This charming cottage is situated just a short distance from Kissimmee's main attractions, making it ideal for exploring the theme parks and other local hotspots. The property consistently receives excellent ratings for location, cleanliness and overall guest experience. The two-bedroom cottage can comfortably accommodate up to four guests and features a unique loft bedroom. Guests can enjoy a private porch, a fully equipped kitchen and a refreshing dip in the heated saltwater pool.
Kissimmee, FL
14/08 – 16/08
SG$325/nighttotal: SG$650 (2 )
Private Hot Tub Near Disney Parks
3 2
house , Kissimmee
This holiday cottage is located in Kissimmee, approximately 13 to 16 kilometres from major Disney attractions such as Walt Disney World Resort, Hollywood Studios, Blizzard Beach Water Park, and Disney Springs, and 13.2 kilometres from Gatorland. This property offers 119 square metres of living space, accommodating up to 10 guests across three bedrooms and two bathrooms, complete with a fully equipped kitchen, air conditioning, a private hot tub, and complimentary WiFi.
9.8 8 reviews
Kissimmee, FL
10/12 – 23/12
SG$173/nighttotal: SG$2249 (13 )
Magical Memories! Splash Pad/pool Resort!
3 2
house , Kissimmee
This townhome in Kissimmee offers excellent access to Walt Disney World, SeaWorld, and Universal Studios, all within a short drive. The 121 square meter property sleeps six across three bedrooms and two bathrooms, featuring a fully equipped kitchen, private patio, on-site laundry, and access to a resort with a pool and hot tub.
9.5 66 reviews
Kissimmee, FL
02/07 – 05/07
SG$320/nighttotal: SG$960 (3 )
*4bd Villa | Relax & Enjoy Near Disney*
4 8
house , Kissimmee
This four-bedroom, three-bathroom townhome is located in the Seven Dwarfs community in Kissimmee, Florida, close to US-192 and a short drive (distance unspecified) from the Disney parks. The fully renovated property, sleeping up to ten guests, boasts a jacuzzi, fitness centre, and access to community swimming pools and tennis courts; a starter kit of toiletries and cleaning supplies is provided.
9.6 5 reviews
Kissimmee, FL
01/07 – 02/07
SG$900/nightfor 1 night
Enchanted Villa With Lake View 6-bedroom In Resort
6 2
house , Kissimmee
This six-bedroom, three-bathroom villa is located in the Lake Berkley Resort in Kissimmee, Florida, approximately 16km from Walt Disney World Resort, 24km from SeaWorld Orlando, and 32km from Universal Orlando Resort's Wizarding World of Harry Potter. The 232 square metre property boasts a Harry Potter-themed interior, a private pool, and access to resort amenities including a clubhouse, lakeside access, and a community pool; it comfortably sleeps 13 guests.
9.4 78 reviews
Kissimmee, FL
01/11 – 15/11
SG$255/nighttotal: SG$3570 (14 )
Close To Disney And All Orlando Attractions Including Outlet Malls And Dining & Minutes To Hwy 192
5 2
house , Kissimmee
This five-bedroom villa is located in Bellavida, Kissimmee, just 2.4 kilometres from Medieval Times and within easy reach of other popular attractions like the 192 Flea Market and Shingle Creek Regional Park. The property has received excellent ratings for its location, cleanliness, and overall experience. The 224 square metre villa comfortably accommodates up to 10 guests and features a private pool, a spacious garden, a fitness centre, and a spa. Guests can enjoy a range of amenities including a fully equipped kitchen, air conditioning, and a terrace, as well as family-friendly features like a water park and a games room.
9.7 15 reviews
Kissimmee, FL
22/07 – 30/07
SG$174/nighttotal: SG$1392 (8 )
3br. Modern Resort-style Townhouse Near Disney
1 5
house , Kissimmee
This centrally located townhouse in Kissimmee places you mere minutes from the entrance of Walt Disney World Resort, Universal Studios Florida, and SeaWorld Orlando, with local shops and restaurants also within a short walk. This family-friendly accommodation offers three bedrooms, two bathrooms, and sleeps up to seven guests, featuring a fully equipped kitchen, air conditioning, a private swimming pool, a jacuzzi, and access to resort amenities including a fitness centre and sports courts.
