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Top Holiday rentals in Kissimmee

Find the Top Holiday rentals 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 51 holiday rentals
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Apartment
MapView on map6.5 km from City Centre
From   US$ 297 /nightSelect
  • Private pool with lake views
  • Full-day security for peace of mind
  • On-site hot tub and massage services
Apartment
MapView on map8.9 km from City Centre1.6 km from Kissimmee Go-Karts
From   US$ 188 /nightSelect
Placed within 3.5 km of Pioneer Village at Shingle Creek, this apartment features a sauna and an outdoor swimming pool.
Holiday home
  • Private Pool
  • Spa Centre
  • Fitness Room
24.1 km from City Centre
From   US$ 152 /nightSelect
  • Private pool with scenic patio views
  • On-site billiards and table tennis available
  • Spa with hot tub and sauna facilities
Apartment
  • Private Balcony
  • Fully Equipped Kitchen
  • Multiple Bathrooms
18.6 km from City Centre
From   US$ 188 /nightSelect
  • Three bedrooms with multiple bathrooms
  • Fully equipped kitchen with dishwasher
  • Private balcony for outdoor space
Holiday home
  • Private Pool
  • Children's Playground
  • Fully Equipped Kitchen
24.0 km from City Centre
From   US$ 282 /nightSelect
  • Private pool for family fun
  • Children's playground on-site
  • Fully equipped kitchen available
Holiday home
  • Private Pool
  • Flat-screen TV
  • Fitness Centre
8.4 km from City Centre1.5 km from Capone's Dinner and Show
From   US$ 419 /nightSelect
  • Private pool for exclusive relaxation
  • Air-conditioned rooms with flat-screen TV
  • Fitness centre for active guests
Holiday home
  • Rooftop Pool
  • Spa and Wellness
  • Children's Playground
23.7 km from City Centre
From   US$ 146 /nightSelect
  • Unique rooftop pool with stunning views
  • On-site spa and wellness center facilities
  • Family-friendly children's playground available
Holiday home
20.4 km from City Centre
From   US$ 124 /nightSelect
Best Buy is 4.5 km from this villa that offers 3 bedrooms along with an equipped kitchenette area.
Holiday home
8.5 km from City Centre1.5 km from Capone's Dinner and Show
From   US$ 274 /nightSelect
Staying at the Luxurious 4Bd Home W/ Pool 4983 Kissimmee means you will be at a 2.6 km distance from Congo River Golf, while enjoying a private swimming pool onsite.
Holiday home
8.3 km from City Centre1.3 km from Capone's Dinner and Show
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.
Holiday home
6.0 km from City Centre400 m from Medieval Times
From   US$ 203 /nightSelect
The Four Bedrooms Townhouse 4563 is set 10 minutes by car from Kissimmee Sports Arena and Rodeo and about 10 minutes' drive from Fantasy Surf.
Apartment
  • 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
Apartment
24.9 km from City Centre
From   US$ 114 /nightSelect
Highlands Reserve Boulevard is 2.3 km from the Hidden Oasis Near Orlando, Disney, Etc. Kissimmee, while West Gate Flea Market is 10 minutes away by car.
Apartment
  • Hot tub
  • Fitness centre
  • Outdoor pool
8.3 km from City Centre1.8 km from Capone's Dinner and Show
From   US$ 203 /nightSelect
  • Private terrace with lake views
  • Year-round outdoor swimming pool
  • On-site water park access
Apartment
20.4 km from City Centre
From   US$ 199 /nightSelect
This apartment, offering 3 bedrooms and 1 bathrooms with a separate toilet, a bath and a shower, is located in the West Kissimmee district.
Holiday home
  • Fitness Centre
  • Outdoor Pool
  • Spa Centre
9.7 km from City Centre
From   US$ 89 /nightSelect
  • Four bedrooms with private entrance
  • On-site fitness centre and spa
  • Outdoor swimming pool open year-round
Holiday home
  • 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
Holiday home
  • Outdoor Pool
  • Golf Course
  • Family Rooms
23.2 km from City Centre
From   US$ 162 /nightSelect
  • Year-round outdoor swimming pool
  • Fully equipped kitchen in each unit
  • On-site golf course available
Holiday home
  • Private Pool
  • Fitness Centre
  • Snack Bar
8.2 km from City Centre1.5 km from Capone's Dinner and Show
From   US$ 242 /nightSelect
  • Private pool with outdoor jacuzzi
  • On-site water park for families
  • Fitness centre for active guests
Holiday home
6.5 km from City Centre900 m from Medieval Times
From   US$ 173 /nightSelect
Located 900 metres from Medieval Times Dinner & Tournament, the charming Crystal Cove Resort features a private swimming pool.
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