Best Holiday rentals and Airbnb offers in Kissimmee, FL
9.7 49 reviews
Kissimmee, FL
28/12 – 09/01
SG$186/nighttotal: SG$2232 (12 )
Family-friendly 2br Condo • Resort Pool • Disney D
1 4
apartment , Kissimmee
This Kissimmee condo, near Walt Disney World, offers easy access to shopping outlets and beaches within a short driving distance – convenient for exploring central Florida. The newly renovated two-bedroom, two-bathroom property sleeps eight guests and boasts a fully equipped kitchen, resort-style amenities including two swimming pools and a fitness centre, plus smart TVs and family-friendly features.
10 5 reviews
Kissimmee, FL
17/08 – 18/08
SG$289/nightfor 1 night
Cloud Nine 1br 15 Min From Kissimmee Main Street
1 1
apartment , Kissimmee
This Kissimmee apartment offers convenient access to Walt Disney World® Resort, Aquatica, and Typhoon Lagoon water park, as well as shopping at Old Town and Disney Springs, though precise distances aren't specified. The self-catering flat comprises one bedroom, one bathroom, sleeps two guests, and includes a microwave, dishwasher, washing machine, air conditioning, a terrace, garden, parking, and a swimming pool.
9.1 13 reviews
Kissimmee, FL
28/12 – 02/01
SG$622/nighttotal: SG$3110 (5 )
8br Group-friendly Villa | Private Pool
8 11
apartment , Kissimmee
This eight-bedroom villa in a gated Kissimmee community is situated 11km from Walt Disney World, 19km from Universal Studios Florida, 18km from SeaWorld Orlando, and just 0.3km from Medieval Times Dinner & Tournament. Sleeping sixteen guests, this spacious property boasts a private pool (heating available for £40/day, 12-24 hour notice required), a dedicated playroom, a cinema room, and a fitness centre, alongside a fully equipped kitchen and five bathrooms.
9.0 59 reviews
Kissimmee, FL
25/12 – 03/01
SG$700/nighttotal: SG$6300 (9 )
Last Minute Disney Getaway! Townhouse With Private Pool. Book Now! #49423
4 11
apartment , Kissimmee
Storey Lake Resort 640 is a family-friendly vacation home in Kissimmee, located within 5km of Capone's Dinner Show, Kissimmee Go-Karts, and the 192 Flea Market, with Medieval Times just 4km away. The property has excellent ratings for location, cleanliness, and overall user experience. This four-bedroom holiday home can accommodate up to 11 guests and features a private pool, a fully equipped kitchen, three bathrooms, and a washing machine. Relax and enjoy the outdoor pool, spa, fitness centre, and other amenities, including a garden, terrace, and concierge services.
10 6 reviews
Kissimmee, FL
03/07 – 05/07
SG$737/nighttotal: SG$1474 (2 )
Near Disney! Themed Rooms\/arcade\/pool & Hot Tub\/gated Resort
5 10
resort , Kissimmee
This five-bedroom, four-bathroom holiday home, part of the 'Themed Home Near Disney! Pool/spa/game Room/resort' offer, is situated near North Poinciana Boulevard and US 192 in Kissimmee, Florida, approximately 14-24 km from Walt Disney World Resort and 24 km from Universal Studios Florida. The property boasts a private pool and hot tub, a games room with air hockey and arcade games, and access to Terra Verde Resort amenities including a zero-entry pool, mini-golf, and a fitness centre; it comfortably sleeps eleven guests.
9.4 72 reviews
Kissimmee, FL
25/12 – 03/01
SG$565/nighttotal: SG$5085 (9 )
Fancy Lakefront 4br Near Disney W/ Themed Bedrooms
1 11
apartment , Kissimmee
This Kissimmee townhouse, near the US 192 corridor, is approximately 24 kilometres from Walt Disney World Resort and other attractions. Sleeping up to 12 guests, this four-bedroom, three-bathroom property boasts a private pool, fully equipped kitchen, free Wi-Fi, and access to Terra Verde Resort amenities including a pool, jacuzzi, and fitness centre.
9.7 164 reviews
Kissimmee, FL
31/10 – 07/11
SG$231/nighttotal: SG$1617 (7 )
*Just Remodeled* Amazing 3 Bedroom Villa - Hot Tub
3 2
apartment , Kissimmee
This private vacation villa is located in Kissimmee, just 24 kilometres from Disney World, making it a convenient base for exploring the theme parks and other attractions. The villa has received excellent ratings for its location, cleanliness, and overall user experience. The villa spans 116 square metres and comfortably accommodates eight guests. It offers a range of amenities including a private hot tub with a lake view, a fully equipped kitchen, a fitness centre, a sauna, a spa, a swimming pool, and a jacuzzi.