9.7 38 reviews
Kissimmee, FL
01/07 – 02/07
SG$147/nightfor 1 night
Hermosa Habitación Para Pareja
1 2
house , Kissimmee
This self-contained Kissimmee property, approximately 32km from Walt Disney World Resort, offers easy access to other Orlando attractions including SeaWorld and Universal Orlando Resort. The one-bedroom, one-bathroom house sleeps two guests and includes a private kitchen with fridge, freezer, and microwave, air conditioning, parking, and private laundry facilities.
9.9 346 reviews
Kissimmee, FL
03/10 – 17/10
SG$123/nighttotal: SG$1722 (14 )
Bitty Bliss Tiny House| Near Disney & Universal
1 2
house , Kissimmee
This charming cottage is located in Kissimmee, just a 20-minute drive from both Disney and Universal Studios, with shopping and restaurants within a 5-minute drive. It has consistently received excellent ratings for its location, cleanliness, and overall guest experience. The cottage features one bedroom with a queen-sized bed, a comfortable queen-sized sofa bed in the living area, and can accommodate up to four guests. The property offers a range of amenities, including a private swimming pool, a well-equipped kitchen, a relaxing porch, and access to a fitness centre and laundry facilities.
Kissimmee, FL
18/07 – 20/07
SG$332/nighttotal: SG$664 (2 )
Peaceful Palms Stay For 6
1 2
house , Kissimmee
This holiday home is situated in Kissimmee, offering convenient access to attractions such as Gatorland (approximately 11.6 kilometres), Disney Springs (approximately 14.6 kilometres), and Disney's Boardwalk (approximately 16.1 kilometres). This property offers 3 bedrooms, 3 bathrooms, a fully equipped kitchen with a dishwasher and oven, and accommodates up to 7 guests, with amenities including air conditioning, a swimming pool, a garden, a fitness centre, a water park, complimentary WiFi, and on-site parking, all within a floor area of 121 square metres.
9.6 11 reviews
Kissimmee, FL
20/07 – 29/07
SG$312/nighttotal: SG$2808 (9 )
4 Bedrooms/ 3 Bathrooms Storey Lake (2625 Rt)
1 7
house , Kissimmee
This four-bedroom, three-bathroom Kissimmee holiday home is situated in the Storey Lake Resort community, a short 11km drive from Walt Disney World, 24km from SeaWorld, and 35km from Universal Studios Florida. The property boasts a private screened pool with a child safety fence, resort-style amenities including a lazy river and waterslides, and comfortably sleeps eight guests with a fully equipped kitchen and laundry facilities.
8.6 39 reviews
Kissimmee, FL
01/08 – 06/08
SG$197/nighttotal: SG$985 (5 )
The Villas At Seven Dwarfs - 2624 Mickey Villa - Near Disney - Water Park
3 4
house , Kissimmee
This Kissimmee villa is situated approximately 11 kilometres from Disney Springs, Hollywood Studios, and Blizzard Beach, offering convenient access to other attractions such as Gatorland and Disney's Wide World of Sports. Sleeping up to 17 guests, this three-bedroom, two-bathroom property boasts free Wi-Fi, private parking, and is a non-smoking family-friendly home close to Disney's Boardwalk and Orlando International Airport (30km).
Best Kissimmee, FL villas and holiday homes with a pool
Among the 8901 accommodations in Kissimmee, FL, here are the 4 best villas and holiday homes with a pool
9.6 111 reviews
Kissimmee, FL
28/08 – 05/09
SG$236/nighttotal: SG$1888 (8 )
Orlando Family Villa Upgraded In 2026
4 12
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.
