This luxury 15-bedroom villa in Kissimmee is situated between 11.9 and 15.1 kilometres from attractions such as Gatorland, Disney Springs, Disney's Wide World of Sports, and Disney's Boardwalk, with Orlando International Airport located 22.5 kilometres away. This expansive property offers a private swimming pool and 16 bathrooms, accommodating up to 26 guests with complimentary WiFi and a fully equipped kitchen, perfect for large family holidays or group stays near Orlando's theme parks.
10 2 reviews
Kissimmee, FL
17/08 – 18/08
240 €/nightfor 1 night
Super Boho - At Lake Toho Fishing Vintage Vibes
2 1
house , Kissimmee
This two-bedroom Kissimmee holiday home is located less than 0.8km from the city centre and under 8km from Gatorland, with SeaWorld and Disney Springs within a 21km radius. The 71 square metre property offers a spacious layout sleeping up to six guests, boasting a fully equipped kitchen with modern appliances, air conditioning, Wi-Fi, and pet-friendly accommodation.
9.8 8 reviews
Kissimmee, FL
17/07 – 19/07
207 €/nighttotal: 414 € (2 )
Laoxury 3bd Townhome Pool Front In Brilliant Kissimmee
3 3
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.
9.6 111 reviews
Kissimmee, FL
16/07 – 19/07
382 €/nighttotal: 1146 € (3 )
Free Resort Access, Private Pool Near Disney 2966
4 8
house , Kissimmee
This four-bedroom house is located in Kissimmee, just 13 kilometres from Gatorland and 13 kilometres from Disney Springs. The 178 square metre property offers a private pool, a Jacuzzi, a bar and a fitness centre, perfect for families or groups of friends.
9.7 164 reviews
Kissimmee, FL
31/10 – 07/11
155 €/nighttotal: 1085 € (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.
9.0 12 reviews
Kissimmee, FL
05/07 – 04/08
49 €/nighttotal: 1470 € (30 )
Waterfront/kayakfishing/neardisney&laketohoa/pets
1 2
house , Kissimmee
This peaceful Kissimmee apartment is situated directly opposite the National Golf Club, offering easy walking access to local supermarkets, restaurants, and shops. The one-bedroom, one-bathroom property sleeps two guests and features a California King bed, a comfortable sofa, a fully equipped kitchen including fridge-freezer and microwave, and a spacious yard with water access for kayaking and boating on a natural lake; internet and air conditioning are also provided.
9.9 89 reviews
Kissimmee, FL
03/07 – 05/07
385 €/nighttotal: 770 € (2 )
Enchanted Themed-house At Storey Lake
4 5
house , Kissimmee
This four-bedroom Storey Lake Resort apartment in Kissimmee, Florida, is ideally located approximately 8km from Walt Disney World Resort, 11km from SeaWorld Orlando, and a short drive from Universal Orlando Resort. The self-catering property sleeps twelve guests and boasts a private heated pool with screened lanai, themed bedrooms (Mario Bros, Minions), a Mickey Mouse bathroom, access to two resort clubhouses with water parks, and includes baby gear (upon request).
9.6 199 reviews
Kissimmee, FL
27/06 – 04/07
152 €/nighttotal: 1064 € (7 )
Open Dates For March - Resort Acess
3 2
resort , Kissimmee
This smoke-free vacation home is located in Kissimmee, within a 15-minute walk of Capone's Dinner Show and Kissimmee Go-Karts, and within 5km of Shingle Creek Regional Park and Medieval Times. The resort has excellent user, location, and cleanliness ratings. This 185 square metre property has three bedrooms and can accommodate six guests. The villa is fully equipped with a kitchen, laundry facilities, two bathrooms, a television, a garden, and a swimming pool.
9.9 42 reviews
Kissimmee, FL
26/07 – 30/07
94 €/nighttotal: 376 € (4 )
Cozy Apartment In S Orlando, Approx. 20 Minutes Away From Disney And Universal.
