Top Holiday rentals in Kissimmee

Find the Top Holiday rentals in Kissimmee – 20+ Quality Options from Leading Providers

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22 Guests, 1 Room
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1-20 out of 28 holiday rentals
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6 adults
3 bedrooms
3 beds
MapView on map6.8 km from City Centre500 m from Capone's Dinner and Show
From   US$ 108 /nightSelect
  • Family-friendly with picnic area
  • On-site activities like fishing and tennis
  • Relaxing garden views throughout property
10 adults
4 bedrooms
5 beds
MapView on map20.7 km from City Centre
From   US$ 10 /nightSelect
  • On-site H2O waterpark for families
  • Outdoor swimming pool with bar
  • Full-service on-site spa facilities
Apartment
  • Heated Pool
  • Fitness Centre
  • Outdoor Spa
24.4 km from City Centre
From   US$ 125 /nightSelect
  • Family-friendly villa accommodations
  • Outdoor heated pool with scenic view
  • On-site fishing and hiking activities
  • Fitness centre
  • Jacuzzi
  • Fishing
7.9 km from City Centre1.4 km from Kissimmee Go-Karts
From   US$ 75 /nightSelect
  • Heated outdoor swimming pool
  • On-site tennis court
  • Hot tub and sauna facilities
  • Outdoor pool
  • Tennis court
  • Fitness center
4.2 km from City Centre
From   US$ 90 /nightSelect
  • Heated outdoor pools and kids' pool
  • On-site tennis court and fitness center
  • Private hot tub and garden views
  • Tennis Courts
  • Children's Play Area
  • Private Garage
9.7 km from City Centre1000 m from Fantasy Surf
From   US$ 119 /nightSelect
  • Self-catering villas with private pools
  • Community clubhouse with tennis courts
  • Lakeside pool with sun loungers
  • Hot tub
  • Game area
  • Sun loungers
25.2 km from City Centre
From   US$ 139 /nightSelect
  • Private entrance with full-day security
  • Outdoor swimming pool with sun loungers
  • Hot tub and picnic area available
  • Hot tub
  • Sauna
  • Tennis court
25.1 km from City Centre
From   US$ 169 /nightSelect
  • Heated outdoor pool with views
  • Wellness amenities including yoga classes
  • 3 living rooms for entertainment
  • Game Room
  • Fitness Centre
  • Outdoor Pool
9.6 km from City Centre700 m from Fantasy Surf
From   US$ 317 /nightSelect
  • Four bedrooms with dedicated game room
  • Private entrance for added privacy
  • Outdoor swimming pool with garden views
  • Outdoor Pool
  • Golf Course
  • Family Rooms
23.2 km from City Centre
From   US$ 153 /nightSelect
  • Year-round outdoor swimming pool
  • Fully equipped kitchen in each unit
  • On-site golf course available
  • Private Pool
  • Outdoor Dining
  • Heated Pool
26.2 km from City Centre
From   US$ 165 /nightSelect
  • Private pool for exclusive relaxation
  • Four bedrooms for family gatherings
  • Heated outdoor pool year-round
  • Private pool
  • Spa centre
  • Kids' play
6.8 km from City Centre600 m from Capone's Dinner and Show
From   US$ 195 /nightSelect
  • Private pool and garden
  • On-site spa and wellness centre
  • Kids pool and play area
  • Outdoor Pool
  • Golf Course
  • Electric Kettle
10.1 km from City Centre500 m from Orange World
From   US$ 144 /nightSelect
  • Heated outdoor swimming pool
  • On-site golf course availability
  • Outdoor dining area for guests
  • Private Pool
  • Fitness Centre
  • Kids Play Area
6.9 km from City Centre500 m from Capone's Dinner and Show
From   US$ 95 /nightSelect
  • Private pool with stunning garden views
  • Fitness center with various activities
  • Kids pool and play area available
  • Fitness Centre
  • Mini Golf
  • Kids Pool
8.5 km from City Centre1.4 km from Fantasy Surf
From   US$ 185 /nightSelect
  • Outdoor swimming pool with kids area
  • Mini golf and water park access
  • Fully equipped kitchen for families
Holiday home
  • Private Pool
  • Fitness Centre
  • Snack Bar
8.2 km from City Centre1.2 km from Fantasy Surf
From   US$ 308 /nightSelect
  • Private pool with outdoor jacuzzi
  • On-site water park for families
  • Fitness centre for active guests
  • Fitness centre
  • Private entrance
  • Fully equipped kitchen
10.1 km from City Centre200 m from Orange World
From   US$ 204 /nightSelect
  • Air-conditioned holiday home with privacy
  • Fully equipped kitchen and laundry facilities
  • Fitness centre on-site for guests
  • Fitness Centre
  • Outdoor Pool
  • Spa Centre
9.7 km from City Centre800 m from Fantasy Surf
From   US$ 89 /nightSelect
  • Four bedrooms with private entrance
  • On-site fitness centre and spa
  • Outdoor swimming pool open year-round
8.3 km from City Centre800 m from Fantasy Surf
From   US$ 178 /nightSelect
This villa is located 4 km from Give Kids The World Village and offers 4 bedrooms together with an outdoor swimming pool.
  • Private Pool
  • Spa Centre
  • Game Room
6.3 km from City Centre
From   US$ 182 /nightSelect
  • Private pool with lake view
  • On-site water park access
  • Two outdoor swimming pools
  • 1
  • 2