Kissimmee Holiday Homes

Compare 274 Kissimmee holiday homes and Airbnbs with private pools and full kitchens. Check rates and photos, then book the home that fits your trip

Check-in
Fri, 13 Nov
Check-out
Sat, 14 Nov
Rooms and Guests2 Guests, 1 room
Check-in
Fri, 13 Nov
-
Check-out
Sat, 14 Nov
Rooms and Guests2 Guests, 1 room
1Filter & Sort
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Check-in
Fri, 13 Nov
-
Check-out
Sat, 14 Nov
Rooms and Guests2 Guests, 1 room
1Filter & Sort
View map
View map
1-20 out of 273
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
Private Pool HomesHoliday home
6.7
Nice
10 adults
5 bedrooms
5 beds
Map
16.2 mi from City Center
Private PoolOutdoor PoolKids Pool
  • Private pool in each home
  • Garden-view holiday homes
  • Kids pool with spa access
FromUS$ 137 /nightSelect
8.8
Great
10 adults
4 bedrooms
5 beds
Map
12.9 mi from City Center
Water ParkPool BarSpa Center
  • On-site H2O Waterpark
  • Outdoor pool with pool bar
  • Full-service spa and beauty
FromUS$ 10 /nightSelect
8.8
Great
Map
3.6 mi from City Center1506 yd from Kissimmee Value Outlet Shops
Private PoolHeated PoolHot Tub/Jacuzzi
  • Private pool in each townhouse
  • Fully equipped kitchen with appliances
  • Heated outdoor pool and hot tub
FromUS$ 116 /nightSelect
7.9
Very good
6 adults
3 bedrooms
3 beds
Map
4.2 mi from City Center489 yd from Capone's Dinner and Show
Hot tubWater parkFitness center
  • Private hot tub in each villa
  • Pool with a view and garden
  • On-site water park access
FromUS$ 108 /nightSelect
9.0
Perfect
Map
6.0 mi from City Center910 yd from Fantasy Surf
Outdoor PoolGames RoomFull Kitchen
  • Year-round outdoor swimming pool
  • On-site games and play area
  • Full kitchen and washer included
FromUS$ 76 /nightSelect
9.3
Perfect
Map
14.9 mi from City Center
Outdoor poolHot tubFull kitchen
  • 18-minute drive to Disney parks
  • Full kitchen in every apartment
  • Outdoor pool and hot tub
FromUS$ 130 /nightSelect
8.6
Great
Map
11.4 mi from City Center1.4 mi from Savanna Club Golf Course
Shared KitchenGarden ViewPet Friendly
  • Shared kitchen for guest use
  • Garden views from room
  • Pets allowed on property
FromUS$ 45 /nightSelect
8.9
Great
Map
15.0 mi from City Center
Private PoolWater ParkSpa Center
  • Private pool with lake views
  • On-site water park access
  • Private entrance for privacy
FromUS$ 250 /nightSelect
9.3
Perfect
10 adults
5 bedrooms
5 beds
Map
12.4 mi from City Center
Private PoolOutdoor DiningPrivate Terrace
  • Private pool with outdoor dining area
  • Fully equipped kitchen and terrace
  • Private check-in and check-out
FromUS$ 160 /nightSelect
9.1
Perfect
8 adults
2 bedrooms
4 beds
Map
5.3 mi from City Center1544 yd from Fantasy Surf
Water ParkPool BarWater Slide
  • Free water park access included
  • 5-minute drive to Disney parks
  • Pool bar with water slide
FromUS$ 248 /nightSelect
7.7
Very good
Map
11.5 mi from City Center
Water ParkFull KitchenTennis Court
  • On-site water park with slides
  • Full kitchens in each unit
  • Tennis court and bike hire
FromUS$ 178 /nightSelect
8.9
Great
Map
14.9 mi from City Center
Pool barWater slideHot tub
  • Lake-view balcony with hot tub
  • Pool bar with water slide
  • Tennis and table tennis courts
FromUS$ 186 /nightSelect
8.9
Great
8 adults
4 bedrooms
4 beds
Map
5.3 mi from City Center697 yd from Fantasy Surf
Private PoolHot TubFitness Center
  • Private pool and hot tub
  • Near Disney Springs and parks
  • Full kitchen and BBQ included
FromUS$ 297 /nightSelect
9.3
Perfect
Map
3.1 mi from City Center1.1 mi from Osceola County Stadium
Water ParkFree ParkingFully Equipped Kitchen
  • Themed Harry Potter holiday home
  • Water park on-site access
  • Pets allowed with free parking
FromUS$ 571 /nightSelect
9.4
Perfect
Map
5.8 mi from City Center406 yd from Fantasy Surf
Water ParkSolariumPublic Bath
  • Four outdoor pools with water park
  • Solarium and public bath on-site
  • Free private parking and security
FromUS$ 144 /nightSelect
7.2
Very good
Map
12.5 mi from City Center
Water slideTennis courtIndoor pool
  • 3 miles to Disney parks
  • Indoor and outdoor pools
  • Full kitchen and dressing room
FromUS$ 262 /nightSelect
7.4
Very good
Map
14.6 mi from City Center
Heated PoolGame RoomBBQ Grill
  • Private heated PoolSpa
  • Game room & billiards
  • Close to Disney parks
FromUS$ 428 /nightSelect
5.8
Needs improvement
Map
2.6 mi from City Center1.1 mi from Chambers Neighborhood Ctr
Private PoolFull KitchenPlayground
  • Private pool at home
  • Near Disney World & parks
  • Children's playground on-site
FromUS$ 90 /nightSelect
7.9
Very good
8 adults
3 bedrooms
4 beds
Map
6.0 mi from City Center992 yd from Fantasy Surf
Full KitchenTennis CourtKids Play Area
  • Self-catering with full kitchen
  • Community lakeside pool
  • Private 2-car garage
FromUS$ 90 /nightSelect
8.9
Great
Map
13.9 mi from City Center
Private PoolSaunaFitness Center
  • Sleeps up to 10 guests
  • Private pool with garden views
  • On-site sauna and fitness room
FromUS$ 118 /nightSelect
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Kissimmee holiday homes offer more than just a place to sleep-they are designed for families and groups who want extra space, privacy, and resort-style amenities. From compact 3-bedroom townhomes to sprawling 8-bedroom villas, these rentals come with fully equipped kitchens, private pools, and separate living areas. Many properties sit within gated communities like Veranda Palms or Cumbrian Lakes, placing you minutes from Disney World, Gatorland, and SeaWorld. Budgets vary, but with nightly rates often starting under $150, these homes deliver more square footage and flexibility than a standard hotel room.

For travelers who prioritize entertainment, look at options like Margaritaville Cottages Orlando by Rentyl, which features an on-site waterpark, pool bar, and spa, or Sonoma Resort's 7-bedroom home with a private pool and wellness center. For a quieter retreat, Formosa Garden Pool Home offers a private pool and games room at a budget-friendly price. Popular areas to consider include Celebration, Reunion Resort, and the US-192 corridor, all within 10-15 km of major attractions. When booking, check for free cancellation, parking, and whether the pool is heated-especially during winter months. Top-rated properties like The Bear's Den Resort Orlando even include an infinity pool, waterpark, and multiple restaurants for a true all-in-one stay.