swimming pool
  • Child friendly
FREE PHONE CALLS AND WIFILuxurious 3 bedroom/2 bathroom, fully equipped Condo is located in the exclusive gated community of Windsor Palms, Kissimmee, less than 3 miles from Walt Disney World. A perfect location for all that Central Florida has to offer eg The Parks of  …see more

from £63 / night

£390 - £695 / week

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from £63 / night

55

Beautifully furnished condo 10 minutes from Disney - Cane Island condo sleeps 6

Kissimmee / Cane Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This ground floor apartment is first class. Compare staying here with staying in a Disney Hotel and you will be astonished. Half the price of a 'moderate' Disney Resort but twice as much space as a 'Deluxe' Resort. Not only will you be saving mone  …see more

from £49 / night

£343 / week

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from £49 / night

(1) Very Good 

20

Lovely Condo,NEW MATTRESSES,WIFI,4 miles to Disney - Kissimmee City condo sleeps 6

Kissimmee / Kissimmee City

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This spacious 3 bedrooms and 2 bedrooms vacation home includes the Following Amenities: 4 miles to Disney , 1 King Bed, 1 Queen Bed, 2 Twin Beds, COMMUNITY has heated pool, spa, fitness center, theater room, basketball and tennis court and children playground, Complemen  …see more

from £65 / night

£432 - £649 / week

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from £65 / night

42

Minion Cove - Windsor Hills Resort condo sleeps 6

Kissimmee / Windsor Hills Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
3 Bedroom 2 Bathroom Condo Sleeps 6 Welcome to Minion Cove, our 3 bedroom 2 bathroom condo located in the beautiful 5 star gated community of Windsor Hills located less than 2 miles from the main gates of Walt Disney World. Windsor Hills is one of the newest and greates  …see more

from £65 / night

£420 - £909 / week

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from £65 / night

46

Perfect Home @ Disney - Kissimmee condo sleeps 7

Central Florida / Kissimmee

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome home dear ! ! ! A perfect home@Disney within amazing community, location and spacious rooms. First of all, Location & Community ! Our condo is within a famous Windsor Palm Resort Community, which is often viewed as one of the best resorts in the area. Yo  …see more

from £56 / night

£312 - £390 / week

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from £56 / night

(6) Excellent 

18

Lighthouse Keys Spa and resort - Kissimmee condo sleeps 8

Central Florida / Kissimmee

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our condo is located in Kissimmee within the community of lighthouse Keys It is constantly in the top two for accommodation in the area on trip advisor. Ultimate in luxury and can sleep 6 comfortably and up to eight. Perfect for family holiday, golf trip. Fifteen minu  …see more

from £114 / night

£756 / week

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from £114 / night

16

DISNEY HOLIDAY CONDO ON A LUXURY RESORT - Legacy Dunes Resort condo sleeps 8

Kissimmee / Legacy Dunes Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Gorgeous fully furnished 4 bed 2 bath corporate rental apartment Orlando, FLLocation: Legacy DunesAbsolutely gorgeous, 4-bed, 2-bath condo located in the fabulous Resort Style privately gated community of Legacy Dunes. It comes fully furnished to accommodate 8 persons v  …see more

from £70 / night

£450 - £715 / week

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from £70 / night

37

1308 Caribe Suite - Kissimmee condo sleeps 6

Central Florida / Kissimmee

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
Condo 1308 is based in the Caribe Cove Resort. Our luxurious condo with ample amenities will comfort you, making Caribe Cove a great place to retreat to for a long-awaited vacation. Caribe Cove Resort is perfect for your vacation and holidays. Condo 1308 features abou  …see more

from £91 / night

£637 / week

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from £91 / night

62

Bahama Bay Resort Condo. Florida - Kissimmee condo sleeps 6

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool
3 bed 2 bath luxury condominium (apartment) in the spacious Bahama Bay Resort. The resort is in a tropical setting, about 15 minutes from the theme parks. It offers 4 outdoor heated swimming pools with in-ground Jacuzzis and sun loungers, a children's splash play a  …see more

from £60 / night

£400 - £720 / week

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from £60 / night

(13) Excellent 

28

Luxurious 3 Bedroom Club Cortile Condo with a Balc - Kissimmee condo sleeps 6

Central Florida / Kissimmee

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our superb condition 3 bed 2 bath condo has a 6 person maximum occupancy at Club Cortile Resort, a luxury gated resort with a 4,000 sq ft clubhouse, community pool with jacuzzi, tennis court, fitness centre, movie theatre, internet room and kids playground. Perfect loca  …see more

from £39 / night

£268 - £344 / week

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from £39 / night

(17) Excellent 

20

Rainforest Place Condo with a Terrace, Tennis Court, and Pool - Lindfields condo sleeps 8