1 2
apartment , Southchase
This Southchase apartment is situated within 9.6km of the Florida Mall, Orlando Kart Center, and Osceola Performing Arts Center, offering easy access to major attractions. The one-bedroom, one-bathroom flat sleeps four guests and features a kitchenette with refrigerator, microwave and stovetop, in-unit laundry, a Jacuzzi, and parking; nearby recreational options include Shingle Creek Regional Park and The Ritz-Carlton Golf Club.
9.7 269 reviews
Kissimmee, FL
09/09 – 19/09
113 €/nighttotal: 1130 € (10 )
Fully Remodeled Stylish 3/2 Condo, Close To The Parks
3 6
apartment , Kissimmee
This Kissimmee condo is ideally situated within 5km of attractions including Kissimmee Go-Karts, Capone's Dinner & Show, and Medieval Times, offering convenient access to the 192 Flea Market and Shingle Creek Regional Park. The three-bedroom, two-bathroom apartment boasts a fully equipped kitchen, in-unit laundry, a private terrace, and access to a swimming pool, jacuzzi, sauna, and fitness centre; on-site BBQ facilities are also available.
10 1 review
Kissimmee, FL
27/06 – 04/07
156 €/nighttotal: 1092 € (7 )
3 Bedroom 3 Bathroom Terra Verde 4766
3 2
house , Kissimmee
This Kissimmee holiday home is conveniently located approximately 13.7 kilometres from Disney's Wide World of Sports and Gatorland, and less than 14.5 kilometres from Disney's Hollywood Studios and Blizzard Beach Water Park. The 119 square metre property boasts three bedrooms, three bathrooms, sleeps up to 15 guests, and includes a private pool, fitness centre, and fully equipped kitchen; nearby amenities include a water park and outdoor play equipment.
9.6 20 reviews
Kissimmee, FL
21/07 – 31/07
120 €/nighttotal: 1200 € (10 )
4 Bedroom 3 Bathroom Villas At Seven Dwarfs 1-101
1 4
house , Kissimmee
This Kissimmee holiday home, located in the Villas at Seven Dwarfs resort, is approximately 16km from Walt Disney World, 26km from SeaWorld, and 34km from Universal Studios. The spacious four-bedroom, three-bathroom property sleeps eight guests and boasts a private pool, access to a clubhouse with a Tiki bar and resort amenities, plus in-house washer/dryer, baby equipment, and high-speed internet.
Best family friendly Kissimmee, FL holiday rentals
Among the 15321 accommodations in Kissimmee, FL, here are the 4 best family friendly rentals
9.6 112 reviews
Kissimmee, FL
13/09 – 18/09
212 €/nighttotal: 1060 € (5 )
Orlando Family Villa Upgraded In 2026
4 4
house , Kissimmee
This four-bedroom villa is located just 1.6 kilometres from Medieval Times and the 192 Flea Market in Kissimmee, a popular tourist destination in Florida. It is highly rated by previous guests and offers a comfortable and convenient base for exploring the area. The 143 square metre villa comfortably sleeps up to ten guests and offers a range of amenities, including a private pool, a fully equipped kitchen, a fitness centre, a tennis court, and a garden. Guests can also enjoy a relaxing soak in the jacuzzi or simply unwind on the terrace and soak up the Florida sunshine.
10 1 review
Kissimmee, FL
02/07 – 06/07
798 €/nighttotal: 3192 € (4 )
362 M² Villa ∙ 9 Bedrooms ∙ 19 Guests
9 17
house , Kissimmee
This expansive 9-bedroom villa, located in the Storey Lake Resort, offers convenient access to Orlando's theme parks, being just 8 kilometres from Walt Disney World, 11 kilometres from SeaWorld, and 16 kilometres from Universal Studios, with a supermarket 1.6 kilometres away and a shopping mall 3.2 kilometres away. This 362 square metre holiday home, designed for up to 19 guests, features a private screened pool with a hot tub, a games room with air hockey, pool, foosball, and arcade machines, alongside access to extensive 5-star resort amenities including a communal pool, waterslides, and a lazy river.