9.6 83 reviews
Kissimmee, FL
27/06 – 04/07
SG$183/nighttotal: SG$1281 (7 )
Euphoria Family 2br Suite | Resort Pool • Disney A
1 2
apartment , Kissimmee
This Kissimmee condo, near Disney World and a short drive from shopping outlets and beaches, offers convenient access to major attractions. The two-bedroom, two-bathroom property sleeps eight guests, boasting a king suite, two double beds, a fully equipped kitchen including a Keurig coffee maker, multiple smart TVs, and resort amenities such as two swimming pools, a hot tub, and a fitness centre.
9.0 4 reviews
Kissimmee, FL
10/07 – 12/07
SG$910/nighttotal: SG$1820 (2 )
Modern 6br Home - Pool Bbq Hot Tub - Near Disney
6 14
house , Kissimmee
This six-bedroom, six-bathroom villa is situated in Kissimmee, Florida, conveniently located 12km from Gatorland and approximately 14-16km from various Walt Disney World attractions including Disney Springs and ESPN Wide World of Sports. The 285 square metre property boasts a private pool, hot tub, and barbecue facilities, comfortably accommodating up to 17 guests with amenities including free Wi-Fi and ample parking.
9.4 29 reviews
Kissimmee, FL
15/07 – 27/08
SG$162/nighttotal: SG$6966 (43 )
Once Upon A Stay
3 4
house , Kissimmee
This holiday home in the gated Fiesta Key community, Kissimmee, is conveniently located just a short drive from Walt Disney World Resort, Universal Orlando Resort, and SeaWorld. This pet-friendly villa accommodates up to seven guests across three bedrooms, featuring resort-style amenities such as a swimming pool and fitness centre, alongside a screened patio overlooking a pond and themed rooms including a Mario-themed bedroom with a slide.
9.8 215 reviews
Kissimmee, FL
04/07 – 01/08
SG$162/nighttotal: SG$4536 (28 )
3br-private Jacuzzi-resort Amenities-7 Mls Disney
1 4
apartment , Kissimmee
This three-bedroom townhouse is situated in the Terra Verde Resort, Kissimmee, offering convenient access to Disney World and other theme parks. The 2.5-bathroom property sleeps six guests and boasts a private hot tub, BBQ, fully equipped kitchen, and access to resort amenities including a heated pool, spa, and fitness centre.
9.4 133 reviews
Kissimmee, FL
24/12 – 05/01
SG$282/nighttotal: SG$3384 (12 )
Special Rates Available In Sep And Oct Of 2025
4 6
house , Kissimmee
This four-bedroom, three-bathroom villa is situated in the Terra Verde Resort community in Kissimmee, Florida, offering convenient access to Walt Disney World Resort, Disney's Hollywood Studios, and Epcot, all within a short driving distance. The 149 square metre (1600 square foot) property boasts a private swimming pool, jacuzzi, and tennis court, sleeping up to eight guests and including a fully equipped kitchen; a $25 resort fee applies.
Best family friendly Kissimmee, FL holiday rentals
Among the 15321 accommodations in Kissimmee, FL, here are the 4 best family friendly rentals
9.9 79 reviews
Kissimmee, FL
13/12 – 03/01
SG$259/nighttotal: SG$5439 (21 )
Contemporary & Family Friendly Resort Home
1 6
house , Kissimmee
This three-bedroom, two-bathroom townhouse in a gated Kissimmee community is situated approximately 24 kilometres from Walt Disney World Resort, Universal Orlando Resort, and SeaWorld. The property boasts a private patio overlooking a nature reserve, a fully equipped kitchen, in-unit laundry, and resort-style amenities including a swimming pool, jacuzzi, fitness centre and children's play area, accommodating up to six guests.
9.8 8 reviews
Kissimmee, FL
24/07 – 26/07
SG$306/nighttotal: SG$612 (2 )
Laoxury 3bd Townhome Pool Front In Brilliant Kissimmee
3 6
apartment , Kissimmee
This three-bedroom townhome in Kissimmee offers convenient access to Walt Disney World Resort, including Epcot and Disney's Hollywood Studios, and is located under 1 kilometre from Old Town and Disney Springs. This family-friendly accommodation sleeps six guests, featuring air conditioning, a kitchen with a fridge, microwave, and dishwasher, and direct access to a communal swimming pool.
