Holiday Houses in Kissimmee

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Location

  • United States
  • Florida
  • Central Florida
  • Kissimmee

Location

  • All locations
  • Bellavida Resort (13)
  • Calabria, Orlando (2)
  • Cane Island (4)
  • Chatham Park (1)
  • Compass Bay (13)
  • Coral Cay (7)
  • Country Creek (2)
  • Creekside (1)
  • Crescent Lakes (13)
  • Crestwynd Bay (3)
  • Crystal Cove Resort (5)
  • Cumbrian Lakes (10)
  • Doral Woods (5)
  • Eagle Pointe (10)
  • Emerald Isle Kissimmee (53)
  • Encantada Resort (5)
  • Fiesta Key (5)
  • Formosa Gardens (8)
  • Hamilton's Reserve (2)
  • Indian Creek (13)
  • Indian Point (3)
  • Indian Ridge (3)
  • Indian Ridge Oaks (4)
  • Kissimmee City (34)
  • Lake Berkley (23)
  • Lake Marion (3)
  • Legacy Dunes Resort (4)
  • Liberty Village (5)
  • Lindfields (17)
  • Lucaya Village (2)
  • Oak Island Cove (3)
  • Oak Island Harbor (3)
  • Orange Lake Resort (9)
  • Paradise Palms (29)
  • Regal Oaks (10)
  • Remington (2)
  • Rolling Hills at Formosa (3)
  • Seasons Resort (7)
  • Sunset Lakes (9)
  • Terra Verde Resort (18)
  • The Hamlets (3)
  • Trafalgar Village (7)
  • Tuscany, Florida (2)
  • Venetian Bay Villages (9)
  • Veranda Palms (6)
  • Villasol (3)
  • Vista del lago (2)
  • Westside (2)
  • Windsor Hills Resort (27)
  • Windsor Palms (22)
  • Winward Cay (5)

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4,388 Holiday homes

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

1 / 33

Central Florida / Kissimmee

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £91 / night

£636 - £904 / week

Book Book View

from £91 / night

(17) Excellent 

1 / 51

Kissimmee / Villasol

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 55 km; Swimming pool;
 …see more

from £99 / night

£0 / week

Book Book View

from £99 / night

(4) Excellent 

1 / 18

Central Florida / Kissimmee

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £60 / night

£425 - £650 / week

Book Book View

from £60 / night

(22) Excellent 

1 / 56

Kissimmee / Doral Woods

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £125 / night

£750 - £950 / week

Book Book View

from £125 / night

(8) Excellent 

1 / 46

Kissimmee / Indian Point

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
 …see more

from £75 / night

£525 - £700 / week

Book Book View

from £75 / night

(5) Very Good 

1 / 84

Central Florida / Kissimmee

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £111 / night

£775 - £962 / week

Book Book View

from £111 / night

1 / 56

Kissimmee / Kissimmee City

3 bedroomsSleeps 83 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Great for children of all ages ; Air conditioning;
 …see more

from £75 / night

£525 - £560 / week

Book Book View

from £75 / night

(8) Excellent 

1 / 48

Central Florida / Kissimmee

5 bedroomsSleeps 11Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £111 / night

£695 - £1062 / week

Book Book View

from £111 / night

(13) Very Good 

1 / 37

Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Ask owner if suitable for children; Air conditioning; Pets welcome;
 …see more

from £99 / night

£690 - £957 / week

Enquire Enquire View

from £99 / night

1 / 4

Central Florida / Kissimmee

3 bedroomsSleeps 127 nights min stay

  • 3 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £176 / night

£1222 / week

Book Book View

from £176 / night

1 / 28

Emerald Island 4B/2B near Disney, pool, game room

Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Tropical Paradise Villa is in the most sought after gated Emerald Island Resort located 2.5 miles from Disney's doorstep. It has four bedrooms, two baths, a private screened-in pool with a game room. FAMILY ROOM The bright and spacious open concept living area spor  …see more

from £75 / night

£0 / week

Enquire Enquire View

from £75 / night

1 / 57

Central Florida / Kissimmee

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Suitable for children age 5+; Air conditioning;
 …see more

from £184 / night

£1283 - £1881 / week

Book Book View

from £184 / night

(22) Excellent 

1 / 27

Central Florida / Kissimmee

3 bedroomsSleeps 83 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Nearest beach 90 km; Swimming pool; Not suitable for children;
 …see more

from £76 / night

£530 - £743 / week

Book Book View

from £76 / night

1 / 40

Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £100 / night

£688 - £917 / week

Book Book View

from £100 / night

1 / 32

Central Florida / Kissimmee

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £61 / night

£423 - £530 / week

Book Book View

from £61 / night

(6) Very Good 

1 / 22

Kissimmee / Regal Oaks

4 bedroomsSleeps 83 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £60 / night