Kissimmee / Lindfields

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Fully fitted kitchen with large fridge, icemaker, cooker, microwave and automatic dishwaster All cookware Bed and bath linens Beach towels, toys and parasols. Washer and dryer Ironing board and iron Cable TV in the living room and main bedroom with access to more than 7  …see more

from £60 / night

£397 / week

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from £60 / night

15

Kissimmee / Kissimmee City

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £92 / night

£642 / week

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from £92 / night

18

FLORIDA,ORLANDO,Laguna Bay - Kissimmee condo sleeps 8

Central Florida / Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Ideally located for exploring all the theme parks, shopping malls / outlets, restaurant / themed eating places, Laguna Bay Villas are ideal for your holiday in Disney area of Orlando, Florida. Well equipped and with extra features over the standard level this condo is  …see more

from £40 / night

£280 / week

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from £40 / night

9

Grand Palms Circle, Kissimmee - Oak Island Cove condo sleeps 6

Kissimmee / Oak Island Cove

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful 3 Bedroomed Upper Level Condo (sleeps 8) on Grand Palms Circle, Kissimmee - 10 minutes drive to all Disney Parks and approximately 30 minutes drive to Universal and Seaworld Parks. Located on a lovely complex just off the 192 in a community called Lindfields.  …see more

from £58 / night

£359 - £504 / week

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from £58 / night

18

2B-Villa Near Disney - Multi-Units Available!! - Kissimmee condo sleeps 6

Central Florida / Kissimmee

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Charming resort located within minutes of Disney and area attractions. The villa consists of a Bed #1: King Size Bed, Bed #2: (2) Twin Size Beds and a Queen sleeper sofa. Accommodates up to 6 guests. 2 Full Bathrooms w/Shower & Tub; Linens; 3 Televisions; DVD Players; I  …see more

from £61 / night

£420 / week

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from £61 / night

26

Central Florida / Kissimmee

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly

 …see more

from £108 / night

£756 / week

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from £108 / night

32

Central Florida / Kissimmee

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £99 / night

£649 / week

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from £99 / night

22

2 BEDROOM 2 BATH CONDO VILLA CLOSE TO DISNEY WORLD - Kissimmee condo sleeps 6

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 £131 / night

£917 / week

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from £131 / night

6

Central Florida / Kissimmee

2 8 2 nights min

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

 …see more

from £104 / night

£688 / week

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from £104 / night

32

Central Florida / Kissimmee

4 8 3 nights min

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

 …see more

from £83 / night

£578 / week

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from £83 / night

30

Central Florida / Kissimmee

3 8 1 night min

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

 …see more

from £76 / night

£516 / week

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from £76 / night

22

Central Florida / Kissimmee

2 6 Min stay varies

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

 …see more

from £58 / night

£390 - £554 / week

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from £58 / night

(5) Excellent 

23

Central Florida / Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £46 / night

£336 - £348 / week

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from £46 / night

18

Central Florida / Kissimmee

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £68 / night

£476 / week

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from £68 / night

5

Central Florida / Kissimmee

3 8 7 nights min

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

 …see more

from £131 / night

£913 / week

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from £131 / night

(1) Excellent 

29

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £54 / night

£459 - £512 / week

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from £54 / night

30

Kissimmee / Lake Marion

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 126 km
  • Swimming pool

 …see more

from £42 / night

£294 / week

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from £42 / night

4

Central Florida / Kissimmee

3 6 Min stay varies

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

 …see more

from £73 / night

£481 - £642 / week

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from £73 / night

15

Central Florida / Kissimmee

3 6 3 nights min

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

 …see more

from £58 / night

£401 / week

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from £58 / night

(2) Excellent 

5

Kissimmee / Windsor Palms

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly

 …see more

from £58 / night

£489 / week

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from £58 / night

9

Central Florida / Kissimmee

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly

 …see more

from £77 / night

£535 / week

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from £77 / night

20

Central Florida / Kissimmee

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Beach / lakeside relaxation
  • Air conditioning

 …see more

from £107 / night

£707 / week

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from £107 / night

14

Kissimmee / Lindfields

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £84 / night

£588 - £936 / week

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from £84 / night

(5) Very Good 

36

Kissimmee / Kissimmee City

3 8 3 nights min

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

 …see more

from £58 / night

£401 / week

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from £58 / night

Top Destination reviews

Lovely Kissimmee Home with Gameroom and Pool
Home from home.

The villa is in a fantastic location for all the attractions and the gated community is set in an attractive environment. The photos do not do it justice- we were blown away with the space and quality of this lovely villa. It has homely touches,oth … see more
Superb 4 Bedroom town house 3 miles from Disney
Great value and location

This townhome is great value with a great location at Emerald Island Resort. We had stayed in the local area a number of times previously so know it well, choosing it for its close proximity to Disney. The townhome was clean and well presented on ar … see more
One of the closest communities to Disney!
Close to Disney, a villa that caters for everyone!

We stayed here with our 8 year old in July 2016. From the time we booked to the time we returned Tracey (the owner) could not have been more helpful. Emails responded to promptly, very thoughtful communication and information throughout. We arr … see more
Disney Lakeside Villa with WiFi and a Pool, Kissimmee
Fantastic!

This was like home from home , clean , beautiful furnished,very relaxing, child friendly, lovely veiws from pool ect, can't wait to go back. … see more
DORAL WOODS SECLUDED VILLA
Best Florida Villa - by far !!!

We have spent many many weeks at this villa and when it isn't available for our trips to Florida nothing we stay at compares !!! It is a great villa, owned by an owner who cares. Well equipped, south facing, very private, safe with a real florida f … see more
holiday villa golf nearby WindsorHills Resort
Lovely villa

Very good if you are visiting Disney parks they are very close by. The villa was in a very nice neighbourhood also it was well maintained. Also the security gates made us feel very secure. Slightly further away from International Drive area but … see more

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