9.0 63 reviews
Kissimmee, FL
14/08 – 16/08
SG$505/nighttotal: SG$1010 (2 )
Cozy Family 4-bedroom Bella Vida Home Near Disney World
4 6
house , Kissimmee
This spacious villa is located in the Bella Vida Resort, just 6 kilometres from Walt Disney World and within walking distance of a shopping centre with restaurants and a Walmart. It has received excellent ratings for location, cleanliness and user experience. The property spans 191 square metres and comfortably accommodates up to 12 guests in its four bedrooms. The villa boasts a private pool and spa, a fully equipped kitchen, a games room, a patio with sun loungers and an outdoor table, a covered lanai and a private screened-in pool area.
9.7 254 reviews
Kissimmee, FL
08/08 – 15/08
SG$231/nighttotal: SG$1617 (7 )
Veranda Palms Luxurious Home W/pool & Near Disney
4 4
house , Kissimmee
This four-bedroom house is located in Veranda Palms, a community near Disney and all amusement parks in Kissimmee, just a short drive from US-192. The property has consistently received excellent ratings from previous guests for its location, cleanliness, and overall experience. The spacious home can comfortably accommodate up to eight guests, making it ideal for families or groups of friends. Amenities include a private heated pool, a Jacuzzi, a fitness centre, and a garden, offering a range of activities and relaxation options.
9.6 155 reviews
Kissimmee, FL
26/07 – 30/07
SG$432/nighttotal: SG$1728 (4 )
Seasons Villa 6 Bedrooms, 4 Masters And Water View
6 8
house , Kissimmee
This six-bedroom villa is located in Kissimmee, just 12 kilometres from Gatorland and 14 kilometres from Disney's Wide World of Sports, making it an ideal base for exploring the area's attractions. It has consistently received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay. The spacious villa, spanning 263 square metres, comfortably accommodates up to 13 guests. It boasts a private pool and hot tub, a fully equipped kitchen, a terrace with lake views, and a garden, offering a relaxing and enjoyable experience for families and groups.
Best family friendly Kissimmee, FL villas and holiday home
Among the 8901 accommodations in Kissimmee, FL, here are the 4 best family friendly villas and holiday homes
9.5 43 reviews
Kissimmee, FL
26/07 – 30/07
SG$388/nighttotal: SG$1552 (4 )
5br/5ba Game/pool Villa 9 Miles To Disney
5 8
house , Kissimmee
This five-bedroom, five-bathroom Kissimmee villa is ideally situated near Shingle Creek Regional Park, less than 5km from attractions including Capone's Dinner Show, the 192 Flea Market, and Medieval Times. The property boasts a private pool, Jacuzzi, and game room, comfortably accommodating up to ten guests and offering free Wi-Fi, a fully equipped kitchen, and on-site laundry facilities.
10 1 review
Kissimmee, FL
23/06 – 30/06
SG$233/nighttotal: SG$1631 (7 )
Cozy Kissimmee Hideaway
1 2
house , Kissimmee
This detached house in Kissimmee is conveniently located between 12.2 and 16.1 kilometres from major Orlando attractions such as Gatorland, Disney's Wide World of Sports, Disney's Boardwalk, and Disney's Blizzard Beach Water Park, offering free private parking and complimentary WiFi. This accommodation provides a fully equipped kitchen, air conditioning, and a terrace, with a generous floor area of 1000 square meters and capacity for up to 15 guests.
10 4 reviews
Kissimmee, FL
17/07 – 19/07
SG$486/nighttotal: SG$972 (2 )
Comfortable House With Hot Tub Close To Disney
5 3
house , Kissimmee
This spacious five-bedroom Kissimmee villa is ideally located approximately 16-18 kilometres from Walt Disney World Resort, Gatorland, and Disney Springs. The 241-square-metre property boasts a private pool, hot tub, and terrace, comfortably accommodating up to 23 guests with five bathrooms and a fully equipped kitchen; enjoy nearby attractions including outdoor dining.
