Holiday Houses in Kissimmee

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20,392 Holiday homes

Luxury Villa on Golf Course, 10 min. from Disney!

Kissimmee house

5 bedrooms / 4 bathrooms / sleeps 12

from £244 / night

£1,703 / week

Luxury 6 Bed Pool Villa Close to Disney

Kissimmee house

6 bedrooms / 4 bathrooms / sleeps 12

from £252 / night

£1,747 / week

Windsor Hills - 6 Bedroom Luxury Villa, 5 Minutes from Disney

Kissimmee villa

6 bedrooms / 4 bathrooms / sleeps 12

2

from £213 / night

£1,238 / week

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

Kissimmee house

4 bedrooms / 2 bathrooms / sleeps 8

5

Responds fast! avg. 2 hours 34 minutes

from £101 / night

£706 / week

DisneyHomesFlorida

Kissimmee house

4 bedrooms / 2 bathrooms / sleeps 10

from £115 / night

£798 / week

Villa with private pool near DisneyWorld

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 6

1

from £92 / night

£640 / week

Four Bedroom home near Disney/Orlando

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 8

2

from £80 / night

£619 / week

Encantada Resort, private pool, near Disney 4B/3B

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 8

2

Responds fast! avg. 2 hours 34 minutes

from £89 / night

£619 / week

Luxurious 3 Bedroom Townhome-1.5 miles from Disney

Kissimmee villa

3 bedrooms / 3 bathrooms / sleeps 7

38

Responds fast! avg. 2 hours 20 minutes

from £84 / night

£575 / week

Kissimmee Townhouse 4 bedrooms

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 8

19

Responds fast! avg. 2 hours 58 minutes

from £106 / night

£671 - £1,060 / week

A stunning pool home in Kissimmee, Disney Paradi

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 9

22

Responds fast! avg. 2 hours 26 minutes

from £119 / night

£802 - £916 / week

Disney World 2 Miles

Kissimmee condo

2 bedrooms / 2 bathrooms / sleeps 5

6

from £78 / night

£504 / week

Lake Berkley Holiday Villa with FREE pool heating.

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 8

27

from £85 / night

£624 - £882 / week

From $80/nt,Close to Disney,Seaworld,Convention Center,4br Townhome with Hot Tub

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 10

6

Responds fast! avg. 2 hours 20 minutes

from £80 / night

£558 / week

Lakefront, gated 4Br/3Ba, 6mile to Disney, Private Jacuzzi, Free WiFi/Cable TV

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 10

7

Responds fast! avg. 2 hours 58 minutes

from £76 / night

£527 / week

Amazing Disney Condo, Pool & Hot tub Onsite

Kissimmee condo

3 bedrooms / 2 bathrooms / sleeps 6

64

Responds fast! avg. 1 hour 24 minutes

from £57 / night

£264 - £422 / week

New Opening 5Br/3Ba Hot Tub/Lake View,Close Disney,Seaworld,Convention Center

Kissimmee townhouse

5 bedrooms / 3 bathrooms / sleeps 12

13

Responds fast! avg. 2 hours 20 minutes

from £86 / night

£761 - £885 / week

Stunning Sunset Villa includes WiFi, Grill, Gameroom

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 8

21

Responds fast! avg. 3 hours 12 minutes

from £115 / night

£659 - £1,781 / week

Veranda Palms Villa

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 8

28

Responds fast! avg. 1 hour 59 minutes

from £115 / night

£773 - £916 / week

Bay Head Villa, Great 3 Bedroom near Golf Courses and Theme Parks

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 8

31

from £75 / night

£544 - £945 / week

3 Bedroom Vacation Home in Kissimmee Pet-Friendly

Kissimmee house

3 bedrooms / 2 bathrooms / sleeps 6

28

from £71 / night

£465 / week

Beautiful Lakeside Villa With Pool; WiFi

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 6

37

from £86 / night

£602 / week

2636TW- Veranda Palms

Kissimmee house

6 bedrooms / 5 bathrooms / sleeps 13

2

from £120 / night

£838 / week

1.5 M to Disney,From $70/nt,3BR 1600 sqft Townhome

Kissimmee apartment

3 bedrooms / 3 bathrooms / sleeps 8

33

Responds fast! avg. 2 hours 5 minutes

from £76 / night

£527 / week

FIVE STAR 3BR Pool Home, ROKU Apps, HBO, GamesRm, WiFi, BBQ,Clean,Disney/Orlando

Kissimmee house

3 bedrooms / 2 bathrooms / sleeps 7

11

Responds fast! avg. 2 hours 37 minutes

from £102 / night

£712 / week

NEW! 4/3 Private Town Home at Storey Lake Resort-Near Disney Theme Parks

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 9 minutes

from £114 / night

£798 / week

Any Week in (JANUARY-APRIL) $1300 (includes TAXES & Final Cleaning)

Kissimmee house

4 bedrooms / 5 bathrooms / sleeps 10

16

from £123 / night

£795 - £1,148 / week

Enchanting Star Lake View House Pool, and Jacuzzi

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 10

13

from £149 / night

£1,042 / week

Pat and Ron's Holiday Home, Relaxing Retreat

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 6

39

from £87 / night

£607 / week

RVH_042R Contemporary Luxury

Kissimmee house

3 bedrooms / 2 bathrooms / sleeps 6

from £79 / night

£551 / week

Indian Point, on Praire Point Boulevard,

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 8

49

Responds fast! avg. 2 hours 57 minutes

from £86 / night

£602 - £630 / week

The Charming Mickey's Tree House,

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 9

8

from £89 / night

£619 - £752 / week

Furnished 4 Bedroom Villa for Rent

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 10

from £177 / night

£818 / week

Windsor Hills Luxury pool house/2 miles to Disney

Kissimmee house

6 bedrooms / 4 bathrooms / sleeps 13

5

Responds fast! avg. 1 hour 31 minutes

from £176 / night

£1,238 - £1,591 / week

Lake View Villa, WiFi, and Pool

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 8

10

from £62 / night

£436 / week

Christine’s Villa

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 55 minutes

from £73 / night

£508 / week

Fantasy Pool Home

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 8

52

Responds fast! avg. 2 hours 12 minutes

from £102 / night

£712 / week

Fresh poolvilla with free WI-FI and BBQ

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 8

13

from £98 / night

£681 / week

Luxury 3 Bed Villa on gated community

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 6

13

from £98 / night

£703 - £929 / week

Kissimmee Windsor at Westside's "The Second Star to the Right" vacation home

Kissimmee villa

7 bedrooms / 6 bathrooms / sleeps 17

5

Responds fast! avg. 2 hours 0 minutes

from £221 / night

£1,548 / week

Viewing 40 of 20,392
rentals in Kissimmee