9.8 156 reviews
Kissimmee, FL
15/07 – 19/07
177 €/nighttotal: 708 € (4 )
Enjoy Disney From This 3 Bed, A Perfect Resort For The Family!
3 1
apartment , Kissimmee
This family-friendly house is located in Kissimmee, just 1.6 kilometres from Capone's Dinner Show and Kissimmee Go-Karts, and within 5 kilometres of 192 Flea Market and Lake Buena Vista Factory Stores. It has excellent user, location and cleanliness ratings. The house offers 120 square metres of space and includes three bedrooms. It comes with a range of amenities, including a swimming pool, Jacuzzi, sauna, spa, fitness centre, tennis court, and a fully equipped kitchen.
10 107 reviews
Kissimmee, FL
24/07 – 26/07
244 €/nighttotal: 488 € (2 )
Free Early Check-in For Reservations Starting April: 13, 14, 15, 20, 21, 22, 27.
3 4
apartment , Kissimmee
This modern townhouse is located in Kissimmee, within a gated community, just a short drive from Old Town and Disney Springs™, making it a convenient base for exploring the area’s attractions. The property has received excellent reviews from previous guests, highlighting its comfort and amenities. This spacious home offers 135 square metres of living space and comfortably accommodates up to eight guests across three bedrooms and three bathrooms. The property features a fully equipped kitchen, a private patio, a swimming pool, a jacuzzi, and a range of entertainment options, including multiple smart TVs and a gaming console, ensuring a relaxing and enjoyable stay for all.
Best Kissimmee, FL holiday rentals with parking
9.0 2 reviews
Kissimmee, FL
28/12 – 02/01
278 €/nighttotal: 1390 € (5 )
Spacious 7br, 4.5 Ba Retreat With Pool (164)
7 11
house , Kissimmee
This seven-bedroom Kissimmee holiday home is ideally situated within 5km of Give Kids the World Village, the 192 Flea Market, and Medieval Times, and 4km from Shingle Creek Regional Park. The 263 square metre property boasts five bathrooms, sleeps fourteen guests, and includes a fully equipped kitchen, swimming pool, sauna, spa, tennis court, and on-site water park and games room.
9.6 111 reviews
Kissimmee, FL
13/09 – 18/09
230 €/nighttotal: 1150 € (5 )
The Villa At Terra Verde
6 4
house , Kissimmee
The Villa at Terra Verde is situated in Kissimmee, just nine miles from both Gatorland and Disney's Wide World of Sports, making it a convenient base for exploring the area's attractions. This property has consistently received excellent ratings for location, cleanliness, and overall user experience. This spacious six-bedroom villa can comfortably accommodate up to 13 guests, offering plenty of room for families or groups of friends. The villa boasts a private pool and patio, a fully equipped kitchen, and a range of wellness amenities including a sauna, hot tub, and fitness room, ensuring a relaxing and enjoyable stay.
9.1 60 reviews
Kissimmee, FL
21/12 – 26/12
399 €/nighttotal: 1995 € (5 )
Fun Packed 5 Bedroom Villa With Private Pool/spa, Games Room & Grill
5 6
house , Kissimmee
This Lake Berkley residence is situated approximately 1.6km from Medieval Times and the 192 Flea Market, and within 4.8km of Shingle Creek Regional Park and Give Kids the World Village. This 217 square metre, five-bedroom property boasts two bathrooms, a private pool, Jacuzzi, and spa, alongside free Wi-Fi, parking and access to an on-site fitness centre and tennis court.