9.7 71 reviews
Kissimmee, FL
10/07 – 18/07
SG$320/nighttotal: SG$2560 (8 )
Fantastic Mickey House Waterpark Near Disney 2572
4 7
apartment , Kissimmee
This four-bedroom, three-bathroom townhouse is located in the Story Lake Resort Community in Kissimmee, Florida, a short drive (a few kilometres) from Walt Disney World's theme parks. The self-catering property sleeps eight guests and boasts a private screened pool with optional heating, a fully equipped kitchen, Smart TVs, Wi-Fi, and access to a nearby water park; child safety pool fencing is provided.
9.6 130 reviews
Kissimmee, FL
13/09 – 23/09
SG$250/nighttotal: SG$2500 (10 )
Sunset Villa, Minutes From Disney. Exclusive 4 Bed, 2.5 Bath Pool Home
4 2
apartment , Kissimmee
This Kissimmee holiday home boasts a waterfront location, less than 5km from Green Meadows Petting Farm, Give Kids the World Village, and Shingle Creek Regional Park, offering convenient access to family attractions. The 169 square metre property sleeps eight guests across four bedrooms and two and a half bathrooms, featuring a private pool, fully equipped kitchen, laundry facilities, and access to an on-site water park, fitness centre, and games room.
Best Kissimmee, FL holiday rentals with parking
10 1 review
Kissimmee, FL
03/07 – 05/07
SG$402/nighttotal: SG$804 (2 )
5 Mi To Wdw! Spacious Resort Escape W/ Pool Access
1 10
house , Kissimmee
This Kissimmee villa is situated a mere 8 kilometres from Walt Disney World, with Hollywood Studios 12 kilometres away and the Wide World of Sports 11.5 kilometres distant, also offering convenient access to Disney Springs (10.8 kilometres) and Gatorland (11.5 kilometres). This 155 square metre holiday home accommodates up to 27 guests across 3 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, complimentary WiFi, air conditioning, a private entrance, and access to a shared swimming pool and hot tub, all located 24 kilometres from Orlando International Airport.
Kissimmee, FL
26/06 – 27/06
SG$723/nightfor 1 night
4824 Resort Pool House Disney Universal Orlando
5 15
apartment , Hunters Creek
This five-bedroom, four-bathroom holiday home, '4824 Resort Pool House Disney Universal Orlando', is situated in Kissimmee, near Storey Lake, a short drive (under 15km) from Walt Disney World and less than 9 minutes from Vineland Premium Outlets. The 216-square-metre property boasts a private pool, access to Storey Lake Resort's amenities (including a water park and lazy river), Disney-themed bedrooms, and comfortably sleeps up to 15 guests.
9.5 103 reviews
Kissimmee, FL
02/07 – 05/07
SG$428/nighttotal: SG$1284 (3 )
Beautiful Lake View Golf Home 2723
4 7
apartment , Kissimmee
This four-bedroom holiday home is located near a lake in Kissimmee, just a short distance from Remington Golf Club, Osceola Center for the Arts, and Osceola Flea and Farmers Market. Guests have consistently rated this property as excellent for its location, cleanliness, and overall experience. The property comfortably accommodates up to eight guests and features a fully equipped kitchen, four bathrooms, and a dining area. Enjoy the private pool, terrace, and stunning lake views, or explore nearby golf courses, attractions, and local markets.
8.2 79 reviews
Kissimmee, FL
02/07 – 05/07
SG$359/nighttotal: SG$1077 (3 )
Amazing 32 Townhome With Lake View At Terra Verde!!
3 2
house , Kissimmee
This three-bedroom townhome in the Terra Verde community of Kissimmee is located under 17.7km from Walt Disney World and 14km from Gatorland. The 120 square metre property boasts a fully equipped kitchen, private parking, a swimming pool, and a fitness centre, sleeping up to six guests and offering lake views.
Frequently asked questions about holiday rentals in Kissimmee, FL
What should a first-time visitor not miss in Kissimmee?
You've got to check out the theme parks like Walt Disney World and Universal Orlando Resort. They're a must-see for any first-timer. And don't forget to visit the Kennedy Space Center Visitor Complex for a glimpse into space exploration.
