Villas and Holiday homes in Kissimmee, FL

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Kissimmee, FL villas
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8901 Villa rentals in Kissimmee, FL

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

Orlando Family Villa Upgraded In 2026 - Kissimmee, FL
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.
Cozy Family 4-bedroom Bella Vida Home Near Disney World - Kissimmee, FL
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.
Veranda Palms Luxurious Home W/pool & Near Disney - Kissimmee, FL
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.
Seasons Villa 6 Bedrooms, 4 Masters And Water View - Kissimmee, FL
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

5br/5ba Game/pool Villa 9 Miles To Disney - Kissimmee, FL
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.
Cozy Kissimmee Hideaway - Kissimmee, FL
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.
Comfortable House With Hot Tub Close To Disney - Kissimmee, FL
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.
2614 Veranda Palms - Kissimmee, FL
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.

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Best Kissimmee, FL villas and holiday homes with parking

Cozy Townhouse With Private Pool In Kissimmee - Kissimmee, FL
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.
3br Home At Fiesta Key Near Disney - Kissimmee, FL
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.
201 Hideaway Beach 4 Beds - Pool&spa - Kissimmee, FL
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.
Luxury Themed Room Villa W/private Pool & Playground! Gameroom.  Pool Table - Kissimmee, FL
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

Amazing Premium 4 Bedr 5* Resort Unit Near Disney - Kissimmee, FL
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.
Modern 4br Home With Private Pool Near Disney - Kissimmee, FL
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.
Bikini Bottom - 4 Bed Disney Pool Home - Kissimmee, FL
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.
Stars Align Storey Lake By Shine Villas Villa - Kissimmee, FL
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.
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