Kissimmee, FL
13/07 – 17/07
SG$541/nighttotal: SG$2164 (4 )
2614 Veranda Palms
1 15
house , Kissimmee
This Kissimmee holiday home is situated 12.4km from Disney Springs and 12.6km from Gatorland, offering easy access to various Disney theme parks within a 13km radius. Sleeping up to 29 guests, this one-bedroom property boasts six bathrooms, a private pool, free parking, free Wi-Fi, a fully equipped kitchen including a dishwasher and microwave, and in-unit laundry facilities.
Frequently asked questions about villa rentals in Kissimmee, FL
What indoor activities for families are available in Kissimmee on rainy days?
On a rainy day, head to the Museum of Illusions, which is fun for all ages. You can also check out the indoor activities at the WonderWorks or the Orlando Science Center, which is just a short drive away.
Kissimmee is a great place for all sorts of activities. Of course, the theme parks are a big draw, but you can also enjoy a round of golf at one of the many courses, go on a airboat ride through the Everglades, or visit the Osceola County Welcome Center and Museum, which tells the story of the area.
What are the best villa rentals with a pool in Kissimmee, FL?
What are the advantages of renting a house or a villa in Kissimmee
Renting a villa or house gives you more space and privacy than a hotel. They often have a private pool, which is perfect for families, and you can save money by cooking some of your own meals. There are some great villa rentals near the Celebration area, which is a lovely, planned community.
What are the best villa rentals with a jacuzzi in Kissimmee, FL?
What food festivals or culinary events take place in and around Kissimmee?
Kissimmee has a great food scene! There's the annual Florida Strawberry Festival in Plant City, which is a bit of a drive, but worth it. You can also check out the Kissimmee Restaurant Week, which happens twice a year, and features special menus and deals at local restaurants.
What are the best villa rentals for families and kids in Kissimmee, FL?
What exclusive experiences are available when visiting Kissimmee?
For a truly exclusive experience, you can book a private dinner at Victoria & Albert's at Disney's Grand Floridian Resort & Spa. It's a world-class restaurant with a prix fixe menu. You could also try a private tour of the theme parks, which gives you a chance to see everything without the crowds.
What are the best pet friendly villa rentals in Kissimmee, FL?
Which part of Kissimmee would be ideal for a villa rental?
The Celebration area is a popular choice for villa rentals. It's a beautiful, planned community with a lot of family-friendly amenities. The area around Disney's Animal Kingdom is also a good option, as it's close to the theme park and has a lot of restaurants and shops.
What are the best villa rentals with parking in Kissimmee, FL?
Best Kissimmee, FL villas and holiday homes with parking
10 1 review
Kissimmee, FL
22/06 – 06/07
SG$270/nighttotal: SG$3780 (14 )
Cozy Townhouse With Private Pool In Kissimmee
3 4
house , Kissimmee
This Kissimmee townhouse is located in a well-connected area, offering convenient access to local attractions and amenities. This 120 square meter villa sleeps 19 guests and features a private swimming pool, a garden, a fitness centre, and a kitchen with a fridge, microwave oven, and dishwasher, with complimentary Wi-Fi and on-site parking.
Kissimmee, FL
06/11 – 08/11
SG$333/nighttotal: SG$666 (2 )
3br Home At Fiesta Key Near Disney
3 2
house , Kissimmee
This 171 square metre villa in Kissimmee is situated within Fiesta Key Resort, offering convenient access to attractions like Gatorland (15 kilometres) and Disney's Wide World of Sports (16 kilometres). This air-conditioned property accommodates up to 12 guests across 3 bedrooms, boasting a fully equipped kitchen with a dishwasher and oven, complimentary WiFi, a private balcony, and on-site parking.