Kissimmee, FL
15/07 – 31/08
275 €/nighttotal: 113300 € (412 )
1200 Sq Ft 2 Bedroom 2 Bath , Orlando Fl
2 3
apartment , Doctor Phillips
This Doctor Phillips apartment, situated 0.16 km from Dr P Phillips Hospital and within 4.8 km of ICON Park and the Orange County Convention Centre, offers easy access to major attractions. The 111-square-metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes a full kitchen, balcony, swimming pool, jacuzzi, fitness centre, and tennis court, plus limited housekeeping.
Frequently asked questions about holiday rentals in Kissimmee, FL
Which neighborhood in Kissimmee should you consider for a vacation rental?
If you're looking for a vacation rental, the area around Celebration is a good bet. It's close to the theme parks and has a lovely, family-friendly atmosphere with plenty of restaurants and shops. You might also consider the Reunion area, which offers a good range of luxury rentals.
What are the best Airbnb and holiday 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.
What are the top family-friendly attractions in Kissimmee?
Kissimmee is a haven for families! You've got the big hitters like Disney World, Universal Studios, and SeaWorld, but don't forget about the smaller attractions like Gatorland, the Dinosaur World, and the Fun Spot America amusement park. These offer a different experience from the big theme parks and are great for all ages.
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.
When is the best time to book a vacation rental in Kissimmee?
To get the best deals, book your vacation rental well in advance, especially if you're travelling during peak season, which is typically from mid-December to mid-April. You can also try booking during the shoulder season (April-May and September-October) for better rates and fewer crowds.
What are the best holiday 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.
What events or festivals should visitors check out in and around Kissimmee?
Kissimmee has a vibrant events calendar throughout the year. The Osceola County Fair in February is a local favourite, and the Epcot International Food & Wine Festival in the autumn is a massive event that attracts visitors from all over. You can find a full list of events on the Kissimmee Convention and Visitors Bureau website.
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?
There are plenty of free and budget-friendly activities in Kissimmee. Head to the Lakefront Park for a picnic and a stroll, or visit the Kissimmee Air Museum for a glimpse into aviation history. The Osceola Heritage Park also offers free events throughout the year.
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 authentic Floridian cuisine, try the Dixie Crossroads in Titusville, just a short drive from Kissimmee. They're famous for their seafood, especially their stone crab claws. If you're looking for something closer to Kissimmee, try the Bob Evans restaurant on West Irlo Bronson Memorial Highway for a taste of classic American comfort food.
What are the best walking or cycling routes in Kissimmee?
The East Lake Tohopekaliga Loop is a great option for a leisurely bike ride, offering scenic views of the lake and the surrounding nature. For a shorter walk, the Celebration Town Center is a lovely area to stroll around, with its charming shops and restaurants.
Are there pet-friendly attractions in Kissimmee?
Yes, many attractions in Kissimmee are pet-friendly. The Promenade at Celebration is a great place to walk your dog, and the Osceola Heritage Park often hosts dog-friendly events. Check with individual attractions for their pet policies before you go.
Destinations nearby
Best Kissimmee, FL holiday rentals with a balcony
Kissimmee, FL
05/07 – 04/08
129 €/nighttotal: 3870 € (30 )
Comfortable 4br At Lake Berkley Near Disney
4 2
apartment , Kissimmee
This Kissimmee holiday home is situated within 3km of Medieval Times, the 192 Flea Market, and Shingle Creek Regional Park, and within 5km of Give Kids the World Village and Kissimmee Go-Karts. The 121 square metre property boasts three bedrooms, three bathrooms, sleeps eight guests, and includes a private pool, terrace, fitness centre, and fully equipped kitchen.
Kissimmee, FL
03/07 – 05/07
409 €/nighttotal: 818 € (2 )
Modern Resort Getaway 9 Mi To Disney Parks!
4 5
house , Kissimmee
This Kissimmee holiday villa is located 11.5 kilometres from Disney Springs and 12.4 kilometres from Gatorland. This 230 square metre holiday home offers accommodation for up to 25 guests, featuring 4 bedrooms, 4 bathrooms, a kitchen equipped with a fridge, microwave oven, and dishwasher, air conditioning, a swimming pool, a hot tub, a garden, and parking, with free Wi-Fi provided.