What are the best Airbnb and vacation rentals in Kissimmee, FL?
What types of vacation rentals can I find in Kissimmee?
You can find all kinds of vacation rentals in Kissimmee, Florida. There are entire houses, apartments, bungalows and cottages you can rent out, as well as more unique vacation rentals, such as cabins, tree houses, or tiny houses. We can help you find the right vacation rental for your stay in Kissimmee.
Which neighborhood in Kissimmee should you consider for a vacation rental?
The area around Old Town is a popular choice. It's close to the theme parks, restaurants, and shops. For a quieter stay, consider the Reunion Resort area, which has plenty of luxury villas with private pools.
What are the most popular Airbnbs in Kissimmee, FL?
Kissimmee is world-famous for its theme parks, like Walt Disney World Resorts, Seaworld Parks & Resorts, and Universal Orlando Resort. However, there is much more to Kissimmee than theme parks. You can get out in nature, go fishing, ride a hot air balloon, go on an airboat adventure through the Central Florida Everglades, visit a Native American Village, go horse riding and more. You can also catch a game with the Orlando Solar Bears or get a round of golf in. There is something for everyone in Kissimmee.
What are the top family-friendly attractions in Kissimmee?
Besides the theme parks, the Gatorland is always a hit with kids. It's home to alligators, crocodiles, and other reptiles. And don't forget about the Aquatica, SeaWorld's waterpark, for a fun day in the sun.
What are the best vacation rentals with a pool in Kissimmee, FL?
Top attractions in Kissimmee include Old Town, where you'll find a Ferris wheel, ride attractions like a roller coaster, a classic merry-go-round and more. You can visit Old Town for free anytime, and there are many places to eat and drink. Medieval Times Dinner and Tournament is another popular attraction, where you're welcomed into the king's court for a four-course feast and a show complete with jousting and more. Then, of course, there's Walt Disney World, which needs no introduction.
When is the best time to book a vacation rental in Kissimmee?
The busiest time is during the school holidays, so book well in advance if you're travelling then. If you're flexible, you can find good deals in the shoulder seasons, like spring and autumn.
What are the best rentals for families and kids in Kissimmee, FL?
It's easy to get around Kissimmee, as you'll find a range of transportation options, from taxis and rideshares like Uber and Lyft to shuttles and LYNX, the public transportation system for Central Florida mostly consisting of local bus services.
What are the best budget-friendly activities in Kissimmee?
A walk around Lakefront Park is a great way to enjoy the outdoors without spending a fortune. You can also visit the Polk Museum of Art for a free afternoon of culture.
What are the best rentals or Airbnbs with a jacuzzi in Kissimmee, FL?
The best time to come to Kissimmee is between January and April, as there is little rain and the temperatures are warm, but not too hot.
What are the best restaurants with local dishes in Kissimmee?
For a taste of Florida, try the seafood at The Boathouse Restaurant on the shores of Lake Tohopekaliga. If you're craving something a bit more casual, head to The Dixie Crossroads for their famous fried chicken.
What are the best walking or cycling routes in Kissimmee?
The Shingle Creek Trail is a great option for a leisurely walk or bike ride. It's a paved trail that runs along the Shingle Creek, offering scenic views of the natural surroundings.
Are there pet-friendly attractions in Kissimmee?
You can take your furry friend to the Celebration Town Center, which has a dog park and plenty of shops and restaurants that welcome pets. The Celebration Farmers Market is also a great place to visit with your dog.
What are the benefits of choosing a vacation rental in Kissimmee?
Vacation rentals offer more space and privacy compared to hotels. They often come with amenities like a private pool and a kitchen, which can save you money on dining out.
What are the top sports attractions and facilities in Kissimmee?
Kissimmee is home to the Silver Spurs Arena, which hosts rodeos and other events. For golf enthusiasts, there are several championship courses in the area, including the Reunion Resort.
Destinations nearby
Best Kissimmee, FL holiday rentals with a balcony
Kissimmee, FL
01/07 – 08/07
SG$213/nighttotal: SG$1491 (7 )
3br House At Lake Berkley Resort
1 6
house , Kissimmee
This detached residence in Kissimmee's Lake Berkley Resort is situated approximately 14.5 kilometres from Disney's Hollywood Studios and Disney Springs, and 11.6 kilometres from Disney's Wide World of Sports, with Gatorland 11.6 kilometres away. This property accommodates up to 11 guests with 3 bedrooms and 3 bathrooms, featuring a private outdoor swimming pool, a fully equipped kitchen including a dishwasher and oven, complimentary WiFi, and exclusive access to Lake Berkley Resort amenities such as a bar and children's playground.