£420 / week

Book Book View

from £60 / night

1 / 51

Kissimmee / Eagle Pointe

4 bedroomsSleeps 85 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 115 km; Swimming pool;
 …see more

from £129 / night

£767 - £790 / week

Book Book View

from £129 / night

(6) Excellent 

1 / 73

Central Florida / Kissimmee

3 bedroomsSleeps 84 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
 …see more

from £77 / night

£535 - £2291 / week

Book Book View

from £77 / night

1 / 21

Central Florida / Kissimmee

4 bedroomsSleeps 123 nights min stay

  • 4 bedrooms
  • Sleeps 12
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £65 / night

£0 / week

Book Book View

from £65 / night

(2) Very Good 

1 / 70

Central Florida / Kissimmee

5 bedroomsSleeps 123 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min stay
Key info: Great for children of all ages ; Air conditioning; No pets allowed;
 …see more

from £109 / night

£760 - £913 / week

Book Book View

from £109 / night

1 / 30

Central Florida / Kissimmee

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Suitable for children age 5+; Air conditioning;
 …see more

from £172 / night

£1203 - £1470 / week

Book Book View

from £172 / night

1 / 16

5 bedroomsSleeps 12Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Great for children of all ages ; No pets allowed;
 …see more

from £93 / night

£646 - £1380 / week

Book Book View

from £93 / night

1 / 24

Central Florida / Kissimmee

5 bedroomsSleeps 12Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
 …see more

from £114 / night

£797 - £1064 / week

Book Book View

from £114 / night

1 / 52

Central Florida / Kissimmee

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £84 / night

£0 / week

Book Book View

from £84 / night

1 / 35

Central Florida / Kissimmee

6 bedroomsSleeps 14Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Great for children of all ages ; No pets allowed;
 …see more

from £161 / night

£0 / week

Book Book View

from £161 / night

(1) Excellent 

1 / 10

Central Florida / Kissimmee

3 bedroomsSleeps 123 nights min stay

  • 3 bedrooms
  • Sleeps 12
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £62 / night

£0 / week

Book Book View

from £62 / night

(17) Excellent 

1 / 20

Central Florida / Kissimmee

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £75 / night

£525 - £625 / week

Book Book View

from £75 / night

1 / 39

Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £92 / night

£642 - £1123 / week

Book Book View

from £92 / night

(15) Very Good 

1 / 66

Kissimmee / Lindfields

2 bedroomsSleeps 54 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 90 km; Swimming pool;
 …see more

from £50 / night

£350 / week

Book Book View

from £50 / night

1 / 16

Central Florida / Kissimmee

4 bedroomsSleeps 82 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £88 / night

£0 / week

Book Book View

from £88 / night

1 / 23

Central Florida / Kissimmee

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £76 / night

£530 - £743 / week

Book Book View

from £76 / night

(6) Excellent 

1 / 58

Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
 …see more

from £84 / night

£569 - £684 / week

Book Book View

from £84 / night

1 / 34

Kissimmee / Crescent Lakes

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £97 / night

£679 / week

Book Book View

from £97 / night

1 / 34

Central Florida / Kissimmee

3 bedroomsSleeps 53 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £76 / night

£530 - £743 / week

Book Book View

from £76 / night

(3) Very Good 

1 / 19

Central Florida / Kissimmee

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 0 km; Swimming pool; Great for children of all ages ;
 …see more

from £65 / night

£476 / week

Book Book View

from £65 / night

(1) Excellent 

1 / 19

Kissimmee / Indian Creek

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £80 / night

£636 / week

Book Book View

from £80 / night

1 / 24

Central Florida / Kissimmee

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Suitable for children age 5+; Air conditioning;
 …see more

from £107 / night

£642 - £1123 / week

Book Book View

from £107 / night

1 / 39

Central Florida / Kissimmee

4 bedroomsSleeps 9Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Nearest beach 150 km; Swimming pool; Great for children of all ages ;
 …see more

from £77 / night

£504 - £657 / week

Book Book View

from £77 / night

1 / 52

Central Florida / Kissimmee

3 bedroomsSleeps 84 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min stay
Key info: Great for children of all ages ; Air conditioning; No pets allowed;
 …see more

from £54 / night

£375 / week

Book Book View

from £54 / night

(8) Excellent 

1 / 23

Central Florida / Kissimmee

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 97 km; Swimming pool; Great for children of all ages ;
 …see more

from £81 / night

£535 - £668 / week

Book Book View

from £81 / night

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