Top Vacation homes in Kissimmee

Find the Top Vacation homes in Kissimmee – 50+ Quality Options from Leading Providers

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Rooms & Guests
22 Guests, 1 Room
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21-40 out of 52 vacation homes
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8 adults
3 bedrooms
4 beds
MapView on map6.0 mi from City Center
From   US$ 110 /nightSelect
  • Community lakeside pool access
  • Private pool options available
  • On-site tennis courts available
17 adults
7 bedrooms
8 beds
MapView on map5.0 mi from City Center1700 yd from Capone's Dinner and Show
From   US$ 378 /nightSelect
  • On-site water park for family fun
  • Multiple outdoor pools with slides
  • Fitness center with diverse activities
Holiday home
  • Private pool
  • Game room
  • Fitness centre
15.0 mi from City Center
From   US$ 152 /nightSelect
  • Private pool with patio and views
  • On-site billiards and table tennis games
  • Full day security and 24-hour reception
Holiday home
  • Private Pool
  • Game Room
  • Children's Playground
14.9 mi from City Center
From   US$ 282 /nightSelect
  • Private pool for relaxation and fun
  • Fully equipped kitchen for family meals
  • Children's playground for family entertainment
Holiday home
  • Rooftop Pool
  • Kids Club
  • Spa Centre
14.8 mi from City Center
From   US$ 146 /nightSelect
  • Rooftop pool with pool views
  • On-site spa and wellness centre
  • Kids club and playground
  • Hot Tub
  • Kids' Pool
  • Fitness Center
4.3 mi from City Center500 yd from Capone's Dinner and Show
From   US$ 95 /nightSelect
  • Private hot tub with garden views
  • Fun kids' pool and play areas
  • On-site fitness center and activities
  • Private Pool
  • Fitness Centre
  • Outdoor Pool
5.2 mi from City Center1700 yd from Capone's Dinner and Show
From   US$ 419 /nightSelect
  • Private pool for exclusive enjoyment
  • Four spacious bedrooms for families
  • Fitness centre for active lifestyle
  • Swimming Pool
  • Hot Tub
  • Outdoor Kitchen
12.7 mi from City Center
From   US$ 124 /nightSelect
  • Outdoor pool and hot tub
  • Fully equipped kitchen for convenience
  • Outdoor dining area for relaxation
  • Private Pool
  • Fitness Centre
  • Water Park
3.7 mi from City Center400 yd from Medieval Times
From   US$ 203 /nightSelect
  • Private pool with garden views
  • Fitness centre and water park access
  • Four spacious bedrooms available
  • Hot tub
  • Kids' pool
  • Tennis court
2.6 mi from City Center
From   US$ 95 /nightSelect
  • Private hot tub and sauna
  • Access to kids' play area
  • Multiple outdoor pools
  • Private Pool
  • Spa Centre
  • Water Park
5.3 mi from City Center1600 yd from Capone's Dinner and Show
From   US$ 274 /nightSelect
  • Private pool with garden views
  • Four comfortable bedrooms for families
  • On-site water park for entertainment
  • Private Pool
  • Fitness Centre
  • Aqua Park
5.4 mi from City Center1.2 mi from Capone's Dinner and Show
From   US$ 232 /nightSelect
  • Private pool with garden views
  • Fitness centre for active stays
  • On-site water park access
  • Private Pool
  • On-site Spa
  • Game Room
5.1 mi from City Center1400 yd from Capone's Dinner and Show
From   US$ 178 /nightSelect
  • Private pool with lake view
  • On-site spa and fitness centre
  • Proximity to Orlando attractions
  • Private Pool
  • Heated Pool
  • Golf Course
16.3 mi from City Center
From   US$ 165 /nightSelect
  • Private pool with outdoor dining area
  • Fully equipped kitchen for convenience
  • Heated pool available year-round
  • Private Pool
  • Spa Centre
  • Game Room
15.0 mi from City Center
From   US$ 238 /nightSelect
  • Private pool with lake views
  • On-site spa and wellness center
  • Proximity to cycling and fishing activities
  • Gameroom
  • Hot tub
  • Private pool
14.6 mi from City Center
From   US$ 509 /nightSelect
  • Private PS5 gameroom with billiards
  • Relaxing hot tub for guests
  • Spacious 9-bedroom villa available
  • Game Room
  • Outdoor Pool
  • Fitness Centre
6.0 mi from City Center
From   US$ 130 /nightSelect
  • Game room with entertainment options
  • Outdoor swimming pool and kids' area
  • Fully equipped kitchen for family meals
  • Private Pool
  • Spa Centre
  • Fitness Centre
3.9 mi from City Center
From   US$ 182 /nightSelect
  • Private pool with lake view
  • On-site water park access
  • Fully equipped kitchen
Holiday home
  • Private Pool
  • Fitness Centre
  • Snack Bar
5.1 mi from City Center1600 yd from Capone's Dinner and Show
From   US$ 238 /nightSelect
  • Private pool for exclusive enjoyment
  • On-site fitness centre for active guests
  • Water park for family entertainment
  • Fitness Centre
  • Outdoor Pool
  • Spa Centre
6.0 mi from City Center
From   US$ 89 /nightSelect
  • Private entrance for added privacy
  • Fully equipped kitchen for convenience
  • On-site fitness centre and spa