9.8 11 reviews
Kissimmee, FL
02/07 – 05/07
SG$318/nighttotal: SG$954 (3 )
9 Mi To Disney: Resort Getaway W\/ Private Patio!
3 2
resort , Kissimmee
This Kissimmee holiday home is situated within 1.6km of Medieval Times dinner theatre and the 192 Flea Market, and within 4.8km of Shingle Creek Regional Park and Osceola Square Mall. This three-bedroom property, boasting 120 square metres of floor space, comfortably sleeps eight guests and includes a private pool, jacuzzi, and fully equipped kitchen; enjoy nearby attractions such as the flea market and regional park.
8.6 49 reviews
Kissimmee, FL
26/06 – 01/07
SG$192/nighttotal: SG$960 (5 )
Disney Adjacent
2 2
apartment , Kissimmee
This two-bedroom apartment is situated just a short distance from Plaza del Sol Kissimmee, Fun 'N' Wheels Fun Park, and the 192 Flea Market, offering easy access to a range of attractions and entertainment options. Guests consistently rate the property highly for its cleanliness, location, and overall experience. The apartment is spacious and comfortable, accommodating up to six guests. It features a fully-equipped kitchen, a private terrace, a swimming pool, a fitness centre, and a tennis court, ensuring a relaxing and enjoyable stay.
Kissimmee, FL
05/07 – 04/08
SG$116/nighttotal: SG$3480 (30 )
The Ideal Getaway V
3 2
house , Kissimmee
This detached villa in Kissimmee is located 11.59 kilometres from Gatorland and within 14 kilometres of major Disney attractions including Disney's Wide World of Sports, Disney Springs, and Disney's Hollywood Studios. This 120 square metre holiday home accommodates six guests across three bedrooms and three bathrooms, featuring air conditioning, complimentary Wi-Fi, a fully equipped kitchen with a microwave and dishwasher, and a private balcony.
Best Kissimmee, FL holiday rentals with air conditioning
8.5 24 reviews
Kissimmee, FL
03/07 – 09/07
SG$232/nighttotal: SG$1392 (6 )
Ideal 3 Br Resort Villa With Laundry
3 2
apartment , Kissimmee
This Kissimmee resort villa offers a superb location, approximately 13.7 kilometres from both Disney's Wide World of Sports and Gatorland. The 111-square-metre self-catering apartment sleeps up to 11 guests, boasting three bedrooms, three bathrooms, a fully equipped kitchen, and access to on-site amenities including a swimming pool, jacuzzi, fitness centre, and tennis court.
9.9 60 reviews
Kissimmee, FL
24/07 – 26/07
SG$391/nighttotal: SG$782 (2 )
Indulge In Luxurious Home Near Disney
1 4
apartment , Kissimmee
This Kissimmee holiday home, located minutes (approximately 5-10km) from Walt Disney World Resort and Universal Orlando Resort, offers easy access to major theme parks and nearby shopping. The spacious property boasts a 5-bedroom, 4-bathroom layout sleeping up to 8 guests, complete with a private screened pool, barbecue, patio furniture, Wi-Fi, Netflix, cable TV, and a laundry room.
9.4 80 reviews
Kissimmee, FL
02/07 – 05/07
SG$427/nighttotal: SG$1281 (3 )
Villa W/ Pvt Pool & Bbq + Games | 15 Min Disney
1 7
house , Kissimmee
This four-bedroom, three-bathroom house in the Crystal Cove resort is situated approximately 9.6km from the Walt Disney World entrance in the Orlando, Florida Disney area. The self-catering property sleeps ten guests and boasts a private pool, game room, in-house laundry, and access to Crystal Cove resort amenities, including a club.
8.8 8 reviews
Kissimmee, FL
19/07 – 21/07
SG$283/nighttotal: SG$566 (2 )
Kissimmee Escape ~ 10 Mi To Disney World!
3 2
apartment , Kissimmee
This Kissimmee holiday home is situated less than 2km from Medieval Times and the 192 Flea Market, and within 5km of Shingle Creek Regional Park and Give Kids the World Village. The 120 square metre property boasts three bedrooms, three bathrooms, sleeps six guests, and includes a private swimming pool, jacuzzi, and fully equipped kitchen; laundry facilities are also available.