9.6 200 reviews
Kissimmee, FL
03/07 – 05/07
415 €/nighttotal: 830 € (2 )
The Eazy Breezy House - 4br W/ Heated Pool
4 5
house , Kissimmee
This Kissimmee holiday home, located approximately 11-16km from Walt Disney World Resort and Disney Springs, offers easy access to major attractions including Gatorland, 12km away. The property boasts a spacious layout with four bedrooms, three bathrooms, a private heated pool, free Wi-Fi, and private parking; ideal for families or groups of up to eight guests.
8.9 59 reviews
Kissimmee, FL
28/08 – 05/09
296 €/nighttotal: 2368 € (8 )
Sw/minions/marvel Themed/resort Access/disney!
9 12
apartment , Kissimmee
This nine-bedroom Kissimmee holiday home, offering the 'Ultimate Vacation Home With Pool, Resort Amenities, Near Disney & Orlando Attractions', is situated less than 1.6km from Shingle Creek Regional Park and Capone's Dinner Theatre, and within 3.2km of Kissimmee Go-Karts and the 192 Flea Market. The property boasts a private pool, on-site water park, fitness centre, games room, and barbecue facilities, accommodating up to 16 guests with seven bathrooms and concierge services.
Best Kissimmee, FL holiday rentals with air conditioning
9.4 85 reviews
Kissimmee, FL
31/07 – 01/09
123 €/nighttotal: 3936 € (32 )
Upgrade All, 24 Hrs Gated Guard Community, Lakeview, Spa, Bbq, Near Parks
3 2
apartment , Kissimmee
This waterfront holiday home is located in Kissimmee, just under 5km from Medieval Times, Give Kids the World Village, and Kissimmee Go-Karts, offering a peaceful escape from the city's hustle and bustle. The property has consistently received excellent user ratings, highlighting its appeal to travellers. This 3-bedroom, 3-bathroom villa spans 119 square metres and comfortably accommodates up to 8 guests. The home features a range of amenities, including a private pool, jacuzzi, sauna, fitness centre, tennis court, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.
Kissimmee, FL
02/07 – 05/07
108 €/nighttotal: 324 € (3 )
Newly Remodeled Tiny Home 20 Minutes From Disney!~
1 2
cabin , Kissimmee
This luxurious tiny home, available for rent in Kissimmee, is situated within a resort community, offering convenient access to the area's major theme parks and attractions. This well-appointed cabin accommodates two guests and features a recently remodelled interior with a custom kitchen and bathroom, air conditioning, internet, and a communal swimming pool and fitness centre.
9.1 260 reviews
Kissimmee, FL
08/09 – 12/09
189 €/nighttotal: 756 € (4 )
Dluxx Townhouse With Splash Pool At Le Reve 1144
5 2
house , Kissimmee
This Kissimmee townhome is conveniently located just a short drive from popular attractions like Gatorland and Disney Springs, making it an ideal base for exploring the area. The property consistently receives excellent ratings for its cleanliness, location, and overall user experience. The townhome offers a comfortable and well-equipped space for your stay, featuring a private pool, a balcony, a fully equipped kitchen, and a host of amenities including free Wi-Fi, air conditioning, and parking. Guests can enjoy a relaxing dip in the pool, prepare meals in the kitchen, or simply unwind on the balcony, taking in the fresh air and views.
10 3 reviews
Kissimmee, FL
24/07 – 26/07
134 €/nighttotal: 268 € (2 )
Modern 3br Townhome Retreat
3 4
apartment , Kissimmee
This central Kissimmee flat offers convenient access to local attractions, with major tourist destinations a short commute away. This pet-friendly accommodation sleeps 8 guests, featuring 3 bathrooms and a kitchen, with air conditioning for comfort, and is situated within easy reach of amenities and entertainment.