8.5 20 reviews
Kissimmee, FL
18/07 – 20/07
SG$565/nighttotal: SG$1130 (2 )
201 Hideaway Beach 4 Beds - Pool&spa
4 6
house , Kissimmee
This spacious four-bedroom villa is situated in Kissimmee, Florida, conveniently located approximately 13km from Gatorland, 16km from Disney Springs, and 16km from Disney's Wide World of Sports. The 186 square metre property boasts a private pool, spa, and tennis court, accommodating up to 15 guests and offering a fully equipped kitchen, three bathrooms, and family-friendly amenities including an indoor play area, outdoor play equipment, and a kids' pool.
9.2 54 reviews
Kissimmee, FL
27/12 – 03/01
SG$425/nighttotal: SG$2975 (7 )
Luxury Themed Room Villa W/private Pool & Playground! Gameroom. Pool Table
4 7
house , Kissimmee
This four-bedroom villa is located in Magic Landings, Kissimmee, just 1.5 kilometres from Osceola Heritage Park and Osceola County Stadium, and less than 2 kilometres from Silver Spurs Arena and Houston Astros Spring Training. This property has received excellent ratings for location, cleanliness, and overall user experience. The villa offers 232 square metres of space, comfortably accommodating up to eight guests. It includes a private pool, a garden, barbecue grills, a fully equipped kitchen, a fireplace, and a patio, making it perfect for family vacations or group getaways.
Best Kissimmee, FL villas and holiday homes with a garden
9.7 70 reviews
Kissimmee, FL
03/07 – 05/07
SG$352/nighttotal: SG$704 (2 )
Amazing Premium 4 Bedr 5* Resort Unit Near Disney
1 7
house , Kissimmee
This newly renovated four-bedroom townhouse is situated in a gated resort community in Kissimmee, Florida, approximately 6.4 kilometres from Walt Disney World. The property sleeps eight guests and boasts a fully equipped kitchen, private swimming pool, fitness centre, and access to resort amenities including a heated pool, tennis courts, and a children's play area.
9.8 77 reviews
Kissimmee, FL
13/07 – 18/07
SG$325/nighttotal: SG$1625 (5 )
Modern 4br Home With Private Pool Near Disney
4 6
house , Kissimmee
This Kissimmee holiday home, located in the Storey Lake Resort, is just 26km from Walt Disney World and 39km from Universal Studios Florida. The four-bedroom, three-bathroom property sleeps twelve guests, boasting a private pool (with optional heating), access to the resort's clubhouses with lazy river and water slides, a fully equipped kitchen, and a fitness centre.
8.0 18 reviews
Kissimmee, FL
03/07 – 05/07
SG$600/nighttotal: SG$1200 (2 )
Bikini Bottom - 4 Bed Disney Pool Home
4 7
house , Kissimmee
This four-bedroom house is ideally located in Kissimmee, just 13 kilometres from Gatorland and 16 kilometres from Disney Springs, making it a convenient base for exploring the area’s many attractions. The property has received very good user ratings, an excellent location rating, and an OK cleanliness rating. The house spans 144 square metres and offers a comfortable living space for families or groups. Guests can enjoy a range of amenities including a private pool and tennis court, a bar, a hot tub, a fully equipped kitchen, a children's playground, table tennis, free Wi-Fi, private parking, and the option to heat the pool for an additional fee.
9.5 90 reviews
Kissimmee, FL
14/10 – 18/10
SG$494/nighttotal: SG$1976 (4 )
Stars Align Storey Lake By Shine Villas Villa
6 11
house , Kissimmee
This six-bedroom Kissimmee villa is ideally situated approximately 13 kilometres from Disney Springs and Gatorland, offering easy access to other attractions including Hollywood Studios, Blizzard Beach, Wide World of Sports Complex, and the Boardwalk. This spacious 344-square-metre property boasts a private pool, jacuzzi, and fitness centre, alongside a fully equipped kitchen, laundry facilities, and free Wi-Fi; perfect for large families or groups seeking a comfortable and convenient base for exploring the theme parks.